bluuebunny/crossref_metadata_2025 huggingface dataset:
LC-MS-MS Identification and Determination of the Flavone-C-Glucoside Vicenin-2 in Rat Plasma Samples Following Intraperitoneal Administration of Lychnophora Extract
Authors: Jabor Valquiria A. Polisel , Soares Denis Melo , Diniz Andrea , de Souza Glória Emilia Petto , Lopes Norberto Peporine
Published: March 2019

The flavone C-glucoside, vicenin-2, in semi-purified extracts of the leaves of Lychnophora ericoides was quantified in rat plasma samples using a method based on reversed-phase high performance liquid chromatography coupled to tandem mass spectrometry. Vicenin-2 was analyzed on a LiChrospher® RP18 column using an isocratic mobile phase consisting of a mixture of methanol: water (30:70, v/v) plus 2.0% glacial acetic acid at a flow rate of 0.8 mL min−1. Genistein was used as internal standard. The mass spectrometer was operated in positive ionization mode and analytes were quantified by multiple reaction monitoring at m/z 595 > 457 for vicenin-2 and m/z 271 > 153 for internal standard. Prior to the analysis, each rat plasma sample was acidified with 200 μL of 50 mmol L−1 acetic acid solution and extracted by solid-phase extraction using a C18 cartridge. The absolute recoveries were reproducible and the coefficients of variation values were lower than 5.2%. The method was linear over the 12.5 – 1500 ng mL−1 concentration range and the quantification limit was 12.5 ng mL−1. Within-day and between-day assay precision and accuracy were studied at three concentration levels (40, 400 and 800 ng mL−1) and were lower than 15%. The developed and validated method seems to be suitable for analysis of vicenin-2 in plasma samples obtained from rats that receive a single i.p. dose of 200 mg kg-1 vicenin-2 extract.
An antiproliferative xanthone of Symphonia pauciflora from the Madagascar rainforest
Authors: Pan Ende , Cao Shugeng , Brodie Peggy J. , Miller James S. , Rakotodrajaona Rolland , Ratovoson Fidy , Birkinshaw Chris , Andriantsiferana Rabodo , Rasamison Vincent E. , Kingston David G. I.
Published: March 2019

Investigation of a Malagasy endemic plant identified as Symphonia pauciflora Baker (Clusiaceae) for antiproliferative activities against the A2780 ovarian cancer cell line led to the isolation of a new compound identified as 2-(3,3-dimethylallyl)-7-methoxy-1,5,6-trihydroxy-2″″,2″″-dimethylpyrano(6″″,5″″:3,4) xanthone (1) and the two known guttiferones A (2) and I (3). The structure elucidation of 1 was based on the analysis of its 1D and 2D NMR and mass spectral data. Compound 1 showed good antiproliferative activity with an IC50 value of 3.8 μM against the A2780 human ovarian cancer cell line, while the known guttiferone analogues (2 and 3) exhibited moderate activities with IC50 values of 8.3 μM and 7.8 μM, respectively.
Structure Determination of Two New Monocillin I Derivatives
Authors: Zhan Jixun , Wijeratne E. M. Kithsiri , Gunatilaka A. A. Leslie
Published: March 2019

Biotransformation of monocillin I (1) by Beauveria bassiana ATCC 7159 was investigated. Two new derivatives 2 and 3 were isolated and identified on the basis of the spectroscopic data. Compounds 2 and 3 are synthesized by hydration at 10,11-double bond and hydrolysis of 14,15-epoxide, respectively. The R configuration of 11-OH in 2 was established by the modified 2-methoxy-2-trifluoromethylphenylacetic acid (MTPA) method. The conversion of 1 to 2 and 3 was reconstituted in an acid solution, indicating that the formation of 2 and 3 is an acid-catalyzed instead of an enzymatic process.
Beauvericin from the Endophytic Fungus, Fusarium redolens, Isolated from Dioscorea zingiberensis and Its Antibacterial Activity
Authors: Xu Lijian , Wang Jihua , Zhao Jianglin , Li Peiqin , Shan Tijiang , Wang Jingguo , Li Xiaolin , Zhou Ligang
Published: March 2019

From the fungal endophyte, Fusarium redolens Dzf2, isolated from rhizomes of the Chinese medicinal plant Dioscorea zingiberensis, beauvericin was obtained by TLC in combination with bioautographic antibacterial assay. The compound was identified by spectroscopic and physicochemical means. The median effective inhibitory concentration (IC50) values of beauvericin against six test bacteria ( Bacillus subtilis, Staphylococcus haemolyticus, Pseudomonas lachrymans, Agrobacterium tumefaciens, Escherichia coli and Xanthomonas vesicatoria) were between 18.4 and 70.7 μg/mL. The beauvericin content of F. redolens Dzf2 mycelia was 9.60 mg/g dw, and beauvericin yield 62.4 mg/L. The obtained results show the potential use of the endophytic fungus for its biological role in providing its host plant with protection, as well as the possible development of beauvericin as an antibacterial.
Simultaneous HPLC Determination of Three Bioactive Alkaloids in the Asian Medicinal Plant Stephania rotunda
Authors: Bory Sothavireak , Bun Sok-Siya , Baghdikian Béatrice , Mabrouki Fathi , Cheng Sun Kaing , Elias Riad , Bun Hot , Ollivier Evelyne
Published: March 2019

A reliable high-performance liquid chromatography (HPLC) method coupled with photodiode array detection has been developed and validated for the determination of three major alkaloids: cepharanthine, tetrahydropalmatine and xylopinine in Stephania rotunda Lour. (Menispermaceae) collected in Cambodia. The chromatographic separation was carried out on a Symmetry C8 column (250 mm x 4.6 mm, 5 μm, Waters), with an isocratic solvent system of 25 mM potassium phosphate buffer (pH 3.5) – acetonitrile. UV detection was performed at 282 nm. Good linear behavior over the investigated concentration ranges was observed with values of r2>0.9964 for all the analytes. The method was reproducible with intra- and inter-day variations of less than 3.91%. The mean recoveries of the analytes ranged from 95.7 to 104.6%. The proposed method was linear, accurate, precise and specific. The validated method was successfully applied to quantify the three alkaloids in various parts of Stephania rotunda and in tubers collected from different Cambodian regions. The results indicated that the developed HPLC method could be used for the quality control of S. rotunda.
Flavonoids from Erythrina vogelii (Fabaceae) of Cameroon
Authors: Ali Muhammad Imran , Ahmed Zeeshan , Waffo Alain Francois Kamdem , Ali Muhammad Shaiq
Published: March 2019

