Abstract:
The present invention relates to  Coix  seed oil extracted from  Semen Coicis , pharmaceutical preparations thereof, and the use thereof in the treatment of tumors and inflammation. Specifically, the  Coix  seed oil contains 5 diglyceride and 8 triglyceride ingredients in the following mass percentages: 1,3-diolein 0.40-0.58%, 1-linolein-3-olein 0.91-1.31%, 1,2-diolein 0.24-0.35%, 1-olein-2-linolein 0.66-0.95%, 1,2-dilinolein 0.33-0.47%, trilinolein 4.87-6.99%, 1-olein-2,3-dilinolein 13.00-18.69%, 1-palmitin-2,3-dilinolein 5.25-7.54%, 1,3-diolein-2-linolein 13.23-19.02%, 1-palmitin-2-linolein-3-olein 10.26-14.75%, 1,3-dipalmitin-2-linolein 2.28-3.28%, triolein 14.44-20.76% and 1-palmitin-2,3-diolein 8.06-11.58%.

Description:
CROSS REFERENCE TO RELATED PATENT APPLICATION 
     The present application claims a priority of the Chinese patent application CN201410342342.1 with filing date Jul. 18, 2014, which application is incorporated herein by reference. 
     FIELD OF THE INVENTION 
     The present invention relates to the pharmaceutical field, specifically, the present invention relates to  Coix  seed oil, pharmaceutical preparations thereof, the process for the preparation of same and the use thereof in the treatment of tumors and inflammation. 
     BACKGROUND OF THE INVENTION 
       Coix  seeds are dried ripe seeds of  Coix lacryma - jobi  L. var  ma - yuen  (Roman.),  Stapf , a genus of plant in the Poaceae family. It is a dampness-eliminating drug and has been used as a medicinal and edible plant for a long time. Modern researches have found that  Coix  seeds have many pharmacological effects, such as analgesic anti-inflammatory, immunomodulatory, anti-ulcer, hypolipidemic and anti-obesity effects. In recent years, researchers around the world have studied the chemical composition of the  Coix  seed by using TLC, HPLC-MS, GC, etc., and found a variety of active ingredients in it, including coixenolide, triglycerides, fatty acids, lactams,  coix  lactones, saccharides, sterols and triterpenoids. Among them, esters are the first discovered components having anti-tumor activities and the most reported chemical composition attracting the most attention. Kanglaite injection, in which the active ingredient is  Coix  seed oil, has been widely used in present Chinese clinical applications, but the  Coix  seed oil used in the Kanglaite injection comprises complex components. In addition to triglycerides, it also contains monoglycerides, diglycerides and fatty acid esters, etc. This will inevitably be a great challenge for the quality control in the practical production process and the safety in clinical applications. 
     In the present invention, the raw material  Coix  seed powder underwent supercritical carbon dioxide extraction, basification, neutral alumina purification and kaolin purification, etc., to afford an effective part,  Coix  seed oil. With the active ingredients&#39; isolation and identification, it is determined that the  Coix  seed oil comprises mainly eight triglyceride components and 5 diglyceride components. Further determination of physicochemical constants has confirmed the optimal acid value, iodine value, saponification value, refractive index and specific gravity, etc. The use of the  Coix  seed oil of the invention in medication has advantages such as the confirmed composition of ingredients, ensuring quality stability in every batch in the industrial production. 
     SUMMARY OF THE INVENTION 
     The first aspect of the invention is to provide a  Coix  seed oil extracted from  Semen Coilis . The  Coix  seed oil contains 5 diglyceride and 8 triglyceride ingredients in the following mass percentages: 1,3-diolein 0.40-0.58%, 1-linolein-3-olein 0.91-1.31%, 1,2-diolein 0.24-0.35%, 1-olein-2-linolein 0.66-0.95%, 1,2-dilinolein 0.33-0.47%, trilinolein 4.87-6.99%, 1-olein-2,3-dilinolein 13.00-18.69%, 1-palmitin-2,3-dilinolein 5.25-7.54%, 1,3-diolein-2-linolein 13.23-19.02%, 1-palmitin-2-linolein-3-olein 10.26-14.75%, 1,3-dipalmitin-2-linolein 2.28-3.28%, triolein 14.44-20.76% and 1-palmitin-2,3-diolein 8.06-11.58%. 
     Preferably, mass percentage contents of the above 5 diglyceride and 8 triglyceride ingredients are: 1,3-diolein 0.45-0.55%, 1-linolein-3-olein 1.03-1.25%, 1,2-diolein 0.27-0.33%, 1-olein-2-linolein 0.75-0.91%, 1,2-dilinolein 0.37-0.45%, trilinolein 5.47-6.69%, 1-olein-2,3-dilinolein 14.63-17.88%, 1-palmitin-2,3-dilinolein 5.90-7.21%, 1,3-diolein-2-linolein 14.88-18.19%, 1-palmitin-2-linolein-3-olein 11.55-14.11%, 1,3-dipalmitin-2-linolein 2.57-3.14%, triolein 16.25-19.86% and 1-palmitin-2,3-diolein 9.07-11.08%. 
     More preferably, mass percentage contents of the above 5 diglyceride and 8 triglyceride ingredients are: 1,3-diolein 0.49-0.51%, 1-linolein-3-olein 1.12-1.16%, 1,2-diolein 0.29-0.31%, 1-olein-2-linolein 0.81-0.85%, 1,2-dilinolein 0.40-0.42%, trilinolein 5.96-6.20%, 1-olein-2,3-dilinolein 15.93-16.58%, 1-palmitin-2,3-dilinolein 6.43-6.69%, 1,3-diolein-2-linolein 16.20-16.87%, 1-palmitin-2-linolein-3-olein 12.57-13.09%, 1,3-dipalmitin-2-linolein 2.79-2.91%, triolein 17.69-18.42% and 1-palmitin-2,3-diolein 9.87-10.27%. 
     The above contents refer to the mass percentage contents of diglyceride and triglyceride compounds in the  Coix  seed oil. 5 diglyceride and 8 triglyceride monomer compounds can be separated by using preparative chromatography from the  Coix  seed oil prepared by the following steps, and their contents can be obtained by weighing and calculating the products. They can also be obtained according to conventional analytic methods in the art. 
     The  Coix  seed oil has the following physicochemical constants based on the fatty oils: specific gravity at 20 0.916-0.920, refractive index at 20° C. 1.471-1.474, acid value&lt;0.2, iodine value 100-106, saponification value 186-195. 
     The  Coix  seed oil of the invention can be prepared by a refining process of crude  Coix  seed oil extracted by supercritical carbon dioxide extraction, 
     wherein: 
     the process of the supercritical carbon dioxide extraction comprises steps of: 
     crushing  Coix  seeds into 10 mesh-80 mesh powder and extracting same using a supercritical CO 2  extraction system in which  Coix  seed powder is put in 600 L×2 extractors; the CO 2  preheater, extractor and separation column are heated by jacketed circulating hot water to make the extraction temperature and separation temperature to reach 33-45° C. and 30-45° C., respectively; the outlet temperatures of separator I and separator II are kept at 20-50° C. and 15-35° C., respectively; the liquid CO 2  is pressed at a flow rate of 1-3 t/h into the CO 2  preheater via a high pressure pump, turning into a fluid in supercritical state; in the extractor, an oil is extracted into the CO 2  fluid at a pressure of 19-23 Mpa; then the CO 2  fluid with this oil enters the separation column in which the pressure is controlled to 7-10 Mpa to separate this oil; the CO 2  gas out from the separation column enters sequentially into separator I and separator II in which the pressure is sustained at 5-7 Mpa and 4-6 Mpa, respectively; impurities such as water separated therefrom are discarded; the CO 2  gas returns to liquid CO 2  for reuse through a condenser; and a continuous extraction for 2-3 h affords the crude  Coix  seed oil; and 
     the refining process comprises steps of: 
     adding petroleum ether (bp. 60° C.-90° C.) into the  Coix  seed oil obtained by the supercritical CO 2  extraction in an amount of 60% of the oil weight; adding 2% NaOH aqueous solution in an amount ranging from 36% to 56% of the oil weight according to the acid value; after stirring the mixture for 10 min and standing for 18-24 h, removing the lower niger layer; washing the upper layer with purified water and letting stand for 18-24 h; after the removal of the lower waste water, washing the upper layer again; after another standing for 40-50 h, removing the lower waste water; and demulsifying the upper layer with acetone in an amount of 70%-90% of the oil weight; after standing for 2-4 h, removing the lower waste acetone and adding 3% to 8% of activated neutral alumina by weight of crude oil in the upper oil layer; stirring the mixture for 30 min, then filtering off the precipitation; heating the filtrate and adding 2% to 6% of activated kaolin by weight of crude oil; stirring the mixture for 30 min at 40-50° C. and then filtering off the precipitation; concentrating the filtrate under a reduced pressure to recover the solvent, then washing again with purified water; after standing for 1-2 h, removing the lower waste water and heating the upper oil layer and vacuum drying it under nitrogen atmosphere; then adding 8 to 12% activated neutral alumina by weight of crude oil and stirring the mixture and allowing to stand at a cold place; after filtrating, concentrating the filtrated oil via heating under vacuum in a nitrogen atmosphere and sterilizing the oil via dry heat sterilization under vacuum at 160-170° C. for 1-2 h; after cooling, filtering the oil through a 0.2 μm microporous membrane; then split charging the obtained  Coix  seed oil in 500 mL glass infusion bottles, nitrogenizing and sealing the bottles. 
     Preferably, the refining process comprises steps of: 
     adding petroleum ether (bp. 60° C.-90° C.) into the  Coix  seed oil obtained by the supercritical CO 2  extraction in an amount of 60% of the oil weight; adding 2% NaOH aqueous solution in an amount ranging from 36% to 56% of the oil weight according to the acid value; after stirring the mixture for 10 min and standing for 20 h, removing the lower niger layer; washing the upper layer with purified water and letting stand for 22 h; after the removal of the lower waste water, washing the upper layer again; after standing for another 46 h, removing the lower waste water; demulsifying the upper layer with acetone in an amount of 70%-90% by weight of the crude oil and standing for 3 h; removing the lower waste acetone and adding 5% of activated neutral alumina by weight of crude oil in the upper oil layer; stirring the mixture for 30 min, then filtering off the precipitation; heating the filtrate, and adding 4% of activated kaolin by weight of crude oil; stirring the mixture for 30 min at 40-50° C., and then filtering off the precipitation; concentrating the filtrate under a reduced pressure to recover the solvent, then washing again with purified water; after standing for 1 h, removing the lower waste water; heating the upper oil layer and vacuum drying it in nitrogen atmosphere; then adding 8%-12% activated neutral alumina, stirring the mixture and allowing to stand at a cold place; after filtration, concentrating the filtrated oil via heating under vacuum in a nitrogen atmosphere and sterilizing the concentrated oil via dry heat sterilization under vacuum at 160-170° C. for 2 h; after cooling, filtering the oil through a 0.2 μm microporous membrane; then split charging the obtained  Coix  seed oil in 500 mL glass infusion bottles, nitrogenizing and sealing the bottles. 
     The  Coix  seed oil of the invention is a yellowish clear liquid with a light odor and a light taste. It is highly soluble in petroleum ether or chloroform, freely soluble in acetone, slightly soluble in ethanol, but insoluble in water. 
     The  Coix  seed oil prepared based on the above methods was detected according to the method in the appendix of “Pharmacopoeia of the People&#39;s Republic of China” (2010 edition) Volume I. Physicochemical constants thereof are: specific gravity at 20 0.916-0.920, refractive index at 20° C. 1.471-1.474, acid value&lt;0.2, iodine value 100-106, saponification value 186-195. The acid value according to the Pharmacopoeia refers to the weight of potassium hydroxide (in milligrams) needed to neutralize free fatty acids contained in 1 gram of fats, fatty oils, or other similar substances. In the quality study of oil products, acid value is an important evaluation. As far as the  Coix  seed oil of the invention, the acid value is less than 0.2. By the optimization of the preparation process such as supercritical extraction parameters and the purification process like basification,  Coix  seed oil was prepared with the following advantages: on the one hand, it has a very low content of free fatty acid impurities, which means a high product quality; on the other hand, it gathers a great amount of active ingredients of diglycerides and triglycerides in high purity, and the types of diglycerides and triglyceride ingredients therein are determinate, and the contents thereof are stable. In addition, other physicochemical constants, such as saponification value, iodine value, etc., measured between batches of samples, had a small range of variation. It further illustrates that the  Coix  seed oil of the invention has a stable quality and a safer clinical use. The preparation method of the invention gives a stable product with a high yield and a low cost. It is suitable for the industrial production in view of the safety and controllability. 
     The second aspect of the invention is to provide a pharmaceutical preparation containing  Coix  seed oil, specifically, it comprises a therapeutically effective amount of the  Coix  seed oil of the invention and one or more pharmaceutically acceptable carriers. 
     Pharmaceutically acceptable carriers can be selected from pharmaceutical conventional dilutions, excipients, fillers, emulsifiers, binders, lubricants, absorption accelerators, surfactants, disintegrants, lubricants and antioxidants, if necessary, flavoring agents, sweeteners, preservative and/or coloring agents 
     Pharmaceutically acceptable carriers can be selected from one or more in the group consists of: mannitol, sorbitol, sodium metabisulfite, sodium bisulfite, sodium thiosulfate, cysteine hydrochloride, thioglycolic acid, methionine, soybean lecithin, vitamin C, vitamin E, EDTA disodium, EDTA calcium sodium, monovalent alkali metal carbonate, acetate, phosphate or its aqueous solution, hydrochloric acid, acetic acid, sulfuric acid, phosphoric acid, amino acids, sodium chloride, potassium chloride, sodium lactate, ethylparaben solution, benzoic acid, potassium sorbate, chlorhexidine acetate, xylitol, maltose, glucose, fructose, dextran, glycine, starch, sucrose, lactose, mannitol, silicic derivatives, cellulose and its derivatives, alginates, gelatin, polyvinyl pyrrolidone, glycerin, Tween 80, agar-agar, calcium carbonate, calcium bicarbonate, surfactants, polyethylene glycol, cyclodextrin, β-cyclodextrin, phospholipid material, kaolin, talc, and calcium stearate or magnesium stearate. 
     Pharmaceutical preparation can be oral solid preparations, oral liquid preparations or injections. 
     Preferably, the oral solid preparation is selected from any one of capsules, tablets, dripping pills, granules, and concentrated pills; the oral liquid preparation is selected from any one of aqueous or oily suspensions, solutions, emulsions, syrups or elixirs, and a dry product that may be reconstructed by water or other suitable carrier before use; and the injection is selected from any one of nano suspensions, liposomes, emulsions, lyophilized powder for injection and aqueous injection. 
     More preferably, the injection comprises the following components: the  Coix  seed oil of the invention 50-350 g, soybean lecithin for injection or soybean lecithin acceptable for injection 10-40 g, glycerin for injection or glycerin acceptable for injection 15-50 g, and water for injection adds to 1000 mL. 
     The injection of the invention can be prepared by a method comprising steps of: 
     adding appropriate amount of water for injection to a formulated amount of soybean lecithin for injection or soybean lecithin acceptable for injection; dispersing the mixture with a high shear dispersing emulsifier to give a dispersion without bulks or granules; adding a formulated amount of glycerin for injection or glycerin acceptable for injection; then adding water for injection to a specified amount, and stirring the mixture to give a water phase; 
     weighing a formulated amount of  Coix  seed oil; heating the weighed oil and the water phase separately to 60-70° C., then mixing them and emulsifying the mixture in a high pressure homogenizer, in which the low pressure is 5-12 MPa and the high pressure is 25-50 MPa; repeating the cycle of homogenization for 3-6 times until the amount of particles below 2 μm is no less than 95% and particles above 5 μm are undetectable; if necessary, using NaOH or HCl to adjust the pH to 4.8 to 8.5, preferably 6.8 to 7.0, most preferably 6.8; and 
     filtering the resulting homogeneous emulsion by nitrogen pressure through a microporous filter of 3 μm or less; filling the emulsion, nitrogenizing, sterilizing and cooling to afford the injection. 
     The capsule of the invention comprises the following components:  Coix  seed oil 200-800 g, antioxidant(s) and/or emulsifier(s) 0.20-0.60 g for 1000 capsules. 
     The capsule of the invention can be prepared by a method comprising steps of: 
     preparing glue solution: weighing gelatin, purified water, glycerin and a preservative at a weight ratio of 1:0.6-1.2:0.3-0.8:0.0001-0.01; adding glycerin, purified water and preservative (selected from any one of 10% ethylparaben solution, benoic acid, potassium sorbate and chlorhexidine acetate) sequentially into a glue melting tank; heating to 70° C.-90; then adding gelatin and constantly stirring the mixture under vacuum until the gelatin is completely dissolved; filtering the glue solution and storing the filtered glue solution at 56-62 for use; 
     preparing drug liquid: adding formulated amount of  Coix  seed oil, antioxidant (Vitamin E) and/or emulsifier (Tween 80) into an dosing tank, and stirring the mixture constantly until being homogeneously mixed; and 
     pressing capsules: choosing proper pellet dies according to the capsule size; pressing capsules in a tempreture of 15-30 and a relative humidity of less than 35%; drying the pressed and shaped capsules; after removing capsules of abnormal size, washing the normal capsules with 95% medicinal ethanol, and drying them continuously till the moisture content is less than 12%; visually inspecting and removing unqualified capsules; finally printing and packaging to afford the capsules. 
     It is demonstrated, in pharmacodynamic experiments, that the  Coix  seed oil of the invention and the pharmaceutical preparation thereof have shown different degrees of inhibition on a variety of human tumor cell lines. Thus, the  Coix  seed oil of the invention and pharmaceutical preparations thereof can be used as therapeutical drugs of neoplastic diseases. 
     Therefore, another aspect of the invention is to provide a method of the treatment of a tumor or an inflammation in a mammal (including human), comprising administering to the mammal (including human) in need a therapeutically effective amount of the  Coix  seed oil of the invention or a pharmaceutical preparation thereof. 
     The  Coix  seed oil of the invention or the pharmaceutical preparation thereof can be administered alone or in combination with a chemotherapeutic drug selected from one or more of platinums, alkylating agents, difluoro nucleosides, antibiotics, cytotoxics and/or hormons. 
     Preferably, platinum is selected from cisplatin and carboplatin, the alkylating agent is selected from cyclophosphamide, the difluoro nucleoside is selected from gemcitabine hydrochloride, the antibiotics are selected from mitoxantrone, mitomycin, the cytotoxics are selected from docetaxel, paclitaxel, and the hormone is selected from leuprorelin acetate. Said cancer refers to lung cancer, liver cancer, pancreatic cancer, prostate cancer, ovarian cancer, breast cancer, sarcomatoid carcinoma or cancer sarcoma, in early, middle or late stage; and the inflammation can be prostatic hyperplasia. 
     The following experimental data are used to illustrate anti-tumor or antiinflammation benefical effects of the  Coix  seed oil of the invention and the pharmaceutical preparations thereof. 
     I. Inhibition of  Coix  Seed Oil and Preparations Thereof on 8 Human Tumor Cell Lines in MTT Method In Vitro 
     A. Experimental Materials and the Preparation Thereof 
     
         
         
           
             (1) Cell lines: PANC-1 (human pancreatic cancer cells), SKOV3 (human ovarian cancer cells), MCF-7 (human breast cancer cells), Bcap-37 (human breast cancer cells), SMMC-7721 (human hepatic cancer cells), HepG-2 (human hepatic cancer cells), A549 (human lung cancer cells) and H460 (human lung cancer cells), storaged and passaged maintainably in Research and Evaluation Center for Pharmacology, Shanghai Institute of Pharmaceutical Industry; 
             (2) DMEM complete medium supplied with 10% newborn calf serum (GIBCO BRL), 1% of penicillin (100 U/mL)+streptomycin (100 μg/mL); 
             (3) 0.25% trypsin solution, purchased from Invitrogen Corp. and storaged at −20; 
             (4) Phosphate buffer (PBS): NaCl 8 g, KCl 0.2 g, Na 2 HPO 4  1.15 g and KH 2 PO 4  0.2 g, dissolved in 1 L double-distilled water and autoclaved at 121 for 20 min, then storaged at 4; 
             (5) MTT (AMRESCO) solution: 5 mg/ml in PBS; 
             (6) Formazan crystal dissolving solution: SDS 10 g, isobutanol 5 ml and concentrated hydrochloric acid 0.1 ml, dissolved in 100 ml of deionized double distilled water. 
           
