bluuebunny/crossref_metadata_2025 huggingface dataset:
Zerumbone Induces G2/M Cell Cycle Arrest and Apoptosis via Mitochondrial Pathway in Jurkat cell Line
Authors: Rahman Heshu Sulaiman , Rasedee Abdullah , Chartrand Max Stanley , Othman Hemn Hassan , Yeap Swee Keong , Namvar Farideh
Published: March 2019

This investigation determined the anticancer properties of zerumbone (ZER) on the human T-cell (Jurkat) line using the MTT assay, microscopic evaluations, flow cytometric analyses, and caspase activity estimations. The results showed that ZER is selectively cytotoxic to Jurkat cells in a dose and time-dependent manner with IC50 of 11.9 ± 0.2, 8.6 ± 0.5 and 5.4 ± 0.4 μg/mL at 24, 48 and 72 hours of treatment, respectively. ZER did not produce an adverse effect on normal human peripheral blood mononuclear cells (PBMC). ZER is not as cytotoxic as doxorubicin, which imposed an inhibitory effect on Jurkat cells with IC50 of 2.1 ± 0.2, 1.8 ± 0.15, 1.5 ± 0.07 μg/mL after 24, 48 and 72 hours treatment, respectively. ZER significantly (P<0.05 ) arrested Jurkat cells at the G2/M phase of the cell cycle. The antiproliferative effect of ZER on Jurkat cells was through the apoptotic intrinsic pathway via the activation of caspase-3 and -9. The results showed that ZER can be further developed into a safe chemotherapeutic compound for the treatment of cancers, especially leukemia.
An HPLC Evaluation of Cytochalasin D Biosynthesis by Xylaria arbuscula Cultivated in Different Media
Authors: Amaral Luciana da S. , Rodrigues-Filho Edson , Santos Carolina A. A. , de Abreu Lucas M. , Pfenning Ludwig H.
Published: March 2019

A quantitative profile of cytochalasin D production by Xylaria arbuscula was followed by growing the fungus in rice, Czapek, Czapek enriched with yeast extract, wheat, and corn. This cytochalasin producer, X. arbuscula, was collected as an endophytic fungus from healthy tissues of Cupressus lusitanica (Cupressaceae). A new HPLC method was developed using a synthetic N-acetyl-L-phenylalanine ethyl ester as internal standard, which showed a good correlation coefficient (r2 = 0.9995). The results varied from 6.40 to 39.55 mg per 100 g of culture medium, with wheat being the best medium for cytochalasin D production. The level of any free amino acids in the medium, not necessarily phenylalanine, appeared to be an important factor to enhance cytochalasin D biosynthesis.
Antibacterial Activities of Oxyprenylated Chalcones and Napthtoquinone against Helicobacter pylori
Authors: Bodet Charles , Burucoa Christophe , Rouillon Steeve , Bellin Nicolas , Taddeo Vito Alessandro , Fiorito Serena , Genovese Salvatore , Epifano Francesco
Published: March 2019

In this study, we synthesized and characterized the antibacterial activity of three naturally occurring oxyprenylated chalcones {xinjiachalcone A (1), (2 E)-1-{2,6-dihydroxy-4-[(3-methylbut-2-enyl)oxy]phenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one (2), (2 E)-1-{2,6-dihydroxy-4-[(3-methylbut-2-enyl)oxy]phenyl}-3-phenylprop-2-en-1-one (3), and lawsone 2-isopentenyl ether (4)}. Using several strains of Helicobacter pylori, including clinical ones, minimum inhibitory concentration (MIC) values and bactericidal activities of these compounds were determined. Xinjiachalcone A (1), active principle of Glycyrrhiza inflata Batalin, was the most effective compound, showing both a low MIC and a strong bactericidal activity against H. pylori. This study suggests that these compounds represent potential natural molecules for the prevention and treatment of H. pylori associated diseases.
Isolation of β-Indomycinone Guided by Cytotoxicity Tests from Streptomyces sp. IFM11607 and Revision of its Double Bond Geometry
Authors: Tsukahara Kentaro , Toume Kazufumi , Ito Hanako , Ishikawa Naoki , Ishibashi Masami
Published: March 2019

The antibiotic β-indomycinone was isolated from Streptomyces sp. IFM11607 by cytotoxicity-guided fractionation against human gastric adenocarcinoma AGS cells, and the geometry of its Δ17,18-double bond was revised from E to Z based on the coupling constant.
Daurichromenic Acid-producing Oxidocyclase in the Young Leaves of Rhododendron dauricum
Authors: Taura Futoshi , Iijima Miu , Lee Jung-Bum , Hashimoto Toshihiro , Asakawa Yoshinori , Kurosaki Fumiya
Published: March 2019

Rhododendron dauricum L., a flowering tree popular in Hokkaido, produces daurichromenic acid (DCA), a terpenophenol with a potent anti-HIV activity. The DCA-producing enzyme, named DCA synthase, could be detected in the soluble protein fraction prepared from the young leaves of R. dauricum. DCA synthase catalyzed oxidocyclization of the farnesyl group of grifolic acid to form (+)-DCA as the major reaction product. The DCA synthase reaction proceeds without the need for any cofactors and coenzymes except for molecular oxygen. Interestingly, these catalytic properties of DCA synthase are quite similar to those reported for cannabinoid synthases in the marijuana plant Cannabis sativa L.
Chemical Composition of the Leaf Oil of Actephila excelsa from Vietnam
Authors: Dai Do N. , Thang Tran D. , Thin Dau B. , Ogunwande Isiaka A.
Published: March 2019

Fresh leaves of Actephila excelsa (Dazl.) Muell. from Vietnam were steam distilled to produce an oil in a yield of 0.15% (v/w). The essential oil was analyzed by a combination of capillary gas chromatography-flame ionization detection (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). The main constituents of the oil were the sesquiterpenes γ-elemene (25.7%) and β-caryophyllene (11.2%). Other significant compounds were methyl salicylate (5.8%), benzyl benzoate (5.2%), ( E, E)-farnesylacetone (4.9%), anisole (4.7%), sabinene (4.1%) and menthone (4.0%). This is the first report on the volatile constituents of this plant.
Chemical Composition of the Essential Oil of the Local Endemics Centaurea davidovii and C. parilica (Asteraceae, sect. Lepteranthus) from Bulgaria
Authors: Maggio Antonella , Riccobono Luana , Bancheva Svetlana , Bruno Maurizio , Senatore Felice
Published: March 2019