A new flavone, vogeol, and a new isoflavone, vogliiol, have been isolated from Erythrina vogelii, a Cameroonian medicinal plant, along with seven known constituents (salvigenin, carpachromene, euchrenone b10 scandenone, 5,4′-dihydroxy-8-(3″″-methylbut-2″″-enyl)-2″′-(4″′-hydroxy-4″′-methylethyl)-furano-[4″′,5″′:6,7] isoflavone, erythrivarone C, and 5,7,4′-trihydroxy-6-[3″″-methylbut-3″″-enyl]-flavone). Their structures were elucidated by spectroscopic methods.
Antioxidant Effects of Secondary Metabolites from Geranium psilostemon
Authors: Şöhretoğrlu Didem , Sabuncuoğrlu Suna Atasayar , Sakar M. Koray , Özgüneş Hilal , Sterner Olov
Published: March 2019

An investigation was made of the effects on endogenous antioxidant enzyme activities and H2O2-induced lipid peroxidation inhibition in human red blood cells of the crude MeOH extract and its EtOAc, n-BuOH, and H2O sub-extracts obtained from aerial parts of Geranium psilostemon Ledeb., as well as compounds isolated from the most active EtOAc extract. Gallic acid (1), methyl gallate (2), pusilagin (3), 1,3,6-tri- O-galloyl-β-glucopyranoside (4), 1,2,3,4,6-penta- O-galloyl-β-glucopyranoside (5), kaempferol (6), quercetin (7), kaempferol 7- O-α-rhamnopyranoside (8), and quercetin 7- O-α-rhamnopyranoside (9) were isolated from the aerial parts of the title plant, and their structures identified from spectroscopic (UV, 1D- and 2D- NMR) and spectrometric (TOF-MS) data. All extracts and isolated compounds inhibited H2O2-induced lipid peroxidation and also enhanced the activity of superoxide dismutase (SOD) and catalase (CAT).
Formadienoate-A and B: Two New Long Chained Feruloyl Esters from Clerodendrum formicarum (Lamiaceae) of Cameroon
Authors: Ali Muhammad Shaiq , Ahmed Zeeshan , Ali Muhammad Imran , Ngoupayo Joseph
Published: March 2019

The ethanol extract of the leaves of Clerodendrum formicarum Gürke, a Lameacious plant of Cameroon, afforded two new long-chained esters named formadienoate-A (1) and B (2) along with two known constituents which have been obtained for the first time from C. formicarum. They include: hexacosyl-( E)-ferulate (3) and 26-hydroxyhexacosyl-( E)-ferulate (4). Structures of all the isolated constituents have been elucidated with the aid of 1D and 2D NMR spectroscopic techniques.
Composition of the Essential Oil of Argania spinosa (Sapotaceae) Fruit Pulp
Authors: Harhar Hicham , Gharby Said , Ghanmi Mohamed , Monfalouti Hanae El , Guillaume Dominique , Charrouf Zoubida
Published: March 2019

The composition of the essential oil from the fresh and dried pulp of the fruit of Argania spinosa (Skeels) L. has been studied. Camphor was the major component in both oil types, but in addition, the fresh fruit oil had significant amounts of 1,8-cineole, endo-borneol, and 2-(4-methylcyclohex-3-enyl)-propan-2-ol., and the dried pulp oil 3,5-dimethyl-4-ethylidene-cyclohex-2-ene-1-one, 1,8-cineole, and 2-methylbutanoic acid. The presence of camphor and 1,8-cineole in argan fruit essential oil suggests that it could be used locally as an insect repellent, offering an output for argan fruit pulp that is at present a waste product.
Comparative Composition of Four Essential Oils of Oregano Used in Algerian and Jordanian Folk medicine
Authors: Berrehal Djemaa , Boudiar Tarek , Hichem Lakhal , Khalfallah Assia , Kabouche Ahmed , Al-Freihat Ahmad , Ghannadi Alireza , Sajjadi Ebrahim , Mehrabani Mitra , Safaei-Ghomi Jawad , Kabouche Zahia
Published: March 2019

The essential oils obtained from Origanum glandulosum Desf., collected from two different localities of north-eastern Algeria, Constantine and Jijel, and from O. syriacum var. syriacum grown at El-Aghwar (northern Jordan) and El-Shubak (southern Jordan), were analyzed by GC-MS. p-Cymene (6.6% and 7.5%) and γ-terpinene (13.4% and 14.5%) were found in O. glandulosum grown at Constantine and Jijel, respectively, in addition to the major components thymol (34.2%, 51.1%) and carvacrol (30.5%, 6.8%). The oil of O. syriacum L. var syriacum (Boiss.) Ietswaart from El-Shubak was mainly represented by thymol (51.8%) and carvacrol (34.4%), while the oil from El-Aghwar was a thymol-chemotype (72.4%), along with γ-terpinene (7.8%) and p-cymene (5.4%).
The Effects of Maturity on Chilli Pepper Volatile Components Determined by SDE, GC-MS and HPLC
Authors: Liu Rong , Xiong Ke , Dai Xiongze , Wang Li , Liu Zhimin , Xue Wentong
Published: March 2019

The volatile components of a Chinese chilli pepper (Capsicum annuum L. var. longum Sendt) were identified at different levels of ripeness. The peppers at the green, ripening, and full color stages were investigated by simultaneous distillation extraction (SDE) combined with gas chromatography and mass spectrometry (GC–MS). Principal component analysis (PCA) was used to analyze the main factors at each of the stages studied. Eighty-one volatile components were identified and quantified in this study. Twenty-two compounds were found at the green stage, forty-four at the ripening stage, and sixty-one at the full color stage. Qualitative and quantitative discrepancies were observed at the different levels of ripeness. Hexanal, 2-hexenal and propanoic acid-2-methyl-hexyl ester were the most abundant components at the green stage, while 2-pentanol was important at the ripening stage, and 3-hexen-1-ol was related to the full color stage.
Antifungal Activity of Saponin-rich Extracts of Phytolacca dioica and of the Sapogenins Obtained through Hydrolysis
Authors: Liberto Melina Di , Svetaz Laura , Furlán Ricardo L. E. , Zacchino Susana A. , Delporte Carla , Novoa Marco A. , Asencio Marcelo , Cassels Bruce K.
Published: March 2019