         
       
    
     B. Experimental Method 
     The inhibition effects of samples on the above-mentioned cell lines were detected by using MTT method. The specific procedures were as follows: 
     (1) Cell culture: (a) Storaged cells were taken out from the liquid nitrogen, thawed quickly in a 37 water bath, then aseptically transferred into 6 ml of cellular medium in a 10 ml centrifugal tube, centrifuged at 1000 rpm for 5 min. The supernatant was discarded, then the precipitated cells were re-suspensed in 5-6 ml cellular media by pipetting and transferred into a flask in a 37 incubator for cell culture; (b) Next day, the flask was taken out from the incubator and the used medium was discarded, then the cells were incubated in 5-6 ml fresh medium in the 37 incubator; (c) On the third day, the flask was taken out from the incubator and the used medium was discarded, then 2-3 ml of PBS (pH7.4) was added into the flask with rocking for cleaning it and the used PBS was discarded. Such a cellular cleaning step was repeated once again. 3-5 drops of 0.25% trypsin solution were added into the flask with sloshing, thus well-distributed in it. The flask was capped and placed in a 37 incubator for about 3 min, and the separation of cells from the flask wall was observed under the microscope. 2 ml of cellular medium was added and cells were separated completely from the flask wall by pipetting, then the cell suspension was transferred into 2 separate clean flasks, each containing 5-6 ml medium. The cell suspension was well-distributed by pipetting, then the flask was placed in a 37 incubator. (d) Step (c) was repeated every other day. In the whole cultivation process, adherent cells were not allowed to grow too dense and suspension cells were always maintained at a logarithmic growth stage. 
     (2) Preparation of the sample and the control: A proper amount of sample of  Coix  seed oil (oil of Job&#39;s tears seed) was dissolved in DMSO to obtain a solution in a concentration of 10 mg/ml. This solution was diluted in a gradient dilution with PBS to obtain a set of sample solutions in the concentration of 10 mg/ml, 5000 μg/ml, 2500 μg/ml, 1250 μg/ml, 625 μg/ml and 312.5 μg/ml, respectively. 
     (3) Each diluted sample solution was added into duplicated wells of a 96 well flat-bottom microplate (10 μl/well). The correspondingly diluted DMSO solutions, as controls, were added into the wells of the microplate. 
     (4) Cells in a logarithmic growth stage were trypsinized and washed, then re-suspended in the medium containing 10% calf serum. The number of living cells was counted in Trypan blue dye exclusion method and cell suspensions were adjusted into a density of 2×10 5  cell/ml. 
     (5) The cell-contained 96 well flat-bottom microplate was placed in a 37 incubator and cells were incubated under 5% CO 2  for 48 h. 
     (6) 20 μl of 5 mg/ml MTT solution was added into each well and cells were incubated continuously in the incubator for 3-4 h. 
     (7) 100 μl of crystal dissolving solution was added into each well and cells were incubated continuously in the incubator overnight, so as to dissolve the resulted formazan crystals sufficiently. Then, the absorbance value was measured at 570 nm for each well. 
     (8) Based on absorbance values, inhibition rates on the cell growth were calculated for sample groups of various concentrations. The calculation formula was as follows:
 
(1−mean absorbance of experimental wells/mean absorbance of control wells)×100%
 
     C. Experimental Results 
     
       
         
               
             
               
               
             
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
             
           
               
                 TABLE 1 
               
             
             
               
                   
               
               
                 Inhibition rates of samples in various concentrations 
               
               
                 on the cell growth in 8 cell lines (%) 
               
             
          
           
               
                   
                 Concentration of Sample 
               
             
          
           
               
                 Cell line 
                 1000 μg/ml 
                 500 μg/ml  
                 250 μg/ml 
                 125 μg/ml 
                 62.5 μg/ml 
                 31.25 μg/ml 
               
               
                   
               
             
          
           
               
                 PANC-1 
                 98.77 
                 73.83 
                 26.24 
                 18.93 
                 15.96 
                 2.95 
               
               
                 SKOV3 
                 98.85 
                 59.52 
                 26.70 
                 16.43 
                 3.43 
                 1.31 
               
               
                 MCF-7 
                 98.47 
                 65.68 
                 23.29 
                 11.85 
                 7.02 
                 0.42 
               
               
                 Bcap-37 
                 99.63 
                 73.03 
                 36.34 
                 17.34 
                 2.29 
                 1.40 
               
               
                 SMMC-7721 
                 98.54 
                 70.73 
                 39.44 
                 22.37 
                 14.70 
                 3.12 
               
               
                 HepG-2 
                 98.47 
                 65.35 
                 38.30 
                 26.22 
                 16.02 
                 1.07 
               
               
                 A549 
                 99.02 
                 74.97 
                 56.85 
                 42.61 
                 22.00 
                 1.48 
               
               
                 H460 
                 97.16 
                 73.47 
                 56.36 
                 44.13 
                 18.45 
                 7.14 
               
               
                   
               
             
          
         
       
     
     
       
         
               
             
               
               
               
             
               
               
               
               
             
               
               
               
               
             
           
               
                 TABLE 2 
               
             
             
               
                   
               
               
                 IC 50  values of samples in 8 cell lines in vitro (μg/ml) 
               
             
          
           
               
                   
                 Sample 
                   
               
             
          
           
               
                   
                   
                   
                 Positive control 
               
               
                   
                 Cell line 
                 Coix seed oil 
                 (Taxol) 
               
               
                   
               
             
          
           
               
                   
                 PANC-1 
                 213.1 
                 0.44 
               
               
                   
                 SKOV3 
                 262.8 
                 0.22 
               
               
                   
                 MCF-7 
                 275.5 
                 0.18 
               
               
                   
                 Bcap-37 
                 220.7 
                 0.28 
               
               
                   
                 SMMC-7721 
                 205.9 
                 0.41 
               
               
                   
                 HepG-2 
                 222.5 
                 0.45 
               
               
                   
                 A549 
                 173.2 
                 0.46 
               
               
                   
                 H460 
                 166.9 
                 0.49 
               
               
                   
               
             
          
         
       
     
     D. Conclusion 
     The  Coix  seed oil of the invention in various concentrations has shown the inhibition on 8 human tumor cell lines in different degrees. 
     2. Inhibition Rate of the Injection of the Invention on the Growth of A549 Human Lung Cancer Transplanted in Nude Mice 
     A. Experimental Materials 
     The injection of the invention (10 g/100 ml), Cisplatin (Qilu Phamaceutical Co., Ltd), blank fat emulsion and normal saline 
     B. Experimental Method 
     A549 Human lung cancer cells cryopreserved in liquid nitrogen were recovered, and incubated in a 37 incubator under 5% CO 2 . After being subcultured, cells in a logarithmic growth stage were distributed with normal saline to be a cell suspension in a concentration of 1-2×10 7  cells/ml. The cell suspension was inoculated into BALB/C nude mice (SPF grade, 18-20 g, 6 weeks old, male) subcutaneously at right axillary. The tumor tissues were aseptically taken from the 2 nd  generation of xenograft model of A549 human lung cancer in a vigorous growth stage and cut into small uniform pieces in the size of 1-2 mm 3 . The right axillary of each nude mouse was inoculated one piece subcutaneously via a trocar. When the inoculated tumor could be touched, the mice were randomly grouped and administered according to the experimental design program. All contacted feed, padding, cages and equipment, etc., should be autoclaved prior to use. The nude mice were fed in a laminar flow rack. Tumor sizes and animal weights were observed and tested dynamically. Mice in each group were sacrificed 3 weeks later or so, and tumors were surgically removed and weighed. The inhibition rate on tumor was calculated according to the following formula:
 
Inhibition rate %=[(Mean tumor weight of the control group−mean tumor weight of the treatment group)/mean tumor weight of the control group]×100%;
 
     Q value of antitumor effect in drug combination was calculated according to Jin&#39;s formula:
 
 Q=E   a+b /( E   a   +E   b   −E   a   ×E   b )
 
Wherein E a+b =the tumor inhibition rate of drug combination, E a  or E b =the tumor inhibition rate of drug A or drug B, respectively. If Q value=0.85-1.15, an additive effect (+) was shown; if Q value&gt;1.15, a synergistic effect (++) was shown.
 
     C. Experimental Results 
     
       
         
               
             
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 3 
               
             
             
               
                   
               
               
                 Efficacy of anti-tumor on Xenograft model of A549 human lung cancer 
               
               
                 inoculated subcutaneously in nude mice 
               
             
          
           
               
                   
                   
                   
                 Number 
                 Weight of 
                 Weight of 
                   
                   
               
               
                   
                   
                 Dosage 
                 of animal  
                 animal (g) 
                 tumor (g) 
                 Inhibition 
                   
               
               
                 Sample group 
                 Dosage 
                 regimen 
                 start/end 
                 start/end 
                   x  ± SD 
                 Rate % 
                 Q 
               
               
                   
               
             
          
           
               
                 The injection 
                 25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.2/24.3  
                 0.623 ± 0.19** 
                 52.87 
                   
               
               
                 The injection 
                 12.5  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.1/25.2 
                 0.788 ± 0.19** 
                 40.39 
                   
               
               
                 The injection 
                 6.25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.6/25.3 
                 0.845 ± 0.15** 
                 36.08 
                   
               
               
                 The injection + 
                 (25  
                 ml + 
                 iv ×  
                 10 qd + 
                 6/6 
                 20.1/25.3 
                 0.458 ± 0.10** 
                 65.36 
                 0.8987 
               
               
                 Cisplatin 
                 1  
                 mg)/kg 
                 ip ×  
                 7 qd 
                   
                   
                   
                   
                   
               
               
                 The injection + 
                 (12.5  
                 ml + 
                 iv ×  
                 10 qd + 
                 6/6 
                 20.2/24.5  
                 0.501 ± 0.11** 
                 62.10 
                 0.9480 
               
               
                 Cisplatin 
                 1  
                 mg)/kg 
                 ip ×  
                 7 qd 
                   
                   
                   
                   
                   
               
               
                 The injection + 
                 (6.25  
                 ml + 
                 iv ×  
                 10 qd + 
                 6/6 
                 20.1/25.4 
                 0.558 ± 0.11** 
                 57.79 
                 0.9172 
               
               
                 Cisplatin 
                 1  
                 mg)/kg 
                 ip ×  
                 7 qd 
                   
                   
                   
                   
                   
               
               
                 Cisplatin 
                 1  
                 mg/kg 
                 ip ×  
                 7 qd 
                 6/6 
                 20.2/24.0  
                 0.765 ± 0.11** 
                 42.13 
                   
               
               
                 Cisplatin 
                 2  
                 mg/kg 
                 ip ×  
                 7 qd 
                 6/6 
                 20.4/23.1  
                 0.181 ± 0.06** 
                 86.31 
                   
               
               
                 Blank fat 
                 25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.1/26.5 
                 1.325 ± 0.34  
                 — 
                   
               
               
                 emulsion 
                   
                   
                   
                   
                   
                   
                   
                   
                   
               
               
                 Control (NS) 
                 25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.3/26.6 
                 1.322 ± 0.32  
                 — 
               
               
                   
               
               
                  *P &lt; 0.05, 
               
               
                 **P &lt; 0.01, compared with NS negative control group. 
               
             
          
         
       
     
     D. Experimental Conclusion 
     It is shown that the injection of the invention (25 ml/kg, 12.5 ml/kg and 6.25 ml/kg, iv×10 qd) has a significant tumor inhibition effect on the growth of A549 human lung cancer transplanted in nude mice. 
     It is shown that the tumor inhibition effect of the co-administration of the injection of the invention with cisplatin was significantly stronger than that of the injection of the invention or that of cisplatin, alone, on A549 human lung cancer transplanted in nude mice, i.e., the co-administration has shown a significant additive effect. 
     3. The Tumor Inhibition Rate of the Injection of the Invention on the Growth of QGY Human Hepatoma Transplanted in Nude Mice 
     A. Experimental Materials 
     The injection of the invention (10 g/100 ml), Adriamycin (Pfizer Italia S.r.1), blank fat emulsion and normal saline 
     B. Experimental Method 
     QGY human hepatoma cells cryopreserved in liquid nitrogen were recovered, and incubated in a 37 incubator under 5% CO 2 . Other steps were the same as mentioned in 2-B. 
     C. Experimental Results 
     
       
         
               
             
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 4 
               
             
             
               
                   
               
               
                 Efficacy of anti-tumor on Xenograft model of QGY human hepatoma 
               
               
                 inoculated subcutaneously in nude mice 
               
             
          
           
               
                   
                   
                   
                 Number 
                 Weight of 
                 Weight of 
                   
                   
               
               
                   
                   
                 Dosage 
                 of animal 
                 animal (g) 
                 tumor (g) 
                 Inhibition 
                   
               
               
                 Sample group 
                 Dosage 
                 regimen 
                 start/end 
                 start/end 
                   x  ± SD 
                 rate % 
                 Q 
               
               
                   
               
             
          
           
               
                 The injection 
                 25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 21.4/25.6 
                 0.680 ± 0.18** 
                 41.18 
                   
               
               
                 The injection 
                 12.5  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 21.4/25.2 
                 0.787 ± 0.15** 
                 31.92 
                   
               
               
                 The injection 
                 6.25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 21.5/24.9 
                 0.790 ± 0.18*  
                 31.66 
                   
               
               
                 The injection + 
                 (25  
                 ml +  
                 Iv ×  
                 10 qd + 
                 6/6 
                 21.8/24.9 
                 0.502 ± 0.16** 
                 56.57 
                 0.8870 
               
               
                 Adriamycin 
                 1  
                 mg)/kg 
                 ip ×  
                 7 qd 
                   
                   
                   
                   
                   
               
               
                 The injection + 
                 (12.5  
                 ml + 
                 iv ×  
                 10 qd + 
                 6/6 
                 21.5/24.7 
                 0.598 ± 0.15** 
                 48.27 
                 0.8312 
               
               
                 Adriamycin 
                 1  
                 mg)/kg 
                 ip ×  
                 7 qd 
                   
                   
                   
                   
                   
               
               
                 The injection + 
                 (6.25  
                 ml + 
                 iv ×  
                 10 qd + 
                 6/6 
                 21.8/24.7 
                 0.627 ± 0.12** 
                 45.76 
                 0.7902 
               
               
                 Adriamycin 
                 1  
                 mg)/kg 
                 ip ×  
                 7 qd 
                   
                   
                   
                   
                   
               
               
                 Adriamycin 
                 1  
                 mg/kg 
                 ip ×  
                 7 qd 
                 6/6 
                 21.3/24.6 
                 0.712 ± 0.18** 
                 38.41 
                   
               
               
                 Adriamycin 
                 2  
                 mg/kg 
                 ip ×  
                 7 qd 
                 6/6 
                 21.8/23.1 
                 0.338 ± 0.17** 
                 70.76 
                   
               
               
                 Blank fat 
                 25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 21.6/26.9 
                 1.125 ± 0.15  
                 — 
                   
               
               
                 mulsion 
                   
                   
                   
                   
                   
                   
                   
                   
                   
               
               
                 NS 
                 25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 21.5/26.7 
                 1.156 ± 0.24  
                 — 
               
               
                   
               
               
                  *P &lt; 0.05, 
               
               
                 **P &lt; 0.01, compared with negative control group (NS). 
               
             
          
         
       
     
     D. Experimental Conclusion 
     It is shown that the injection of the invention (25 ml/kg, 12.5 ml/kg and 6.25 ml/kg, iv×10 qd) has a significant tumor inhibition effect on the growth of QGY human hepatoma transplanted in nude mice. 
     It is shown that the tumor inhibition effect of the co-administration of the injection of the invention with Adriamycin was significantly stronger than that of the injection of the invention or Adriamycin, alone, on QGY human hepatoma transplanted in nude mice. 
     4. The Tumor Inhibition Rate of the Injection of the Invention on LM-3 Human Hepatoma Transplanted in Nude Mice 
     A. Experimental Materials 
     The injection of the invention (10 g/100 ml), cyclophosphamide (Jiangsu Hengrui Medicine Co., Ltd), blank fat emulsion and normal saline 
     B. Experimental Method 
     LM-3 human hepatoma cells cryopreserved in liquid nitrogen were recovered, and incubated in a 37 incubator under 5% CO 2 . Other steps were the same as mentioned in 2-B. 
     C. Experimental Results 
     
       
         
               
             
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 5 
               
             
             
               
                   
               
               
                 Efficacy of anti-tumor on Xenograft model of LM-3 human hepatoma 
               
               
                 inoculated subcutaneously in nude mice 
               
             
          
           
               
                   
                   
                   
                 Number 
                 Weight of 
                 Weight of 
                   
                   
               
               
                   
                   
                 Dosage 
                 of animal 
                 animal (g) 
                 tumor (g) 
                 Inhibition 
                   
               
               
                 Sample group 
                 Dosage 
                 regimen 
                 start/end 
                 start/end 
                   x  ± SD 
                 rate % 
                 Q 
               
               
                   
               
             
          
           
               
                 The injection 
                 25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.2/26.3 
                 1.043 ± 0.16** 
                 32.05 
                   
               
               
                 The injection 
                 12.5  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.3/26.2 
                 1.092 ± 0.28** 
                 28.86 
                   
               
               
                 The injection 
                 6.25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.4/27.0 
                 1.251 ± 0.27** 
                 18.50 
                   
               
               
                 The injection + 
                 (25  
                 ml + 
                 iv ×  
                 10 qd + 
                 6/6 
                 20.4/26.6 
                 0.755 ± 0.13** 
                 50.81 
                 0.9972 
               
               
                 cyclophosphamide 
                 15  
                 mg)/kg 
                 ip ×  
                 7 qd 
                   
                   
                   
                   
                   
               
               
                 The injection + 
                 (12.5  
                 ml + 
                 iv ×  
                 10 qd + 
                 6/6 
                 20.3/28.1 
                 0.778 ± 0.17** 
                 49.32 
                 1.0137 
               
               
                 cyclophosphamide 
                 15  
                 mg)/kg 
                 ip ×  
                 7 qd 
                   
                   
                   
                   
                   
               
               
                 The injection + 
                 (6.25  
                 ml + 
                 iv ×  
                 10 qd + 
                 6/6 
                 20.4/25.8 
                 0.862 ± 0.19** 
                 43.84 
                 1.0648 
               
               
                 cyclophosphamide 
                 15  
                 mg)/kg 
                 ip ×  
                 7 qd 
                   
                   
                   
                   
                   
               
               
                 cyclophosphamide 
                 15  
                 mg/kg 
                 ip ×  
                 7 qd 
                 6/6 
                 20.7/24.8 
                 1.108 ± 0.09** 
                 27.82 
                   