In the present study the chemical compositions of the essential oils from aerial parts of Centaurea davidovii Urum. and C. parilica Stoj. & Stef., both endemic to Bulgaria, were evaluated by GC and GC-MS. The main components of C. davidovii were β-eudesmol (13.9%), spathulenol (13.3%), caryophyllene oxide (10.1%) and ( Z)-phytol (5.4%). The main components of C parilica were hexadecanoic acid (39.2%), ( Z, Z)-9,12-octadecadienoic acid (11.9%), caryophyllene oxide (6.8%) and spathulenol (6.6%). In order to compare the essential oils composition of these taxa and of related species a PCA analysis was carried out.
Chemical Composition and Antifungal Activity of the Essential Oils of Schinus weinmannifolius Collected in the Spring and Winter
Authors: Hernandes Camila , Taleb-Contini Silvia H. , Bartolomeu Ana Carolina D. , Bertoni Bianca W. , França Suzelei C. , Pereira Ana Maria S.
Published: March 2019

Reports on the chemical and pharmacological profile of the essential oil of Schinus weinmannifolius do not exist, although other Schinus species have been widely investigated for their biological activities. This work aimed to evaluate the chemical composition and antimicrobial activity of the essential oil of S. weinmannifolius collected in the spring and winter. The essential oils were extracted by hydrodistillation, analyzed by GC/MS and submitted to microdilution tests, to determine the minimum inhibitory concentration. The oils displayed different chemical composition and antimicrobial action. Bicyclogermacrene and limonene predominated in the oils extracted in the winter and spring, respectively, whereas only the latter oil exhibited antifungal activity.
Antiproliferative and Antimalarial Sesquiterpene Lactones from Piptocoma antillana from Puerto Rico [1]
Authors: Liu Yixi , Rakotondraibe L. Harinantenaina , Brodie Peggy J. , Wiley Jessica D. , Cassera Maria B. , Goetz Michael , Kingston David G. I.
Published: March 2019

Bioassay-directed fractionation of an antiproliferative ethanol extract of the leaves and twigs of Piptocoma antillana (Asteraceae) afforded two new goyazensolide-type sesquiterpene lactones named 5- O-methyl-5-epiisogoyazensolide (1) and 15- O-methylgoyazensolide (2), together with the known compounds 1-oxo-3,10-epoxy-8-(2-methylacryloxy)-15-acetoxygermacra-2,4,11(13)-trien-6(12)-olide (3) and 5-epiisogoyazensolide (4). The structure elucidation of all compounds was carried out based on NMR and mass spectroscopic data analyses. The relative and absolute configurations of all the isolated compounds were determined from their CD and NOESY NMR spectra. Compounds 1–4 showed moderately potent antiproliferative activities against A2780 ovarian cancer cells, with IC50 values of 1.5 ±0.5, 0.6 ± 0.3, 1.62 ± 0.05, and 1.56 ± 0.04 μM, respectively. They also displayed antimalarial activity against Plasmodium falciparum, with IC50 values of 6.2 ± 0.5, 2.2 ± 0.5, 8.0 ± 0.4, and 9.0 ± 0.6 μM, respectively.
History of Gymnemic acid, a Molecule that does not Exist
Authors: Zarrelli Armando , Romanucci Valeria , Gravante Raffaele , Di Marino Cinzia , Di Fabio Giovanni
Published: March 2019

In the literature there are hundreds of articles, the first dating back to 1866 and the last to 2014, on gymnemic acid, isolated from Gy mnema sylvestre, from its isolation to the determination of its biological activities. Gymnemic acid has a CAS number but its structure is not specified. Studies during the second half of the 1970s clearly demonstrated that what was being referred to as gymnemic acid is actually a very complex mixture of dozens of substances, belonging to different classes of natural compounds. This plant, whose infusions or complex mixtures of its metabolites are the basis for many formulas sold in pharmacies and by herbalists, has anti-diabetic and slimming effects. It is certainly misleading to talk about gymnemic acid as a specific molecule. There may be doubts about the exact composition of the products, and consequently about their origin and the claimed effects.
Two New Alkaloids from Melodinus suaveolens
Authors: Lu Fan , Liu Pan , Yin Shan-Shan , Zhang Jun , Wang Jing
Published: March 2019

Two new Melodinus-type alkaloids, 15 β-hydroxy-14,15-dihydroscandine (1) and 14,15-dihydroscandine (2), together with 6 known ones were isolated from Melodinus suaveolens. The structures of the new compounds were identified from spectroscopic (NMR, UV, IR, CD) and mass spectrometric data and Mosher's method. The new compounds exhibited significant, dose-dependent inhibition of the production of lipopolysaccharide (LPS)-induced NO, IL-6 and IL-8 in mice macrophages.
Streptomycin Hydrazone Derivatives: Synthesis and Molecular Recognition in Aqueous Solution
Authors: Fuentes-Martínez Juan P. , Gutiérrez-Rodríguez Diana , García Edgar Rogel , Rivera-Márquez Karla I. , Medrano Felipe , Torres-Ángeles Oscar , Castillo-Vargas Evelin , Montaño Blanca E. Duque , Godoy-Alcántar Carolina
Published: March 2019

Five hydrazone derivatives of streptomycin were synthetized (D0h, D1ph, D2bt, D3dctf, D4ag) and characterized by IR, 1H and 13C NMR spectroscopy, mass spectrometry and elemental analysis. Protonation constants were determined by potentiometry for all derivatives. D1ph and D2bt derivatives were investigated as receptors of dicarboxylates and adenine nucleotides in aqueous solution by potentiometric and 1H NMR titrations. D1ph and D2bt derivatives have the highest affinity with AMP and ATP, respectively, which shows that electrostatic forces are not always the dominant factor in binding of streptomycin derivatives with nucleotides, but the conformational fit between them. Calculated structures at the DFT level of the D1ph derivative bonded with either AMP or ADP showed that the complexes are stabilized by the formation of multiple interactions with the receptors. The antibiotic activity of the derivatives was explored and compared with native streptomycin.
Chemical Constituents from Pterocarpus soyauxii
Authors: Su Zushang , Wang Ping , Yuan Wei , Li Shiyou
Published: March 2019

