bluuebunny/crossref_metadata_2025 huggingface dataset:
HPTLC Method for the Quantitative Determination of ar-Turmerone and Turmerone in Lipid Soluble Fraction from Curcuma longa
Authors: Jain Vikas , Prasad Vure , Singh Satwayan , Pal Raghwendra
Published: March 2019

A simple, sensitive and precise high-performance thin-layer chromatographic (HPTLC) method was developed and validated for the analysis of ar-turmerone and turmerone, the major constituents of the lipid soluble fraction of the herbal medicament (HM) obtained from the rhizomes of Curcuma longa (turmeric). The separation was carried out on HPTLC aluminum plates precoated with silica gel 60F-254, with n-hexane:ethyl acetate (9.8:0.2 v/v) as mobile phase. Densitometric analysis of ar-turmerone and turmerone was carried out in the absorbance mode at 254 nm. This system was found to give compact spots for ar-turmerone and turmerone (Rf values 0.5 ± 0.05; 0.6 ± 0.04, respectively). A good linear regression relationship between peak areas and the concentrations was obtained over the range of 100–600 ng/spot, with correlation coefficients of 0.997 and 0.998 for ar-turmerone and turmerone, respectively. The limit of detection and quantification was found to be 20 and 40 ng/spot for ar-turmerone and turmerone, respectively. The method was further validated for precision and recovery. The RSD values of the precision were in the range 0.49–1.33% and spike recoveries were 99.9 and 100.0% for ar-turmerone and turmerone, respectively. Analysis of different batches of HM using the above method gave ar-turmerone and turmerone contents in the range of 25–30% and 30–38%. The developed HPTLC method can be applied for identification and quantitative determination of ar-turmerone and turmerone in the lipid soluble fractions of turmeric.
Tom J. Mabry's Natural Products Chemistry Program: 1960–2007
Authors: Calabria Lalita M. , Mabry Tom J.
Published: March 2019

This paper presents an overview of Dr. Mabry's accomplishments in his career as a natural product chemist, first at the University of Zürich as a post-doctoral fellow, and from 1962, as a faculty member at the University of Texas at Austin in the Department of Botany until the late 1990s, when the Biological Sciences programs at UT-Austin were completely reorganized. From then until his retirement in 2006, he was a member of the Molecular Cell and Developmental Biology faculty.
Efficient Synthesis of the Insect Elicitor Volicitin and Biologically Active Analogs
Authors: Krishnamachari Venkat , Xie Xitao , Zhu Shifang , Wei Han-Xun , Paré Paul W
Published: March 2019

An improved and efficient copper (I) mediated coupling procedure was used to synthesize N-(17-hydroxylinolenoyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore pest beet army worm, and its biologically active analogs.
Sulfated Triterpene Glycosides from Zygophyllum Fabago
Authors: Ahmad Viqar Uddin , Khan Saleha Suleman , Ahmed Amir , Khan Afsar , Farooq Umar , Arshad Saima , Sener Bilge , Erdemogluc Nurgun
Published: March 2019

From the aerial parts of Zygophyllum fabago from Turkey, two new sodium salts of sulfated glycoside derivatives of ursolic acid, named as zygofaboside A (1) and zygofaboside B (2) have been isolated. Their structures were elucidated through spectral studies, including 2D-NMR spectroscopic experiments (HMQC, HMBC, COSY and NOESY).
Application of High-Performance Liquid Chromatography for Simultaneous Identification of Integristerone A, 20-Hydroxyecdysone, Ecdysone and 2-Deoxy-20-hydroxyecdysone
Authors: Rybin Viatcheslav , Boltenkov Eugene , Novozhilova Elena
Published: March 2019

Conditions for separation and identification of integristerone A (1), 20-hydroxyecdysone (2), ecdysone (3) and 2-deoxy-20-hydroxyecdysone (4) by reversed-phase HPLC with UV and mass-selective detection at atmospheric pressure chemical ionization have been developed. Correlation between quasi-molecular ions fragmentation and structure peculiarities of the studied ecdysteroids has been shown. Application of these conditions for the analysis of extract from the inflorescences of Serratula komarovii made it possible to reveal and to identify compounds 1, 2 and 4.
Sigmoidine L, A New Antibacterial Flavonoid from Erythrina Sigmoidea (Fabaceae)
Authors: Kouam Jacques , Etoa François-Xavier , Mabeku Laure BrigitteKouitcheu , Fomum Zacharias Tanee
Published: March 2019

Chemical analyses of the stem bark of Erythrina sigmoidea (Fabaceae) yielded a new flavonoid, designated sigmoidin L (1), the known erythrinasinate, E-p-coumaric acid docosylester, and 3′-prenylnaringinin, reported here for the first time for the stem bark of E.sigmoidea. The structure of 1 was established by chemical and spectroscopic means as 5,7, 3′,4′-tetrahydroxy-5′-[3″-methyl-4″-oxobut-(1″Z) enyl]flavanone. Sigmoidin L exhibited significant antibacterial potency in vitro against Staphylococus aureus and Proteus vulgaris.
Two New Apigenin Glycosides from Cephalotaxus Harringtonia Var. Harringtonia
Authors: Mendiratta(Nee Chugh) Anju , Dayal Rameshwar , Bartley John P.
Published: March 2019

Apigenin and its two new glycosides namely apigenin-5-O-β-D-glucopyranosyl-(2→1)-α-L-rhamnopyranoside and apigenin-5-O-β-D-(6″-acetylglucopyranosyl-(2→1)-α-L-rhamnopyranoside have been isolated and characterized from the needles of Cephalotaxus harringtonia var. harringtonia.
Tracking of β-Lactoglobulin Binding Compounds with Biofingerprinting Chromatogram Analysis of Natural Products
Authors: Riihimäki Laura , Vuorela Pia
Published: March 2019