               
               
                 cyclophosphamide 
                 30  
                 mg/kg 
                 ip ×  
                 7 qd 
                 6/6 
                 20.5/25.0 
                 0.265 ± 0.12** 
                 82.74 
                   
               
               
                 Blank fat emulsion 
                 25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.4/27.8 
                 1.557 ± 0.30  
                 — 
                   
               
               
                 NS 
                 25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.6/28.0 
                 1.535 ± 0.28  
                 — 
               
               
                   
               
               
                  *P &lt; 0.05, 
               
               
                 **P &lt; 0.01, compared with negative control group (NS). 
               
             
          
         
       
     
     D. Experimental Conclusion 
     It is shown that the injection of the invention (25 ml/kg, 12.5 ml/kg and 6.25 ml/kg, iv×10 qd) has a significant tumor inhibition effect on the growth of LM-3 human hepatoma transplanted in nude mice. 
     It is shown that the tumor inhibition effect of the co-administration of the injection of the invention with cyclophosphamide was significantly stronger than that of the injection of the invention or cyclophosphamide, alone, on LM-3 human hepatoma transplanted in nude mice, i.e., the co-administration has shown a significant additive effect. 
     5. The Tumor Inhibition Rate of the Injection of the Invention on the Growth of SMMC-7721 Human Hepatoma Transplanted in Nude Mice 
     A. Experimental Materials 
     The injection of the invention (10 g/100 ml), gemcitabine hydrochloride (LILLY FRANCE), blank fat emulsion and normal saline 
     B. Experimental Method 
     SMMC-7721 human hepatoma cells cryopreserved in liquid nitrogen were recovered, and incubated in a 37 incubator under 5% CO 2 . Other steps were the same as mentioned in 2-B. 
     C. Experimental Results 
     
       
         
               
             
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 6 
               
             
             
               
                   
               
               
                 Efficacy of anti-tumor on Xenograft model of SMMC-7721 human hepatoma 
               
               
                 inoculated subcutaneously in nude mice 
               
             
          
           
               
                   
                   
                   
                 Number 
                 Weight of 
                 Weight of 
                   
                   
               
               
                   
                   
                 Dosage 
                 of animal 
                 animal (g) 
                 tumor (g) 
                 Inhibition 
                   
               
               
                 Sample group 
                 Dosage 
                 regimen 
                 start/end 
                 start/end 
                   x  ± SD 
                 rate % 
                 Q 
               
               
                   
               
             
          
           
               
                 The injection 
                 25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.4/25.1 
                 0.876 ± 0.13** 
                 49.71 
                   
               
               
                 The injection 
                 12.5  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.4/25.6 
                 0.942 ± 0.21** 
                 45.92 
                   
               
               
                 The injection 
                 6.25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.1/24.8 
                 1.041 ± 0.23** 
                 40.24 
                   
               
               
                 The injection + 
                 (25  
                 ml + 
                 iv ×  
                 10 qd + 
                 6/6 
                 20.5/26.1 
                 0.610 ± 0.09** 
                 64.98 
                 0.8731 
               
               
                 Gemcitabine 
                 25  
                 mg)/kg 
                 iv ×  
                 3 q 3 d 
                   
                   
                   
                   
                   
               
               
                 The injection + 
                 (12.5  
                 ml + 
                 iv ×  
                 10 qd + 
                 6/6 
                 20.9/26.5 
                 0.632 ± 0.14** 
                 63.72 
                 0.8790 
               
               
                 Gemcitabine 
                 25  
                 mg)/kg 
                 iv ×  
                 3 q 3 d 
                   
                   
                   
                   
                   
               
               
                 The injection + 
                 (6.25  
                 ml + 
                 iv ×  
                 10 qd + 
                 6/6 
                 20.4/26.4 
                 0.661 ± 0.16** 
                 62.06 
                 0.8916 
               
               
                 Gemcitabine 
                 25  
                 mg)/kg 
                 iv ×  
                 3 q 3 d 
                   
                   
                   
                   
                   
               
               
                 Gemcitabine 
                 25  
                 mg/kg 
                 iv ×  
                 3 q 3 d 
                 6/6 
                 20.1/25.1 
                 0.886 ± 0.24** 
                 49.14 
                   
               
               
                 Gemcitabine 
                 50  
                 mg/kg 
                 iv ×  
                 3 q 3 d 
                 6/6 
                 20.4/24.2 
                 0.215 ± 0.11** 
                 87.66 
                   
               
               
                 Blank fat 
                 25  
                 ml/kg 
                 Iv ×  
                 10 qd 
                 6/6 
                 20.2/26.1 
                 1.765 ± 0.19  
                   
                   
               
               
                 emulsion 
                   
                   
                   
                   
                   
                   
                   
                   
                   
               
               
                 NS 
                 25  
                 ml/kg 
                 iv ×  
                 10 qd 
                 6/6 
                 20.8/26.9 
                 1.742 ± 0.24  
               
               
                   
               
               
                  *P &lt; 0.05, 
               
               
                 **P &lt; 0.01, compared with negative control group (NS). 
               
             
          
         
       
     
     D. Experimental Conclusion 
     It is shown that the injection of the invention (25 ml/kg, 12.5 ml/kg and 6.25 ml/kg, iv×10 qd) has a significant tumor inhibition effect on the growth of SMMC-7721 human hepatoma transplanted in nude mice. 
     It is shown that the tumor inhibition effect of the co-administration of the injection of the invention with gemcitabine hydrochloride was significantly stronger than that of the injection of the invention or gemcitabine hydrochloride, alone, on SMMC-7721 human hepatoma transplanted in nude mice, i.e., the co-administration has shown a significant additive effect. 
     6. The Inhibition Rate of the Injection of the Invention on 5180 Sarcoma Transplanted in Mice 
     A. Experimental Materials 
     The injection of the invention (10 g/100 ml), Cyclophosphamide (CTX), Mitoxantrone (DHAD), Mitomycin (MMC) and normal saline 
     S180 sarcoma: inoculated in Kunmin mice, 19-21 g, female 
     B. Experimental Method 
     Ascitic fluid of mice having well-grown 5180 sarcoma was diluted with normal saline (1:4) to obtain a cell suspension of about 1-2×10 7  cells/ml. Each mouse was inoculated with 0.2 ml of the suspension subcutaneously at the right axilla, and the mice were grouped randomly. The administration began from the next day according to the dosage program in Table 7. On the tenth day after the inoculation of S180, animals were sacrificed via cervical dislocation and dissected to take out the tumor block. Weights of tumor were compared and inhibition rates were calculated for each group. 
     C. Experimental Results 
     
       
         
               
             
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 7 
               
             
             
               
                   
               
               
                 Efficacy of anti-tumor on S180 sarcoma model in mice 
               
             
          
           
               
                   
                   
                   
                 Number 
                 Weight of 
                   
                   
               
               
                   
                   
                 Dosage 
                 of animal 
                 tumor (g) 
                 Inhibition 
                   
               
               
                 Sample group 
                 Dosage 
                 regimen 
                 start/end 
                   x  ± SD 
                 rate % 
                 Q 
               
               
                   
               
             
          
           
               
                 The injection 
                 25  
                 ml/kg 
                 iv ×  
                 7 
                 10/10 
                 1.18 ± 0.23 
                 25.32*  
                   
               
               
                 The injection + 
                 25  
                 ml/kg + 
                 iv ×  
                 7 + 
                 10/10 
                 0.79 ± 0.14 
                 50.00** 
                 0.8847 
               
               
                 CTX 
                 30  
                 mg/kg 
                 ip ×  
                 2(1, 3) 
                   
                   
                   
                   
               
               
                 CTX 
                 30  
                 mg/kg 
                 Ip ×  
                 2(1, 3) 
                 10/10 
                 0.92 ± 0.21 
                 41.77*  
                   
               
               
                 The injection + 
                 25  
                 ml/kg + 
                 iv ×  
                 7 + 
                 10/10 
                 0.52 ± 0.13 
                 67.09** 
                 1.0627 
               
               
                 DHAD 
                 2  
                 mg/kg 
                 ip ×  
                 2(1, 3) 
                   
                   
                   
                   
               
               
                 DHAD 
                 2  
                 mg/kg 
                 Ip ×  
                 2(1, 3) 
                 10/10 
                 0.78 ± 0.20 
                 50.63** 
                   
               
               
                 The injection + 
                 25  
                 ml/kg + 
                 iv ×  
                 7 + 
                 10/10 
                 0.62 ± 0.12 
                 60.76** 
                 1.1220 
               
               
                 MMC 
                 1.5  
                 mg/kg 
                 ip ×  
                 2(1, 3) 
                   
                   
                   
                   
               
               
                 MMC 
                 1.5  
                 mg/kg 
                 Ip ×  
                 2(1, 3) 
                 10/10 
                 0.97 ± 0.19 
                 38.61*  
                   
               
               
                 Control (NS) 
                 25  
                 ml/kg 
                 iv ×  
                 7 
                 10/10 
                 1.58 ± 0.36 
                 — 
               
               
                   
               
               
                  *P &lt; 0.05, 
               
               
                 **P &lt; 0.01, compared with negative control group (NS). 
               
             
          
         
       
     
     D. Experimental Conclusion 
     It is shown in the results that the injection of the invention in combination with CTX, DHAD or MMC has a tumor inhibition effect that is significantly stronger than that of the injection of the invention or chemotherapy drug alone, i.e., the co-administration has shown a significant additive effect. 
     7. The Inhibition Rate of the Injection of the Invention on W256 Cancer Sarcoma Transplanted in Rats 
     A. Experimental Materials 
     The injection of the invention (10 g/100 ml), Cyclophosphamide (CTX) and normal saline 
     W256 cancer sarcoma: inoculated in Wistar rats, 50-60 g, female 
     B. Experimental Method 
     Ascitic fluid of rats with well-grown W256 cancer sarcoma was diluted with normal saline to obtain a cell suspension of about 1-2×10 7  cells/ml. Each rat was inoculated with 0.2 ml of the suspension at the right axilla subcutaneously. The rats were grouped randomly next day and began administration. Two weeks later, animals were sacrificed and dissected to take out the tumor block. Weights of tumor were compared between each experimental group and the control group and tumor inhibition rates were calculated. 
     C. Experimental Results 
     
       
         
               
             
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 8 
               
             
             
               
                   
               
               
                 Efficacy of anti-tumor on the model of W256 cancer sarcoma in rats 
               
             
          
           
               
                   
                   
                   
                 Number 
                 Weight of 
                   
                   
               
               
                 Sample 
                   
                 Dosage 
                 of animal 
                 tumor (g) 
                 Inhibition 
                   
               
               
                 group 
                 Dosage 
                 regimen 
                 start/end 
                   x  ± SD 
                 rate % 
                 Q 
               
               
                   
               
             
          
           
               
                 CTX 
                 30  
                 mg/kg 
                 iv ×  
                 7 
                 10/8  
                 0.42 ± 0.85 
                 87.68** 
                   
               
               
                 CTX 
                 10  
                 mg/kg 
                 iv ×  
                 2(3, 5) 
                 10/10 
                 2.12 ± 1.22 
                 37.83*  
                   
               
               
                 The injection 
                 20  
                 ml/kg 
                 iv ×  
                 10 
                 10/10 
                 1.44 ± 0.72 
                 57.78** 
                   
               
               
                 The injection + 
                 20  
                 ml/kg + 
                 iv ×  
                 10 + 
                 10/10 
                 0.94 ± 0.32 
                 72.43** 
                 0.9821 
               
               
                 CTX 
                 10  
                 mg/kg 
                 iv ×  
                 2(3, 5) 
                   
                   
                   
                   
               
               
                 The injection 
                 10  
                 ml/kg 
                 iv ×  
                 10 
                 10/10 
                 1.88 ± 0.71 
                 44.87** 
                   
               
               
                 The injection + 
                 10  
                 ml/kg + 
                 iv ×  
                 10 + 
                 10/10 
                 1.02 ± 0.58 
                 70.09** 
                 1.0664 
               
               
                 CTX 
                 10  
                 mg/kg 
                 iv ×  
                 2(3, 5) 
                   
                   
                   
                   
               
               
                 The injection 
                 5  
                 ml/kg 
                 iv ×  
                 10 
                 10/9  
                 2.13 ± 1.19 
                 37.54*  
                   
               
               
                 The injection + 
                 5  
                 ml/kg + 
                 iv ×  
                 10 + 
                 10/10 
                 1.68 ± 0.98 
                 50.73** 
                 0.8293 
               
               
                 CTX 
                 10  
                 mg/kg 
                 iv ×  
                 2(3, 5) 
                   
                   
                   
                   
               
               
                 Control (NS) 
                 20  
                 ml/kg 
                 iv ×  
                 10 
                 10/10 
                 3.41 ± 1.16 
                 — 
               
               
                   
               
               
                  *P &lt; 0.05, 
               
               
                 **P &lt; 0.01, compared with negative control group (NS). 
               
             
          
         
       
     
     D. Experimental Conclusion 
     It is shown in the results that the injection of the invention in combination with CTX has a tumor inhibition effect that is significantly stronger than that of the injection of the invention or the chemotherapy drug alone, i.e., the co-administration has shown a significant additive effect. 
     8. The Tumor Inhibition Rate of the Injection of the Invention on PANC-1 Human Pancreatic Cancer Transplanted in Nude Mice 
     A. Experimental Materials 
     The injection of the invention (10 g/100 ml), Gemcitabine hydrochloride and normal saline 
     PANC-1 human pancreatic cancer cells: inoculated in BALB/C nude mice, 16-18 g, female 
     B. Experimental Method 
     Tumor blocks of well-grown PANC-1 human pancreatic cancer were inoculated subcutaneously in 4-week-old female BALB/C nude mice. The nude mice were grouped randomly and administered. One week after the end of the administration, the mice were sacrificed and dissected. Tumor blocks were taken out and weighed. Differences of tumor weight between each experimental group and the control group were compared and the tumor inhibition rates were calculated. 
     C. Experimental Results 
     
       
         
               
             
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 9 
               
             
             
               
                   
               
               
                 Efficacy of anti-tumor on model of PANC-1 human pancreatic cancer in nude mice 
               
             
          
           
               
                   
                   
                   
                 Number 
                 Weight of 
                   
                   
               
               
                   
                   
                 Dosage 
                 of animal 
                 tumor (g) 
                 Inhibition 
                   
               
               
                 Sample group 
                 Dosage 
                 regimen 
                 start/end 
                   x  ± SD 
                 rate % 
                 Q 
               
               
                   
               
             
          
           
               
                 Gemcitabine 
                 60 
                 mg/kg 
                 iv ×  
                 1 
                 6/6 
                 0.1443 ± 0.081 
                 24.61 
                   
               
               
                 The injection 
                 50 
                 ml/kg 
                 iv ×  
                 10 
                 6/6 
                 0.1491 ± 0.013 
                 22.10 
                   
               
               
                 The injection + 
                 50 
                 ml/kg + 
                 iv ×  
                 10 + 
                 6/6 
                 0.0921 ± 0.043 
                 51.88 
                 1.2570 
               
               
                 Gemcitabine 
                 60 
                 mg/kg 
                 iv ×  
                 1 
                   
                   
                   
                   
               
               
                 Control (NS) 
                 50 
                 ml/kg 
                 iv ×  
                 10 
                 6/6 
                 0.1914 ± 0.087 
                 — 
               
               
                   
               
             
          
         
       
     
     It is shown in the results that the injection of the invention in combination with gemcitabine hydrochloride has a tumor inhibition effect that is significantly stronger than that of the injection of the invention or the chemotherapy drug alone, i.e., the co-administration has shown a significant additive effect. 
     9. The Tumor Inhibition Rate of the Injection of the Invention on FC-3M Human Prostate Cancer Transplanted in Nude Mice 
     A. Experimental Materials 
     The injection of the invention (10 g/100 ml), Leuprolide acetate (Lupron) and normal saline 
     FC-3M human prostate cancer: inoculated in BALB/C nude mice, 17-21 g, male 
     B. Experimental Method 
     Tumor blocks of well-grown FC-3M human prostate cancer were homogenized in normal saline (1:4). Each nude mouse was inoculated with 0.2 ml of the suspension at the right axilla subcutaneously, and the mice were grouped randomly. The administration began from the next day. 21 Days after the inoculation, the mice were sacrificed. Tumor blocks were taken out and weighed. Differences of tumor weight between each experimental group and the control group were compared and the tumor inhibition rates were calculated. 
     C. Experimental Results 
     
       
         
               
             
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 10 
               
             
             
               
                   
               
               
                 Efficacy of anti-tumor on model of FC-3M human 
               
               
                 prostate cancer in nude mice 
               
             
          
           
               
                   
                   
                   
                 Number 
                 Weight of 
                   
                   
               
               
                   
                   
                 Dosage 
                 of animal 
                 tumor (g) 
                 Inhibition 
                   
               
               
                 Sample group 
                 Dosage 
                 regimen 
                 start/end 
                   x  ± SD 
                 rate % 
                 Q 
               
               
                   
               
             
          
           
               
                 Lupron 
                 0.75  
                 ml/kg 
                 iv × 1 
                 6/6 
                 0.98 ± 0.23 
                 36.36** 
                   
               
               
                 Lupron 
                 1.5  
                 ml/kg 
                 iv × 1 
                 6/6 
                 0.76 ± 0.14 
                 50.65** 
                   
               
               
                 The injection 
                 12.5  
                 ml/kg 
                 iv × 10 
                 6/6 
                 1.12 ± 0.24 
                 27.27  
                   
               
               
                 The injection + 
                 12.5  
                 ml/kg + 
                 iv × 10 + 
                 6/6 
                 0.52 ± 0.13 
                 66.23** 
                 1.2330 
               
               
                 Lupron 
                 0.75  
                 ml/kg 
                 iv × 1 
                   
                   
                   
                   
               
               
                 The injection 
                 25  
                 ml/kg 
                 iv × 10 
                 6/6 
                 0.77 ± 0.15 
                 50.00** 
                   
               
               
                 The injection + 
                 25  
                 ml/kg + 
                 iv × 10 + 
                 6/6 
                 0.45 ± 0.16 
                 70.78** 
                 0.9397 
               
               
                 Lupron 
                 1.5  
                 ml/kg 
                 iv × 1 
                   
                   
                   
                   
               
               
                 Control (NS) 
                 25  
                 ml/kg 
                 iv × 10 
                 6/6 
                 1.54 ± 0.20 
                 — 
               
               
                   
               
               
                  *P &lt; 0.05, 
               
               
                 **P &lt; 0.01, compared with the control group. 
               
             
          
         
       
     
     It is shown in the results that the injection of the invention in combination with Lupron has a tumor inhibition effect that is significantly stronger than that of the injection of the invention or the chemotherapy drug alone, i.e., the co-administration has shown a significant additive effect. 
     10. The Tumor Inhibition Rate of the Injection of the Invention on Bcap37 Human Breast Cancer Transplanted in Nude Mice 
     A. Experimental Materials 
     The injection of the invention (10 g/100 ml), Docetaxel injection (Taxotere, 20 mg/vial) and normal saline 
     Bcap-37 human breast cancer: inoculated in BALB/C nude mice (SPF grade), 18-20 g, female 
     B. Experimental Method 
     Tumor blocks of well-grown Bcap-37 human breast cancer were homogenized in normal saline to obtain cell suspensions in the concentration of 1-2×10 7  cells/ml. Each nude mouse was inoculated with 0.2 ml of the suspension at the right axilla subcutaneously, and the mice were grouped randomly. The administration began from the 7th day after the inoculation. 20 Days after the inoculation, the mice were sacrificed. Tumor blocks were taken out and weighed. Differences of tumor weight between each experimental group and the control group were compared, and tumor inhibition rates and Q values were calculated. 
     C. Experimental Results 
     