Three new benzofurans (1–3) and one new isoflavan (4), pteroyanin G, H, I and J, together with 21 known compounds, were isolated from the heartwood of Pterocarpus soyauxii. Their structures were determined by the NMR and MS spectral data in comparison with literature data. Compounds (1–25) did not show cytotoxicity against three human cancer cell lines, A549, Panc-28, and HCT-116 ( GI 50 > 50 μM).
Two New Pyrone Derivatives from the Plant Endophytic Fungus Exserohilum sp
Authors: Li Ruxin , Niu Shubin , Guo Liangdong , Zhang Yang
Published: March 2019

Two new α-pyrones, Exserolide G–H (1–2), together with one known metabolite, stemphypyrone (3), were isolated from the solid-substrate fermentation cultures of the plant endophytic fungus Exserohilum sp. The structures of the new compounds were elucidated primarily by analysis of NMR data. Compounds 1–3 were tested for cytotoxicity against a small panel of human carcinoma cell lines. Compound 1 showed cytotoxicity against HeLa, A549 and HCT116 cells.
Protective Effect of Agave salmiana Fructans in Azoxymethane-Induced Colon Cancer in Wistar Rats
Authors: Dávila-Céspedes Antonio , Juárez-Flores Bertha I. , Pinos-Rodríguez Juan M. , Aguirre-Rivera Juan R. , Oros-Ovalle A. Cuahutemoc , Loyola-Martínez E.D. , Andrade-Zaldívar Hera
Published: March 2019

Colon cancer is a world concerning disease; it shows a high mortality rate and may be related to eating habits. Studies using inulin-like fructans, which are produced as energy supplies by several plants, have demonstrated a chemo-protective effect of these fructans in colon cancer. However, agavins a structurally different type of fructans from the Agave genus with demonstrated prebiotic effects, have been poorly studied for their possible protective effects in cancer. The aim of the present study was to evaluate the effect of Agave fructan-rich diets in colon cancer progress using a rat model and “Agave mezcalero potosino” A. salmiana Otto ex Salm Dick, which is widely distributed in Mexico. Results showed a significant decrease (p<0.05) in early lesions of colon cancer (aberrant crypt foci) compared with the control group. These data suggest that fructans from A. salmiana may contribute to a reduction in the risk of colon cancer as well as inulin-like compounds.
Repellent Constituents of Essential Oil from Citrus wilsonii Stem Barks against Tribolium castaneum
Authors: Wu Yan , Chen Hai-Ping , Wei Jian-Yu , Yang Kai , Tian Zhao-Fu , Li Xiao-Lan , Wang Ping-Juan , Wang Cheng-Fang , Du Shu-Shan , Cai Qian
Published: March 2019

The essential oil obtained from Citrus wilsonii Tanaka stem barks with hydrodistillation was investigated by GC-FID and GC-MS. The main components of the essential oil were identified to be nerol acetate (44.5%), nerol (13.6%), citronellyl propionate (13.5%) and α-terpineol (3.6%). Among them, the four active constituents, predicted with a bioactivity-test, were isolated and identified as nerolacetate, nerol, citronellyl propionate and α-terpineol. It was found that the essential oil of C. wilsonii stem barks possessed strong repellency (86% and 92%, respectively, at 78.6 nL/cm2, after 2 and 4 h treatment) against Tribolium castaneum adults. Repellency of the four active compounds was also determined. Nerolacetate, nerol, citronellyl propionate and α-terpineol were strongly repellent (100%, 100%, 90% and 96%, respectively, at 15.7 nL/cm2, after 2h treatment) against T. castaneum. Nerol exhibited the same level of repellency as the positive control, DEET. The results indicate that the essential oil of C. wilsonii stem barks and its active compounds have the potential to be developed as natural repellents for control of T. castaneum.
Further Degraded Diterpenoids from the Stems of Trigonostemon lii
Authors: Tan Cheng-Jian , Di Ying-Tong , Hao Xiao-Jiang
Published: March 2019

Two degraded diterpenoids, thrigonosomones D and E, were isolated from the stems of Trigonostemon lii. Their structures were established by spectroscopic methods, including extensive 1D- and 2D-NMR experiments.
Antitumor Screening of Pterodon pubescens Terpenic Fraction Indicates High Sensitivity for Lymphocytic Leukemia Cells
Authors: Martino Thiago , Pereira Monica F. , Gayer Carlos R.M. , Dalmau Sergio R. , Coelho Marsen G.P. , Sabino Kátia C.C.
Published: March 2019

Cancer is the second leading cause of human mortality worldwide. Therefore, the search for new drugs or alternative therapy strategies has been required. Anticancer agents have been developed from plants since the 1950s and natural products still represent an important source of new and promising bioactive molecules. This work describes the cytotoxic effects of SF5 on tumor cells of high prevalence in the world and investigated some mechanisms of its antitumor action. The antitumor screening was performed with human lung carcinoma (A549), human breast (MCF-7) and prostate (PC-3) adenocarcinoma and chronic myeloid and acute lymphocytic leukemia cell lines. The acute lymphocytic leukemia Jurkat cells presented high sensitivity to the cytotoxic effects of SF5 (inhibition of 85–90%), compared with either the chronic myeloid leukemia K562 or solid tumor cell lines (lung, breast and prostate). SF5 arrested the cell cycle in G1 phase, which may be related with the observed downregulation of mRNA expression of c-Myc transcription factor at 24 h and 36 h. SF5 treatment induced cytochrome c release from mitochondria to cytosol, leading the Jurkat cells into apoptosis, which was evidenced by the internucleosomal fragmented DNA and increased number of annexin V-FITC positive cells. The SF5 showed high cytotoxicity for lymphocytic leukemia cells and low or none for solid tumor cells, without toxicity for peripheral mononuclear cells of healthy humans. SF5 altered gene expression, arrested the cell cycle and induced apoptosis via the mitochondrial pathway, similar to traditional antineoplastic chemotherapeutic drugs.
Direct Identification and Characterization of Phenolic Compounds from Crude Extracts of Buds and Internodes of Grapevine (Vitis vinifera cv Merlot)
Authors: Qsaib Said , Mateus Nuno , Ikbal Fatima Ez-zohra , Rifai Lala Aicha , de Freitas Victor , Koussa Tayeb
Published: March 2019