The addition of milk to tea has been shown to prevent the vascular protective effects of the tea. Thus we had an interest in evaluating the possible binding of compounds in extracts of black tea, Camellia sinensis (L.) O. Kunze, and nettle, Urtica dioica L, to β-lactoglobulin (βLG), which is the main proteinaceous component of whey. Since our previously miniaturised 96-well plate method based on fluorescence quenching is suitable only for pure compounds, we have developed a method of ultrafiltration sampling combined with HPLC to study the βLG-binding property of the extracts. The method development was made with extract of Piper nigrum L. (black pepper), because its major component is piperine, which has been earlier shown to bind to βLG. The results showed that piperine from P. nigrum was highly and rutin from U. dioica slightly bound to βLG. No components from C. sinensis were bound to βLG. We showed for the first time, that the ultrafiltration/HPLC system can be used in βLG-binding studies with plant extracts. Furthermore, we demonstrated that βLG could bind compounds from extracts and in this way either enhance, or decrease, their health benefits, for example in food preparations.
Antioxidant and Hepatoprotective Effects of Polyphenols in Leaves of Artemisia Princeps Pamp
Authors: Toda Shizuo
Published: March 2019

The leaves of Artemisia princeps Pamp have been used for tea and food in Japan. The polyphenols of the leaves have inhibitory effects against lipid peroxidation and protein fragmentation by free radicals in vitro and an inhibitory effect on galactosamine -lipopolysaccharide induced hepatotoxicity in vivo. The levels of serum glutamic oxaloacetic transaminase and glutamic pyruvic transaminase, lipid peroxidation in serum and liver by hepatotoxity were depressed by polyphenols in A. princeps Pamp. The depression of gluthathione and superoxide dismutase in plasma and liver by hepatotoxity were elevated by polyphenols in A. princeps Pamp. These results demonstrated that polyphenols in A. princeps Pamp have antioxidant and hepatoprotective effects.
Chemical Composition and Antimicrobial Activities of Essential Oils of Four Lines of Origanum Vulgare Subsp. Hirtum (Link) Ietswaart Grown in Hungary
Authors: Veres Katalin , Varga Erzsébet , Schelz Zsuzsanna , Molnár József , Bernáth Jenő , Máthé Imre
Published: March 2019

The essential oils of four lines of Origanum vulgare L. subsp. hirtum (Link) Ietswaart cultivated in Hungary were analysed by GC and GC-MS methods. These oils were found to contain carvacrol, γ-terpinene and p-cymene as main constituents. The antimicrobial activities of the various oils and their authentic individual components were tested on Gram-positive and Gram-negative bacterial strains, two Saccharomyces cerevisiae strains and two Candida albicans strains. No difference in sensitivity was found between Escherichia coli, Staphylococcus epidermidis and the yeast strains tested, but there were marked differences in sensitivity between the proton pump-deficient mutant of E. coli and its wild type as regards the growth inhibition and MIC values.
An Overview of the Genus Nardostachys
Authors: Chatterjee Asima , Dutta Utpal , Bandyopadhyay Debasish , Nayak Anupam , Basak Bidyut , Banerji Avijit , Banerji Julie
Published: March 2019

Nardostachys jatamansi, a medicinally important herb of Nepalese origin, has been used for centuries in the Ayurvedic and Unani systems of medicine. In combination with Marsilea minuta it is being used as an antistress and anticonvulsant drug and also finds use in the treatment of epilepsy. Recently, it has been reported that N. jatamansi, which plays an important role in protecting from cerebral ischemia and liver damage, is also used for the treatment of osteoporosis and hypercalcemia. The other member of the genus Nardostachys, N. chinensis, possesses antifungal and antimalarial properties. It is also used in the treatment of skin dysfunction. A short summary of the chemical constituents of the two species along with their physical and biological properties is reported.
C-Glycosylflavonoids: Identification, Bioactivity and Synthesis
Authors: Rauter Amélia P. , Lopes Rui G. , Martins Alice
Published: March 2019

C-Glycosylflavonoids are a group of compounds widespread in nature which have gained much interest due to their biological properties. This review focuses on the research of the last ten years concerning detection and structural characterization of C-glycosylflavonoids, their bioactivities and synthesis.
Volatile Constituents of Calamintha origanifolia Boiss. Growing Wild in Lebanon
Authors: Formisano Carmen , Rigano Daniela , Napolitano Francesco , Senatore Felice , Arnold Nelly Apostolides , Piozzi Franco , Rosselli Sergio
Published: March 2019

The essential oil of aerial parts of Calamintha origanifolia Boiss. (Lamiaceae), growing wild in Lebanon, was obtained by hydrodistillation and was analysed by GC and GC-MS. 49 compounds, representing 92.2% of the oil, were identified. The major components, belonging to the class of oxygenated monoterpenes, were pulegone (22.5%), isomenthone (12.2%) and piperitenone (9.6%). The oil showed a slight antimicrobial activity against three bacterial strains.
Selective Cytotoxic Activities of Leaf Essential Oils from Monteverde, Costa Rica
Authors: Moriarity Debra M. , Bansal Anita , Cole Ramona A. , Takaku Sayaka , Haber William A. , Setzer William N.
Published: March 2019

The leaf essential oils of Eugenia cartagensis, Myrcia sp. nov. “fuzzy leaf”, Ocotea veraguensis, O. whitei, and Persea americana, have been obtained by hydrodistillation and the essential oil compositions determined by GC-MS. The essential oils have been screened for in-vitro cytotoxic activity against a panel of human tumor cell lines, and each of the species shows selective cytotoxic activity. E. cartagensis was active against HCT-15 and SW 620 human colorectal carcinoma cells, O. veraguensis and Myrcia “fuzzy leaf” were cytotoxic to MDA-MB-231 and MDA-MB-468 mammary adenocarcinoma cells, and O. whitei and Persea americana were toxic to M-14 melanoma cells.
Antibacterial Diterpenes from the Roots of Ceriops tagal
Authors: Chacha Musa , Mapitse Renameditswe , Afolayan Anthony J. , Majinda Runner R. T.
Published: March 2019

Investigation of the roots of Ceriops tagal led to the isolation of a new isopimarane, together with the known diterpenes isopimar-8(14)-en-15,16-diol and erythroxyl-4(17),15(16)-dien-3-one. The structure of the new compound was identified as isopimar-8(14)-en-16-hydroxy-15-one. These structures were determined from extensive spectroscopic data analysis. The isolates were screened for antibacterial activity using the agar dilution method against ten test bacterial strains ( Bacillus cereus, Escherichia coli, Klebsiella pneumoniae, Micrococcus kristinae, Pseudomonas aeruginosa, Salmonella pooni, Serratia marcescens, Staphylococcus aureus, S. epidermidis and Streptococcus pyrogens). Isopimar-8(14)-en-16-hydroxy-15-one exhibited activity, with MIC values of 0.5 mg/mL against Streptococcus pyrogens; 0.25 mg/mL against Salmonella pooni and 0.1 mg/mL against Bacillus cereus, Staphylococcus aureus and Micrococcus kristinae.
Synthesis of Pregnenolone and Methyl Lithocholate Oxalate Derivatives
Authors: Nahar Lutfun , Sarker Satyajit D. , Turner Alan B.
Published: March 2019

Five new steroidal oxalate derivatives, oxalic acid (pregn-5-en-20-one)-3β-yl ethyl ester (2), oxalic acid mono (pregn-5-en-20-one)-3β-yl ester (3), chloro-oxo-acetic acid (5β-cholan-24-oic acid methyl ester)-3α-yl ester (5), oxalic acid mono (5β-cholan-24-oic acid methyl ester)-3α-yl ester (6) and oxalic acid (5β-cholan-24-oic acid methyl ester)-3α-yl ethyl ester (7) were synthesized, respectively, from pregnenolone (1) and methyl lithocholate (4) using excess oxalyl chloride.
Phenolic Glycosides from Phlomis lanceolata (Lamiaceae)
Authors: Nazemiyeh Hossein , Delazar Abbas , Ghahramani Mohammed-Ali , Talebpour Amir-Hossein , Nahar Lutfun , Sarker Satyajit D.
Published: March 2019

Preparative reversed-phase HPLC analyses of the methanol extract of the aerial parts of Phlomis lanceolata afforded three phenolic glycosides including a flavonol glycoside, peterin (1), and two phenylethanoid glycosides, viridoside (2) and peteroside (3). Compounds 1 and 3 are novel natural products. The structures of all three compounds were elucidated by spectroscopic means.
Antioxidant and Membrane Stabilizing Properties of the Flowering Tops of Anthocephalus Cadamba
Authors: Alam M. Ashraful , Ghani Abdul , Subhan Nusrat , Rahman M. Mostafizur , Haque M. Shamsul , Majumder Muntasir M. , Majumder M. Ehsanul H. , Akter Raushan A. , Nahar Lutfun , Sarker Satyajit D.
Published: March 2019

The hydroethanolic extract of Anthocephalus cadamba displayed remarkable antioxidative potential in the 1,1-diphenyl-2-picrylhydrazyl (DPPH), the hydrogen peroxide, the nitric oxide scavenging, the reducing power, the total antioxidant capacity, the lipid peroxidation inhibition (thiobarbituric acid-reactive substances production), and the RBC membrane stabilization assays. While in the DPPH assay the IC50 value of the extract was 146.5 μg/mL, it was 24.8 μg/mL in the nitric oxide scavenging assay.
A Method of Selecting Plants with Anti-inflammatory Potential for Pharmacological Study
Authors: Lin G. David , Li Rachel W. , Myers Stephen P. , Leach David N.
Published: March 2019

In searching for anti-inflammatory agents from Australian medicinal plants, a method of selecting plants with anti-inflammatory potential for chemical and pharmacological study was developed and is described in this paper. The method was based on the cross-referencing of ethnopharmacological information documented in Australian bush medicine and Chinese herbal medicine. Our hypothesis was that plants that have been used in several geographically different cultures for the same or similar medicinal purposes would be highly probable to possess some common chemical and pharmacological properties, and therefore might warrant scientific investigation. The Chinese ethnopharmacological information was used as “standard” references to select Australian plants with anti-inflammatory potential. From 284 plants documented in Australian bush medicine and 882 plants in Chinese herbal medicine, 58 Australian plants and 41 Chinese plants were identified to have potential anti-inflammatory activity. The traditional use of the identified Australian and Chinese plants to treat inflammatory conditions, botanical names, modes of preparation and administration, and chemical constituents were compiled to form a Chinese and an Australian dataset using Microsoft Access. By cross-referencing the ethnobotany, ethnopharmacology and phytochemistry of the plants in the two datasets, fourteen Australian plants were selected for laboratory study. Testing of these plants with respect to inhibitory activity against cyclooxygenases (COX) and lipoxygenases (LOX) showed that the majority of the plants (>85%) exhibited anti-inflammatory activity. Bioassay-guided isolation and spectroscopic identification of active constituents in three species were conducted. Racemosic acid was characterised as a new compound with anti-inflammatory activity from Ficus racemosa, together with a known compound bergenin. Triterpene-fatty acid esters were identified in Tinospora smilacina. HPLC fractions from Clematis pickeringii inhibited COX and LOX and also triggered peroxisome proliferator activated receptors (PPARs). This method of cross-referencing ethnopharmacological information to select plants with anti-inflammatory potential appears to be productive, and may be more widely applicable for the selection of plants for other pharmacological and chemical studies.
Volatile Components from Selected Mexican, Ecuadorian, Greek, German and Japanese Liverworts
Authors: Ludwiczuk Agnieszka , Nagashima Fumihiro , Gradstein Rob S. , Asakawa Yoshinori
Published: March 2019

Twenty-one liverworts from Mexico, Ecuador, Greece, Germany and Japan were extracted with diethyl ether and the crude extracts analyzed by TLC and GC/MS. Several volatile sesqui- and diterpenoids, and also bibenzyls were identified. Many of these compounds are important chemical markers of liverworts genus or family. Sacculatane-type diterpene dialdehydes occur in the Pelliaceae family, while bibenzyls, especially with a prenyl group are characteristic of the Japanese Radula perrottetii. Eudesman-type sesquiterpene lactones and pinguisane-type sesquiterpenoids are significant markers of Frullania tamarisci and Trocholejeunea sandvicensis, respectively. The Greek Fossombronia angulosa contained exactly the same compounds previously found in brown algae. Such chemical similarity suggests that some families of liverworts and algae may have an evolutionary relationship.
Anti-babesial Quassinoids from the Fruits of Brucea Javanica
Authors: Elkhateeb Ahmed , Yamasaki Masahiro , Maede Yoshimitsu , Katakura Ken , Nabeta Kensuke , Matsuura Hideyuki
Published: March 2019

The medicinal plant Brucea javanica (L.) Merr. (Simaroubaceae), grown in China, was examined for anti-babesial properties. The anti-babesial activity of the fruit was found to be attributed to its quassinoid constituents. Ten active compounds were isolated and purified from a chloroform extract. The identities of these compounds were confirmed from NMR spectroscopic and mass spectral data as brusatol (1), bruceantin (2), bruceine A (3), bruceantinol (4), dehydrobruceine B (5), dehydrobrusatol (6), dehydrobruceine A (7), bruceine D (8), bruceoside A (9), and yadanzioside G (10). When tested in vitro against Babesia gibsoni, compounds 1–10 had IC50 values of 0.74, 13.4, 4.0, 12.0, 308.2, 10.5, 835.0, >1000, and >1000 ng/mL, respectively. Compounds 1–4, 6 and 7 had far higher activity than the commercial anti-babesial drug diminazene aceturate, which possesses an IC50 value of 70.5 ng/mL. Except for bruceine A (3), bruceantinol (4) and bruceine D (8), this is the first report of the anti-babesial activity of these isolated quassinoids.
Phytochemical and Microscopic Characterization of the Caribbean Aphrodisiac Bois Bandé: Two New Norneolignans
Authors: Werner Ingrid , Mucaji Pavel , Presser Armin , Kletter Christa , Glasl Sabine
Published: March 2019

Acidic extraction of the stem bark and roots of Chione venosa (SW.) URBAN var. venosa, purchased in Grenada under the vernacular name Bois Bandé, led to the isolation of two new substances of the oxynorneolignan-type. Moreover, TLC- and HPLC-systems were developed in order to determine these substances in crude extracts. Analytical data are indicated for the new compounds, as well as for those substances which were published recently. In the different Caribbean islands different plant sources are used to furnish the aphrodisiac Bois Bandé. On the basis of the presented analytical systems, 14 different samples of Bois Bandé (stem bark and/or root) that were either purchased from local traders or collected at different sites in the Grenadian forest were examined. In addition, an entire macroscopic and microscopic description of the drug is given which, in combination with the phytochemical data, provides a powerful tool to assess the quality of the drug material with regard to its botanical homogeneity.
Struthiolanone: A Flavanone-Resveratrol Adduct from Struthiola Argentea
Authors: Ayers Sloan , Zink Deborah L. , Brand Robert , Pretorius Seef , Stevenson Dennis , Singh Sheo B.
Published: March 2019

Struthiolanone (1), a flavanone-resveratrol adduct, was isolated from Struthiola argentea. Its structure was determined by high-resolution mass spectrometry and 1D- and 2D-NMR spectroscopic techniques. The absolute configuration was determined by comparison of the CD spectrum of biflavonoids. This compound appears to be the first example of a flavanoid-stilbene adduct.
Antialactone: A New γ-Lactone from Antiaris Africana, and its Absolute Configuration Determined from TDDFT CD Calculations
Authors: Bertin Vouffo , Hussain Hidayat , Kouam Simeon F. , Dongo Etienne , Pescitelli Gennaro , Salvadori Piero , Kurtán Tibor , Krohn Karsten
Published: March 2019

Four compounds were isolated from the stem bark of Antiaris africana. One of them, a γ-lactone named antialactone (1a), is reported for the first time as a natural product. The structures were determined by comprehensive analyses of their 1D and 2D NMR spectra and EI MS data. The absolute configuration of antialactone acetate (1b) was established by TDDFT CD calculations and comparison with measured CD spectra. The remaining three known compounds were identified, by comparing their spectroscopic data with those reported in the literature, as lichenxanthone, β-sitosterol, and betulinic acid.
Subereaphenol A, a new Cytotoxic and Antimicrobial Dibrominated Phenol from the Red Sea Sponge Suberea Mollis
Authors: Shaala Lamiaa A. , Khalifa Sherief I. , Mesbah Mostafa K. , Van Soest Rob W. M. , Youssef Diaa T. A.
Published: March 2019

An investigation of the sponge Suberea mollis collected at the Egyptian Red Sea coast afforded a new cytotoxic and antimicrobial dibrominated phenol, subereaphenol A (1), together with the previously reported compounds 2-(3′,5′-dibromo-2′-hydroxy-4′-methoxyphenyl)acetamide (2), dibromoverongiaquinol (3), bromochloroverongiaquinol (4), and 2-(3′,5′-dibromo-4′-ethoxy-1′-hydroxy-4′-methoxy-2′,5′-cyclohexadien-1-yl)acetamide (5). The structure of the compounds was determined by a combination of 1D and 2D NMR techniques and High-resolution mass spectral determinations. Complete and new NMR data for the known compounds has been reported. The cytotoxic and the antimicrobial activities of the compounds are reported.
Argan Oil, Functional Food, and the Sustainable Development of the Argan Forest
Authors: Charrouf Zoubida , Guillaume Dominique
Published: March 2019

For years, in southwestern Morocco, the decline of the argan forest has been accompanied by the concomitant desert encroachment. Preservation of this forest by increasing the economic value of argan tree was proposed twenty years ago, but successful large scale production of certified, high quality argan oil, an edible oil introduced as a functional food, has only been recently achieved. Argan oil is now marketed in most developed countries, despite its elevated price, and protection of the argan forest is now seriously being considered. The aim of this work is to present the recent progress made in argan oil production, the ways explored to commercialize the oil extraction by-products, and recent attempts to use other argan tree parts as part of a long term aim to preserve the argan forest.
Revised Structure by Computational Methods for a Coumarin Isolated from Zanthoxylum Rhoifolium (Rutaceae)
Authors: Rivera Augusto , Rios-Motta Jaime
Published: March 2019

On the basis of theoretical methods using DFT/B3LYP/6-31G* geometries and HF/6-311+G** GIAO NMR predictions, the 13C NMR spectroscopic data of a coumarin from Zanthoxylum rhoifolium was reassigned. The structure was revised to be 4-methoxy-3-(3-methylbut-2-enyl)-2 H-chromen-2-one (4) and not 3-methoxy-4-(3-methylbut-2-enyl)-2 H-chromen-2-one (2), as assumed previously.
Supercritical Extraction of Essential Oil from Ilex Paraguariensis Leaves
Authors: Cassel Eduardo , Vargas Rubem M. F. , Brun Gerti W.
Published: March 2019

Essential oil from mate tea leaves was extracted with supercritical carbon dioxide at 120 bars and temperatures ranging from 323.15K to 343.15K. The experiments were carried out using a high-pressure apparatus in a pilot scale unit. Mathematical modeling was realized using a mass transfer model proposed by Sovová, generating information about unknown parameters for supercritical extraction of essential oil from mate tea leaves, and it was possible to observe agreement between the mathematical model and the experimental data.
Cultivars of Lavandula Lanata Boiss., a Good Source of Lavandulol
Authors: Barrero Alejandro F. , Herrador M. Mar , Arteaga Pilar , Arteaga Jesús F. , Burillo Jesús
Published: March 2019

The chemical composition of the essential oil extracted from aerial parts and flowers of Lavandula lanata autochthonous of Sierra Nevada and of flowers of L. lanata cultivated in the region of Teruel have been carried out. The main components of the oils were the oxygenated monoterpenes camphor, lavandulol, octan-3-one and 1,8-cineol. The percentage of lavandulol in cultivars is superior to 35% and thus they constitute an excellent source of this product of interest in perfumery.
Synthesis of Sesquiterpenes via Silicon-Guided Rearrangement of Epoxydecalins
Authors: Blay Gonzalo , Collado Ana M. , García Begoña , Pedro José R.
Published: March 2019

A survey of the rearrangement of methyldecalins via C-5 carbocation intermediates, with special attention to the silicon-guided rearrangement of epoxydecalins is provided. A TMS group properly positioned on either C-1 or C-9 promotes the acidic rearrangement of 10-methyl-4,5-epoxydecalins and 10-methyl-5,6-epoxydecalins with exclusive migration toward C-5 of the methyl or methylene groups linked directly to C-10. The application of this biomimetic approach to the synthesis of a number of spirocyclic and eremophilane sesquiterpenes is reported.
Anti-inflammatory and Cytotoxic Cycloartanes from Guayule (Parthenium Argentatum)
Authors: Flores-Rosete Graciela , Martínez-Vázquez Mariano
Published: March 2019

The need for the discovery and development of new pharmaceuticals for the treatment of cancer demands that all approaches to drug discovery should be exploited. Among the possible approaches, the one from natural products has made many unique and vital contributions to drug discovery. This mini review focuses on researches made in our laboratory on cycloartanes isolated from Parthenium argentatum, as well as some of its derivatives, in order to obtain potential anti-inflammatory and anti-cancer agents.
Vibrational Circular Dichroism: A New Tool for the Solution-State Determination of the Structure and Absolute Configuration of Chiral Natural Product Molecules
Authors: Nafie Laurence A.
Published: March 2019

Vibrational circular dichroism (VCD) has been used in recent years to determine the absolute configuration of a number of natural product chiral molecules. In this brief review, these applications will be described and the methodology of VCD determination of absolute configuration (AC) will be explained. The principal advantages of VCD versus X-ray crystallography for absolute configuration determination are: 1) only solution-state samples are needed and therefore single crystals are not required, 2) high enantiomeric sample purity is not required, 3) high chemical purity is not required as long as impurities are not chiral and 4) solution-state conformations are obtained as an extra feature of the AC determination.
Inhibitory Activity of α,β-Unsaturated Lactones on Histamine Release from Rat Peritoneal Mast Cells
Authors: Penissi Alicia B. , Rudolph María I. , Vera Mariano E. , Mariani María L. , Ceñal Juan P. , Tonn Carlos E. , Giordano Oscar S. , Piezzi Ramón S.
Published: March 2019

The present study was designed to examine the effects of a sesquiterpene lactone isolated from Artemisia douglasiana Besser (dehydroleucodine, DhL), a xanthanolide sesquiterpene isolated from Xanthium cavanillesii Schouw (xanthatin, Xt) and a semisynthetic butenolide (3-benzyloxymethyl-5 H-furan-2-one, But) on mast cell histamine release induced by compound 48/80. Peritoneal mast cells from male adult Sprague-Dawley rats were purified in Percoll, preincubated in the presence of test lactones (DhL, Xt or But) and then challenged with the mast cell activator compound 48/80. Concentration-response studies of mast cell histamine release evoked by compound 48/80, evaluation of mast cell viability and morphology studies by light microscopy were carried out. Biochemical and morphological studies showed the effectiveness of the above lactones to inhibit secretory responses of rat peritoneal mast cells. The present study provides evidence in favor of the hypothesis that DhL, Xt and But inhibit compound 48/80-induced histamine release from rat peritoneal mast cells. Our findings may provide an insight into the design of novel pharmacological agents that may be used to regulate the mast cell response.
A Convenient Synthesis of the Central Core of Helioporins, seco-Pseudopterosins and Pseudopterosins via BCA-Annulation Sequence
Authors: Esteban Gema , Rincón Rocío , Csákÿ Aurelio G. , Plumet Joaquín
Published: March 2019

A convenient synthesis of the central core of helioporins, seco-pseudopterosins and pseudopterosins in racemic form is reported, using a Suzuki coupling (A-ring formation)-Friedel-Crafts acylation sequence, followed by synthetic elaboration of the resulting tetralone derivative. Key steps of the method are a totally diastereoselective cuprate conjugate addition and a final, spontaneous Friedel-Crafts acylation.
New Guanidine Alkaloids from the Leaves of Verbesina Peraffinis
Authors: Compagnone Reinaldo S. , Bermudez Jhorman , Ibáñez Glorymar , Díaz Beth , Garrido María R. , Israel Anita , Suárez Alírica I.
Published: March 2019

Two new guanidine alkaloids, 1 and 2, were isolated from the methanol extract of the leaf of Verbesina peraffinis, in addition to four known substances: galegine, the methylamide of caffeic acid, galactitol and the flavonoid 3- O-glucosyl-(1–2)-galactoside-5,7,4′ trimethoxy-kaempferol. Their structures were determined on the basis of spectroscopic methods. The antihypertensive activity of the methanolic extract was assayed in rats using a model of hypertension induced by footshock.
Seasonal Phytochemical Variation and Antifungal Evaluation of Different Parts of Epidendrum Mosenii
Authors: Rosa Patrícia Walter , Da Silva Machado Marina , Niero Rivaldo , Zacchino Susana , De Los Ángeles Gette Maria , Monache Franco Delle , Filho Valdir Cechinel
Published: March 2019

Epidendrum mosenii is a Brazilian medicinal plant, traditionally used to treat infections and pains. This study reports on the chemical composition and microbiological properties of different parts and in different seasons of this plant. Results demonstrate that 4,3′,5′-trihydroxy-3-methoxy-dihydrostilbene (1), 4,5-dihydroxy-3,3-dimethoxy-dihydrostilbene (2) and pholidotin (3) were mainly present in the roots in all seasons, and the yield of mass extract increased their recovery in other parts, such as the stem and leaves for compounds (2) and (3), in summer and winter, respectively. The antifungal results indicate that compounds (1) and (2) have interesting activity against Cryptococcus neoformans, Microsporum gypseum, Trychophyton rubrum and Trychophyton mentagrophytes with MIC values between 62.5 and 125 μg/mL. Taken together, these results strongly suggest that the antifungal properties of E. mosenii are related, at least in part, to the presence of dihydrostilbenes 1 and 2, and this is useful for quality control of phytopreparations based on this plant, justifying the popular use of this plant to treat infections.
Toxic Chemical Compounds of the Solanaceae
Authors: Pomilio Alicia B. , Falzoni Elvira M. , Vitale Arturo A.
Published: March 2019

The Solanaceae is comprised of some 2500 species of cosmopolitan plants, especially native to the American continent. They have great value as food, like the well-known potato, tomato and eggplants, and medicines, like species of Atropa, Withania and Physalis, but many plants of this family are toxic, and sometimes lethal to mammals, in particular to man. Some of them also produce hallucinations and perceptual changes. The toxic species of this family are characterized by the occurrence of a variety of chemical compounds, some of which are responsible for the toxicity and lethality observed after ingestion, while others are suspected to be toxic. In this review, the following toxic compounds belonging to different members of the Solanaceae family are described: Tropane alkaloids ( Atropa, Datura, Hyoscyamus, Mandragora); pyrrolidine and pyrrolic alkaloids ( Nierembergia, Physalis, Solanum); protoalkaloids ( Nierembergia); glycoalkaloids ( Lycopersicon, Solanum); nicotine ( Nicotiana); cardenolides ( Cestrum, Nierembergia); capsaicinoids ( Capsicum); kaurene-type tetracyclic diterpenes ( Cestrum); steroidal glycosides ( Cestrum, Solanum); 1,25-dihydroxyvitamin D3 and vitamin D3 ( Cestrum, Solanum, Nierembergia); and withasteroids, withanolides ( Withania), and physalins ( Physalis). Other bioactive chemical constituents of members of this family are sugar esters and lectins. Phenylpropanoids are not included in this paper.
Simultaneous Determination of Nine Bioactive Constituents of Caulis Lonicerae Japonicae by High-Performance Liquid Chromatography Coupled with Mass Spectrometry
Authors: Li Hui-Jun , Qian Zheng-Ming , Li Ping , Ren Mei-Ting , Chen Jun , Xin Gui-Zhong
Published: March 2019

A new high-performance liquid chromatography coupled with mass spectrometry (HPLC-MS) method has been developed for the simultaneous determination of nine major compounds, namely chlorogenic acid (1), caffeic acid (2), sweroside (3), loganin (4), secoxyloganin (5), 3,5-di- O-caffeoyl quinic acid (6), luteolin-7- O-glucoside (7), rutin (8) and 3,4-di- O-caffeoyl quinic acid (9), in Caulis Lonicerae Japonicae (CLJ), a commonly used traditional Chinese medicinal herb. The separation was achieved on a C-18 column (250 × 4.6 mm, 5.0 μm) with a column temperature of 30°C and a flow-rate of 0.8 mL/min. The mobile phase was composed of (A) aqueous formic acid (0.1%, v/v) and (B) methanol, using a gradient elution of 30% B for 0-13 min, 30–40% B for 13–17 min, and 40–49% B for 17–30 min. The limit of detection ( S/ N = 3) ranged from 0.8 to 5.1 ng/mL and the limit of quantification ( S/ N = 10) varied from 3.4 to 16.9 ng/mL. All calibration curves showed good linear regression ( r2 > 0.9976) within the test ranges. The intra- and inter-day precisions, as determined from sample solutions, were below 2.2 and 4.3%, respectively. The recoveries for nine compounds were within 91.3 and 104.2%. This proposed method has been successfully applied to evaluation of commercial samples of CLJ from different markets in China, which provides a new basis of assessment of the quality of the herbal drug.
Comparative Analysis of Microbial and Rat Metabolism of the Total Saponins from Panax notoginseng by HPLC-ESI-MS/MS
Authors: Chen Guang-tong , Yang Min , Tao Si-jia , Lu Zhi-qiang , Zhang Jin-qiang , Huang Hui-lian , Wu Li-jun , Guo De-an
Published: March 2019

The total saponins extracted from the roots of Panax notoginseng have been regarded as the principal components manifesting the pharmacological activities of the drug. In order to compare the similarities and differences of microbial and mammalian metabolism of PNS, liquid chromatography coupled with mass spectrometry and tandem mass spectrometry has been applied to investigate the constituents and metabolites of the microbial transformations by three fungi Absidia coerulea, Acremonium strictum, and Curvularia lunata, and metabolism in rats. A total of thirty-seven peaks were detected and thirty-one peaks were identified by comparing the retention times and MS spectra with those of reference compounds and literature data. Twenty-eight peaks were found both in microbial and rat metabolism samples of PNS. Their structures were identified by comparison of the retention times and MS spectra with those of reference compounds. A number of isomers were identified after the metabolism.
Analysis on the Stability of Total Phenolic Acids and Salvianolic Acid B from Salvia miltiorrhiza by HPLC and HPLC-MSn
Authors: Xu Man , Han Jian , Li Hui-feng , Fan Li , Liu Ai-hua , Guo De-an
Published: March 2019

The stability of salvianolic acid B and total phenolic acids from Salvia miltiorrhiza in water solutions at different temperatures, in buffered aqueous solutions at different pHs and in biological fluids, including simulated gastric and intestinal fluids, were investigated in vitro. The results showed that the degradation of salvianolic acid B was pH- and temperature-dependent. Furthermore, structures of the degradation products of salvianolic acid B and total phenolic acids were elucidated by liquid chromatography-electrospray ion trap mass spectrometry and analysis of the degraded solutions revealed seventeen degradation products. The possible degradation pathway of salvianolic acid B is proposed.
A New Type of Modified Brassinosteroids for Enzyme-linked Immunosorbent Assay
Authors: Khripach Vladimir , Zhabinskii Vladimir , Antonchick Alexey , Litvinovskaya Raissa , Drach Svetlana , Sviridov Oleg , Pryadko Andrey , Novik Tatyana , Matveentsev Vitaliy , Schneider Bernd
Published: March 2019

New modified brassinosteroids (BS) with a full set of specific functional groups and with an additional one at C-26 have been synthesized and used as haptens for enzyme-linked immunosorbent assay. The haptens were conjugated to bovine serum albumin (BSA) and the obtained immunoconjugates were applied for production of polyclonal antibodies. A conjugation of the haptens to horseradish peroxidase (HRP) gave the corresponding enzyme-labeled BS – another principal component for immuno-competitive analysis. The steroids were linked to proteins through spacers at the terminal side chain carbon atom (C-26) that made both the cyclic part and the side chain exposed for recognition by antibodies. It allowed maximization of their sensitivity and for the first time made possible immunochemical distinguishing of the most important group of natural BS, B-lactones, from B-ketones and 6-deoxo derivatives. The synthesis of haptens based on a sequence of transformations starting from stigmasterol included Claisen rearrangement of 22-allylic ethers as a key reaction in the side chain construction.
Isoquinoline Alkaloids and Homoisoflavonoids from Drimiopsis barteri Bak and D. burkei Bak
Authors: Ngamga Dieudonne , Bipa Josephine , Lebatha Pearl , Hiza Christabel , Mutanyatta Joan , Bezabih Merha-Tibeb , Tane Pierre , Abegaz Berhanu M.
Published: March 2019

The powdered bulbs and leaves of Drimiopsis barteri yielded two novel isoquinoline alkaloids: 5-hydroxy-7,2′,3′,4′-tetramethoxy{2H-1-}benzopyran [4,3-c]isoquinoline and 6-hydroxy-7,2′,3′,4′-tetramethoxy{2H-1-}benzopyran [4,3-c]isoquinoline, three new scillascillins: 5,7-dihydroxy-2′,3′,4′-trimethoxyspiro-{2H-1-benzopyran-7′-bicyclo [4.2.0]octa[1,3,5]-triene}-4-one, 5-hydroxy-7,2′,3′,4′-tetramethoxyspiro{2H-1-benzopyran-7′-bicyclo [4.2.0]octa[1,3,5]-triene}-4-one and 5,2′,4′-trihydroxy-7,3′-dimethoxyspiro{2H-1-benzopyran-7′-bicyclo [4.2.0]octa[1,3,5]-triene}-4-one, and a tetrahydroxyhomo-isoflavanone: 5,6,7-trihydroxy-3-(4-hydroxybenzyl)chroman-4-one. The bulbs of Drimiopsis burkei gave three new metabolites: the first scillascillin, mentioned above, and two xanthones: 1,6-dihydroxy-2,3-dimethoxy-8-methylxanthone and 1,4-dihydroxy-2,3,6-trimethoxy-8-methylxanthone. Seventeen known compounds were isolated from both plants. Structures were elucidated based on detailed 1-, and 2D-NMR spectroscopic and MS analyses.
Isolation of Pyranocoumarins from Angelica Gigas
Authors: Reddy V.L. Niranjan , Jadhav Atul N. , Avula Bharathi , Khan Ikhlas A.
Published: March 2019

A mixture of diastereomers of the coumarin glycoside 3′- O-β-D-glucopyranosyl-3′,4′-dihydroxanthyletin (1), along with six known pyranocoumarins, columbianoside (4), marmesin (5), 3′-hydroxy-3′,4′-dihydroxanthyletin (6), decursin (7), decursinol angelate (8), and isoimperatorin (9), were isolated from the roots of Angelica gigas Nakai. The racemic compound 1 was successfully separated by preparative HPLC to obtain a new isomer 3′( S)- O-β-D-glucopyranosyl-3′,4′-dihydroxanthyletin (2), and a known isomer 3′( R)- O-β-D-glucopyranosyl-3′,4′-dihydroxanthyletin (3). The absolute configuration of compounds 2 and 3 was determined by comparison of optical rotation and NMR data of their acid hydrolysis products.
Constituents of Zanthoxylum Flavum and their Antioxidant and Antimalarial Activities
Authors: Ross Samir A. , Krishnaven Kesanapallis , Radwan Mohamed M. , Takamatsu Satoshi , Burandt Charles L.
Published: March 2019

Biologically guided fractionation of the methanolic extract of the roots of Zanthoxylum flavum Vahi. has led to the isolation of 18 constituents: seven coumarins, seven alkaloids, one lignan, two sterols and one triterpene. The isolated compounds have been identified by comparison of their spectral data with those reported. Among the isolates, 14 compounds have been isolated for the first time from Z. flavum. The coumarin oxypeucedanin (6) displayed significant antioxidant activity with an IC50 value of 8.3 μg/mL in the cell-based DCFH-DA assay. The isolated compounds were also evaluated for their antimalarial and cytotoxic activities.
Two New Xanthone Glycosides from Ventilago Leiocarpa Benth
Authors: Wang Li-Li , Zuo Jian-Ping , Ma Lei , Wang Xia-Chang , Hu Li-Hong
Published: March 2019

Two new xanthone glycosides, 8-hydroxy-3-methyl-6-methoxyxanthone-1- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranose (1) and 8-hydroxy-3-methyl-6-methoxyxanthone-1- O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranose (2), together with two known anthraquinones, 1,8-dihydroxy-3-methylanthraquinone (3) and 1,3,8-trihydroxy-6-methylanthraquinone (4), were isolated from the bark of Ventilago leiocarpa Benth. The structures were determined by various NMR spectroscopic and MS analyses. Compounds 1–4 were tested for their inhibitory activities against T and B cell proliferation, and 2 exhibited moderate inhibitory activities against LPS-induced B cell proliferation and ConA-induced T cell proliferation, with IC50 values of 8.8 and 17.9 μM, respectively.
Membrane Activity-Guided Isolation of Antiproliferative and Antiplatelet Constituent from Evodiopanax Innovans
Authors: Tsuchiya Hironori , Tanaka Toshiyuki , Nagayama Motohiko , Oyama Masayoshi , Iinuma Munekazu
Published: March 2019

Bark of Evodiopanax innovans (Araliaceae) was subjected to membrane activity-guided extraction and chromatographic fractionation. The potency to interact with lipid membranes and change their fluidity was determined by measuring fluorescence polarization of liposomal and cell membranes. Plant preparations, including the MeOH extract and the specified fraction, reduced the fluidity of model biomembranes prepared with different phospholipids and cholesterol. Further purification led to the isolation of maltol 3- O-β-glucopyranoside, which inhibited tumor cell growth and platelet aggregation, together with rigidifying the cell membranes as well as the membrane-active antitumor compound (-)-epigallocatechin gallate and doxorubicin. The isolate at 100 μM and 1.0 mM showed growth inhibition of 13–49% against tumor cells cultured for 24 and 48 h. At 1.8–3.6 mM, it also produced 50% inhibition of platelet aggregation induced by collagen, adenosine 5′-diphosphate and thrombin. E. innovans is considered as a medicinal plant containing a potent bioactive constituent that exerts antiproliferative and antiplatelet effects through interaction with cell membranes to modify their fluidity.
O-Methylheptaphylline from Clausena suffruticosa
Authors: Begum Rokeya , Rahman Mohammad S. , Chowdhury A. M. Sarwaruddin , Rahman M. Mukhlesur , Rashid Mohammad A.
Published: March 2019

O-Methylheptaphylline (1), together with capnolactone (2), were isolated from Clausena suffruticosa. The structure of 1 was established unambiguously by a series of 1D and 2D-NMR analyses. The cytotoxic activity of 1 and 2 was determined against brine shrimp nauplii and the LC50 values recorded were 0.56 μg/mL and 7.94 μg/mL, respectively.
The Anti-tumor Effect of the Light Petroleum Extract from Pulsatilla Chinensis (Bunge) Regel
Authors: Zhang Min , Song Zhihang , Wang Dan , Cheng Lin , Jin Wenrong , Zhang Peng , Huo Yang , Ma Zhongjun
Published: March 2019

The crude ethanol extract of Pulsatilla chinensis (Bunge) Regel roots was extracted successively with light petroleum, dichloromethane and n-butanol. The light petroleum fraction (PEF) exhibited potent anti-proliferation activity on HL60 cells with an IC50 value of 14 μg/mL. As a result, ICR mice transplanted with tumor strain S180 were employed for testing the effectiveness of drug administration of PEF. The tumor inhibitory rate was 36.7% at a dose of 20 mg/kg/d, which was higher than the positive control, which produced 31.5% inhibition. However, an unusual phenomenon was observed in that the tumor inhibitory response was reverse dose-dependent since tumor inhibition was only 19.5% at a dose of 180 mg/kg/d. GC-MS revealed that the main components of the PEF were C-19 and C-22 polyunsaturated fatty acids. Previous studies had revealed that polyunsaturated fatty acids exhibit either anti-tumor or tumor promoting activities, and so it is proposed that the effects of PEF on tumor growth is dependent on dosage.
Iridoid Glucosides from Viburnum Macrocephalum
Authors: Tomassini Lamberto , Foddai Sebastiano , Ventrone Antonio , Nicoletti Marcello
Published: March 2019

The phytochemical study of the aerial parts of Viburnum macrocephalum Fortune, an ornamental species of Chinese origin, led to the isolation, together with the phenolic glucoside triandrin, of three iridoid glucosides: the novel 7-cinnamoylpatrinoside (1), and the known 7- p-coumaroylpatrinoside (2) and patrinoside (3).
Chemotaxonomy of Linaria Genus by Nor-Iridoids Distribution
Authors: Serafini Mauro , Piccin Antonella , Stanzione Alessandra , Petitto Valentina , Nicoletti Marcello
Published: March 2019

Recent phytochemical study of several Italian species of Linaria, including rare endemic species, allowed a chemotaxomic approach to the genus based on phylogenetic trends in Lamiiflorae.
A Guaiane Diol from Actinolema Eryngioides
Authors: Özen Hasan Çetin , Pollastro Federica , Appendino Giovanni
Published: March 2019

The seeds from the Umbelliferous Anatolian plant Actinolema eryngioides Fenzl afforded, as a major constituent, the guaiane diol 1, the unusual hydroxylation pattern of which (C-4 and C-7) was established by spectroscopic means.
Isolation and Cytotoxic Activity of Compounds from the Root Tuber of Curcuma Wenyujin
Authors: Wang Dan , Huang Wei , Shi Qiang , Hong Chengtao , Cheng Yiyu , Ma Zhongjun , Qu Haibin
Published: March 2019

Bioassay-directed separation of the light petroleum and methylene chloride extracts of the root tuber of Curcuma wenyujin Y. H. Chen et C. Ling against five cell lines led to the isolation of one hexane derivative, crotepoxide (1), four sesquiterpenes, 4- epi-curcumenol (2), curcumenol (3), curcumadiol (4), and gweicurculactone (5), and three curcuminoids, curcumin (6), demethoxy-curcumin (7), and bisdemethoxycurcumin (8). Compounds 1–5 have not been found previously in C. wenyujin; compounds 2 and 3 were obtained as an epimeric mixture. The structures of the compounds were established on the basis of NMR spectroscopic data. When tested for cytotoxity against cell lines HL-60, HepG2, K562, KB and MCF-7, compounds 5–8 showed better antitumor activity than the others.