       
         
               
             
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 11 
               
             
             
               
                   
               
               
                 Efficacy of anti-tumor on model of Bcap-37 human breast cancer in nude mice 
               
             
          
           
               
                   
                   
                   
                 Number 
                 Weight of 
                   
                   
               
               
                   
                   
                 Dosage 
                 of animal 
                 tumor (g) 
                 Inhibition 
                   
               
               
                 Sample group 
                 Dosage 
                 regimen 
                 start/end 
                   x  ± SD 
                 rate % 
                 Q 
               
               
                   
               
             
          
           
               
                 Control (NS) 
                 25  
                 ml/kg 
                 iv ×  
                 10 
                 10/10 
                 2.94 ± 0.81  
                   
                   
               
               
                 Docetaxel 
                 25  
                 mg/kg 
                 ip ×  
                 1 
                 6/6 
                 1.27 ± 0.88** 
                 56.80 
                   
               
               
                   
                 6.25  
                 ml/kg 
                 iv ×  
                 10 
                 6/6 
                 1.86 ± 0.32** 
                 36.73 
                   
               
               
                 The injection 
                 12.5  
                 ml/kg 
                 iv ×  
                 10 
                 6/6 
                 1.41 ± 0.65** 
                 52.04 
                   
               
               
                   
                 25  
                 ml/kg 
                 iv ×  
                 10 
                 6/6 
                 1.18 ± 0.59** 
                 59.86 
                   
               
               
                 The injection + 
                 6.25  
                 ml/kg + 
                 iv ×  
                 10 + 
                 6/6 
                 0.87 ± 0.45** 
                 70.41 
                 0.9689 
               
               
                 Docetaxel 
                 25  
                 mg/kg 
                 ip ×  
                 1 
                   
                   
                   
                   
               
               
                 The injection + 
                 12.5  
                 ml/kg + 
                 iv ×  
                 10 + 
                 6/6 
                 0.94 ± 0.98** 
                 68.03 
                 0.8581 
               
               
                 Docetaxel 
                 25  
                 mg/kg 
                 ip ×  
                 1 
                   
                   
                   
                   
               
               
                 The injection + 
                 25  
                 ml/kg + 
                 iv ×  
                 10 + 
                 6/6 
                 0.72 ± 0.36** 
                 75.51 
                 0.9135 
               
               
                 Docetaxel 
                 25  
                 mg/kg 
                 ip ×  
                 1 
               
               
                   
               
               
                  *P &lt; 0.05, 
               
               
                 **P &lt; 0.01, compared with the negative control group. 
               
             
          
         
       
     
     The tumor inhibition effects of the injection of the invention in combination with Docetaxel injection were significantly stronger than that of the injection of the invention or Docetaxel, alone, on Bcap-37 human breast cancer transplanted in nude mice. It has been demonstrated in this experiment that the combination of the injection of the invention with Docetaxel has shown a significant additive effect. 
     11. The Tumor Inhibition Rate of the Injection of the Invention on MDA-MB-435 Human Breast Cancer Transplanted in Nude Mice 
     A. Experimental Materials 
     The injection of the invention (10 g/100 ml), Paclitaxel injection (30 mg/5 ml) and normal saline 
     MDA-MB-435 human breast cancer: inoculated in BALB/C nude mice (SPF grade), 18-20 g, female 
     B. Experimental Method 
     Tumor blocks of well-grown MDA-MB-435 cancer were homogenized in normal saline to obtain cell suspensions in the concentration of 1-2×10 7  cells/ml. Each nude mouse was inoculated with 0.2 ml of the suspension at the right axilla subcutaneously, and the mice were grouped randomly. The administration began from the 7th day after the inoculation. 18 Days after the inoculation, the mice were sacrificed. Tumor blocks were taken out and weighed. Differences of tumor weight between each experimental group and the control group were compared, and tumor inhibition rates and Q values were calculated. 
     C. Experimental Results 
     
       
         
               
             
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 12 
               
             
             
               
                   
               
               
                 Efficacy of anti-tumor on the model of MDA-MB-435 
               
               
                 human breast cancer in nude mice 
               
             
          
           
               
                   
                   
                   
                 Number 
                 Weight of 
                   
                   
               
               
                   
                   
                 Dosage 
                 of animal 
                 tumor (g) 
                 Inhibition 
                   
               
               
                 Sample 
                 Dosage 
                 regimen 
                 start/end 
                   x  ± SD 
                 rate % 
                 Q 
               
               
                   
               
             
          
           
               
                 Control (NS) 
                 25  
                 ml/kg 
                 iv ×  
                 10 
                 12/12 
                 2.72 ± 0.39  
                   
                   
               
               
                 Paclitaxel 
                 50  
                 mg/kg 
                 ip ×  
                 1 
                 6/6 
                 1.01 ± 0.33** 
                 62.87 
                   
               
               
                 The injection 
                 6.25  
                 ml/kg 
                 iv ×  
                 10 
                 6/6 
                 1.53 ± 0.26** 
                 43.75 
                   
               
               
                   
                 12.5  
                 ml/kg 
                 iv ×  
                 10 
                 6/6 
                 1.22 ± 0.25** 
                 55.15 
                   
               
               
                   
                 25  
                 ml/kg 
                 iv ×  
                 10 
                 6/6 
                 0.66 ± 0.07** 
                 75.74 
                   
               
               
                 The injection + 
                 6.25  
                 ml/kg + 
                 iv ×  
                 10 + 
                 6/6 
                 0.93 ± 0.48** 
                 65.81 
                 0.8318 
               
               
                 Paclitaxel 
                 50  
                 mg/kg 
                 ip ×  
                 1 
                   
                   
                   
                   
               
               
                 The injection + 
                 12.5  
                 ml/kg + 
                 iv ×  
                 10 + 
                 6/6 
                 0.76 ± 0.45** 
                 72.06 
                 0.8646 
               
               
                 Paclitaxel 
                 50  
                 mg/kg 
                 ip ×  
                 1 
                   
                   
                   
                   
               
               
                 The injection + 
                 25  
                 ml/kg + 
                 iv ×  
                 10 + 
                 6/6 
                 0.48 ± 0.32** 
                 82.35 
                 0.9050 
               
               
                 Paclitaxel 
                 50  
                 mg/kg 
                 ip ×  
                 1 
               
               
                   
               
               
                  *P &lt; 0.05, 
               
               
                 **P &lt; 0.01, compared with the negative control group. 
               
             
          
         
       
     
     The tumor inhibition effects of the injection of the invention in combination with Paclitaxel injection were significantly stronger than that of the injection of the invention or Paclitaxel injection, alone, on MDA-MB-435 human breast cancer transplanted in nude mice. It has been demonstrated in this experiment that the combination of the injection of the invention with Paclitaxel injection has shown a significant additive effect. 
     12. The Clinical Efficacy of the Capsules of the Invention in Combination with Chemotherapy in the Treatment of Ovarian Cancer 
     A. Clinical Data and Treatment Method 
     58 patients suffering from late stage ovarian cancer were randomly divided into two groups: Group I, capsule of the invention and Group II, control. 30 Cases in Group I were treated with TC program (Taxol+Carboplatin) in combination with the capsule of the invention; and 28 cases of the control group were treated with TC program merely. The baseline data of both groups were balanced (p&gt;0.05). Taxol (175 mg/m 2 ) was administered on day 1 and Carboplatin AUC=5 was administered on day 1 and repeated every 3 weeks. 4-6 Cycles of chemotherapy was performed based on patient&#39;s benefit situation. The capsule of the invention (6 capsules, t.i.d.) was administered continuously until the occurrence of disease progression or intolerable toxic and side effects. 
     B. Therapeutic Evaluation 
     (1) Response rate and disease control rate: Short-term effects were evaluated and analyzed every 2 cycles of chemotherapy using RECIST criteria, and the results of evaluation were divided into 4 grades: complete response (CR), partial response (PR), stable disease (SD) and progression of disease (PD). Response rate (RR) was calculated by using CR+PR; and disease control rate (DCR) was calculated by using CR+PR+SD. Therapeutical effects were confirmed for all CR and PR patients four weeks later. 
     (2) Toxic and side effects: Common Terminology Criteria (NCI-CTC AE) version 3.0 was used to analyze adverse effects. Toxic reactions were scored as 0-V grades. 
     C. Results 
     (1) Short-term effects: Group I, the response rate was 46.7% (0 case in CR grade, 14 cases in PR grade, 8 cases in SD grade and 8 cases in PD grade), and the disease control rate was 73.3%; Group II, the response rate was 39.3% (0 case in CR grade, 11 cases in PR grade, 6 cases in SD grade and 11 cases in PD grade), and the disease control rate was 60.7%. Both the response rate and the disease control rate in Group I were significantly higher than those in Group II. 
     (2) Toxic and side effects: It has been shown in the evaluation for 58 patients that the most common toxic and side effects were gastrointestinal reactions, myelosuppression, neurotoxicity, myalgia and arthralgia, etc. The incidences of grade ¾ myelosuppression in the group of the invention (Group I) and the control group (Group II) were 42.5% and 54%, respectively; the incidences of grade ¾ febrile neutropenia/infection in the group of the invention (Group I) and the control group (Group II) were 12% and 19%, respectively. There was no death case in both groups. Nausea, vomiting, neurotoxicity, myalgia and arthralgia were more common in the control group. The incidence of fatigue in the group of the invention was significantly lower than that in the control group. 
     Thus it can be seen that the combination of the capsule of the invention with Taxol+Carboplatin has a higher response rate in the treatment of late stage ovarian cancer and a lower chemotherapy-related toxic reaction, and can effectively improve the patients&#39; life quality. 
     13. The Effect of the Capsule of the Invention on Prostate Hyperplasia Induced by the Implantation of Urogenital Sinus in Mice 
     A. Experimental Materials 
     The capsule of the invention, Prostate Tablet (Cerniton®, PuShiTaiPian) (pollen extracts P5 70 mg, EA10 4 mg), NaCl injection (2.25 g/250 ml; 250 ml/bottle), Pentobarbital sodium, olive oil, penicillin sodium for injection (800,000 units/vial) 
     Animal: ICR mice, clean grade, fasting overnight prior to use. 
     B. Experimental Method 
     Preparation of urogenital sinus: ICR mice in sexual maturity, twenty female and ten male, 25-30 g, were caged in the ratio of female:male=2:1. Every morning, the vulva of each mouse was expanded by using a pincet to inspect whether a vaginal plug appeared. The phenomenon of the appearance of a white emboli pluged in the vagina, which was formed by the solidified semen, indicates that the copulation had occurred. The day when vaginal plug appeared was considered as day 1 of pregnancy. The female mouse, at the 16th days after fertilization, was sacrificed and the 16 day-old embryo was aseptically taken out. The urogenital sinus was placed into a glass petri dish filled with normal saline and reserved. 
     Modeling: Sixty male ICR mice (25-30 g) in sexual maturity were anesthetized with pentobarbital sodium via intraperitoneal injection. The abdoman of each mouse was aseptically incised and the ventral prostate was separated carefully. Urogenital sinus tissues from three 16 days-old fetus of the same strain mice were transplanted into the ventral prostate. 10 mice in the sham operation group were merely punctured in abdomen but not implanted with urogenital sinus tissues. All mice were given penicillin (20,000 units, i.p.) for three days after the operation. 
     Grouping and administering: The mice without abnormalities, three days after the operation, were divided into the following groups: sham operation group, model group, positive control group (Cernilton 60 mg/kg), and groups of the capsule of the invention (high-dose 9 g/kg, middle-dose 3 g/kg and low-dose 1 g/kg). The intragastric administration (0.1 ml/10 g) was performed for 28 days, and the mice in the sham operation group and the model group were merely given with the same volume of olive oil. 
     Detection indexes: (1) body weight, (2) wet weight of ventral prostate and prostate index (wet weight of prostate/body weight), (3) pathological changes of ventral prostate tissues (Scoring criteria is shown in Table 13). 
     
       
         
               
             
               
               
             
               
             
               
               
             
               
             
               
               
             
           
               
                 TABLE 13 
               
               
                   
               
               
                 Scoring criteria of prostate tissue hyperplasia in pathological test 
               
               
                   
               
             
             
               
                 (1) Based on the size of prostatic acinar lumen and 
               
               
                 the amount of secretions in lumen 
               
             
          
           
               
                 −: 
                 Prostatic acinar lumen, in different sizes and irregular forms, with 
               
               
                   
                 pink-dyed secretions; 
               
               
                 +: 
                 Part of prostatic acinar lumen, dilating and tightly stacking, with 
               
               
                   
                 increasing and deepening secretions; 
               
               
                 ++: 
                 Prostatic acinar lumen, obviously dilating and tightly stacking, with 
               
               
                   
                 obviously increasing and deepening secretions; 
               
             
          
           
               
                 (2) Based on the degree of proliferation of fibroblast 
               
               
                 in mesenchyme of prostate 
               
             
          
           
               
                 −: 
                 No or occasional hyperplastic fibroblast in mesenchyme; 
               
               
                 +: 
                 A few hyperplastic fibroblasts in mesenchyme, in scattered 
               
               
                   
                 distribution; 
               
               
                 ++: 
                 Many hyperplastic fibroblasts in mesenchyme; 
               
               
                 +++: 
                 Extensive hyperplastic fibroblasts in mesenchyme, in clusters or 
               
               
                   
                 bundles. 
               
             
          
           
               
                 (3) Based on morphology, arrangement regularity and 
               
               
                 hyperplasia degree of glandular epithelia 
               
             
          
           
               
                 −: 
                 Columnar or cuboidal monolayer glandular epithelia, protruding 
               
               
                   
                 towards acinar lumen to form plicae, with cell nuclei locating at the 
               
               
                   
                 fundus, and arranging regularly; 
               
               
                 +: 
                 Basically normal epithelial morphology, but less regularly 
               
               
                   
                 arranged; 
               
               
                 ++: 
                 Part of the epithelia proliferated from monolayer into bilayer, 
               
               
                   
                 irregularly arranged; 
               
               
                 +++: 
                 Many epithelia proliferated from monolayer into bilayer, or even 
               
               
                   
                 3-4 layers, obviously irregularly arranged. 
               
               
                   
               
             
          
         
       
     
     C. Experimental Results 
     
       
         
               
             
               
               
               
               
             
           
               
                 TABLE 14 
               
             
             
               
                   
               
               
                 Effects on ventral prostate in the model of prostatic hyperplasis induced by 
               
               
                 the implantation of urogenital sinus in mice ( x  ± s, n = 10) 
               
             
          
           
               
                   
                   
                 Wet weight 
                 Ventral prostate 
               
               
                   
                   
                 of ventral 
                 index (mg/10 g 
               
               
                 Group 
                 Dosage 
                 prostate (mg) 
                 body weight) 
               
               
                   
               
               
                 Sham operation 
                 — 
                 17.8 ± 7.0 
                  4.16 ± 1.60 
               
               
                 Model 
                 — 
                 50.1 ± 14.0 ###   
                 12.18 ± 3.74 ###   
               
               
                 Cernilton 
                 60 mg/kg 
                 30.7 ± 9.0** 
                  7.30 ± 2.11** 
               
               
                 Capsule of the invention 
                  9 g/kg 
                 30.9 ± 14.2* 
                  7.25 ± 3.25* 
               
               
                 Capsule of the invention 
                  3 g/kg 
                 32.3 ± 6.2** 
                  7.47 ± 2.42** 
               
               
                 Capsule of the invention 
                  1 g/kg 
                 36.5 ± 8.8* 
                  8.50 ± 2.08* 
               
               
                   
               
               
                   ### P &lt; 0.001 vs Sham operation group; 
               
               
                 *P &lt; 0.05, **P &lt; 0.01 vs Model group, t-test. 
               
             
          
         
       
     
     
       
         
               
             
               
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 15 
               
             
             
               
                   
               
               
                 Effects on prostatic acinar lumen and secretions in lumen of 
               
               
                 ventral prostate in the model of prostatic hyperplasis induced 
               
               
                 by the implantation of urogenital sinus in mice (n = 10) 
               
             
          
           
               
                   
                 Size of prostatic 
               
               
                   
                 acinar lumen and 
               
               
                   
                 secretions in lumen* 
               
             
          
           
               
                   
                 Group 
                 Dosage 
                 − 
                 + 
                 ++ 
               
               
                   
               
             
          
           
               
                   
                 Sham operation 
                 — 
                 10 
                 0 
                 0 
               
               
                   
                 Model 
                 — 
                 1 
                 5 
                 4 
               
               
                   
                 Cernilton 
                 60 mg/kg 
                 4 
                 5 
                 1 
               
               
                   
                 Capsule of the invention 
                  9 g/kg 
                 4 
                 5 
                 0 
               
               
                   
                 Capsule of the invention 
                  3 g/kg 
                 3 
                 4 
                 2 
               
               
                   
                 Capsule of the invention 
                  1 g/kg 
                 2 
                 3 
                 2 
               
               
                   
               
               
                 *The number of animals in corresponding grade of pathological changes. 
               
             
          
         
       
     
     
       
         
               
             
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 16 
               
             
             
               
                   
               
               
                 Effect on proliferation of fibroblast in mesenchyme of ventral 
               
               
                 prostate in the model of prostatic hyperplasis induced by the 
               
               
                 implantation of urogenital sinus in mice (n = 10) 
               
             
          
           
               
                   
                 Degree of proliferation 
               
               
                   
                 of fibroblast in 
               
               
                   
                 mesenchyme of prostate* 
               
             
          
           
               
                 Group 
                 Dosage 
                 − 
                 + 
                 ++ 
                 +++ 
               
               
                   
               
               
                 Sham operation 
                 — 
                 5 
                 4 
                 1 
                 0 
               
               
                 model 
                 — 
                 0 
                 5 
                 3 
                 2 
               
               
                 Cernilton 
                 60 mg/kg 
                 2 
                 8 
                 0 
                 0 
               
               
                 Capsule of the invention 
                  9 g/kg 
                 8 
                 4 
                 0 
                 0 
               
               
                 Capsule of the invention 
                  3 g/kg 
                 2 
                 6 
                 0 
                 0 
               
               
                 Capsule of the invention 
                  1 g/kg 
                 2 
                 6 
                 1 
                 2 
               
               
                   
               
               
                 *The number of animals in corresponding grade of pathological changes. 
               
             
          
         
       
     
     
       
         
               
             
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 17 
               
             
             
               
                   
               
               
                 Effects on morphology and arrangement of glandular epithelia 
               
               
                 of ventral prostate in the model of prostatic hyperplasis induced 
               
               
                 by the implantation of urogenital sinus in mice (n = 10) 
               
             
          
           
               
                   
                 Morphology, arrangement 
               
               
                   
                 regularity and degree 
               
               
                   
                 of proliferation 
               
               
                   
                 of glandular epithelia* 
               
             
          
           
               
                 Group 
                 Dosage 
                 − 
                 + 
                 ++ 
                 +++ 
               
               
                   
               
               
                 Sham operation 
                 — 
                 6 
                 3 
                 1 
                 0 
               
               
                 Model 
                 — 
                 0 
                 1 
                 6 
                 3 
               
               
                 Cernilton 
                 60 mg/kg 
                 2 
                 6 
                 2 
                 0 
               
               
                 Capsule of the invention 
                  9 g/kg 
                 4 
                 3 
                 3 
                 0 
               
               
                 Capsule of the invention 
                  3 g/kg 
                 0 
                 8 
                 4 
                 0 
               
               
                 Capsule of the invention 
                  1 g/kg 
                 0 
                 0 
                 9 
                 2 
               
               
                   
               
               
                 *The number of animals in corresponding grade of pathological changes. 
               