The crude methanol extracts of latent buds and internodes Vitis vinifera L. cv. Merlot were used for the determination of phenolic compounds by a combination of reverse phase HPLC with diode array detection (HPLC-DAD) and mass spectrometry (LC-MS). This method allowed the identification of 9 phenolic compounds without purification or fractionation. These 9 compounds were divided into three groups: procyanidins, flavonols and stilbenes. Detection by HPLC-DAD at different wave lengths of 280 nm to 320 nm, allowed the estimation of concentrations of those compounds. This method permitted, for the first time, both characterization and quantification of polyphenolic compounds in buds of grapevine. Comparison with the results obtained in internodes showed that quercetin, resveratrol tetramer and ε-viniferin had similar levels in buds and internodes while six other compounds identified had higher levels in buds.
Anti-inflammatory and Anti-oxidative Activities of Polyacetylene from Dendropanax dentiger
Authors: Chien Shih-Chang , Tseng Yen-Hsueh , Hsu Wei-Ning , Chu Fang-Hua , Chang Shang-Tzen , Kuo Yueh-Hsiung , Wang Sheng-Yang
Published: March 2019

Dendropanax dentiger has been used as a folk medicine since ancient times. In our current study, we observed that D. dentiger exhibited a significant anti-inflammatory activity, which could efficiently inhibit nitric oxide (NO) production in the lipopolysaccharide (LPS)-induced macrophage inflammation assay. (9 Z,16 S)-16-Hydroxy-9,17-octadecadiene-12,14-diynoic acid (HODA) was isolated from the leaves of D. dentiger following a bioactivity guided fractionation protocol. Our data indicated that HODA significantly inhibited the NO production in LPS-induced RAW 264.7 murine macrophage cells (IC50 = 4.28 μM). Consistent with these observations, the mRNA and protein expression levels of iNOS were also inhibited by HODA in a dose-dependent manner. HODA also reduced the translocation of NF-κB into nuclear fractions. Meanwhile, HODA enhanced Nrf-2 activation and its downstream antioxidant gene HO-1. We concluded that HODA possessed significant anti-inflammatory and anti-oxidative activity; the compound may have a potential for development as a chemoprevention agent.
Antifungal Activity of Plant Extracts against Aspergillus niger and Rhizopus stolonifer
Authors: Surapuram Venkatasaichaitanya , Setzer William N. , McFeeters Robert L. , McFeeters Hana
Published: March 2019

Despite recent advances in antifungal development, fungi remain a devastating threat to human health and compromise viability of the food supply. Plant based antimicrobials represent a vast untapped source with tremendous potential. Herein we present the antifungal properties of more than 50 plant extracts against two important human and agricultural pathogens, Aspergillus niger and Rhizopus stolonifer. Multiple extracts exhibit promising MIC values of less than 100 μg/mL and are reported for both fungal species.
An in vitro Antibacterial Study of Savory Essential Oil and Geraniol in Combination with Standard Antimicrobials
Authors: Miladinović Dragoljub L. , Ilić Budimir S. , Kocić Branislava D. , Miladinović Marija D.
Published: March 2019

The chemical composition and antibacterial activity of Satureja kitaibelii Wierzb. ex Heuff. (savory) essential oil were examined, as well as the association between it and standard antimicrobials: tetracycline and chloramphenicol. The antibacterial activities of geraniol, the main constituent of S. kitaibelii oil, individually and in combination with standard antimicrobials were also determined. The interactions of the essential oil and geraniol with antimicrobials toward five selected strains were evaluated using the microdilution checkerboard assay in combination with chemometric methods. Oxygenated monoterpenes were the most abundant compound class in the oil (59.7%), with geraniol (50.4%) as the major compound. The essential oil exhibited in vitro antibacterial activity against all tested bacterial strains, but the activities were lower than those of the standard antimicrobials. The combinations savory oil-chloramphenicol, savory oil-tetracycline and geraniol-chloramphenicol produced predominantly synergistic interactions (FIC indices in the range 0.21–0.87) and substantial reductions in the MIC values of antimicrobials against Gram-negative bacteria, the pharmacological treatment of which is very difficult nowadays. In the PCA and HCA analyses these combinations form a separate group.
Chemical Composition and Biological Activity of Pulicaria vulgaris Essential Oil from Iran
Authors: Sharifi-Rad Javad , Miri Abdolhossein , Hoseini-Alfatemi Seyedeh Mahsan , Sharifi-Rad Majid , Setzer William N. , Hadjiakhoondi Abbas
Published: March 2019

The present study investigated the chemical composition of the essential oil (EO) from aerial parts (flowering stage) of Pulicaria vulgaris Gaertn. by GC–MS. Also, the antimicrobial activity of the EO against Gram-positive bacteria ( Bacillus cereus and Staphylococcus aureus), Gram-negative bacteria ( Escherichia coli and Pseudomonas aeruginosa) and fungi ( Aspergillus niger and Candida albicans) was tested. In total, 23 compounds were recognized, accounting for 98.08 % of the EO. The main compounds in the EO were thymol (50.22%), p-menth-6-en-2-one (carvotanacetone, 20.2%), thymol isobutyrate (16.88%), menthan-2-one (4.31%), 1-methyl-1,2-propanedione (4.13%), 2,5-dimethoxy- p-cymene (4.01%), myrtenol (1.22%), linalool (1.1%), and β-myrcene (1.9%). Results of antibacterial test of P. vulgaris essential oil showed that all assayed concentrations significantly inhibited the growth of B. cereus, S. aureus, E. coli, and P. aeruginosa at P < 0.05. MIC for B. cereus, S. aureus, E. coli, P. aeruginosa was 17.5, 25.2, 19.4 and 33.2 μg/mL respectively; antifungal screening of the essential oil of P. vulgaris showed that the oil significantly inhibited the growth of A. niger and C. albicans (MIC = 15.5 and 9.9 μg/mL, respectively). Results of cytotoxicity assay showed that the essential oil exhibited a significant cytotoxic activity against both cell lines. In case of MCF-7 and Hep-G2 cell lines, IC50 of the essential oil were 5.36 and 7.16 μμg/ml, respectively. The potent antimicrobial and cytotoxic activities of the EO may be attributed to its high contents of thymol, carvotanacetone and thymol isobutyrate. Antimicrobial and antitumor chemotherapies are showing diminishing effectiveness because of emergence of drug-resistance. Hence, using efficient natural chemotherapeutic agents such as Pulicaria vulgaris essential oil with fewer side effects is an encouraging approach to fight cancer and infectious diseases in medicine, agriculture, food science and related fields.
Novel C-ring Analogs of Ursolic acid: Synthesis and Cytotoxic Evaluation
Authors: Mallavadhani Uppuluri V. , Pattnaik Banita , Suri Nitasha , Saxena Ajit K.
Published: March 2019