A saponin-rich extract of Phytolacca dioica L. berries, its acid hydrolysate, and its major aglycone, phytolaccagenin, were assayed for antifungal activity against ATCC standard cultures of Candida albicans and Cryptococcus neoformans, and against clinical isolates of these fungi. The activity of the extract was either low or negligible, but the hydrolysate, containing the sapogenins, including phytolaccagenin, and also pure phytolaccagenin, showed promising antifungal potency. Hydrolysis of a natural product extract is shown to be a useful modification leading to improved bioactivity.
Cytotoxic Pentacyclic Triterpenoids from Combretum oliviforme
Authors: Wu Xiao-Peng , Han Chang-Ri , Chen Guang-Ying , Yuan Yuan , Xie Jian-Ying
Published: March 2019

Four pentacyclic triterpenoids were obtained from the leaves of Combretum oliviforme Chao, 3β–hydroxyolean–12–en–28–oic acid (1), 23– O–[α-L-(4′-acetylrhamnopyranosyl)]–imberbic acid (2), 23–acetoxy–3β–acetylimberbic acid–29–methyl ester (3), and 23– O–[α-L-rhamnopyranosyl]-1,3β-diacetylimberbic acid (4). Hydrolysis of 2 and 4 gave 23–hydroxyimberbic acid (5). The structures were elucidated by NMR, electrospray ionization mass spectrometry (ESIMS) and comparison with literature data. Compounds 1, 2, 3 and 4 were isolated from C. oliviforme Chao leaves for the first time and 3 for the first time from any natural source. All compounds were tested in vitro for their activity against human lung cancer cell line SPC-A-1, human erythroleukaemic line K562 and human gastric cancer SGC-7901 cells. Compounds 1, 3, 4 and 5 had cytotoxic activity for the three cell lines with IC50 0.69-69.68 μM. These results suggest that the presence of acetyl group in the triterpene aglycone structure plays an essential role for cytotoxic activity.
Bioassay-guided Isolation and Quantification of the α-Glucosidase Inhibitory Compound, Glycyrrhisoflavone, from Glycyrrhiza uralensis
Authors: Li Wei , Li Songpei , Lin Lin , Bai Hong , Wang YingHua , Kato Hiroyoshi , Asada Yoshihisa , Zhang Qingbo , Koike Kazuo
Published: March 2019

The EtOAc extract of the roots of Glycyrrhiza uralensis exhibited α-glucosidase inhibitory activity. Bioassay-guided fractionation resulted in the isolation of an active prenylflavonoid, glycyrrhisoflavone. Its structure was elucidated by NMR and MS analyses. A simple method to prepare glycyrrhisoflavone from the 95% EtOH extract of the roots of G. uralensis was developed by combination of Diaion HP-20 column chromatography (CC), silica gel CC, and preparative HPLC. An HPLC-PDA method was developed for quantitative determination of glycyrrhisoflavone in the roots of G. uralensis. The sample was extracted with MeOH and analyzed using a reversed-phase column with isocratic elution with CH3CN-H2O (0.06% trifluoroacetic acid) (42:58) at a flow rate of 1.2 mL/min, a column temperature of 40°C, and a detection wavelength of 260 nm. The method allowed the determination of glycyrrhisoflavone in the concentration range of 5-500 μg/mL. The relative standard deviation values of the precision and repeatability were 0.3% and 2.0%, respectively. The limits of detection and quantification were 0.5 μg/mL and 5 μg/mL, respectively. The relative recovery rate was 100.2 ± 1.8%. Based on the validation results, the HPLC determination method was found to be precise, accurate, and time conservative. This method was applied successfully to nine different root samples of G. uralensis. The amounts of glycyrrhisoflavone in these samples were 15-93 mg/100 g of dried powdered plant material.
Poly[3-(3,4-dihydroxyphenyl)glyceric Acid] from Anchusa italica Roots
Authors: Barbakadze Vakhtang , Gogilashvili Lali , Amiranashvili Lela , Merlani Maia , Mulkijanyan Karen , Churadze Manana , Salgado Antonio , Chankvetadze Bezhan
Published: March 2019

Elucidation of the main structural unit of a water-soluble, high-molecular weight preparation from the crude polysaccharides of Anchusa italica Retz. roots has been carried out. According to 13C NMR, 1H NMR and 2D heteronuclear 1H/13C HSQC spectral data, the main structural element of the high-molecular, water-soluble preparation was a regularly substituted polyoxyethylene chain, namely poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene]. Most carboxylic groups of this caffeic acid-derived polymer of A. italica are methylated.
Isothymol in Ajowan Essential Oil
Authors: Bekhechi Chahrazed , Boti Jean Brice , Bekkara Fewzia Atik , Abdelouahid Djamel Eddine , Casanova Joseph , Tomi Félix
Published: March 2019

Ajowan is a popular spice that is used in folk medicine in Algeria. Most studies reported that thymol is the main component of the seed oil. Isothymol was reported to be a constituent of essential oil isolated from aerial parts. Using plants harvested in five different locations in north western Algeria, every two weeks during the flowering stage, we demonstrated that isothymol was the major component when the plant was collected near the sea at low altitude and at the beginning of the flowering stage. In other cases, thymol is the predominant constituent.
Flavonoids of Enhydra Fluctuans Exhibit Anticancer Activity against Ehrlich's Ascites Carcinoma in Mice
Authors: Sannigrahi Santanu , Mazumder Upal Kanti , Mondal Arijit , Pal Dilipkumar , Mishra Silpi Lipsa , Roy Souvik
Published: March 2019