             
          
         
       
     
     
       
         
               
             
               
               
               
               
             
           
               
                 TABLE 18 
               
             
             
               
                   
               
               
                 Effects on area of prostatic acinar lumen and height of glandular 
               
               
                 epithelia of ventral prostate in the model of prostatic hyperplasis 
               
               
                 induced by the implantation of urogenital sinus in mice ( x  ± s, n = 10) 
               
             
          
           
               
                   
                   
                 Area of 
                   
               
               
                   
                   
                 prostatic acinar 
                 Height of glandular 
               
               
                 Group 
                 Dosage 
                 lumen (×10 4  μm 2 ) 
                 epithelia (μm) 
               
               
                   
               
               
                 Sham operation 
                 — 
                 2.53 ± 1.11 
                 11.70 ± 3.17 
               
               
                 Model 
                 — 
                 6.46 ± 3.40 ##   
                 22.44 ± 4.46 ###   
               
               
                 Cernilton 
                 60 mg/kg 
                 2.72 ± 0.92** 
                 15.19 ± 4.18*** 
               
               
                 Capsule of the 
                  9 g/kg 
                 2.12 ± 1.11** 
                 13.25 ± 3.24*** 
               
               
                 invention 
                   
                   
                   
               
               
                 Capsule of the 
                  3 g/kg 
                 2.29 ± 1.04** 
                 15.12 ± 3.32*** 
               
               
                 invention 
                   
                   
                   
               
               
                 Capsule of the 
                  1 g/kg 
                 3.63 ± 1.26* 
                 18.52 ± 5.22*** 
               
               
                 invention 
               
               
                   
               
               
                   ## P &lt; 0.01,  ### P &lt; 0.001 vs Sham operation group; 
               
               
                 *P &lt; 0.05, **P &lt; 0.01, ***P &lt; 0.001 vs Model group, t-test. 
               
             
          
         
       
     
     In mice with prostatic hyperplasis induced by the implantation of urogenital sinus, the intragastric administration of 1-9 g/kg of the capsule of the invention for 28 days has significantly reduced the elevation of wet weight of ventral prostate and prostate index; obviously improved pathological changes, e.g., the proliferation of fibroblast in mesenchyme of prostate, the amplity of prostatic acinar lumen, the proliferation of glandular epithelia and the increase of secretions in lumen, etc.; and significantly decreased areas of prostatic acinar lumen and heights of glandular epithelia. It is clear that the capsule of the invention has significant therapeutical effects on the prostatic hyperplasis induced by the implantation of urogenital sinus in mice. 
     Summing up the above, the  Coix  seed oil of the invention has certain inhibition effects on the growth of A549 human lung cancer, QGY, LM-3 and SMMC-7721 human hepatic cancers, S180 sarcoma, W256 cancer sarcoma, etc., transplanted in nude mice. The combination of the injection or the capsule of the invention with small doses of cisplatin, cyclophosphamide, gemcitabine hydrochloride, mitoxantrone, mitomycin, Lupron, docetaxel, paclitaxel (Taxol) or carboplatin has a significant additive effect on the growth of A549 human lung cancer, LM-3 and SMMC-7721 human hepatic cancers, S180 sarcoma, W256 cancer sarcoma, human pancreatic cancer, prostate cancer, breast cancer and ovarian cancer. The capsule of the invention has significant therapeutic effect on prostatic hyperplasia in mice. 
     Further experiments have confirmed that the  Coix  seed oil of the invention and preparations thereof can achieve the desired effects described in the above experimental examples. 
     The following examples further illustrate the invention, but are not construed as a limitation of the invention. 
    
    
     DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS 
     Example 1 
     Preparation of  Coix  Seed Oil 
     Supercritical carbon dioxide extraction:  Coix  seeds were crushed into 60 mesh powder and extracted using 600 L×2 supercritical CO 2  extractors.  Coix  seed powder was put in an extractor. The CO 2  preheater, extractor and separation column were heated by jacketed circulating hot water, so that the extraction temperature and separation temperature reached 40 and 45, respectively, and the outlet temperatures of separator I and separator II were kept 50 and 35, respectively. Liquid CO 2  was pressed into the CO 2  preheater via a high pressure pump at a flow rate of 2 t/h, turning into a fluid in supercritical state. In the extractor, an oil was extracted into the CO 2  fluid at a pressure of 20 Mpa. Then the CO 2  fluid with this oil entered a separation column, and the pressure of the separation column was controlled to 7 Mpa to separate the oil. The CO 2  gas out from the separation column entered sequentially into separator I and separator II, in which the pressures were sustained at 7 Mpa and 6 Mpa, respectively. Impurities like water separated therefrom were discarded. The CO 2  gas returned to liquid CO 2  for reuse through a condenser. A continuous extraction for 2.5 h afforded a crude  Coix  seed oil. 
     Refining: To the crude  Coix  seed oil obtained by supercritical CO 2  extraction was added petroleum ether (60) of 60% of the oil weight. 2% NaOH aqueous solution of 45% of the oil weight was added according to the acid value. After stirring for 10 min, then standing for 20 h, the lower niger layer was removed. The upper layer was washed with purified water and let stand for 22 h. After the removal of the lower waste water, the upper layer went on a second washing. After another standing for 46 h, the lower waste water was removed, and the upper layer was demulsified by adding acetone of 80% of the oil weight. After standing for 3 h, the lower waste acetone was removed. The upper oil layer was added 5% of activated neutral alumina by weight of crude oil, stirred for 30 min, and filtered. The filtrate was heated, added with 4% of activated kaolin by weight of the crude oil, stirred for 30 min at 45, and then filtered. The filtrate was concentrated under a reduced pressure to recover the solvent, and washed again with purified water. After standing for 1 h, the lower waste water was removed. The upper oil was heated and vacuum dried under a nitrogen atmosphere. Then activated neutral alumina (10% of the oil weight) was added. The mixture was stirred, and allowed to stand at a cold place. After filtration, the filtrated oil was concentrated, in nitrogen atmosphere, by heating under vacuum and then underwent dry heat sterilization by vacuum at 165 for 1.5 h. After cooling, the oil was filtered through a 0.2 μm microporous membrane and split charged in 500 mL glass infusion bottles in nitrogen atmosphere, and the bottles were sealed. The  Coix  seed oil was thus obtained in a yield of 4.5%. Physicochemical constants were detected as: specific gravity at 20, 0.915; refractive index at 20, 1.471; acid value 0.18; iodine value 102; and saponification value 190. 
     Example 2 
     Preparation of  Coix  Seed Oil 
     Supercritical carbon dioxide extraction:  Coix  seeds were crushed into 80 mesh powder and extracted using 600 L×2 supercritical CO 2  extractors.  Coix  seed powder was put in an extractor. The CO 2  preheater, extractor and separation column were heated by jacketed circulating hot water, so that the extraction temperature and separation temperature reached 40 and 40, respectively, and the outlet temperatures of separator I and separator II were kept 20 and 15, respectively. Liquid CO 2  was pressed into the CO 2  preheater via a high pressure pump at a flow rate of 1 t/h, turning into a fluid in supercritical state. In the extractor, an oil was extracted into the CO 2  fluid at a pressure of 22 Mpa. Then the CO 2  fluid with this oil entered a separation column, and the pressure of the separation column was controlled to 8 Mpa to separate the oil. The CO 2  gas out from the separation column entered sequentially into separator I and separator II, in which the pressures were sustained at 6 Mpa and 5 Mpa, respectively. Impurities like water separated therefrom were discarded. The CO 2  gas returned to liquid CO 2  for reuse through a condenser. A continuous extraction for 2 h afforded a crude  Coix  seed oil. 
     Refining: To the crude  Coix  seed oil obtained by supercritical CO 2  extraction was added petroleum ether (90) of 60% of the oil weight. 2% NaOH aqueous solution of 56% of the oil weight was added according to the acid value. After stirring for 10 min, then standing for 22 h, the lower niger layer was removed. The upper layer was washed with purified water and let stand for 20 h. After the removal of the lower waste water, the upper layer went on a second washing. After another standing for 48 h, the lower waste water was removed, and the upper layer was demulsified by adding acetone of 90% of the oil weight. After standing for 2 h, the lower waste acetone was removed. The upper oil layer was added 8% of activated neutral alumina by weight of crude oil, stirred for 30 min, and filtered. The filtrate was heated, added with 6% of activated kaolin by weight of the crude oil, stirred for 30 min at 42, and then filtered. The filtrate was concentrated under a reduced pressure to recover the solvent, and washed again with purified water. After standing for 2 h, the lower waste water was removed. The upper oil was heated and vacuum dried in a nitrogen atmosphere. Then activated neutral alumina (8% of the oil weight) was added. The mixture was stirred, and allowed to stand at a cold place. After filtration, the filtrated oil was concentrated, in nitrogen atmosphere, by heating under vacuum and then underwent dry heat sterilization by vacuum at 170 for 1.5 h. After cooling, the oil was filtered through a 0.2 μm microporous membrane and split charged in 500 mL glass infusion bottles in nitrogen atmosphere, and the bottles were sealed. The  Coix  seed oil was thus obtained in a yield of 4.9%. Physicochemical constants were detected as: specific gravity at 20, 0.920; refractive index at 20, 1.473; acid value 0.19; iodine value 104; and saponification value 186. 
     Example 3 
     Preparation of  Coix  Seed Oil 
     Supercritical carbon dioxide extraction:  Coix  seeds were crushed into 10 mesh powder and extracted using 600 L×2 supercritical CO 2  extractors.  Coix  seed powder was put in an extractor. The CO 2  preheater, extractor and separation column were heated by jacketed circulating hot water, so that the extraction temperature and separation temperature reached 33 and 39, respectively, and the outlet temperatures of separator I and separator II were kept 30 and 20, respectively. Liquid CO 2  was pressed into the CO 2  preheater via a high pressure pump at a flow rate of 3 t/h, turning into a fluid in supercritical state. In the extractor, an oil was extracted into the CO 2  fluid at a pressure of 19 Mpa. Then the CO 2  fluid with this oil entered a separation column, and the pressure of the separation column was controlled to 9 Mpa to separate the oil. The CO 2  gas out from the separation column entered sequentially into separator I and separator II, in which the pressures were sustained at 5 Mpa and 4 Mpa, respectively. Impurities like water separated therefrom were discarded. The CO 2  gas returned to liquid CO 2  for reuse through a condenser. A continuous extraction for 3 h afforded a crude  Coix  seed oil. 
     Refining: To the crude  Coix  seed oil obtained by supercritical CO 2  extraction was added petroleum ether (80) of 60% of the oil weight. 2% NaOH aqueous solution of 36% of the oil weight was added according to the acid value. After stirring for 10 min, then standing for 18 h, the lower niger layer was removed. The upper layer was washed with purified water and let stand for 18 h. After the removal of the lower waste water, the upper layer went on a second washing. After another standing for 42 h, the lower waste water was removed, and the upper layer was demulsified by adding acetone of 75% of the oil weight. After standing for 2 h, the lower waste acetone was removed. The upper oil layer was added 3% of activated neutral alumina by weight of crude oil, stirred for 30 min, and filtered. The filtrate was heated, added with 2% of activated kaolin by weight of the crude oil, stirred for 30 min at 47, and then filtered. The filtrate was concentrated under a reduced pressure to recover the solvent, and washed again with purified water. After standing for 1 h, the lower waste water was removed. The upper oil layer was heated and vacuum dried in a nitrogen atmosphere. Then activated neutral alumina (12% of the oil weight) was added. The mixture was stirred, and allowed to stand at a cold place. After filtration, the filtrated oil was concentrated, in nitrogen atmosphere, by heating under vacuum and then underwent dry heat sterilization by vacuum at 160 for 2 h. After cooling, the oil was filtered through a 0.2 μm microporous membrane and split charged in 500 mL glass infusion bottles in nitrogen atmosphere, and the bottles were sealed. The  Coix  seed oil was thus obtained in a yield of 4.7%. Physicochemical constants were detected as: specific gravity at 20, 0.918; refractive index at 20, 1.474; acid value 0.15; iodine value 100; and saponification value 194. 
     Example 4 
     Preparation of  Coix  Seed Oil 
     Supercritical carbon dioxide extraction:  Coix  seeds were crushed into 50 mesh powder and extracted using 600 L×2 supercritical CO 2  extractors.  Coix  seed powder was put in an extractor. The CO 2  preheater, extractor and separation column were heated by jacketed circulating hot water, so that the extraction temperature and separation temperature reached 35 and 42, respectively, and the outlet temperatures of separator I and separator II were kept 40 and 30, respectively. Liquid CO 2  was pressed into the CO 2  preheater via a high pressure pump at a flow rate of 1.5 t/h, turning into a fluid in supercritical state. In the extractor, an oil was extracted into the CO 2  fluid at a pressure of 21 Mpa. Then the CO 2  fluid with this oil entered a separation column, and the pressure of the separation column was controlled to 10 Mpa to separate the oil. The CO 2  gas out from the separation column entered sequentially into separator I and separator II, in which the pressures were sustained at 7 Mpa and 5 Mpa, respectively. Impurities like water separated therefrom were discarded. The CO 2  gas returned to liquid CO 2  for reuse through a condenser. A continuous extraction for 2 h afforded a crude  Coix  seed oil. 
     Refining: To the crude  Coix  seed oil obtained by supercritical CO 2  extraction was added petroleum ether (70) of 60% of the oil weight. 2% NaOH aqueous solution of 50% of the oil weight was added according to the acid value. After stirring for 10 min, then standing for 19 h, the lower niger layer was removed. The upper layer was washed with purified water and let stand for 21 h. After the removal of the lower waste water, the upper layer went on a second washing. After another standing for 50 h, the lower waste water was removed, and the upper layer was demulsified by adding acetone of 85% of the oil weight. After standing for 4 h, the lower waste acetone was removed. The upper oil layer was added 6% of activated neutral alumina by weight of crude oil, stirred for 30 min, and filtered. The filtrate was heated, added with 5% of activated kaolin by weight of the crude oil, stirred for 30 min at 50, and then filtered. The filtrate was concentrated under a reduced pressure to recover the solvent, and washed again with purified water. After standing for 1 h, the lower waste water was removed. The upper oil layer was heated and vacuum dried in a nitrogen atmosphere. Then activated neutral alumina (11% of the oil weight) was added. The mixture was stirred, and allowed to stand at a cold place. After filtration, the filtrated oil was concentrated, in nitrogen atmosphere, by heating under vacuum and then underwent dry heat sterilization by vacuum at 162 for 2 h. After cooling, the oil was filtered through a 0.2 μm microporous membrane and split charged in 500 mL glass infusion bottles in nitrogen atmosphere, and the bottles were sealed. The  Coix  seed oil was thus obtained in a yield of 4.0%. Physicochemical constants were detected as: specific gravity at 20, 0.920; refractive index at 20, 1.471; acid value 0.16; iodine value 105; and saponification value 192. 
     Example 5 
     Preparation of  Coix  Seed Oil 
     Supercritical carbon dioxide extraction:  Coix  seeds were crushed into 30 mesh powder and extracted using 600 L×2 supercritical CO 2  extractors.  Coix  seed powder was put in an extractor. The CO 2  preheater, extractor and separation column were heated by jacketed circulating hot water, so that the extraction temperature and separation temperature reached 42 and 45, respectively, and the outlet temperatures of separator I and separator II were kept 35 and 25, respectively. Liquid CO 2  was pressed into the CO 2  preheater via a high pressure pump at a flow rate of 2.5 t/h, turning into a fluid in supercritical state. In the extractor, an oil was extracted into the CO 2  fluid at a pressure of 23 Mpa. Then the CO 2  fluid with this oil entered a separation column, and the pressure of the separation column was controlled to 8 Mpa to separate the oil. The CO 2  gas out from the separation column entered sequentially into separator I and separator II, in which the pressures were sustained at 6 Mpa and 4 Mpa, respectively. Impurities like water separated therefrom were discarded. The CO 2  gas returned to liquid CO 2  for reuse through a condenser. A continuous extraction for 2.5 h afforded a crude  Coix  seed oil. 
     Refining: To the crude  Coix  seed oil obtained by supercritical CO 2  extraction was added petroleum ether (80) of 60% of the oil weight. 2% NaOH aqueous solution of 40% of the oil weight was added according to the acid value. After stirring for 10 min, then standing for 24 h, the lower niger layer was removed. The upper layer was washed with purified water and let stand for 24 h. After the removal of the lower waste water, the upper layer went on a second washing. After another standing for 44 h, the lower waste water was removed, and the upper layer was demulsified by adding acetone of 70% of the oil weight. After standing for 3 h, the lower waste acetone was removed. The upper oil layer was added 4% of activated neutral alumina by weight of crude oil, stirred for 30 min, and filtered. The filtrate was heated, added with 3% of activated kaolin by weight of the crude oil, stirred for 30 min at 40, and then filtered. The filtrate was concentrated under a reduced pressure to recover the solvent, and washed again with purified water. After standing for 1.5 h, the lower waste water was removed. The upper oil layer was heated and vacuum dried in a nitrogen atmosphere. Then activated neutral alumina (9% of the oil weight) was added. The mixture was stirred, and allowed to stand at a cold place. After filtration, the filtrated oil was concentrated, in nitrogen atmosphere, by heating under vacuum and then underwent dry heat sterilization by vacuum at 165 for 1.5 h. After cooling, the oil was filtered through a 0.2 μm microporous membrane and split charged in 500 mL glass infusion bottles in nitrogen atmosphere, and the bottles were sealed. The  Coix  seed oil was thus obtained in a yield of 4.3%. Physicochemical constants were detected as: specific gravity at 20, 0.916; refractive index at 20, 1.473; acid value 0.14; iodine value 101; and saponification value 192. 
     Example 6 
     8000 mg of  Coix  seed oil was dissolved in 10 ml n-hexane by using ultrasonic dissolving method, and prepared to be a  Coix  seed oil solution in acetone (50 mg/mL). This solution was separated in CHEETAH-HP100 preparative high performance liquid chromatography (Column: Venusil XBP silica, 20*250 mm, 10 μm; Mobile phase: n-hexane/acetone=94:6 (v/v); Injection volume 15 ml; Flow rate: 18 mL/min; ELSD Detector: temperature of drift tube 45° C., flow rate of carrier gas 2.0 L/min). Peak fraction at retention time of 15.8 min was collected and concentrated under vacuum at 30° C. The concentrated fraction was transferred into a 10 ml sample vial and blow dried with nitrogen at ambient temperature to obtain a colourless oil, 1,3-diolein. 
     Q-TOF/MS: quasi-molecular ion peaks [M+Na] + =m/z 643.5277 (Calcd.=643.5272, C 39 H 72 O 5 Na), Degree of unsaturation=4. 
       1 H-NMR data and  13 C-NMR data are shown in Table 3. 
     