Ursolic acid (1), a natural pentacyclic triterpenic acid, afforded a variety of ring-C transformed products (5–11) when treated with N-bromosuccinimide under the influence of a range of protective groups and solvents. The synthesized compounds have been evaluated for cytotoxic activity against prostate PC 3, leukemia THP 1, cervical Hela and lung A-549 cancer cell lines. Among the tested analogs, compounds 5, 8, 9 and 10 showed potent activity against PC 3, THP 1 and Hela cell lines. Especially, compound 10 showed enhanced activity against the Hela cell line than the parent compound. Compounds 5, 8 and 9 showed comparable activities against PC 3 and THP 1 cell lines.
A New Stilbenoid Compound from the Lianas of Gnetum microcarpum
Authors: Azmin Nik Fatini Nik , Ahmat Norizan , Syah Yana M. , Zawawi Nik Khairunissa’ Nik Abdullah , Yusof Mohd Izwan Mohamad
Published: March 2019

A new stilbene, malaysianol E (1), together with five known stilbenes namely gnetol (2), gnetucleistol C (3), gnetucleistol D (4), resveratrol (5) and ε-viniferin (6) were successfully discovered from the acetone extract of the lianas of Gnetum microcapum. The structures of these stilbenes were determined on the basis of spectroscopic (1D and 2D NMR) and MS evidence. This paper describes the structural elucidation of the new compound, malaysianol E. The chemotaxonomic significance of this compound is briefly discussed.
Selective COX-2 Inhibitory Properties of Dihydrostilbenes from Liquorice Leaves–In Vitro Assays and Structure/Activity Relationship Study
Authors: Trombetta Domenico , Giofrè Salvatore V. , Tomaino Antonio , Raciti Roberto , Saija Antonella , Cristani Mariateresa , Romeo Roberto , Siracusa Laura , Ruberto Giuseppe
Published: March 2019

Three dihydrostilbenes belonging to the polyphenol pool characterized in the leaves of Sicilian liquorice ( Glycyrrhiza glabra L.) have been tested for their antioxidant and anti-inflammatory activity. The three dihydrostilbenes (PA-82, GA-23, DO-07) were in vitro tested to evaluate their capability to scavenge the stable radical 1,1-diphenyl-2-picrylhydrazyl (DPPH), and to decrease thromboxane B2 (TxB2) and prostaglandin E2 (PGE2) release in human whole blood samples. On the basis of the observed capability of these compounds to affect the cell COX-1/COX-2 pathway, a molecular docking study was carried out in order to understand in detail the ability of these compounds to bind to COX-1 and COX-2. The results show that the liquorice dihydrostilbenes are preferred ligands for COX-2 rather than for COX-1, providing a good rational for the observed selectivity in ex vivo experiments. Therefore, they appear to be good candidates for employment in human therapy against inflammation-related pathological conditions.
Chemical Composition and Antioxidant Activity of Seed oil of Two Algerian Date Palm Cultivars (Phoenix dactylifera)
Authors: Boukouada Mustapha , Ghiaba Zineb , Gourine Nadhir , Bombarda Isabelle , Saidi Mokhtar , Yousfi Mohamed
Published: March 2019

The fatty acid composition of date seed oil from two different date palm ( Phoenix dactylifera L.) cultivars, locally known as Degla-Baïdha and Tafezouine, were investigated. GC analysis revealed the presence of five dominant fatty acids: oleic C18:1 (46.51; 39.15%), lauric C12:0 (22.1; 28.5%), myristic C14:0 (10.7; 11.4%), palmitic C16:0 (9.6; 8.7%) and linoleic C18:2 (6.9; 6.1%). The oils was characterised by a low content of tocopherols (0.53; 1.41 μg/g). The antioxidant activity of the oils was investigated using the DPPH•(1,1-di-phenyl-2-picryl-hydrazyl) scavenging assay. The oils had a weak bleaching effect on DPPH• free radicals. This study showed that the qualities of the tested oils are highly comparable with those of some commercial seed oils of other plants. Furthermore, a statistical analysis using the hierarchy ascendant classification method was conducted in order to highlight the similarities and/or the differences regarding the contents of the main fatty acids found in some common plants and in the five most famous cultivars of Phoenix dactylifera of south eastern Algeria (Tafezouine, Degla-Baïdha, Deglet-Nour, Ghars, Tamdjouhert).
Volatile Constituents of Murraya koenigii Fresh Leaves Using Headspace Solid Phase Microextraction – Gas Chromatography – Mass Spectrometry
Authors: Sukkaew Sayamol , Pripdeevech Patcharee , Thongpoon Chalermporn , Machan Theeraphan , Wongchuphan Rattana
Published: March 2019