Flavonoids obtained from Enhydra fluctuans (FEF) were screened for anticancer activity against Ehrlich's ascites carcinoma (EAC) bearing Swiss albino mice. The anticancer activity was assessed by measuring the tumor growth response, percentage increase of life span, hematological parameters, lipid peroxidation, and antioxidant enzyme activity, like GSH and CAT. Two flavonoids, baicalein 7- O-glucoside and baicalein 7- O-diglucoside, were isolated from the ethyl acetate fraction. Treatment with FEF caused a significant decrease in the tumor cell volume and increase of life span. All the hematological parameters, malonaldehyde content and antioxidant enzyme activity were restored towards the normal level. FEF was found to be cytotoxic in the in-vitro model.
Pro-coagulant Activity of Phenolic Acids Isolated from Blumea Riparia
Authors: Huang Li , Lin Cuiwu , Li Aiyuan , Wei Baoyao , Teng Jianwen , Li Lue
Published: March 2019

The effects of extracts of the aerial part of Blumea riparia DC. and their phenolic acids on hemostasis were evaluated. The EtOAc fraction showed significantly reduced blood clotting time (CT) and tail bleeding time of transection (BT) of mice in vivo. This fraction contained vanillic acid (1), syringic acid (2), p-coumaric acid (3), caffeic acid (4), and protocatechuic acid (5). Compound 1 reduced prothrombin time (PT), and strengthened mice uterine contractions. Compound 3 reduced CT and the activated partial thromboplastin time (APTT). Compound 5 reduced CT and increased the frequency of mice uterine contraction in a dose-dependent manner. Compound 2 reduced APTT. Compound 4 remarkably strengthened uterine contraction. Taken together, these data suggest that compounds 1, 3, and 5 possess procoagulant activity which jointly synergize blood coagulation via different mechanisms.
Encapsulation and Regeneration of In Vitro Derived Zephyranthes Grandiflora: An Effective Way for Exchange of Germplasm
Authors: Gangopadhyay Moumita , Dewanjee Saikat , Chakraborty Dipjyoti , Bhattacharya Sabita
Published: March 2019

An attempt was made to develop a protocol for the preparation of synthetic seeds using in vitro regenerated, genetically identical bulbs of Zephyranthes grandiflora. Encapsulation was standardized with 4% sodium alginate and 1% sucrose for uniform bulb size with high conversion potential. An optimum storage temperature was found to be 4°C. Synthetic seeds were germinated in MS medium supplemented with benzyladenine (2 mg dm−3) and rooted in the presence of indole-3-butyric acid (1 mg dm−3) in MS medium. Well-rooted plants were transferred to the experimental field with 80% survival after hardening. This study elucidated an efficient technique for exchange of germplasm and ex situ conservation method.
Composition of Essential Oil from Seeds and Cones of Abies Alba
Authors: Wajs Anna , Urbańska Justyna , Zaleśkiewicz Ewa , Bonikowski Radosłtaw
Published: March 2019

The volatile composition of Abies alba Mill. seeds and cone scales has been studied, leading to the determination of 90 volatile constituents. The major component of the seed essential oil was (-)-limonene (about 70%), while that of the cone scale oil was α-pinene (57%). Monoterpene hydrocarbons were predominant in both oils, but the quantitative and qualitative composition of the volatile compounds was specific for each part of the tree.
Virucidal Activity and Chemical Composition of Essential Oils from Aromatic Plants of Central West Argentina
Authors: García Cybele C. , Acosta Eliana G. , Carro Ana C. , Belmonte María C. Fernández , Bomben Renata , Duschatzky Claudia B. , Perotti Marina , Schuff Carola , Damonte Elsa B.
Published: March 2019

The essential oils of seven aromatic plants from central west argentina were isolated by steam distillation and analyzed by a gas chromatography mass spectrometry technique. The oils were screened for cytotoxicity and In Vitro inhibitory activity against herpes simplex virus type 1 (HSV-1), dengue virus type 2 (DENV-2) and Junin virus (JUNV). The oils showed a variable virucidal action according to the virus. JUNV was the least susceptible virus in comparison with HSV-1 and DENV-2. The better relationship between cytotoxicity and inhibitory activity was observed for the essential oil of Lantana grisebachiii (Seckt.) var. grisebachii against DENV-2 and HSV-1 with IC50 (inhibitory concentration 50%) values of 21.1 and 26.1 ppm, respectively. This effect was specific since the selectivity indices (ratio cytotoxicity/virucidal activity) were > 23.7 and > 19.1 for DENV-2 and HSV-1, respectively. Furthermore, the oil from L. grisebachii was also an effective inhibitor of HSV-2 and acyclovir resistant variants of herpes virus. This study demonstrates the effective and selective inhibitory activity of the essential oil from Lantana grisebachii against HSV and DENV by direct virus inactivation.
Neolitsea Sericea Essential Oil Attenuates LPS-induced Inflammation in RAW 264.7 Macrophages by Suppressing NF-κB and MAPK Activation
Authors: Yoon Weon-Jong , Moon Ji-Young , Kang Ji-Yong , Kim Gi-Ok , Lee Nam Ho , Hyun Chang-Gu
Published: March 2019

The chemical composition and antiinflammatory activities of hydrodistilled essential oil from Neolitsea sericea leaves (NSE) have been investigated for the first time. The chemical constituents of NSE were analysed by GC-MS and found to include sericenine (32.3%), sabinene (21.0%), trans-β-ocimene (13.3%), β-caryophyllene (4.8%), and 4-terpineol (4.2%). The effects of NSE on nitric oxide (NO), prostaglandin E2 (PGE2), tumour necrosis factor (TNF)-α, interleukin (IL)-1β, and IL-6 production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages were also examined. Pro-inflammatory cytokine and mediator tests indicated that NSE has excellent dose-dependent inhibitory activities. To further examine the mechanism responsible for the inhibition of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) expression by NSE, we examined the effect of NSE on nuclear factor-κB (NF-κB) activation and the phosphorylation of mitogen-activated protein kinases (MAPK). NSE inhibited NF-κB activation by LPS, and this was associated with the abrogation of IκB-α phosphorylation and subsequent decreases in nuclear p50 and p65 protein levels. Further, the phosphorylation of p38, ERK and JNK was suppressed by NSE in a concentration-dependent manner. These results suggest that NSE exerts antiinflammatory effects in LPS-stimulated RAW 264.7 macrophages by inhibition of NF-κB activation and MAPK phosphorylation, and, therefore, may be useful for treatment of inflammatory diseases.
Microbial Transformation of (-)-Nopol Benzyl Ether: Direct Dihydroxylation of Benzene Ring
Authors: Noma Yoshiaki , Asakawa Yoshinori
Published: March 2019

The biotransformation of (-)-nopol benzyl ether (5) by Aspergillus Niger TBUYN-2 and A. niger Tiegh CBSYN was investigated. A. niger biotransformed 5 to afford (-)-4-oxonopol-2’,4’-dihydroxybenzyl ether (6), and (-)-4-oxonopol (7) as main products. Compound 6 showed strong antioxidant activity (IC50 30.2 μM), which was very similar to that of butyl hydroxyl anisol (BHA).
Volatile Components of Selected Liverworts, and Cytotoxic, Radical Scavenging and Antimicrobial Activities of Their Crude Extracts
Authors: Komala Ismiarni , Ito Takuya , Yagi Yasuyuki , Nagashima Fumihiro , Asakawa Yoshinori
Published: March 2019

Crude extracts of the Tahitian liverworts Mastigophora Diclados and Frullania sp., the Indonesian Frullania sp., Dumortiera hirsuta and Marchantia sp., and the Japanese Porella perrottetiana were investigated chemically by using gas chromatography-mass spectrometry (GC-MS). All extracts contained various volatile sesqui- and diterpenoids and a few aromatic compounds. The Tahitian M. diclados and Frullania sp., and the Indonesian Frullania sp. exhibited cytotoxic activity against HL-60 and KB cell lines. The extracts of the Tahitian M. diclados and the Indonesian Marchantia sp. showed radical scavenging activity, whereas the crude extracts of the Tahitian M. diclados and Frullania sp., and the Indonesian Frullania and Marchantia sp. showed antimicrobial activity against Staphylococcus aureus and Bacillus subtilis.
Antimicrobial Properties of Volatile Phenylpropanes
Authors: Pauli Alexander , Kubeczka Karl-Heinz
Published: March 2019

The examination of antimicrobial structure-activity relationships of 93 volatile phenylpropanes (VPs) and 21 related aromatic compounds revealed a dependence of antimicrobial activity from the kind and number of substituents on the aromatic ring, their substitution pattern and microbial characteristics, such as Gram coloring and strain specific factors. Eugenol isomers were predominantly inhibitory in a concentration range from 25 to 2000 mg/L against all microorganisms tested, which were three strains of Escherichia Coli and Klebsiella pneumoniae, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, Listeria monocytogenes, and Candida albicans. Etherified VPs were either less active or inactive depending on the type of side chain and/or substitution pattern. Differences in the antimicrobial activity of cis- and trans-isomers were observed. Species specific structure-activity relationships exist as was demonstrated with the Gram-negative bacteria (inactivity of E-ortho-eugenol) C. albicans (activity of di- and threefold methoxylated 1-propenylbenzenes), S. aureus and B. subtilis (activity of di-ortho methoxylated phenolic allylbenzenes and hydroquinone derivatives). With regard to the variety of observed specific effects and natural variation of susceptibility towards VPs according to literature reference data, the chances for successful prediction by computational analysis (QSAR) appear to be limited.
Potential Interaction between the Volatile and Non-volatile Fractions on the In Vitro Antimicrobial Activity of Three South African Pelargonium (Geraniaceae) Species
Authors: Lalli Jacqueline Y. , Viljoen Alvaro M. , Van Vuuren Sandy F.
Published: March 2019

Previous studies have reported promising antimicrobial efficacy for the essential oils and solvent extracts of several indigenous Pelargonium species. This study aimed to determine if any pharmacological interaction (e.g. synergism or antagonism) exists between the volatile and non-volatile components when the different fractions were investigated. The antimicrobial activity of the following fractions were tested; the essential oil prepared by hydrodistillation (EO), non-volatile fraction (NV), prepared by extraction of plant material remaining in the distilling apparatus (having no or negligible volatile constituents) and solvent extracts prepared from fresh (FC) and dried (DC) plant material containing both volatile and non-volatile constituents. Pelargonium quercifolium oil was dominated by p-cymene (42.1%) and viridiflorol (16.9%), while P. graveolens and P. tomentosum oil had high levels of isomenthone (84.0 and 58.8%, respectively). Menthone was noted as a major constituent in the P. tomentosum EO sample. It was evident from the results that the presence of volatile constituents in the three species; P. graveolens, P. quercifolium and P. tomentosum is generally not a prerequisite for antimicrobial activity. The most significant variations of antimicrobial activity were noted for P. tomentosum where poorer activity was noted for the FC and EO fractions against Bacillus cereus and Candida albicans. Studies on Staphylococcus aureus, however, showed the converse, where best activity was noted for the FC fraction (3.0 mg/mL). For P. quercifolium, the DC fraction indicated a notable increase in anti-staphylococcal activity (2.0 mg/mL) when compared with the FC (8.0 mg/mL) and EO (16.0 mg/mL) fractions. For P. tomentosum, the FC fraction indicated much lower antimicrobial activity (against both B. cereus and C. albicans) when compared with all other fractions, suggesting that the essential oils may impact negatively on the antimicrobial activity when tested against these two pathogens.
Developing and Characterizing a Mouse Model of Hepatotoxicity Using Oral Pyrrolizidine Alkaloid (Monocrotaline) Administration, with Potentiation of the Liver Injury by Co-administration of LPS
Authors: Abdel-Bakky Mohamed Sadek , Hammad Mohamed A. , Walker Larry A. , Ashfaq Mohammad K.
Published: March 2019

Oral administration of xenobiotics is preferable for research in In Vivo models because it mimics the real life situation of human subjects. Therefore, oral (po) monocrotaline (MCT) (a common contaminant of dietary supplements)/intraperitoneal (ip) lipopolysaccharides (LPS)-induced liver injury possibly imitates idiosyncratic hepatotoxicity in humans. Cytokines, for example interleukin-1β (IL-1β) and transforming growth factor beta (TGF-β) are known to play a role in the development of toxicity and repair processes, respectively. The purpose of this study was to develop and characterize a model of po MCT/ip LPS hepatotoxicity which may elucidate the mechanisms of injury. ND4 male mice were given MCT (200 mg/kg) followed 4 h later by LPS (6 mg/kg). Blood samples were drawn for plasma chemistry and IL-1β. Animals were euthanized and livers were harvested at different time points. We have shown that MCT/LPS cotreatment results in significant elevation of plasma alanine aminotransferase (ALT), CRP, IL-1β and TGF-β. Histopathological evaluation revealed diffuse degenerative injury. In summary, we have established a reproducible in vivo model of hepatotoxicity by po MCT/ip LPS cotreatment that may closely mimic real life idiosyncratic hepatotoxicity.
Terpene Bioconversion – How does its Future Look?
Authors: Krings Ulrich , Berger Ralf Guenter
Published: March 2019

The usage of essential oils as such or of volatile fractions thereof is widespread in the flavor and fragrance industry to aromatize perfumery and cosmetic products, foodstuffs, and many household and pharmaceutical products. The increased market share of convenience food together with consumers’ request for constant high quality and natural products have established a lasting increase in the demand for natural flavorings that cannot be satisfied by the traditional plant materials. This review summarizes selected work on terpene bioconversion / transformation and focuses on recently published papers dealing with novel strains and products, high product yields, intriguing genetic engineering approaches, and integrated bioprocesses. The future perspectives of an industrial realization of a biotechnological production of terpene-derived natural flavors are critically evaluated.
A New Sesquiterpene and other Constituents from Saussurea Lappa Root
Authors: Duan Jin-ao , Hou Pengfei , Tang Yuping , Liu Pei , Su Shulan , Liu Hanqing
Published: March 2019

Five sesquiterpenes, dehydrocostus lactone (1), santamarine (5), β-cyclocostunolide (6), 4α-hydroxy-4β-methyldihydrocostol (7) and 10α-hydroxyl-artemisinic acid (9), along with four other compounds, β-sitosterol (2), daucosterol (3), 5-hydroxy-methyl-furaldehyde (4), and trans-syingin (8), were isolated and identified from the roots of Saussurea lappa (Compositae). Based on previous reports and our study, sesquiterpene derivatives are common and characteristic constituents of the genus Saussurea. Among the nine compounds obtained, 9 is a new sesquiterpene. It is an artemisinic acid derivative, whose structural skeleton has not been reported for Saussurea species before, but artemisinic acid is a common compound in another Compositae species, Artemisia annua. Dehydrocostus lactone (1) is present in high-content and is a possible bioprecursor of 10α-hydroxyartemisinic acid (9).
An Unusual Bisnor-clerodane Diterpenoid from Polyalthia Simiarum
Authors: Kabir Selina , Rahman Mohammad S. , Chowdhury A. M. Sarwaruddin , Hasan Choudhury M. , Rashid Mohammad A.
Published: March 2019

The stem bark of Polyalthia simiarum has yielded a new bisnor-type clerodane diterpenoid, 2-oxo-14,15-bisnor-3,11 E-kolavadien-13-one (1), and three previously known clerodane derivatives, kolavenic acid (2), 16β-hydroxycleroda-3,13(14) Z-dien-15,16-olide (3), and 16-oxocleroda-3,13(14) E-dien-15-oic acid (4). The structures of these compounds were unambiguously determined by extensive NMR studies as well as by comparison with related compounds. Till now this is the second report of the occurrence of any unusual C-18 clerodane diterpenoid from nature. The crude light petroleum extract and the purified compound 3 demonstrated moderate free radical scavenging activity with IC50 values of 21.5 and 23.5 μg/mL, respectively.
Anti-inflammatory Mechanisms of Compounds from Curcuma Mangga Rhizomes using RAW264.7 Macrophage Cells
Authors: Kaewkroek Kanidta , Wattanapiromsakul Chatchai , Tewtrakul Supinya
Published: March 2019

Curcuma mangga extract and its compounds were investigated for their anti-inflammatory mechanisms against nitric oxide (NO) and prostaglandin E2 (PGE2) release using RAW 264.7 cells. From bioassay-guided fractionation, demethoxycurcumin (1) was isolated from the chloroform fraction, whereas 15,16 bisnorlabda-8(17), 11-dien-13-one (2) and ( E)-15,15-diethoxylabda-8(17),12-dien-16-al (3) were from the n-hexane fraction. Bisdemethoxycurcumin (4), the structure of which is similar to that of 1, was also tested. Of the tested compounds, 3 exhibited the highest activity against NO release with an IC50 value of 9.4 μM, followed by 1 (IC50 = 12.1 μM), 4 (IC50 = 16.9 μM) and 2 (IC50 = 30.3 μM). For the effect on PGE2 release, 1 possessed the highest activity (IC50 = 4.5 μM, followed by 4 (IC50 = 5.6 μM), 3 (IC50 = 35.3 μM) and 2 (IC50 = 42.5 μM). The mechanism at transcriptional level revealed that 1, 3 and 4 down-regulated the mRNA expressions of iNOS and COX-2 in a dose-dependent manner, whereas 2 had an effect only on iNOS mRNA. These results indicate that C. mangga and its compounds do exert anti-inflammatory activity. Moreover, this is the first report of the isolation of 3 from C. mangga rhizomes.
New Triterpene Glycosides from Camptosorus Sibiricus
Authors: Li Ning , Xiao Wan , Hou Bailing , Li Xian
Published: March 2019

Two new cycloartane glycosides were isolated from the whole herbs of Camptosorus sibiricus Rupr. By means of chemical and spectroscopic methods (1D and 2D NMR, HRMS, ESIMS), the structures were established as (24 R)-3β,7β,24,25,30-pentahydroxycycloartane-30- O-coumaroyl-3- O-β-D-glucopyranosyl-24- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (1) and (24 R)-3β,7β,24,25,30-pentahydroxy-1-ene-cycloartane 24- O-β-D-glucopyranoside (2). The two new compounds were inactive in vitro against A375-S2 and Hela human tumor cell lines using the MTT method.
Asporyergosterol, A New Steroid from an Algicolous Isolate of Aspergillus Oryzae
Authors: Qiao Ming-Feng , Ji Nai-Yun , Liu Xiang-Hong , Li Fang , Xue Qin-Zhao
Published: March 2019

Asporyergosterol (1), a new steroid with an E double bond between C-17 and C-20, was identified from the culture extracts of Aspergillus oryzae, an endophytic fungus isolated from the marine red alga Heterosiphonia japonica. Moreover, four known steroids including (22 E,24 R)-ergosta-4,6,8(14),22-tetraen-3-one (2), (22 E,24 R)-3β-hydroxyergosta-5,8,22-trien-7-one (3), (22 E,24 R)-ergosta-7,22-dien-3β,5α,6β-triol (4), and (22 E,24 R)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (5) were isolated. Structures of these compounds were unambiguously established by spectroscopic techniques and by comparison with literature values. All the isolates exhibited low activity to modulate acetylcholinesterase (AChE).
Synthesis and Bioactivity of β-Carboline Derivatives
Authors: Li Shengkun , Yang Bing , Zhang Qianliang , Zhang Jiwen , Wang Junru , Wu Wenjun
Published: March 2019

The β-carboline alkaloids possess a wide diversity of important biochemical effects and pharmacological properties. A series of β-carboline derivatives were synthesized from L-tryptophan through the Pictet-Spengler reaction and oxidation of K2Cr2O7 by a sequential one-pot synthesis method. In Vitro antibacterial, insecticidal, and cytotoxic activities of all synthesized compounds were investigated by the tablet diffusion, leaf disc, and MTT methods, respectively. Some of the compounds (1-1, 1-2, 1-3 and 1-12) exhibited obvious antibacterial effects and some (1-3) had significant cytotoxic activities against tumor cells 3LL, MCF-7, BGC-823 and QGY-7701, with IC50 values of 7.79, 5.75, 3.53 and 4.02 μg/mL, respectively. No insecticidal activity against third stage instar larvae of Mythimna separata Walker were observed under the tested concentration.
Antihepatotoxic and Antioxidant Activities of Methanol Extract and Isolated Compounds from Ficus Chlamydocarpa
Authors: Donfack Jean Hubert , Fotso Simo Christophe Colombe , Ngameni Bathelemy , Tchana Angèle N. , Kerr Philip G. , Finzi Paola Vita , Vidari Giovanni , Giardina Silvana , Buonocore Daniela , Ngadjui Bonaventure T. , Moundipa Paul F. , Marzatico Fulvio
Published: March 2019

Free radicals, in particular radical oxygen species (ROS), play an important role in the aetiology and pathogenesis of various diseases. Current research in many countries focuses on the use of local medicinal plants as a promising source of liver protective agents. This paper describes the hepatoprotective effects of the methanol extract and four isolated compounds from Ficus chlamydocarpa on CCl4-induced liver damage, as well as the possible antioxidant mechanisms involved in this protection. The DPPH test, along with the ß-Carotene-Linoleic Acid Model System and Ferric-Reducing Antioxidant Power assays, as well as the inhibition of microsomal lipid peroxidation were used to measure radical-scavenging and antioxidant activities. Pretreatment of rats with the methanol extract of F. chlamydocarpa before CCl4 administration, significantly prevented serum increase of hepatic enzyme markers, glutamate oxaloacetate transaminase (GOT) and glutamate pyruvate transaminase (GPT), in a dose-dependent manner. The hepatoprotection was also associated with a significant enhancement in hepatic reduced glutathione (GSH) and a marked decrease of liver malondialdehyde (MDA). Among the four compounds 1-4, isolated from the methanol extract, α-amyrin acetate (1) and luteolin (4) showed a significant hepatoprotective activity, as indicated by their ability to prevent liver cell death and lactate dehydrogenase (LDH) leakage during CCl4 intoxication.
Anthocyanin-Rich Black Currant Extract Suppresses the Growth of Human Hepatocellular Carcinoma Cells
Authors: Bishayee Anupam , Háznagy-Radnai Erzsébet , Mbimba Thomas , Sipos Péter , Morazzoni Paolo , Darvesh Altaf S. , Bhatia Deepak , Hohmann Judit
Published: March 2019

Dietary antioxidants, such as anthocyanins, are helpful in the prevention and control of various diseases by counteracting the imbalance of oxidative and antioxidative factors in the living systems. Black currant (Ribes Nigrum L., Grossulariaceae) is known to contain high amounts of anthocyanins (250 mg/100 g fresh fruit). Black currant fruits have been used in Asian and European traditional medicine for the treatment of a variety of diseases. Black currant extract has recently been found to be the second most effective amongst nine different berry extracts studied for their free radical scavenging activity. Constituents present in black currant juice have been found to exert a number of health-promoting effects, including immunomodulatory, antimicrobial and antiinflammatory actions, inhibition of low-density lipoprotein, and reduction of cardiovascular diseases. Although antioxidant and antiinflammatory effects of black currant juice could be of value in preventing and treating oxidative stress- and inflammation-driven cancers, no experimental evidence is available to now. The objective of the present study was to evaluate the potential antiproliferative effects of black currant fruit skin extract against HepG2 human liver cancer cells. The aqueous extract yielded an anthocyanin-rich fraction with cyanidin-3 -O-rutinoside as one of the major anthocyanins. This fraction exhibited a potent cytotoxic effect on HepG2 cells and this effect was more pronounced than that of delphinidin and cyanidin, two major aglycones of anthocyanins present in black currant. Our results indicate, for the first time, that black currant skin containing an anthocyanin-rich fraction inhibits the proliferation of liver cancer cells, possibly due to additive as well as synergistic effects. This product could be useful in the prevention and treatment of human hepatocellular carcinoma.
New Coumarin-Hemiterpene Ether Glucosides and a Structurally Related Phenylpropanoic Acid Derivative from Artemisia Armeniaca
Authors: Mojarrab Mahdi , Delazar Abbas , Hamburger Matthias , Potterat Olivier
Published: March 2019

Two new coumarin-hemiterpene ether glucosides, 4’- O-(β-D-glucopyranosyl) desoxylacarol (1), and 5- O-(β-D-glucopyranosyl) lacarol (2), were isolated from the methanolic extract of the aerial parts of Artemisia armeniaca Lam. Their structures were established by means of spectroscopic analysis including 1H- and 2D-NMR, HRESIMS, and acid hydrolysis. In addition, a structurally related phenylpropanoic acid derivative (3) was obtained in small amounts, and its structure tentatively assigned as 3-(4-hydroxy–3-methylbutoxy)-4-methoxy melilotic acid.
Nutritional Value of the Chilean Seaweeds Cryptonemia Obovata and Rhodymenia Corallina
Authors: Ortiz Jaime , Vivanco Juan , Jiménez Paula , Leiva Moisés , Ramírez Leslie , Bustamante Andrés
Published: March 2019

Some nutritional components of the edible seaweeds Cryptonemia obovata and Rhodymenia corallina were determined. The amino acid content ranged from 1.0 ± 0.3 to 4174.2 ± 14.2 mg 100g−1 dry wt in C. obovata and between 0.9 ± 0.3 and 2657.0 ± 13.5 mg 100g−1 dry wt in R. corallina. The most abundant fatty acid in C. obovata was palmitic acid, reaching a value of 36.5 ± 0.2%, while in Rhodymenia corallina the main fatty acid was oleic acid, reaching a value of 24.7 ± 0.07%. Both seaweeds showed an important content of EPA (C20:5ω3). In C. obovata,α-tocopherol was the principal tocol (138.5 ± 4.9 mg kg−1 lipid), while in R. corallina, it was γ-tocotrienol (850.3 ± 9.4 mg kg−1 lipid). Furthermore, β-carotene was the main carotenoid pigment found in C. obovata.
Chemical Composition and Antifungal Activity of Essential Oils of Thuja Sutchuenensis, a Critically Endangered Species Endemic to China
Authors: Lei Huaping , Wang Yonggang , Su Chang , Liang Fengyin , Su Weiwei , Hui Mamie , Shaw Pangchui , Luo Yulong
Published: March 2019

The essential oils from leaves, twigs and stems of large trees and shrub-like trees of Thuja sutchuenensis were extracted by hydrodistillation and supercritical fluid extraction, and analyzed by GC and GC–MS. The essential oil composition differed significantly among the three organs, as well as between large trees and shrub-like trees. Furthermore, consistent with the eastern Asia–North American disjunct distribution of the genus, many differences in the essential oil composition between T. sutchuenensis and other Thuja species were apparent. The essential oils exhibited a certain degree of antifungal activity against six strains of human pathogenic fungi.
4-Deacetylbaccatin III: A Proposed Biosynthetic Precursor of Paclitaxel from the Bark of Taxus Wallichiana
Authors: Nisar Muhammad , Qayum Mughal , Adhikari Achyut , Khan Inamullah , Kaleem Waqar Ahamad , Ali Zulfiqar , Choudhary M. Iqbal
Published: March 2019

4-Deacetylbaccatin III was isolated and characterized from the bark of Taxus wallichiana Zucc. It was previously identified as an intermediate during the synthesis of paclitaxel and was proposed as a precursor for the biosynthesis of paclitaxel. Existence of 4-deacetylbaccatin III in T. wallichiana is strong evidence for the previously proposed biosynthetic pathway of paclitaxel via 4-deacetylbaccatin III.
Identification of Glycyrrhiza Species by Direct Analysis in Real Time Mass Spectrometry
Authors: Fukuda Eriko , Baba Masaki , Iwasaki Noriaki , Uesawa Yoshihiro , Arifuku Kazunori , Kamo Osamu , Tsubono Koji , Okada Yoshihito
Published: March 2019

DART (Direct Analysis in Real Time)-MS is a novel mass spectrometric ion source, and allows the analysis of most compounds at ambient pressure and ground potential by producing [M+H]+ molecular ion species. Using this method, we examined the compounds characteristic of several kinds of licorices. For the analysis of Glycyrrhiza inflata Batalin, the peak at m/z 339 originates mainly from [M+H]+ of licochalcone A (LA), a species-specific compound. This peak was hardly detected in G. glabra Linné and G. uralensis Fischer. These results indicate that G. inflata can be differentiated from the other two species by detection of LA peaks using DART-MS analysis.
Isoflavones from the Mangrove Endophytic Fungus Fusarium sp. (ZZF41)
Authors: Huang Zhongjing , Yang Jianxiang , She Zhigang , Lin Yongcheng
Published: March 2019

A new isoflavone, 5- O-methyl-2′-methoxy-3′-methylalpinumisoflavone (1), together with four known compounds 6-methoxy-5,7,4′-trihydroxyisoflavone (2), 6-methoxy-7,4′-dihydroxyisoflavone (3), (+)-marmesin (4), and 4-methylbenzoic acid carboxymethyl ester (5), were isolated from the mangrove endophytic fungus, Fusarium sp. (ZZF41). Their structures were determined by analysis of spectroscopic data. Compound 1 inhibited HEp-2 and HepG2 cells with IC50 values of 4 and 11 μmol/mL, respectively.
Composition and Antimicrobial Activity of the Leaf and Twig Oils of Litsea Mushaensis and L. linii from Taiwan
Authors: Ho Chen-Lung , Wang Eugene I-Chen , Tseng Yen-Hsueh , Liao Pei-Chun , Lin Chien-Nan , Chou Ju-Ching , Su Yu-Chang
Published: March 2019

The hydrodistilled essential oils of the leaves and twigs of Litsea mushaensis and L. linii were analyzed. Sixty-nine and ninety compounds were identified in the leaf and twig oils, respectively, of L. mushaensis. The main components of the leaf oil were β-eudesmol (24.2%), τ-cadinol (10.2%), α-humulene (10.1%), α-pinene (9.7%), and trans-β-ocimene (6.5%), whereas the main components of the twig oil were trans-β-ocimene (19.5%), α-pinene (12.8%) and cis-β-ocimene (7.7%). With L. linii, 72 and 78 compounds were respectively identified in the leaf and twig oils. The main components of the leaf oil were β-selinene (15.7%), α-selinene (15.5%), β-caryophyllene (12.2%), α-humulene (7.2%), and δ-cadinene (5.6%), and of the twig oil trans-β-ocimene (20.8%), β-selinene (11.4%), α-cadinol (6.0%), δ-cadinene (5.8%), τ-cadinol (5.4%) and β-eudesmol (5.2%). L. mushaensis leaf oil was shown to have excellent antimicrobial and anti-wood-decay fungal activity, superior to the other oils.