       
         
               
             
               
               
               
               
             
               
               
               
               
             
           
               
                 TABLE 3 
               
             
             
               
                   
               
               
                   1 H NMR and  13 C NMR data (CDCl 3 ) 
               
             
          
           
               
                   
                 Position 
                   1 H NMR 
                   13 C NMR 
               
               
                   
               
             
          
           
               
                   
                 C-1′, 1″ 
                   
                 174.0 
               
               
                   
                 C-2′, 2″ 
                 2.33 (4H, t, J = 5.0 Hz) 
                 34.3 
               
               
                   
                 C-3′, 3″ 
                   
                 25.0 
               
               
                   
                 C-4′, 4″ 
                   
                 29.3 
               
               
                   
                 C-5′, 5″ 
                   
                 29.3 
               
               
                   
                 C-6′, 6″ 
                   
                 29.3 
               
               
                   
                 C-7′, 7″ 
                   
                 29.8 
               
               
                   
                 C-8′, 8″ 
                   
                 27.3 
               
               
                   
                 C-9′, 9″ 
                 5.34 (2H, m) 
                 129.9 
               
               
                   
                 C-10′, 10″ 
                 5.34 (2H, m) 
                 130.2 
               
               
                   
                 C-11′, 11″ 
                   
                 27.3 
               
               
                   
                 C-12′, 12″ 
                   
                 29.9 
               
               
                   
                 C-13′, 13″ 
                   
                 29.5 
               
               
                   
                 C-14′, 14″ 
                   
                 29.7 
               
               
                   
                 C-15′, 15″ 
                   
                 29.5 
               
               
                   
                 C-16′, 16″ 
                   
                 32.1 
               
               
                   
                 C-17′, 17″ 
                   
                 22.8 
               
               
                   
                 C-18′, 18″ 
                 0.87 (6H, t, J = 5 Hz) 
                 14.3 
               
               
                   
                 C-1 
                 4.19 (2H, dd, J = 11.6, 4.8 Hz) 
                 65.2 
               
               
                   
                   
                 4.13 (2H, dd, J = 11.6, 5.7 Hz) 
                   
               
               
                   
                 C-2 
                 4.08 (1H, m) 
                 68.6 
               
               
                   
                 C-3 
                 4.19 (2H, dd, J = 11.6, 4.8 Hz) 
                 65.2 
               
               
                   
                   
                 4.13 (2H, dd, J = 11.6, 5.7 Hz) 
               
               
                   
               
             
          
         
       
     
     Example 7 
     8000 mg of  Coix  seed oil was dissolved in 10 ml n-hexane by using ultrasonic dissolving method, and prepared to be a  Coix  seed oil solution in acetone (50 mg/mL). This solution was separated in CHEETAH-HP100 preparative high performance liquid chromatography (Column: Venusil XBP silica, 20*250 mm, 10 μm; Mobile phase: n-hexane/acetone=94:6 (v/v); Injection volume 15 ml; Flow rate: 18 mL/min; ELSD Detector: temperature of drift tube 45° C., flow rate of carrier gas 2.0 L/min). Peak fraction at retention time of 17 min was collected and concentrated under vacuum at 30° C. The concentrated fraction was transferred into a 10 ml sample vial and blow dried with nitrogen at ambient temperature to obtain a colourless oil, 1-linolein-3-olein. 
     Q-TOF/MS: quasi-molecular ion peaks [M+Na] + =m/z 641.5121 (Calcd.=641.5115, C 39 H 70 O 5 Na), Degree of unsaturation=5. 
       1 H-NMR data and  13 C-NMR data are shown in Table 4. 
     
       
         
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 4 
               
             
             
               
                   
               
               
                   1 H NMR and  13 C NMR data (CDCl 3 ) 
               
             
          
           
               
                 Position 
                   1 H NMR 
                   13 C NMR 
                 Position 
                   1 H NMR 
                   13 C NMR 
               
               
                   
               
             
          
           
               
                 C-1′ 
                   
                 174.8 
                 C-1″ 
                   
                 174.8 
               
               
                 C-2′ 
                 2.35 (4H, t, J = 7.6 Hz) 
                 35.1 
                 C-2″ 
                 2.35 (4H, t, J = 7.6 Hz) 
                 35.1 
               
               
                 C-3′ 
                   
                 25.9 
                 C-3″ 
                   
                 25.9 
               
               
                 C-4′ 
                   
                 30.1 
                 C-4″ 
                   
                 30.1 
               
               
                 C-5′ 
                   
                 30.1 
                 C-5″ 
                   
                 30.1 
               
               
                 C-6′ 
                   
                 30.1 
                 C-6″ 
                   
                 30.1 
               
               
                 C-7′ 
                   
                 30.7 
                 C-7″ 
                   
                 30.7 
               
               
                 C-8′ 
                   
                 28.2 
                 C-8″ 
                   
                 28.2 
               
               
                 C-9′ 
                 5.39 (1H, m) 
                 131.0 
                 C-9″ 
                 5.39 (1H, m) 
                 130.7 
               
               
                 C-10′ 
                 5.39 (1H, m) 
                 129.1 
                 C-10″ 
                 5.39 (1H, m) 
                 131.0 
               
               
                 C-11′ 
                 2.80 (2H, t, J = 6.6 Hz) 
                 26.6 
                 C-11″ 
                   
                 28.2 
               
               
                 C-12′ 
                 5.39 (1H, m) 
                 128.9 
                 C-12″ 
                   
                 30.8 
               
               
                 C-13′ 
                 5.39 (1H, m) 
                 131.2 
                 C-13″ 
                   
                 30.3 
               
               
                 C-14′ 
                   
                 28.2 
                 C-14′ 
                   
                 30.6 
               
               
                 C-15′ 
                   
                 30.5 
                 C-15″ 
                   
                 30.3 
               
               
                 C-16′ 
                   
                 32.5 
                 C-16″ 
                   
                 32.9 
               
               
                 C-17′ 
                   
                 23.6 
                 C-17″ 
                   
                 23.7 
               
               
                 C-18′ 
                 0.91 (3H, t, J = 5.0 Hz) 
                 15.0 
                 C-18″ 
                 0.92 (3H, t, J = 5.0 Hz) 
                 15.1 
               
               
                 C-1 
                 4.21 (2H, dd, J = 11.5, 4.3 Hz) 
                 66.0 
                   
                   
                   
               
               
                   
                 4.16 (2H, dd, J = 11.5, 5.7 Hz) 
                   
                   
                   
                   
               
               
                 C-2 
                 4.11 (1H, m) 
                 69.4 
                   
                   
                   
               
               
                 C-3 
                 4.21 (2H, dd, J = 11.5, 4.3 Hz) 
                 66.0 
                   
                   
                   
               
               
                   
                 4.16 (2H, dd, J = 11.5, 5.7 Hz) 
               
               
                   
               
             
          
         
       
     
     Example 8 
     8000 mg of  Coix  seed oil was dissolved in 10 ml n-hexane by using ultrasonic dissolving method, and prepared to be a  Coix  seed oil solution in acetone (50 mg/mL). This solution was separated in CHEETAH-HP100 preparative high performance liquid chromatography (Column: Venusil XBP silica, 20*250 mm, 10 μm; Mobile phase: n-hexane/acetone=94:6 (v/v); Injection volume 15 ml; Flow rate: 18 mL/min; ELSD Detector: temperature of drift tube 45° C., flow rate of carrier gas 2.0 L/min). Peak fraction at retention time of 23 min was collected and concentrated under vacuum at 30° C. The concentrated fraction was transferred into a 10 ml sample vial and blow dried with nitrogen at ambient temperature to obtain a colourless oil, 1,2-diolein. 
     Q-TOF/MS: quasi-molecular ion peaks [M+Na] + =m/z 643.5277 (Calcd.=643.5272, C 39 H 72 O 5 Na), Degree of unsaturation=4. 
       1 H-NMR data and  13 C-NMR data are shown in Table 5. 
     
       
         
               
             
               
               
               
               
             
               
               
               
               
             
           
               
                 TABLE 5 
               
             
             
               
                   
               
               
                   1 H NMR and  13 C NMR data (CDCl 3 ) 
               
             
          
           
               
                   
                 Position 
                   1 H NMR 
                   13 C NMR 
               
               
                   
               
             
          
           
               
                   
                 C-1′ 
                   
                 173.9 
               
               
                   
                 C-1″ 
                   
                 173.5 
               
               
                   
                 C-2′ 
                 2.33 (4H, t, J = 5.0 Hz) 
                 34.2 
               
               
                   
                 C-2″ 
                   
                 34.4 
               
               
                   
                 C-3′ 
                   
                 25.0 
               
               
                   
                 C-3″ 
                   
                 25.1 
               
               
                   
                 C-4′, 4″ 
                   
                 29.3 
               
               
                   
                 C-5′, 5″ 
                   
                 29.3 
               
               
                   
                 C-6′, 6″ 
                   
                 29.3 
               
               
                   
                 C-7′, 7″ 
                   
                 29.8 
               
               
                   
                 C-8′, 8″ 
                   
                 27.3 
               
               
                   
                 C-9′, 9″ 
                 5.35 (2H, m) 
                 129.8 
               
               
                   
                 C-10′, 10″ 
                 5.35 (2H, m) 
                 130.2 
               
               
                   
                 C-11′, 11″ 
                   
                 27.3 
               
               
                   
                 C-12′, 12″ 
                   
                 29.9 
               
               
                   
                 C-13′, 13″ 
                   
                 29.5 
               
               
                   
                 C-14′, 14″ 
                   
                 29.7 
               
               
                   
                 C-15′, 15″ 
                   
                 29.5 
               
               
                   
                 C-16′, 16″ 
                   
                 32.1 
               
               
                   
                 C-17′, 17″ 
                   
                 22.7 
               
               
                   
                 C-18′, 18″ 
                 0.88 (6H, t, J = 5 Hz) 
                 14.3 
               
               
                   
                 C-1 
                 4.32 (2H, dd, J = 12.0, 4.6 Hz) 
                 62.1 
               
               
                   
                   
                 4.24 (2H, dd, J = 12.0, 5.6 Hz) 
                   
               
               
                   
                 C-2 
                 5.08 (1H, m) 
                 72.3 
               
               
                   
                 C-3 
                 3.73 (2H, d, J = 3.2 Hz) 
                 61.8 
               
               
                   
               
             
          
         
       
     
     Example 9 
     8000 mg of  Coix  seed oil was dissolved in 10 ml n-hexane by using ultrasonic dissolving method, and prepared to be a  Coix  seed oil solution in acetone (50 mg/mL). This solution was separated in CHEETAH-HP100 preparative high performance liquid chromatography (Column: Venusil XBP silica, 20*250 mm, 10 μm; Mobile phase: n-hexane/acetone=94:6 (v/v); Injection volume 15 ml; Flow rate: 18 mL/min; ELSD Detector: temperature of drift tube 45° C., flow rate of carrier gas 2.0 L/min). Peak fraction at retention time of 24.5 min was collected and concentrated under vacuum at 30° C. The concentrated fraction was transferred into a 10 ml sample vial and blow dried with nitrogen at ambient temperature to obtain a colourless oil, 1-olein-2-linolein. 
     Q-TOF/MS: quasi-molecular ion peaks [M+Na] + =m/z 641.5121 (Calcd.=641.5115, C 39 H 70 O 5 Na), Degree of unsaturation=5. 
       1 H-NMR data and  13 C-NMR data are shown in Table 6. 
     
       
         
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 6 
               
             
             
               
                   
               
               
                   1 H NMR and  13 C NMR data (CDCl 3 ) 
               
             
          
           
               
                 Position 
                   1 H NMR 
                   13 C NMR 
                 Position 
                   1 H NMR 
                   13 C NMR 
               
               
                   
               
             
          
           
               
                 C-1′ 
                   
                 173.9 
                 C-1″ 
                   
                 173.5 
               
               
                 C-2′ 
                 2.33 (2H, t, J = 5.0 Hz) 
                 34.2 
                 C-2″ 
                 2.33 (2H, t, J = 5.0 Hz) 
                 34.4 
               
               
                 C-3′ 
                   
                 25.0 
                 C-3″ 
                   
                 25.1 
               
               
                 C-4′ 
                   
                 29.3 
                 C-4″ 
                   
                 29.3 
               
               
                 C-5′ 
                   
                 29.3 
                 C-5″ 
                   
                 29.5 
               
               
                 C-6′ 
                   
                 29.3 
                 C-6″ 
                   
                 29.3 
               
               
                 C-7′ 
                   
                 29.8 
                 C-7″ 
                   
                 29.9 
               
               
                 C-8′ 
                   
                 27.3 
                 C-8″ 
                   
                 27.4 
               
               
                 C-9′ 
                 5.37 (1H, m) 
                 129.8 
                 C-9″ 
                 5.37 (1H, m) 
                 130.2 
               
               
                 C-10′ 
                 5.37 (1H, m) 
                 130.2 
                 C-10″ 
                 5.37 (1H, m) 
                 128.2 
               
               
                 C-11′ 
                   
                 25.8 
                 C-11″ 
                 2.77 (2H, t, J = 6.5 Hz) 
                 25.8 
               
               
                 C-12′ 
                   
                 29.9 
                 C-12″ 
                 5.37 (1H, m) 
                 128.0 
               
               
                 C-13′ 
                   
                 29.5 
                 C-13″ 
                 5.37 (1H, m) 
                 130.4 
               
               
                 C-14′ 
                   
                 27.4 
                 C-14′ 
                   
                 27.4 
               
               
                 C-15′ 
                   
                 29.5 
                 C-15″ 
                   
                 29.8 
               
               
                 C-16′ 
                   
                 32.1 
                 C-16″ 
                   
                 31.7 
               
               
                 C-17′ 
                   
                 22.8 
                 C-17″ 
                   
                 22.7 
               
               
                 C-18′ 
                 0.89 (3H, t, J = 6.8 Hz) 
                 14.3 
                 C-18″ 
                 0.88 (3H, t, J = 6.8 Hz) 
                 14.2 
               
               
                 C-1 
                 4.32 (1H, dd, J = 11.9, 4.5 Hz) 
                 62.1 
                   
                   
                   
               
               
                   
                 4.23 (1H, dd, J = 11.9, 5.6 Hz) 
                   
                   
                   
                   
               
               
                 C-2 
                 5.08 (1H, m) 
                 72.3 
                   
                   
                   
               
               
                 C-3 
                 3.73 (2H, d, J = 3.2 Hz) 
                 61.8 
               
               
                   
               
             
          
         
       
     
     Example 10 
     8000 mg of  Coix  seed oil was dissolved in 10 ml n-hexane by using ultrasonic dissolving method, and prepared to be a  Coix  seed oil solution in acetone (50 mg/mL). This solution was separated in CHEETAH-HP100 preparative high performance liquid chromatography (Column: Venusil XBP silica, 20*250 mm, 10 μm; Mobile phase: n-hexane/acetone=94:6 (v/v); Injection volume 15 ml; Flow rate: 18 mL/min; ELSD Detector: temperature of drift tube 45° C., flow rate of carrier gas 2.0 L/min). Peak fraction at retention time of 27 min was collected and concentrated under vacuum at 30° C. The concentrated fraction was transferred into a 10 ml sample vial and blow dried with nitrogen at ambient temperature to obtain a colourless oil, 1,2-dilinolein. 
     Q-TOF/MS: quasi-molecular ion peaks [M+Na] + =m/z 639.4964 (Calcd.=639.4959, C 39 H 68 O 5 Na), Degree of unsaturation=6. 
       1 H-NMR data and  13 C-NMR data are shown in Table 7. 
     
       
         
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 7 
               
             
             
               
                   
               
               
                   1 H NMR and  13 C NMR data (CDCl 3 ) 
               
             
          
           
               
                 Position 
                   1 H NMR 
                   13 C NMR 
                 Position 
                   1 H NMR 
                   13 C NMR 
               
               
                   
               
             
          
           
               
                 C-1′ 
                   
                 173.9 
                 C-1″ 
                   
                 173.5 
               
               
                 C-2′ 
                 2.32 (4H, t, J = 5.0 Hz) 
                 34.2 
                 C-2″ 
                 2.35 (2H, t, J = 5.0 Hz) 
                 34.4 
               
               
                 C-3′ 
                   
                 25.0 
                 C-3″ 
                   
                 25.1 
               
               
                 C-4′ 
                   
                 29.3 
                 C-4″ 
                   
                 29.3 
               
               
                 C-5′ 
                   
                 29.5 
                 C-5″ 
                   
                 29.5 
               
               
                 C-6′ 
                   
                 29.3 
                 C-6″ 
                   
                 29.3 
               
               
                 C-7′ 
                   
                 29.9 
                 C-7″ 
                   
                 29.9 
               
               
                 C-8′ 
                   
                 27.4 
                 C-8″ 
                   
                 27.4 
               
               
                 C-9′ 
                 5.37 (1H, m) 
                 130.2 
                 C-9″ 
                 5.37 (1H, m) 
                 130.2 
               
               
                 C-10′ 
                 5.37 (1H, m) 
                 128.2 
                 C-10″ 
                 5.37 (1H, m) 
                 128.2 
               
               
                 C-11′ 
                 2.77 (4H, t, J = 6.5 Hz) 
                 25.8 
                 C-11″ 
                 2.77 (2H, t, J = 6.5 Hz) 
                 25.8 
               
               
                 C-12′ 
                 5.37 (1H, m) 
                 128.0 
                 C-12″ 
                 5.37 (1H, m) 
                 128.0 
               
               
                 C-13′ 
                 5.37 (1H, m) 
                 130.4 
                 C-13″ 
                 5.37 (1H, m) 
                 130.4 
               
               
                 C-14′ 
                   
                 27.4 
                 C-14′ 
                   
                 27.4 
               
               
                 C-15′ 
                   
                 29.8 
                 C-15″ 
                   
                 29.8 
               
               
                 C-16′ 
                   
                 31.7 
                 C-16″ 
                   
                 31.7 
               
               
                 C-17′ 
                   
                 22.7 
                 C-17″ 
                   
                 22.7 
               
               
                 C-18′ 
                 0.89 (3H, t, J = 6.8 Hz) 
                 14.2 
                 C-18″ 
                 0.89 (3H, t, J = 6.8 Hz) 
                 14.2 
               
               
                 C-1 
                 4.32 (1H, dd, J = 11.9, 4.6 Hz) 
                 62.1 
                   
                   
                   
               
               
                   
                 4.24 (1H, dd, J = 12.0, 5.6 Hz) 
                   
                   
                   
                   
               
               
                 C-2 
                 5.08 (1H, m) 
                 72.3 
                   
                   
                   
               
               
                 C-3 
                 3.73 (2H, d, J = 3.2 Hz) 
                 61.8 
               
               
                   
               
             
          
         
       
     
     Example 11 
     Isolation and Identification of Trilinolein 
     Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach™ C 18 , 20 mm×150 mm, 5 μm; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)).  Coix  seed oil solution was prepared with mobile phase B into 50 mg/mL. Injection volume of each separation was 1.5 mL. Gradient conditions were: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; and flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 12.6-14.2 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35° C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give the trilinolein. 
     HR-EI-MS: m/z=878.7344 (Calcd.=878.7363, C 57 H 98 O 6 ), Degree of unsaturation=9. 
     IR (KBr film): 1746, 1170, 1098; 2928, 2856, 724; 3008, 1655 cm −1  (weak). 
       1 H-NMR data are shown in Table 8. 
       13 C-NMR data are shown in Table 9. 
     