The volatile components of Murraya koenigii fresh leaves, collected from Surat Thani province, Thailand were studied by using headspace (HS) solid-phase microextraction (SPME) coupled with gas chromatography-mass spectrometry (GC-MS). The four fibers employed to extract the volatiles were polydimethylsiloxane (PDMS), polydimethylsiloxane-divinylbenzene (PDMS-DVB), carboxane-polydimethylsiloxane (CAR-PDMS) and polydimethylsiloxane-divinylbenzene-carboxane (PDMS-DVB-CAR). The volatile constituents of M. koenigii fresh leaves were also extracted by hydrodistillation and analyzed by GC-MS. Fifty-one compounds were identified by these fibers. Five major compounds, γ–terpinene, β-caryophyllene, β-phellandrene, α-selinene and α-pinene, were detected in all fibers. The PDMS-DVB-CAR fiber was considered as the best for trapping key volatiles of M. koenigii fresh leaves.
Constituents, Antibacterial and Antioxidant Activities of Essential Oils from Trachelospermum jasminoides Flowers
Authors: Pansanit Acharavadee , Pripdeevech Patcharee
Published: March 2019

The present work reports the chemical compositions, antibacterial and antioxidant activities of essential oils from T. jasminoides flowers collected from two different geographical areas, Chiang Rai and Chiang Mai, Thailand. The essential oil of T. jasminoides from the Chiang Rai area had 99 compounds representing 97.9% of the total oil composition, with E-nerolidol and α-phellandrene as the major constituents. In contrast, the essential oil of T. jasminoides collected from the Chiang Mai area contained 93 components representing 94.8% of the total oil, with trans-linalool oxide and citronellol as the major compounds. Flower oils of T. jasminoides exhibited greater antibacterial activities against Gram-negative bacteria than Gram-positive bacteria. Both oils displayed antioxidant activities.
UV-protective Effects of Phytoecdysteroids from Microsorum grossum Extracts on Human Dermal Fibroblasts
Authors: Ho Raimana , Teai Taivini , Meybeck Alain , Raharivelomanana Phila
Published: March 2019

Microsorum grossum (Polypodiaceae), locally called metuapua'a, is one of the most frequently used fern species in Polynesian traditional medicine. Fronds or rhizomes of this species are common ingredients of popular medicine recipes to cure various ailments. M. grossum frond and rhizome extracts contain, as their main bioactive components, phytoecdysteroids such as 20-hydroxyecdysone, known to have many interesting biological activities and considered to be adaptogenic compounds [1]. The skin-active effect of M. grossum extract was investigated in two ways on human dermal fibroblasts: a transcriptomic study with c-DNA array for gene expression modulation and a Stress Induced Premature Senescence (SIPS) test. The total extract of M. grossum up-regulates Heme Oxygenase 1 (HO1), an enzyme which protects cells from oxidative stress and which is responsible for skin photoimmunoprotection. The present paper also reports that premature senescence of human skin induced by repeated UV irradiations can be prevented by an ecdysteroid fraction of M. grossum. Our data indicate that extracts of M. grossum could protect skin against oxidative stresses and suggest that they could be used as innovative active cosmetic ingredients.
Pterandric Acid – its Isolation, Synthesis and Stereochemistry
Authors: Haleem Muhammad A. , Capellari Simone C. , Sympson Beryl B. , Marsaioli Anita J.
Published: March 2019

Some plant families have a specialized type of pollination system, with floral lipid rewards for pollinators, which is common. In neotropical Malpighiaceae species like Pterandra pyroidea, this specialized type of pollination system is apparently shifting from floral oils/lipids to pollen reward. Mass spectrometric analysis (GC/MS-EI) indicated that P. pyroidea floral oil has a unique chemical composition, i.e., few fatty acid constituents possessing acetoxy groups at positions 5 and 7, which is distinct from the other floral oils of sympatric Malpighiaceae species. The structure of the major floral oil constituent, a novel fatty acid, a nti-5,7-diacetoxydocosanoic acid, was confirmed based on synthesis, mass fragmentation, and 1H and 13C NMR analyses; the compound is herein named pterandric acid.
Pulvinulin A, Graminin C, and cis-Gregatin B – New Natural Furanones from Pulvinula sp. 11120, a Fungal Endophyte of Cupressus arizonica
Authors: Wijeratne E. M. Kithsiri , Xu Yaming , Arnold A. Elizabeth , Gunatilaka A. A. Leslie
Published: March 2019

Three new natural furanones, pulvinulin A (1), graminin C (2), and cis-gregatin B (3), together with the known fungal metabolites, graminin B (4) and 10-norparvulenone (5), were isolated from Pulvinula sp. 11120, an endophytic fungal strain occurring in healthy foliage of Cupressus arizonica (Arizona cypress). The structures of 1 and 2 were elucidated by the analysis of their spectroscopic data and chemical interconversions, and that of 3 was determined by comparison with data for synthetic cis-gregatin B. Comparison of spectroscopic data of 4 and 5 with those reported identified them as graminin B and 10-norparvulenone, respectively. Metabolites 1–4 exhibited antibacterial activity against E. coli.
Cytotoxic Active Constituents of Essential Oils of Curcuma longa and Curcuma zanthorrhiza
Authors: Schmidt Erich , Ryabchenko Boris , Wanner Juergen , Jäger Walter , Jirovetz Leopold
Published: March 2019

The polar and apolar fractions of Curcuma longa and C. zanthorriza enriched by ar-turmerone, ar-curcumene and xanthorrizol were screened for cytotoxic activity against the HeLa cell line. Actinomycin D and curcumin were used as reference samples, both known for their cytotoxic properties. Amongst all fractions tested, the xanthorrizol fraction (CC50: 26.1±1.9 μM) showed the strongest cytotoxic properties similar to those of curcumin (CC50: 8.1±1.7 μM). Further studies also revealed that the cytotoxic effects of the extracts and pure compounds are caused by apoptosis induction identified by the cleaved form of PARP protein
Natural Flavonoids as Potential Herbal Medication for the Treatment of Diabetes Mellitus and its Complications
Authors: Chen Jian , Mangelinckx Sven , Adams An , Wang Zheng-tao , Li Wei-lin , De Kimpe Norbert
Published: March 2019

Diabetes mellitus, together with its various complications, is becoming a serious threat to human health. Natural products are secondary metabolites widely distributed in plants, having a broad range of biological activities. The development of antidiabetic medication from natural products, especially those originating from plants with a traceable folk-usage history in treating diabetes, is receiving more attention. Many studies highlighted not only the benefits of natural flavonoids with hypoglycemic effects, but also their importance in the management of diabetic complications. This review describes selected natural flavonoids that have been validated for their hypoglycemic properties, together with their mechanisms of action. Also discussed are their activities in the treatment of diabetic complications demonstrated via laboratory diabetic animal models, in vitro and clinical trials using human subjects. Published papers from 2000 to date on flavonoids and diabetes were covered through accessing Web of Science and multiple databases for biomedical sciences. The major potential benefits of natural flavonoids discussed in this review clearly suggest that these substances are lead compounds with sufficient structural diversity of great importance in the antidiabetic drug developing process.
Antitumor Constituents of the Wetland Plant Nymphoides peltata: A Case Study for the Potential Utilization of Constructed Wetland Plant Resources
Authors: Du Yuanda , Wang Renqing , Zhang Haijie , Liu Jian
Published: March 2019

The efficient utilization of plant resources is a necessary and important measure for sustainable management of constructed wetlands. Screening bioactive metabolites from wetland plants could reveal potential solutions for the utilization of constructed wetland plant resources. In this study, the constructed wetland macrophyte Nymphoides peltata was screened for constituents with antitumor activity. The secondary metabolites of N. peltata were extracted and separated by MCI gel, silica gel, and Sephadex gel column chromatography. Antitumor tests were then carried out with MTT assay against the human prostate cancer cell PC3 and the human osteosarcoma cell U2OS. The secondary metabolite group with the most significant antitumor activity was further examined, and four constituents were obtained and identified. This study provides a scientific basis for the potential efficient utilization of N. peltata and other constructed wetland plant resources.
Protective Effect of Silymarin against Rapamycin-induced Apoptosis and Proliferation Inhibition in Endothelial Progenitor Cells
Authors: Zhang Peng , Han Guohua , Gao Pei , Qiao Kun , Ren Yusheng , Liang Chun , Leng Bing , Wu Zonggui
Published: March 2019

For this study, peripheral blood samples were collected from human volunteers. Mononuclear cells (MNC) were separated by density centrifugation and were induced to differentiate into endothelial progenitor cells (EPCs) in vitro. Different concentrations of rapamycin and silymarin were introduced to the EPCs over 24 hours and then EPCs were analyzed for proliferation, migration, apoptosis and angiogenesis. Compared with the control group, rapamycin (1, 10, 100 ng/mL) inhibited the proliferation and migration of EPCs in a concentration dependent manner ( P<0.05). Silymarin (50, 100 μg/mL) enhanced the proliferation and migration of EPCs and inhibited apoptosis in a concentration dependent manner ( P<0.05). By adding rapamycin (1 ng/mL) and silymarin (25, 50, 100 μg/mL) over 24 hours, silymarin inhibited the pro-apoptotic effect of rapamycin on EPCs, and reversed the inhibition of proliferation, migration and angiogenesis of EPCs by rapamycin ( P<0.05).
Essential Oil Constituents of Etlingera yunnanensis and Hornstedtia sanhan grown in Vietnam
Authors: Chau Dao T. M. , Dai Do N. , Hoi Tran M. , Thai Tran H. , Thang Tran D. , Ogunwande Isiaka A.
Published: March 2019

The chemical composition of the essential oils obtained from the hydrodistillation of different parts of Etlingera yunnanensis (T.L. Wu &S.J. Chen) R.M. Sm. and Hornstedtia sanhan M.F. Newman (Zingiberaceae) grown in Vietnam are reported. The analysis was performed by means of a gas chromatography-flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC-MS). The essential oil of the leaves of E. yunnanensis comprised mainly germacrene D (19.2%), β-pinene (11.6%), and α-amorphene (11.2%), while that of the stems was rich in β-pinene (23.7%), 1,8-cineole (11.0%) and α-pinene (9.6%). The major components of the root oil of E. yunnanensis were β-pinene (31.9%), α-pinene (13.7%) and 1,8-cineole (9.4%). However, α-pinene (25.9%, 36.3% and 14.1% for leaves, stems and roots, respectively), β-pinene (9.7%, 11.8% and 7.2% for leaves, stems and roots, respectively) and limonene (22.1%, 24.6% and 16.2% for leaves, stems and roots, respectively) were the major compounds of H. sanhan. In addition, α-humulene (15.9%) was present in larger amounts in the leaf oil while the root oil contained the largest proportion of methyl chavicol (43.7%).
Chrysanthemum indicum Attenuates Cisplatin-induced Nephrotoxicity both in vivo and in vitro
Authors: Kim Tae-Won , Kim Young-Jung , Park So-Ra , Seo Chang-Seob , Ha Hyekyung , Shin Hyeun-Kyoo , Jung Ju-Young
Published: March 2019

Chrysanthemum indicum Linné has been used in traditional medicine to treat various inflammatory diseases in East Asia. The aim of the present study was to investigate the protective effect of C. indicum ethanol extract (CILE) against cisplatin-induced nephrotoxicity. An HPLC-photodiode array method was used for fingerprint analysis of the CILE and ten major constituents were quantitatively analyzed. The protective effect of CILE on cisplatin-induced nephrotoxicity was assessed using both in vitro (porcine kidney cell; PK15 cell) and in vivo (Sprague Dawley rat) experiments. In the in vitro study, CILE enhanced PK15 cell viability after cisplatin treatment with recovered antioxidant status. Moreover, the increased p53 expression after cisplatin treatment was decreased in the CILE pretreated cells. In the in vivo study, SD rats were treated for 28 consecutive days with CILE (0, 100, 300 and 500 mg/kg). On day 23, a single dose of cisplatin (5 mg/kg) was injected to induce nephrotoxicity. The CILE pretreated group showed recovered serum renal function index with ameliorated oxidative stress. Histopathological alterations and apoptosis in the kidney were also decreased in CILE pretreated rats. Taken together, CILE could attenuate cisplatin-induced nephrotoxicity and might be a beneficial agent for acute renal failure management.
Foliar Flavonoids from Tanacetum vulgare var. boreale and their Geographical Variation
Authors: Uehara Ayumi , Akiyama Shinobu , Iwashina Tsukasa
Published: March 2019

Foliar flavonoids of Tanacetum vulgare var. boreale were isolated. Eight flavonoid glycosides, 7- O-glucosides of apigenin, luteolin, scutellarein and 6-hydroxyluteolin, and 7- O-glucuronides of apigenin, luteolin, chrysoeriol and eriodictyol were identified. Moreover, eight flavonoid aglycones, apigenin, luteolin, hispidulin, nepetin, eupatilin, jaceosidin, pectolinarigenin and axillarin were also isolated and identified. The flavonoid composition of two varieties of T. vulgare, i.e. var. boreale and var. vulgare, were compared. All samples of var. boreale and one sample of var. vulgare had the same flavonoid pattern, and could be distinguished from almost all the samples of var. vulgare. Thus, the occurrence of chemotypes, which are characterized by either the presence or absence of scutellarein 7- O-glucoside, eriodictyol 7- O-glucuronide and pectolinarigenin was shown in T. vulgare sensu lato.
Flavonoids and their Qualitative Variation in Calystegia soldanella and Related Species (Convolvulaceae)
Authors: Murai Yoshinori , Setoguchi Hiroaki , Ono Eiichiro , Iwashina Tsukasa
Published: March 2019

Coastal species are exposed to severe environmental stresses, e.g. salt and UV-B. The plants adapt themselves to such harsh environment by controlling morphological features and chemical defense systems. Flavonoids are known as efficient anti-stress polyphenols produced by plants. Most flavonoids show antioxidant activity, and their properties are important for plants to survive under high-stress conditions such as those in a coastal area. Among the compounds, ortho-dihydroxylated flavonoids act as strong antioxidants. In this survey, we elucidated the flavonoid composition of a seashore species Calystegia soldanella, which is distributed not only on the seashore, but also by the inland freshwater lake, Lake Biwa. Seven flavonol glycosides, i.e. quercetin 3- O-rutinoside, 3- O-glucoside, 3- O-rhamnoside and 3- O-apiosyl-(1→2)-[rhamnosyl-(1→6)-glucoside], and kaempferol 3- O-rutinoside, 3- O-glucoside and 3- O-rhamnoside were isolated from the leaves of C. soldanella. In addition, it was shown that the quercetin (Qu) to kaempferol (Km) ratio of coastal populations was higher than that of lakeshore populations. In general, these differences of Qu/Km ratio depend on flavonoid 3′-hydroxylase (F3′H) transcription. RT-PCR analysis suggested that F3′H of C. soldanella is regulated translationally or post-translationally, but not transcriptionally. Furthermore, quantitative and qualitative differences in flavonoid composition occurred among three Calystegia species, C. soldanella, C. japonica and C. hederacea.
Two New Isoflavanones from the Roots of Erythrina variegata
Authors: Tanaka Hitoshi , Atsumi Ikunori , Hasegawa Motori , Hirata Miyuki , Sakai Tatsuko , Sato Masaru , Yamaguchi Ryozo , Tateishi Yoichi , Tanaka Toshiyuki , Fukai Toshio
Published: March 2019

Two new isoflavanones, eryvarins Y (1) and Z (2), together with three known compounds (3–5) were isolated from the roots of Erythrina variegata. The structures of 1 and 2 were established on the basis of spectroscopic data. The new compounds are peculiar isoflavanones, possessing both a 3-methylbut-2-en-1-yl group and a 2-hydroxy-3-methylbut-3-en-1-yl group. Among the isolates, orientanol E (5) exhibited potent antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) strains.
Concise Synthesis of N,N-Dimethyltryptamine and 5-Methoxy-N,N-dimethyltryptamine Starting with Bufotenine from Brazilian Anadenanthera ssp
Authors: Moreira Leandro A. , Murta Maria M. , Gatto Claudia C. , Fagg Christopher W. , Santos Maria L. dos
Published: March 2019

Bufotenine (1, 5-hydroxy- N,N-dimethyltryptamine) was isolated from seeds of Anadenanthera spp., a tree widespread in the Brazilian cerrado, using an efficient acid-base shakeout protocol. The conversion of bufotenine into N,N-dimethyltryptamine (4) and 5-methoxy- N,N-dimethyltryptamine (5) was accomplished through an innovative and short approach featuring the use of novel bufotenine-aminoborane complex (7). Furthermore, an easy methodology for conversion of bufotenine into 5-hydroxy -N,N,N-trimethyltryptamine (6) was well-established. This is the first study that highlights bufotenine as a resource for the production of N, N-dimethyltryptamines for either pharmacological and toxicological investigations or for synthetic purposes.
A New Cytotoxic Cytochalasin from the Endophytic Fungus Trichoderma harzianum
Authors: Chen Huiqin , Daletos Georgios , Okoye Festus , Lai Daowan , Dai Haofu , Proksch Peter
Published: March 2019

The new natural product 4′-hydroxy-deacetyl-18-deoxycytochalasin H (1), together with the known deacetyl-18-deoxycytochalasin H (2) and 18-deoxycytochalasin H (3) were obtained from the endophytic fungus Trichoderma harzianum isolated from leaves of Cola nitida. The structure of the new compound was unambiguously determined by 1D and 2D NMR spectroscopy, and by HRESIMS measurements, as well as by comparison with the literature. Compounds 1-3 showed potent cytotoxic activity against the murine lymphoma (L5178Y) cell line and against human ovarian cancer (A2780 sens and A2780 CisR) cell lines (IC50 0.19–6.97 μM). The A2780 cell lines included cisplatin-sensitive (sens) and -resistant (R) cells.
The Search for Antifungals from Amazonian Trees: A Bio-Inspired Screening
Authors: Basset Charlie , Eparvier Véronique , Espindola Laila S.
Published: March 2019

The anti-fungal activity of 60 extracts from 15 tree species in the French Guiana rainforest against human and wood-rotting fungi was studied. In this way (+)-mopanol (1) was isolated from the ethyl acetate extract of Peltogyne sp. (Caesalpiniaceae) wood. This work demonstrated that (1) the natural durability of wood can indeed guide the search for antifungal agents, (2) that extracts selected in this bio-inspired process exhibit a broad spectrum of antifungal activity and (3) that the method allows for the isolation of strongly active antifungals.