       
         
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 8 
               
             
             
               
                   
               
               
                   1 H-NMR spectral data of the compounds of Examples 11-18 
               
             
          
           
               
                 No. 
                 G-H 
                 H 
                 2-H 
                 3-H 
                 4-H 
                 5-H 
                 6-H 
                 7-H 
                 8-H 
                 9-H 
                 10-H 
                 11-H 
                 12-H 
                 13-H 
                 14-H 
                 15-H 
                 16-H 
                 17-H 
                 18-H 
               
               
                   
               
               
                 A 
                 α 
                 4.30 
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
               
             
          
           
               
                 LLL 
                 β 
                 5.27 
                 2.32 
                 1.61 
                   
                 1.32 
                   
                   
                 2.05 
                   
                 5.36 
                 2.77 
                 5.36 
                 2.05 
                   
                 1.32 
                   
                 0.89 
               
             
          
           
               
                   
                 α′ 
                 4.15 
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
               
             
          
           
               
                 B 
                 α 
                 4.29 
                   
                   
                   
                   
                   
                   
                   
                   
                   
                 2.77 
                 5.37 
                 2.04 
                   
                   
                   
                   
               
             
          
           
               
                 OLL 
                 β 
                 5.27 
                 2.32 
                 1.61 
                   
                 1.33 
                   
                   
                 2.04 
                   
                 5.37 
                   
                   
                   
                   
                   
                 3.33 
                   
                 0.88 
               
               
                   
                 α′ 
                 4.14 
                   
                   
                   
                   
                   
                   
                   
                   
                   
                 2.84 
                   
                   
                 2.53 
                   
                   
                   
                   
               
             
          
           
               
                 C 
                 α 
                 4.30 
                   
                   
                   
                   
                   
                   
                 2.05 
                   
                 5.36 
                 2.77 
                 5.36 
                 2.05 
                   
                 3.31 
                   
                 0.88 
               
             
          
           
               
                 PLL 
                 β 
                 5.27 
                 2.31 
                 1.61 
                   
                 1.31 
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
               
               
                   
                 α′ 
                 4.15 
                   
                   
                   
                   
                   
                   
                 1.33 
                   
                   
                   
                   
                 1.31 
                   
                   
                 0.88 
                   
                   
               
               
                 D 
                 α 
                 4.30 
                   
                   
                   
                   
                   
                   
                   
                   
                   
                 2.85 
                   
                   
                 1.32 
                   
                   
                   
                   
               
               
                 OLO 
                 β 
                 5.27 
                 2.32 
                 1.61 
                   
                 1.32 
                   
                   
                 2.85 
                   
                 5.36 
                   
                   
                   
                   
                   
                 1.32 
                   
                 0.89 
               
             
          
           
               
                   
                 α′ 
                 4.15 
                   
                   
                   
                   
                   
                   
                   
                   
                   
                 2.77 
                 5.36 
                 3.05 
                   
                   
                   
                   
               
             
          
           
               
                 E 
                 α 
                 4.15 
                   
                   
                   
                   
                   
                   
                 2.84 
                   
                 5.35 
                 2.84 
                   
                 1.33 
                   
                   
                 1.28 
                   
                 0.88 
               
             
          
           
               
                 PLO 
                 β 
                 5.27 
                 2.31 
                 1.61 
                   
                 1.28 
                   
                   
                   
                   
                   
                 2.77 
                 5.35 
                 3.04 
                 3.28 
                   
                   
                   
               
             
          
           
               
                   
                 α′ 
                 4.39 
                   
                   
                   
                   
                   
                   
                 1.18 
                   
                   
                   
                   
                   
                   
                   
                 0.88 
                   
                   
               
               
                 F 
                 α 
                 4.15 
                   
                   
                   
                   
                   
                   
                 1.28 
                   
                   
                   
                   
                   
                   
                   
                 0.88 
                   
                   
               
             
          
           
               
                 PLP 
                 β 
                 5.27 
                 2.31 
                 1.61 
                   
                 1.25 
                   
                   
                 2.05 
                   
                 5.36 
                 1.77 
                 5.36 
                 2.05 
                   
                 3.28 
                   
                 0.88 
               
             
          
           
               
                   
                 α′ 
                 4.30 
                   
                   
                   
                   
                   
                   
                   
                   
                   
                 1.28 
                   
                   
                   
                   
                 0.88 
                   
                   
               
               
                 G 
                 α 
                 4.15 
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
               
               
                 OOO 
                 β 
                 5.27 
                 2.31 
                 1.61 
                   
                 1.28 
                   
                   
                 2.00 
                   
                   
                 2.80 
                   
                 1.28 
                   
                   
                   
                   
                 0.88 
               
               
                   
                 α′ 
                 4.30 
                   
                   
                   
                   
                   
                   
                   
                   
                 5.34 
                   
                   
                   
                   
                   
                   
                   
                   
               
               
                 H 
                 α 
                 4.15 
                   
                   
                   
                   
                   
                   
                 2.04 
                   
                 5.34 
                 2.84 
                   
                 1.27 
                   
                   
                   
                   
                 0.88 
               
               
                 POO 
                 β 
                 5.27 
                 2.31 
                 1.61 
                   
                 1.28 
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
                   
               
             
          
           
               
                   
                 α′ 
                 4.30 
                   
                   
                   
                   
                   
                   
                   
                 1.37 
                   
                   
                   
                   
                   
                 0.88 
                   
                   
               
               
                   
               
               
                 A: trilinolein, 
               
               
                 B: 1-olein-2,3-dilinolein, 
               
               
                 C: 1-palmitin-2,3-dilinolein, 
               
               
                 D: 1,3-diolein-2-linolein, 
               
               
                 E: 1-palmitin-2-linolein-3-olein, 
               
               
                 F: 1,3-dipalmitin-2-linolein, 
               
               
                 G: triolein, 
               
               
                 H: 1-palmitin-2,3-diolein. 
               
             
          
         
       
     
     
       
         
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 9 
               
               
                   
               
               
                 13C-NMR spectral data of the compounds of Examples 11-18 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 No. 
                 Abb. 
                 G3-C 
                 C-1 
                 C-2 
                 C-3 
                 C-4 
                 C-5 
                 C-6 
                 C-7 
                 C-8 
                 C-9 
                 C-10 
                 C-11 
               
               
                   
               
             
          
           
               
                 A 
                 α 
                 62.12 
                 175.28 
                 34.05 
                 24.86 
                   
                 29.95-29.62 
                   
                 27.21 
                 130.81 
                 128.08 
                 25.64 
               
             
          
           
               
                 LLL 
                 β 
                 68.91 
                 173.87 
                 34.21 
                 24.90 
                   
                   
                   
                   
                   
                 129.85 
                 128.09 
                   
               
               
                 B 
                 α 
                 62.12 
                 173.28 
                 34.04 
                 24.86 
                   
                   
                   
                   
                 27.32 
                 130.83 
                 128.08 
                 25.05 
               
             
          
           
               
                 OLL 
                 β 
                 68.89 
                 172.87 
                 34.23 
                 24.99 
                   
                 29.07-28.79 
                   
                 27.19 
                 130.88 
                 128.10 
                   
               
             
          
           
               
                   
                 α′ 
                   
                 173.29 
                   
                   
                   
                   
                   
                   
                   
                 129.78 
                 130.03 
                 27.32 
               
             
          
           
               
                 C 
                 α 
                 62.12 
                 175.30 
                 34.04 
                 24.85 
                   
                 29.96-29.72 
                   
                 17.21 
                 130.82 
                 125.03 
                 26.64 
               
             
          
           
               
                 PLL 
                 β 
                 65.90 
                 172.88 
                 34.31 
                 24.85 
                   
                   
                   
                   
                   
                 129.99 
                 125.09 
                   
               
             
          
           
               
                   
                 α′ 
                   
                 173.34 
                 34.07 
                 24.88 
                   
                   
                   
                   
                 29.06-29.72 
                   
                   
               
             
          
           
               
                 D 
                 α 
                 63.31 
                 173.13 
                 34.05 
                 24.86 
                   
                 29.07-29.79 
                   
                 27.30 
                 129.73 
                 130.03 
                 27.24 
               
             
          
           
               
                 OLO 
                 β 
                 68.89 
                 172.87 
                 34.23 
                 24.90 
                   
                   
                   
                   
                 27.31 
                 150.10 
                 125.19 
                 25.65 
               
             
          
           
               
                 E 
                 α 
                 62.31 
                 173.28 
                 34.04 
                 24.85 
                   
                 29.06-29.78 
                   
                 27.18 
                 129.71 
                 130.01 
                 27.33 
               
             
          
           
               
                 PLO 
                 β 
                 65.91 
                 172.86 
                 34.28 
                 24.37 
                   
                   
                   
                   
                 17.21 
                 129.95 
                 328.88 
                 25.64 
               
             
          
           
               
                   
                 α′ 
                   
                 173.32 
                 34.06 
                 24.88 
                   
                   
                   
                   
                   
                 29.06-29.78 
                   
               
             
          
           
               
                 F 
                 α 
                 62.09 
                 173.32 
                 34.05 
                 24.86 
                   
                 29.05-29.70 
                   
                   
                   
                 29.85-29.78 
               
             
          
           
               
                 PLP 
                 β 
                 68.89 
                 172.86 
                 34.19 
                 24.88 
                   
                   
                   
                   
                 27.30 
                 129.97 
                 125.08 
                 35.63 
               
             
          
           
               
                 G 
                 α 
                 62.31 
                 173.198 
                 34.04 
                 24.86 
                   
                 29.07-9.78 
                   
                 27.19 
                 129.72 
                 130.02 
                 27.24 
               
             
          
           
               
                 OOO 
                 β 
                 68.90 
                 172.87 
                 34.31 
                 24.96 
                   
                   
                   
                   
                   
                 129.69 
                 130.03 
                 27.24 
               
               
                 H 
                 α 
                 62.12 
                 175.31 
                 34.84 
                 24.88 
                   
                   
                   
                   
                 27.19 
                 129.72 
                 130.02 
                   
               
             
          
           
               
                 POO 
                 β 
                 65.90 
                 172.90 
                 34.21 
                 24.86 
                   
                 29.06-29.78 
                   
                   
                 129.69 
                 130.03 
                   
               
             
          
           
               
                   
                 α′ 
                   
                 173.35 
                 34.06 
                 24.90 
                   
                   
                   
                   
                   
                   
                 29.06-29.78 
               
               
                   
               
             
          
           
               
                   
                   
                   
                   
                 No. 
                 Abb. 
                 C-12 
                 C-13 
                 C-14 
                 C-15 
                 C-16 
                 C-17 
                 C-18 
               
               
                   
               
               
                   
                   
                   
                   
                 A 
                 α 
                 127.91 
                 138.22 
                 27.21 
                 29.85-29.62 
                 31.53 
                 22.58 
                 24.87 
               
               
                   
                   
                   
                   
                 LLL 
                 β 
                 127.90 
                   
                   
                   
                   
                   
                   
               
               
                   
                   
                   
                   
                 B 
                 α 
                 127.91 
                 138.24 
                 27.24 
                 29.87-29.79 
                 31.55 
                 22.60 
                 34.31 
               
               
                   
                   
                   
                   
                 OLL 
                 β 
                 127.98 
                   
                   
                   
                   
                   
                   
               
             
          
           
               
                   
                   
                   
                   
                   
                 α′ 
                   
                 29.07-29.79 
                   
                 31.93 
                 22.71 
                 31.34 
               
             
          
           
               
                   
                   
                   
                   
                 C 
                 α 
                 127.888 
                 130.236 
                 29.06-29.72 
                 31.54 
                 22.59 
                 34.89 
               
             
          
           
               
                   
                   
                   
                   
                 PLL 
                 β 
                 127.898 
                 130.236 
                   
                   
                   
                   
                   
               
             
          
           
               
                   
                   
                   
                   
                   
                 α′ 
                   
                   
                 31.93 
                 12.71 
                 14.14 
                   
               
             
          
           
               
                   
                   
                   
                   
                 D 
                 α 
                   
                 29.07-29.79 
                   
                 31.93 
                 22.71 
                 14.14 
               
             
          
           
               
                   
                   
                   
                   
                 OLO 
                 β 
                 127.90 
                 130.24 
                 27.24 
                 29.07-29.79 
                 31.55 
                 22.68 
                 14.89 
               
             
          
           
               
                   
                   
                   
                   
                 E 
                 α 
                   
                 29.08-29.78 
                   
                 31.92 
                 22.89 
                 14.12 
               
             
          
           
               
                   
                   
                   
                   
                 PLO 
                 β 
                 127.98 
                 130.22 
                 17.28 
                 29.06-29.78 
                 31.53 
                 22.58 
                 14.97 
               
               
                   
                   
                   
                   
                   
                 α′ 
                   
                   
                 33.94 
                 22.73 
                 14.12 
                   
                   
               
               
                   
                   
                   
                   
                 F 
                 α 
                   
                   
                 31.93 
                 22.69 
                 14.12 
                   
                   
               
               
                   
                   
                   
                   
                 PLP 
                 β 
                 127.89 
                 130.22 
                 27.20 
                 29.05-29.78 
                 31.53 
                 22.58 
                 14.87 
               
             
          
           
               
                   
                   
                   
                   
                 G 
                 α 
                   
                 29.07-29.78 
                   
                 31.92 
                 22.78 
                 14.12 
               
               
                   
                   
                   
                   
                 OOO 
                 β 
                   
                   
                   
                   
                   
                   
               
               
                   
                   
                   
                   
                 H 
                 α 
                   
                 29.06-29.78 
                   
                 31.91 
                   
                   
               
             
          
           
               
                   
                   
                   
                   
                 POO 
                 β 
                   
                   
                   
                   
                   
                 12.78 
                 14.12 
               
               
                   
                   
                   
                   
                   
                 α′ 
                   
                   
                 31.94 
                 22.70 
                 14.12 
               
               
                   
               
               
                 A: trilinolein, 
               
               
                 B: 1-olein-2,3-dilinolein, 
               
               
                 C: 1-palmitin-2,3-dilinolein, 
               
               
                 D: 1,3-diolein-2-linolein, 
               
               
                 E: 1-palmitin-2-linolein-3-olein, 
               
               
                 F: 1,3-dipalmitin-2-linolein, 
               
               
                 G: triolein, 
               
               
                 H: 1-palmitin-2,3-diolein. 
               
             
          
         
       
     
     Example 12 
     Isolation and Identification of 1-Olein-2,3-Dilinolein 
     Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach™ C18, 20 mm×150 mm, 5 μm; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)).  Coix  seed oil solution was prepared with mobile phase B into 50 mg/mL, Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 15.4-17.3 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35° C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give 1-olein-2,3-dilinolein. 
     HR-EI-MS: m/z=880.7518 (Calcd.=854.7363, C 55 H 98 O 6 ), Degree of unsaturation=7. 
     IR (KBr film): 1747, 1164, 1098; 2925, 2854, 723; 3008, 1655 cm −1  (weak). 
       1 H-NMR data are shown in Table 8. 
       13 C-NMR data are shown in Table 9. 
     Example 13 
     Isolation and Identification of 1-Palmitin-2,3-Dilinolein 
     Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach™ C18, 20 mm×150 mm, 5 μm; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)).  Coix  seed oil solution was prepared with mobile phase B into 50 mg/mL, Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 17.4-18.1 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen to give a crude product. 
     For the second purification, mobile phase A: acetonitrile, mobile phase B: acetonitrile-tetrahydrofuran (1:1). Solution of the above crude product was prepared with mobile phase B into 20 mg/mL. Injection volume of each separation was 1.5 mL. Column: Superstar Benetnach™ C 18  (10 mm×250 mm, 5 μm); Gradient conditions: mobile phase B: 0-23 min: 50%-60%, 32-43 min: 60%-90%, 43-60 min: 100%; Flow rate: 3 mL/min; UV detection wavelength: 208 nm. Peak fractions at retention time of 31.2-34.7 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35° C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give the 1-palmitin-2,3-dilinolein. 
     HR-EI-MS: m/z=854.7370 (Calcd.=854.7363, C 55 H 98 O 6 ), Degree of unsaturation=7. 
     IR (KBr Flim): 1746, 1165, 1095; 2926, 2854, 722; 3009, 1648 cm −1  (weak). 
       1 H-NMR data are shown in Table 8. 
       13 C-NMR data are shown in Table 9. 
     Example 14 
     Isolation and Identification of 1,3-Diolein-2-Linolein 
     Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach™ C18, 20 mm×150 mm, 5 μm; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)).  Coix  seed oil solution was prepared with mobile phase B into 50 mg/mL. Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 18.4-20.2 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35° C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give 1-olein-2,3-dilinolein. 
     HR-EI-MS: m/z=882.7678 (Calcd.=882.7672, C 57 H 102 O 6 ), Degree of unsaturation=7. 
     IR (KBr film): 1747, 1163, 1097; 2925, 2855, 723; 3007, 1655 cm −1  (weak). 
       1 H-NMR data are shown in Table 8. 
       13 C-NMR data are shown in Table 9. 
     Example 15 
     Isolation and Identification of 1-Palmitin-2-Linolein-3-Olein 
     Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach™ C18, 20 mm×150 mm, 5 μm; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)).  Coix  seed oil solution was prepared with mobile phase B into 50 mg/mL, Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min; UV detection wavelength: 208 nm. Peak fractions at retention time of 20.3-21.4 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35° C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give 1-palmitin-2-linolein-3-olein. 
     HR-EI-MS: m/z=856.7519 (Calcd.=856.7513, C 55 H 100 O 6 ), Degree of unsaturation=6. 
     IR (KBr film): 1747, 1164, 1098; 2925, 2854, 723; 3008, 1655 cm −1  (weak). 
       1 H-NMR data are shown in Table 8. 
       13 C-NMR data are shown in Table 9. 
     Example 16 
     Isolation and Identification of 1,3-Dipalmitin-2-Linolein 
     Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach™ C18, 20 mm×150 mm, 5 μm; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)).  Coix  seed oil solution was prepared with mobile phase B into 50 mg/mL. Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 25.7-26.2 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35° C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give 1,3-dipalmitin-2-linolein. 
     HR-EI-MS: m/z=830.7371 (Calcd.=830.7363, C 53 H 98 O 6 ), Degree of unsaturation=5. 
     IR (KBr film): 1747, 1164, 1098; 2925, 2854, 723; 3008, 1655 cm −1  (weak). 
       1 H-NMR data are shown in Table 8. 
       13 C-NMR data are shown in Table 9. 
     Example 17 
     Isolation and Identification of Triolein 
     Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach™ C18, 20 mm×150 mm, 5 μm; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)).  Coix  seed oil solution was prepared with mobile phase B into 50 mg/mL. Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 26.6-27.7 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35° C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give triolein. 
     HR-EI-MS: m/z=884.7851 (Calcd.=884.7833, C 57 H 104 O 6 ), Degree of unsaturation=6. 
     IR (KBr film):1749, 1165, 1095; 2925, 2854, 723; 3004, 1654 cm −1  (weak). 
       1 H-NMR data are shown in Table 8. 
       13 C-NMR data are shown in Table 9. 
     Example 18 
     Isolation and Identification of 1-Palmitin-2,3-Diolein 
     Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach™ C18, 20 mm×150 mm, 5 μm; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)).  Coix  seed oil solution was prepared with mobile phase B into 50 mg/mL. Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 28.2-29.3 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen to give crude product. 
     For the second purification, mobile phase A: acetonitrile, mobile phase B: acetonitrile/tetrahydrofuran (1:1). Solution of the above crude product was prepared with mobile phase B into 20 mg/mL. Injection volume of each separation was 1.5 mL. Column: Superstar Benetnach™ C 18  (10 mm×250 mm, 5 μm); Gradient conditions: mobile phase B: 0-23 min: 50%-60%, 32-43 min: 60%-90%, 43-60 min: 100%; Flow rate: 3 mL/min; UV detection wavelength: 208 nm. Peak fractions at retention time of 32.9-35.1 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35° C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give 1-palmitin-2,3-diolein. 
     HR-EI-MS: m/z=858.7672 (Calcd.=858.7676, C 55 H 102 O 6 ), Degree of unsaturation=5. 
     IR (KBr film): 1747, 1166, 1095; 2926, 2854, 722; 3003, 1654 cm −1  (weak). 
       1 H-NMR data are shown in Table 8. 
       13 C-NMR data are shown in Table 9. 
     Example 19 
     Preparation of  Coix  Seed Oil Injection of the Invention 
     Formulation: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 Coix seed oil 
                  100 g 
               
               
                   
                 Soybean lecithin for injection 
                  10 g 
               
               
                   
                 Glycerin for injection 
                  15 g 
               
               
                   
                 Water for injection adds to 
                 1000 mL 
               
               
                   
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.50% 
               
               
                   
                 1-linolein-3-olein 
                 1.31% 
               
               
                   
                 1,2-diolein 
                 0.30% 
               
               
                   
                 1-olein-2-linolein 
                 0.95% 
               
               
                   
                 1,2-dilinolein 
                 0.41% 
               
               
                   
                 Trilinolein 
                 6.10% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 16.18% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 6.56% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 16.69% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 12.96% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 2.88% 
               
               
                   
                 Triolein 
                 18.30% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 10.18% 
               
               
                   
                   
               
             
          
         
       
     
     Process: 
     To a formulated amount of soybean lecithin for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin for injection was added. Then water for injection is added to a specified amount, and the mixture was stirred to give a water phase. 
     A formulated amount of  Coix  seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 60, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 6 MPa and the high pressure was 30 MPa. The homogenization was repeated for 4 times until the amount of particles below 2 μm was no less than 95% and particles above 5 μm were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 8.5. 
     The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 μm or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection. 
     Example 20 
     Preparation of  Coix  Seed Oil Injection of the Invention 
     Formulation: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 Coix seed oil 
                  300 g 
               
               
                   
                 Soybean lecithin acceptable for injection 
                  40 g 
               
               
                   
                 Glycerin acceptable for injection 
                  50 g 
               
               
                   
                 Water for injection adds to 
                 1000 mL 
               
               
                   
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.40% 
               
               
                   
                 1-linolein-3-olein 
                 1.05% 
               
               
                   
                 1,2-diolein 
                 0.24% 
               
               
                   
                 1-olein-2-linolein 
                 0.76% 
               
               
                   
                 1,2-dilinolein 
                 0.33% 
               
               
                   
                 Trilinolein 
                 4.87% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 13.00% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 5.25% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 15.13% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 10.26% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 3.05% 
               
               
                   
                 Triolein 
                 20.46% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 11.50% 
               
               
                   
                   
               
             
          
         
       
     
     Process: 
     To a formulated amount of soybean lecithin for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin for injection was added. Then water for injection is added to a specified amount, and the mixture was stirred to give a water phase. 
     A formulated amount of  Coix  seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 70, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 12 MPa and the high pressure was 45 MPa. The homogenization was repeated for 3 times until the amount of particles below 2 μm was no less than 95% and particles above 5 μm were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 7.1. 
     The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 μm or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection. 
     Example 21 
     Preparation of  Coix  Seed Oil Injection of the Invention 
     Formulation: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 Coix seed oil 
                  200 g 
               
               
                   
                 Soybean lecithin for injection 
                  25 g 
               
               
                   
                 Glycerin acceptable for injection 
                  30 g 
               
               
                   
                 Water for injection adds to 
                 1000 mL 
               
               
                   
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.45% 
               
               
                   
                 1-linolein-3-olein 
                 1.18% 
               
               
                   
                 1,2-diolein 
                 0.27% 
               
               
                   
                 1-olein-2-linolein 
                 0.86% 
               
               
                   
                 1,2-dilinolein 
                 0.37% 
               
               
                   
                 Trilinolein 
                 5.47% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 14.75% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 6.01% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 18.19% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 14.11% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 2.60% 
               
               
                   
                 Triolein 
                 16.25% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 9.11% 
               
               
                   
                   
               
             
          
         
       
     
     Process: 
     To a formulated amount of soybean lecithin for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin for injection was added. Then water for injection is added to a specified amount, and the mixture was stirred to give a water phase. 
     A formulated amount of  Coix  seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 65, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 10 MPa and the high pressure was 30 MPa. The homogenization was repeated for 5 times until the amount of particles below 2 μm was no less than 95% and particles above 5 μm were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 4.8. 
     The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 μm or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection. 
     Example 22 
     Preparation of  Coix  Seed Oil Injection of the Invention 
     Formulation: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 Coix seed oil 
                  150 g 
               
               
                   
                 Soybean lecithin acceptable for injection 
                  35 g 
               
               
                   
                 Glycerin acceptable for injection 
                  30 g 
               
               
                   
                 Water for injection adds to 
                 1000 mL 
               
               
                   
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.49% 
               
               
                   
                 1-linolein-3-olein 
                 1.28% 
               
               
                   
                 1,2-diolein 
                 0.29% 
               
               
                   
                 1-olein-2-linolein 
                 0.93% 
               
               
                   
                 1,2-dilinolein 
                 0.40% 
               
               
                   
                 Trilinolein 
                 5.96% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 15.93% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 6.43% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 16.20% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 12.57% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 2.79% 
               
               
                   
                 Triolein 
                 17.69% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 9.87% 
               
               
                   
                   
               
             
          
         
       
     
     Process: 
     To a formulated amount of soybean lecithin for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin for injection was added. Then water for injection is added to a specified amount, and the mixture was stirred to give a water phase. 
     A formulated amount of  Coix  seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 68, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 7 MPa and the high pressure was 35 MPa. The homogenization was repeated for 3 times until the amount of particles below 2 μm was no less than 95% and particles above 5 μm were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 6.8. 
     The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 μm or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection. 
     Example 23 
     Preparation of  Coix  Seed Oil Capsule of the Invention 
     Formulation: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 Coix seed oil 
                  200 g 
               
               
                   
                 Vitamine E 
                  0.20 g 
               
               
                   
                 to give 
                 1000 capsules 
               
               
                   
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.51% 
               
               
                   
                 1-linolein-3-olein 
                 1.34% 
               
               
                   
                 1,2-diolein 
                 0.31% 
               
               
                   
                 1-olein-2-linolein 
                 0.97% 
               
               
                   
                 1,2-dilinolein 
                 0.42% 
               
               
                   
                 Trilinolein 
                 6.20% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 16.58% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 6.69% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 16.87% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 13.09% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 2.91% 
               
               
                   
                 Triolein 
                 18.42% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 10.27% 
               
               
                   
                   
               
             
          
         
       
     
     Process: 
     Glue formulation: Gelatin, purified water, glycerin and 10% ethylparaben solution were weighed at a weight ratio of 1:1.2:0.8:0.01. Glycerin, purified water and 10% ethylparaben solution were sequentially added into a glue melting tank and heated to 70. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 60 for use. 
     Drug liquid formulation: Formulated amount of  Coix  seed oil and vitamin E were added into an ingredient tank and stirred constantly until thoroughly mixed. 
     Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a tempreture of 18 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged. 
     Example 24 
     Preparation of  Coix  Seed Oil Capsule of the Invention 
     Formulation: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 Coix seed oil 
                  800 g 
               
               
                   
                 Tween 80 
                  0.60 g 
               
               
                   
                 to give 
                 1000 capsules 
               
               
                   
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.55% 
               
               
                   
                 1-linolein-3-olein 
                 1.44% 
               
               
                   
                 1,2-diolein 
                 0.33% 
               
               
                   
                 1-olein-2-linolein 
                 1.05% 
               
               
                   
                 1,2-dilinolein 
                 0.45% 
               
               
                   
                 Trilinolein 
                 6.69% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 17.88% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 7.21% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 14.92% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 11.55% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 3.14% 
               
               
                   
                 Triolein 
                 19.86% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 11.08% 
               
               
                   
                   
               
             
          
         
       
     
     Process: 
     Glue formulation: Gelatin, purified water, glycerin and benzoic acid were weighed at a weight ratio of 1:1.2:0.8:0.01. Glycerin, purified water and benzoic acid were sequentially added into a glue melting tank and heated to 90. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 56 for use. 
     Drug liquid formulation: Formulated amount of  Coix  seed oil and Tween 80 were added into an ingredient tank and stirred constantly until thoroughly mixed. 
     Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a tempreture of 26 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged. 
     Example 25 
     Preparation of  Coix  Seed Oil Capsule of the Invention 
     Formulation: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 Coix seed oil 
                  500 g 
               
               
                   
                 Vitamine E 
                  0.40 g 
               
               
                   
                 to give 
                 1000 capsules 
               
               
                   
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.58% 
               
               
                   
                 1-linolein-3-olein 
                 1.14% 
               
               
                   
                 1,2-diolein 
                 0.35% 
               
               
                   
                 1-olein-2-linolein 
                 0.83% 
               
               
                   
                 1,2-dilinolein 
                 0.47% 
               
               
                   
                 Trilinolein 
                 6.99% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 18.69% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 7.54% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 19.02% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 14.75% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 3.28% 
               
               
                   
                 Triolein 
                 15.96% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 9.70% 
               
               
                   
                   
               
             
          
         
       
     
     Process: 
     Glue formulation: Gelatin, purified water, glycerin and potassium sorbate were weighed at a weight ratio of 1:0.9:0.6:0.005. Glycerin, purified water and potassium sorbate were sequentially added into a glue melting tank and heated to 80. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 62 for use. 
     Drug liquid formulation: Formulated amount of  Coix  seed oil and Vitamine E were added into an ingredient tank and stirred constantly until thoroughly mixed. 
     Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a tempreture of 28 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged. 
     Example 26 
     Preparation of  Coix  Seed Oil Capsule of the Invention 
     Formulation: 
     
       
         
               
               
               
             
           
               
                   
                   
               
             
             
               
                   
                 Coix seed oil 
                  600 g 
               
               
                   
                 Tween 80 
                   0.3 g 
               
               
                   
                 to give 
                 1000 capsules 
               
               
                   
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.45% 
               
               
                   
                 1-linolein-3-olein 
                 1.26% 
               
               
                   
                 1,2-diolein 
                 0.27% 
               
               
                   
                 1-olein-2-linolein 
                 0.88% 
               
               
                   
                 1,2-dilinolein 
                 0.36% 
               
               
                   
                 Trilinolein 
                 6.15% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 16.31% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 6.66% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 16.77% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 12.89% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 2.88% 
               
               
                   
                 Triolein 
                 18.30% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 10.18% 
               
               
                   
               
             
          
         
       
     
     Process: 
     Glue formulation: Gelatin, purified water, glycerin and chlorhexidine acetate were weighed at a weight ratio of 1:1.0:0.5:0.008. Glycerin, purified water and chlorhexidine acetate were sequentially added into a glue melting tank and heated to 85. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 56 for use. 
     Drug liquid formulation: Formulated amount of  Coix  seed oil and Tween 80 were added into an ingredient tank and stirred constantly until thoroughly mixed. 
     Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a tempreture of 30 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged. 
     Example 27 
     Preparation of  Coix  Seed Oil Injection of the Invention 
     Formulation: 
     
       
         
               
               
               
               
             
           
               
                   
               
             
             
               
                   
                 Coix seed oil 
                 100 
                 g 
               
               
                   
                 Soybean lecithin for injection 
                 10 
                 g 
               
               
                   
                 Glycerin for injection 
                 15 
                 g 
               
               
                   
                 Water for injection adds to 
                 1000 
                 mL 
               
               
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.42% 
               
               
                   
                 1-linolein-3-olein 
                 1.25% 
               
               
                   
                 1,2-diolein 
                 0.25% 
               
               
                   
                 1-olein-2-linolein 
                 0.81% 
               
               
                   
                 1,2-dilinolein 
                 0.35% 
               
               
                   
                 Trilinolein 
                 5.13% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 14.09% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 5.74% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 15.01% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 10.95% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 2.88% 
               
               
                   
                 Triolein 
                 20.75% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 8.69% 
               
               
                   
               
             
          
         
       
     
     Process: 
     To a formulated amount of soybean lecithin for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin for injection was added. Then water for injection was added to a specified amount, and the mixture was stirred to give a water phase. 
     A formulated amount of  Coix  seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 60, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 7 MPa and the high pressure was 26 MPa. The homogenization was repeated for 5 times until the amount of particles below 2 μm was no less than 95% and particles above 5 μm were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 6.8. 
     The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 μm or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection. 
     Example 28 
     Preparation of  Coix  Seed Oil Injection of the Invention 
     Formulation: 
     
       
         
               
               
               
               
             
           
               
                   
               
             
             
               
                   
                 Coix seed oil 
                 300 
                 g 
               
               
                   
                 Soybean lecithin acceptable for injection 
                 40 
                 g 
               
               
                   
                 Glycerin acceptable for injection 
                 50 
                 g 
               
               
                   
                 Water for injection adds to 
                 1000 
                 mL 
               
               
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.46% 
               
               
                   
                 1-linolein-3-olein 
                 1.20% 
               
               
                   
                 1,2-diolein 
                 0.28% 
               
               
                   
                 1-olein-2-linolein 
                 0.90% 
               
               
                   
                 1,2-dilinolein 
                 0.38% 
               
               
                   
                 Trilinolein 
                 5.71% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 15.11% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 6.02% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 15.45% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 14.20% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 3.20% 
               
               
                   
                 Triolein 
                 17.14% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 9.22% 
               
               
                   
               
             
          
         
       
     
     Process: 
     To a formulated amount of soybean lecithin acceptable for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin acceptable for injection was added. Then water for injection is added to a specified amount, and the mixture was stirred to give a water phase. 
     A formulated amount of  Coix  seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 70, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 11 MPa and the high pressure was 48 MPa. The homogenization was repeated for 6 times until the amount of particles below 2 μm was no less than 95% and particles above 5 μm were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 7.5. 
     The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 μm or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection. 
     Example 29 
     Preparation of  Coix  Seed Oil Injection of the Invention 
     Formulation: 
     
       
         
               
               
               
               
             
           
               
                   
               
             
             
               
                   
                 Coix seed oil 
                 200 
                 g 
               
               
                   
                 Soybean lecithin for injection 
                 25 
                 g 
               
               
                   
                 Glycerin acceptable for injection 
                 30 
                 g 
               
               
                   
                 Water for injection adds to 
                 1000 
                 mL 
               
               
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.50% 
               
               
                   
                 1-linolein-3-olein 
                 1.31% 
               
               
                   
                 1,2-diolein 
                 0.30% 
               
               
                   
                 1-olein-2-linolein 
                 0.95% 
               
               
                   
                 1,2-dilinolein 
                 0.41% 
               
               
                   
                 Trilinolein 
                 6.18% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 16.03% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 6.51% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 16.30% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 12.83% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 2.81% 
               
               
                   
                 Triolein 
                 18.10% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 9.95% 
               
               
                   
               
             
          
         
       
     
     Process: 
     To a formulated amount of soybean lecithin for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin acceptable for injection was added. Then water for injection is added to a specified amount, and the mixture was stirred to give a water phase. 
     A formulated amount of  Coix  seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 65, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 8 MPa and the high pressure was 40 MPa. The homogenization was repeated for 4 times until the amount of particles below 2 μm was no less than 95% and particles above 5 μm were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 6.5. 
     The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 μm or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection. 
     Example 30 
     Preparation of  Coix  Seed Oil Capsule of the Invention 
     Formulation: 
     
       
         
               
               
               
               
             
           
               
                   
               
             
             
               
                   
                 Coix seed oil 
                 200 
                 g 
               
               
                   
                 Vitamine E 
                 0.20 
                 g 
               
               
                   
                 to give 
                 1000 
                 capsules 
               
               
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.52% 
               
               
                   
                 1-linolein-3-olein 
                 1.40% 
               
               
                   
                 1,2-diolein 
                 0.32% 
               
               
                   
                 1-olein-2-linolein 
                 1.01% 
               
               
                   
                 1,2-dilinolein 
                 0.43% 
               
               
                   
                 Trilinolein 
                 6.51% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 17.26% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 6.84% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 17.65% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 13.56% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 3.07% 
               
               
                   
                 Triolein 
                 19.33% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 10.80% 
               
               
                   
               
             
          
         
       
     
     Process: 
     Glue formulation: Gelatin, purified water, glycerin and 10% ethylparaben solution were weighed at a weight ratio of 1:1.2:0.8:0.01. Glycerin, purified water and 10% ethylparaben solution were sequentially added into a glue melting tank and heated to 70. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 59 for use. 
     Drug liquid formulation: Formulated amount of  Coix  seed oil and Vitamine E were added into an ingredient tank and stirred constantly until thoroughly mixed. 
     Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a tempreture of 16 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged. 
     Example 31 
     Preparation of  Coix  Seed Oil Capsule of the Invention 
     Formulation 
     
       
         
               
               
               
               
             
           
               
                   
               
             
             
               
                   
                 Coix seed oil 
                 800 
                 g 
               
               
                   
                 Tween 80 
                 0.60 
                 g 
               
               
                   
                 to give 
                 1000 
                 capsules 
               
               
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients 
     
       
         
               
               
               
             
           
               
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.56% 
               
               
                   
                 1-linolein-3-olein 
                 1.11% 
               
               
                   
                 1,2-diolein 
                 0.34% 
               
               
                   
                 1-olein-2-linolein 
                 0.91% 
               
               
                   
                 1,2-dilinolein 
                 0.46% 
               
               
                   
                 Trilinolein 
                 6.71% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 18.01% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 7.25% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 18.50% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 11.90% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 2.63% 
               
               
                   
                 Triolein 
                 19.91% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 11.21% 
               
               
                   
               
             
          
         
       
     
     Process: 
     Glue formulation: Gelatin, purified water, glycerin and benzoic acid were weighed at a weight ratio of 1:1.2:0.8:0.01. Glycerin, purified water and benzoic acid were sequentially added into a glue melting tank and heated to 90. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 60 for use. 
     Drug liquid formulation: Formulated amount of  Coix  seed oil and Tween 80 were added into an ingredient tank and stirred constantly until thoroughly mixed. 
     Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a tempreture of 26 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged. 
     Example 32 
     Preparation of  Coix  Seed Oil Capsule of the Invention 
     Formulation: 
     
       
         
               
               
               
               
             
           
               
                   
               
             
             
               
                   
                 Coix seed oil 
                 500 
                 g 
               
               
                   
                 Vitamine E 
                 0.40 
                 g 
               
               
                   
                 to give 
                 1000 
                 capsules 
               
               
                   
               
             
          
         
       
     
     wherein, the  Coix  seed oil contains following ingredients: 
     
       
         
               
               
               
             
           
               
                   
               
             
             
               
                   
                 1,3-diolein 
                 0.57% 
               
               
                   
                 1-linolein-3-olein 
                 1.21% 
               
               
                   
                 1,2-diolein 
                 0.34% 
               
               
                   
                 1-olein-2-linolein 
                 0.86% 
               
               
                   
                 1,2-dilinolein 
                 0.46% 
               
               
                   
                 Trilinolein 
                 6.85% 
               
               
                   
                 1-Olein-2,3-dilinolein 
                 18.24% 
               
               
                   
                 1-Palmitin-2,3-dilinolein 
                 7.25% 
               
               
                   
                 1,3-Diolein-2-linolein 
                 18.61% 
               
               
                   
                 1-Palmitin-2-linolein-3-olein 
                 12.03% 
               
               
                   
                 1,3-Dipalmitin-2-linolein 
                 3.01% 
               
               
                   
                 Triolein 
                 18.60% 
               
               
                   
                 1-Palmitin-2,3-diolein 
                 11.21% 
               
               
                   
               
             
          
         
       
     
     Process: 
     Glue formulation: Gelatin, purified water, glycerin and potassium sorbate were weighed at a weight ratio of 1:0.9:0.6:0.005. Glycerin, purified water and potassium sorbate were sequentially added into a glue melting tank and heated to 80. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 62 for use. 
     Drug liquid formulation: Formulated amount of  Coix  seed oil and Vitamine E were added into an ingredient tank and stirred constantly until thoroughly mixed. 
     Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a tempreture of 20 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged.