bluuebunny/crossref_metadata_2025 huggingface dataset:
Full Assignments of the 1H, 13C and 15N Magnetic Resonance Spectra of Two Porphyrin Compounds
Authors: Chen Qi-Feng , Wang Yao-Nan , Wang Ling , Jian Xi-Xian , Chen Dong-Lin , Zhao Ming , Wang Feng-Peng
Published: March 2019

Two chlorin derivatives, rhodochlorin dimethyl ester (7) and chlorin-e6 trimethyl ester (8), were prepared from methyl pheophobide a (6) through base-degradation of the E ring and methylation of the carboxylic acids. Full assignments of the 1H, 13C and 15N magnetic resonance spectra of compounds 7 and 8 were made by 2D NMR techniques (1H-1H COSY, 1H-13C HMQC, 1H-13C HMBC, 1H-15N HMBC).
The Effects of Salacia reticulata on Anti-Cellular Oxidants and Melanogenesis Inhibition in α-MSH-stimulated and UV Irradiated B16 Melanoma Cells
Authors: Sirwannalert Prasit , Kariya Ryusho , Suzu Ikuko , Okada Seiji
Published: March 2019

The purposes of this study were to investigate the inhibitory effects of Salacia reticulata Tul. root extract on cellular oxidants and melanogenesis in B16 melanoma cells. Cells treated with non-toxic doses of S. reticulata root extract were investigated for their effects on melanogenesis, cellular tyrosinase activity and cellular oxidant scavenging activity. The results indicated that S. reticulata extract inhibited melanin synthesis and tyrosinase activity in α-MSH-induced or UV-irradiated B16 melanoma cells in a dose dependent manner. Additionally, the extract also exhibited anti-cellular oxidants in UV-induced radical melanoma cells. Altogether, these results suggested that S. reticulata root extract has roles in suppression of melanogenesis and oxidant inhibition. S. reticulata root extract may be a potential source for the development of pharmaceutical products for treatment of skin hyperpigmentation disorders.
Anti-oxidant, Anti-inflammatory and Anti-proliferative Activities of Moroccan Commercial Essential Oils
Authors: Aazza Smail , Lyoussi Badiaa , Megías Cristina , Cortés-Giraldo Isabel , Vioque Javier , Figueiredo A. Cristina , Miguel Maria G.
Published: March 2019

Essential oils (EO) possess antimicrobial, anti-inflammatory, insect repellent, anti-cancer, and antioxidant properties, among others. In the present work, the antioxidant, anti-inflammatory and anti-proliferative activities of Moroccan commercial EOs (Citrus aurantium, C. Union, Cupressus sempervirens, Eucalyptus globulus, Foeniculum vulgare and Thymus vulgaris) were evaluated and compared with their main constituents. T. vulgaris EO showed the best free radicals scavenging capacity. This EO was also the most effective against lipid peroxidation along with C. limon and F. vulgare EOs. C. sempervirens EO was the most effective in scavenging NO free radicals, whereas C. limon EO showed the best chelating power. Not all of the major compounds of the EO were responsible for the whole activity of the EOs. T. vulgaris EO showed the best anti-proliferative activity against THP-1 cells in contrast to that of F. vulgare. The antioxidant and anti-inflammatory activities of the EOs were plant species dependent and not always attributable to the EOs main components. Nevertheless, the EOs anti-proliferative activities were more related to their main components, as with T. vulgaris, C. limon, E. globulus and C. sempervirens.
Prediction of Anticancer Activity of Diterpenes Isolated from the Paraiban Flora through a PLS Model and Molecular Surfaces
Authors: Scotti Luciana , Scotti Marcus T. , Ishiki Hamilton , Junior Francisco J. B. M. , dos Santos Paula F. , Tavares Josean F , da Silva Marcelo S.
Published: March 2019

The aim of this work was to predict the anticancer potential of 3 atisane, and 3 trachylobane diterpene compounds extracted from the roots of Xylopia langsdorffiana. The prediction of anticancer activity as expressed against PC-3 tumor cells was made using a PLS model built with 26 diterpenes in the training set. Significant statistical measures were obtained. The six investigated diterpenes were applied to the model and their activities against PC-3 cells were calculated. All the diterpenes were active, with atisane diterpenes showing the higher pIC50 values. In human prostate carcinoma PC-3 cells, the apoptosis mechanism is related to an inhibition of IKK/NF-κB. Antioxidant potential implies a greater electronic molecular atmosphere (increased donor electron capacity), which can reduce radical reactivity, and facilitate post donation charge accommodation. Molecular surfaces indicated a much greater electronic cloud over atisane diterpenes.
Torrubiellone E, an Antimalarial N-Hydroxypyridone Alkaloid from the Spider Pathogenic Fungus Torrubiella longissima BCC 2022
Authors: Isaka Masahiko , Haritakun Rachada , Intereya Kamolphan , Thanakitpipattana Donnaya , Hywel-Jones Nigel L.
Published: March 2019

Torrubiellone E (1), a new N-hydroxypyridone alkaloid, was isolated from the spider pathogenic fungus Torrubiella longissima BCC 2022, together with the known compounds, torrubiellones A (2) and B (3), and JBIR-130 (4). Compound 1 exhibited antimalarial activity against Plasmodium falciparum K1 with an IC50 value of 3.2 μg/mL, while it also showed weak cytotoxic activities.
Chemical Components of Ardisia splendens Leaves and Their Activity against Coxsackie A16 Viruses
Authors: Van Nguyen Thi Hong , Vien Trinh Anh , Nhiem Nguyen Xuan , Van Kiem Phan , Van Minh Chau , Long Pham Quoc , Anh Luu Tuan , Cuong Nguyen Manh , Song Jae-Hyoung , Ko Hyun-Jeong , Kim Nanyoung , Park Seon Ju , Kim Seung Hyun
Published: March 2019

Using a combination of chromatographic methods, one new flavonol glycoside, myricetin 3,7-di-O-α-L-rhamnopyranoside (1), and nine known compounds myricitrin (2), quercetin 3,7-di-O-α-L-rhamnopyranoside (3), quercitrin (4), desmanthin-1 (5), myricetin 3-O -(3″-O-galloyl)-α-L-rhamnopyranoside (6), (+)-catechin (7), benzyl O-β-D-glucopyranoside (8), 2-phenylethyl O-β-D-glucopyranoside (9), and corilagin (10) were isolated from the leaves of Ardisia splendens Pit. Based on an in vitro test against Coxsackie viruses A16 by SRB assay, only compounds 2, 5, and 10 exhibited activity against Coxsackie viruses A16 with IC50 values of 40.1, 32.2, and 30.5 μM, respectively. This result suggested that compounds 2, 5, and 10 might be potential agents for treating hand, foot and mouth diseases.
Two New Diphenylmethyl-substituted Xanthones from Securidaca longepedunculata
Authors: Dibwe Dya Fita , Awale Suresh , Kadota Shigetoshi , Morita Hiroyuki , Tezuka Yasuhiro
Published: March 2019

Two new diphenylmethyl-substituted xanthones, named muchimangins K (1) and L (2), have been isolated from the roots of Securidaca longepedunculata (Polygalaceae) collected in the Democratic Republic of Congo. Their structures were established by analyses of the spectral data, including 2D NMR spectra, to be l,3,6,8-tetrahydroxy-2,5-dimethoxy-4-[l-(2,4,5-trimethoxyphenyl)-1-phenylmethyl]xanthone (1) and l,3,6-trihydroxy-4,7-dimethoxy-2-[l-(2,4,5-trimethoxyphenyl)-1-phenylmethyl]xanthone (2).
Pro-inflammatory Cytokines and Nitric Oxide Inhibitory Constituents from Cassia occidentalis Roots
Authors: Patel Neeraj K , Pulipaka Sravani , Dubey Shashi P. , Bhutani Kamlesh K
Published: March 2019

The anti-inflammatory and cytotoxic activity of thirty-six extracts of nine Indian medicinal plants were determined by measuring the inhibition of production of nitric oxide (NO), interleukin 1beta (IL-1β) and tumor necrosis factor alpha (TNF-α) in lipopolysaccharide (LPS) stimulated RAW 264.7 cells. Their cytotoxic activity against macrophages was determined by MTT assay. The ethyl acetate (EtOAc) extract of Cassia occidentalis L. (roots) (IC50= 21.3 to 43.1 μg/mL) and Mimosa pudica (whole plant) (IC50 = 31.7 to 47.2 μg/mL) and the dichloromethane (DCM) extract of Leucas cephalotes (whole plant) (IC50= 46.8 to 49.3 μg/mL) exhibited significant anti-inflammatory activity by in vitro inhibition of the production of TNF-α, IL-1β and NO in LPS stimulated RAW 264.7 cells. Furthermore, the five compounds isolated from the ethyl acetate extract of Cassia occidentalis roots were found to suppress LPS-induced IL-1β, TNF-α and NO production in a concentration-dependent manner in these cells at IC50 values ranging from 22.5 to 97.4 μM. Emodin and chrysophanol were also found active in inhibiting pro-inflammatory cytokines in vivo. These findings justify an ethnopharmacological use of C occidentalis roots as an effective herbal remedy for the treatment and prevention of inflammation and associated ailments.
Phloroglucinol Derivatives Present an Antidepressant-like Effect in the Mice Tail Suspension Test (TST)
Authors: Duarte Mônica Oliveira , Lunardelli Soraia , Kiekow Cíntia Janine , Stein Ana Cristina , Müller Liz , Stolz Eveline , Rates Stela Maris Kuze , Gosmann Grace
Published: March 2019

The antidepressant-like effects of phloroglucinol and seven synthetic related derivatives were investigated using the tail suspension test (TST) in mice. Compounds 2-methyl-1-[2,4,6-trihydroxy-3-(2-methylpropanoyl)phenyl] propan-1-one (5), 1-(2,4,6-trihydroxyphenyl)ethan-1-one (6), 1-(3-acetyl-2,4,6-trihydroxyphenyl)ethan-1-one (7), 2-methyl-1-[2,4,6-trihydroxy-3-(2-methylpropanoyl)-5-{[2,4,6-trihydroxy-3,5-bis(2-methylpropanoyl)phenyl]methyl} phenyl] propan-1-one (9) and 1-{3-acetyl-5-[(3,5-diacetyl-2,4,6-trihydroxyphenyl)methyl]-2,4,6-trihydroxyphenyl}ethan-1-one (10), containing acyl groups, decreased the immobile behavior of mice treated orally with equimolar doses of imipramine 20 mg/kg, with no alterations in locomotor activity as assessed by the open-field test. These results suggest that these phloroglucinol derivatives could represent a new molecular model in the search for antidepressant drugs.
Glycosylation of Artepillin C with Cultured Plant Cells of Phytolacca americana
Authors: Shimoda Kei , Kubota Naoji , Uesugi Daisuke , Hamada Hiroki
Published: March 2019

Biotransformation of artepillin C was investigated using cultured plant cells as biocatalysts. Artepillin C was converted into its 4- and 9-β-D-glucosides, and 4,9-β-D-diglucoside by cultured cells of Phytolacca americana. In contrast, cultured Ipomoea batatas cells glucosylated artepillin C to only its 4- and 9-β-D-glucosides.
Trichocladinols I-K, Oxatricyclic and Oxabicyclic Polyketides from Trichocladium opacum
Authors: Su Manyun , Chen Shenxi , Liu Xingzhong , Pei Yuehu
Published: March 2019

Three new polyketides, trichocladinols I-K (1-3) with oxabicyclic (1 and 3) and oxatricyclic (2) skeletons, together with three known metabolites, massarilactone G (4), massarigenin D (5), and rosigenin (6), were isolated from the solid-substrate fermentation cultures of the ascomycete fungus Trichocladium opacum. The structures of the new compounds were elucidated primarily by analysis of NMR data. The absolute configurations of 1-3 were deduced from circular dichroism (CD) data. Compounds 1-3 were tested for cytotoxicity against five human carcinoma cell lines, HeLa, A549, MCF-7, HCT116, and T24. Compound 1 showed a weak cytotoxic effect against HeLa cells, but 2 and 3 were inactive.
Anti-Legionella Activity of Essential Oil of Satureja cuneifolia
Authors: Dunkić Valerija , Mikrut Antonija , Bezić Nada
Published: March 2019

The essential oil of Satureja cuneifolia Ten. was characterized by a high concentration of the phenolic compounds carvacrol (21.3%) and thymol (9.2%). The in vitro activity of the essential oil against Legionela pneumophila serogroups (SG) 1 and 2-15 and Legionella spp. from different sources, using micro-dilution, showed that L. pneumofila is sensitive to the oil, with MICs ranging from 0.12 to 0.5%, v/v, and a MBC at 0.5 to 1%, v/v. The essential oil of S. cuneifolia was effective in the reduction of Legionellosis infections.
Synthesis and Insecticidal Activities of Novel Nitrogenous Derivatives of Celangulin-V
Authors: Zhang Jiwen , Cui Lihui , Li Longbo , Hu Zhan , Zhang Qianliang , Hu Zhaonong , Wu Wenjun
Published: March 2019

In order to develop new biorational pesticides and clarify the potential structural factors needed for the biological activity of celangulin-V analogues, thirty novel nitrogenous derivatives were designed and synthesized. The single crystal structure of celangulin-V is reported for the first time and provides a more accurate structure than that previously reported. The structures of all the new derivatives were confirmed by either NMR or ESI-MSn analysis. Insecticidal activities of these compounds were tested against the third-instar larvae of Mythimna separata. One derivative (1–6) showed higher insecticidal activity than celangulin-V, with a KD50 of 231.2 μg.g–1, while two compounds (2–13 and 2–14) exhibited lower insecticidal activities; the others revealed no activity at a concentration of 20 mg mL−1. The results support the view that celangulin-V has the potential to be a lead structure of semi-synthetic green insecticides.
Stereo and Regioselective Microbial Reduction of the Clerodane Diterpene 3,12-Dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene
Authors: Mafezoli Jair , Oliveira Maria C. F. , Paiva José R. , Sousa Antônio H. , Lima Mary A. S. , Júnior José N. Silva , Barbosa Francisco G. , Wijeratne E. M. Kithsiri , Gunatilaka A. A. Leslie
Published: March 2019

The biotransformation of the clerodane diterpene, 3,12-dioxo-15,16-epoxy-4-hydroxy-cleroda-13(16),14-diene (1), obtained from Croton micans var. argyroglossum (Baill.) Müll., was investigated for the first time. Whole cells of Cunninghamella echinulata and Rhizopus stolonifer were used as enzymatic systems, and with both fungi the only biotransformation product obtained was the new ent-neo-clerodane diterpene (3 R,4 S,5 S,8 S,9 R,10 S)-3,4-dihydroxy-15,16-epoxy-12-oxo-cleroda-13(16),14-diene (2a). The absolute stereochemistry of 2a was inferred by comparison of its optical rotation with those of the chemical reduction product of 1 and its quasienantiomer 2c.
Chromatographic Fingerprint Combined with Content of Asperosaponin VI and Antioxidant Activity for Quality Evaluation of Wine-fried Dipsaci Radix
Authors: Song Li , Wang Shaoyun , Duan Xiaoju , Liu Xinhua , Li Zhaofang , Nie Lei , Chu Guangyi
Published: March 2019

Dipsaci Radix, the dry root of Dipsacusasper Wall. ex Henry, is a commonly used traditional Chinese medicine (TCM). A novel comprehensive method was proposed for quality evaluation of wine-fried Dipsaci Radix by an integrated data including three aspects of information: high performance liquid chromatography (HPLC) fingerprint, asperosaponin VI content and antioxidant activity (AA). Various indicators including fingerprint similarity, asperosaponin VI content and AA were respectively employed for quality assessment of processed Dipsaci Radix samples. Results showed that considerable differences existed in quality of processed samples with different processing conditions according to three indicators. Among the factors affecting quality of wine-fried Dipsaci Radix, heating temperature was the most influential factor based on analysis of variance (ANOVA), and should be cautiously controlled. The three evaluation indicators respectively used for optimization of processing technology suggested different optimal conditions of wine-frying. Therefore, a combined indicator based on three evaluation indicators was used for determination of optimal processing condition. Multivariate statistical methods such as Hierarchical Clustering Analysis (HCA) and Principal Components Analysis (PCA) were both employed to classify the processed samples for quality evaluation. To more comprehensively evaluate the quality of wine-fried Dipsaci Radix, HPLC fingerprint combined with content of asperosaponin VI and AA may be a reasonable and practical approach.
Revised NMR Data for 9-O-Demethylgalanthine: An Alkaloid from Zephyranthes robusta (Amaryllidaceae) and its Biological Activity
Authors: Šafratová Marcela , Novák Zdeněk , Kulhánková Andrea , Kuneš Jiří , Hrabinová Martina , Jun Daniel , Macáková Kateřina , Opletal Lubomír , Cahlíková Lucie
Published: March 2019

Ongoing studies of Zephyranthes robusta resulted in the isolation of the lycorine-type alkaloid previously called carinatine and 10- O-demethylgalanthine. The NMR data given previously for this compound were revised and completed by two-dimensional 1H-1H and 1H-13C chemical shift correlation experiments. The name of the isolated compound was corrected to 9- O-demethylgalanthine in accordance with the currently used system of numbering of lycorine-type alkaloids. 9- O-Demethylgalanthine and galanthine, a previously isolated alkaloid from Z. robusta, were inactive in acetylcholinesterase/butyrylcholinesterase assays (IC50 > 500 μM), but showed important prolyl oligopeptidase inhibition activity.
Chemical Constituents of Dendrobium venustum and their Antimalarial and Anti-herpetic Properties
Authors: Sukphan Prapapun , Sritularak Boonchoo , Mekboonsonglarp Wanwimon , Lipipun Vimolmas , Likhitwitayawuid Kittisak
Published: March 2019

A MeOH extract from the whole plant Dendrobium venustum exhibited significant antimalarial and anti-herpetic activities. Bioassay-guided isolation of the plant extract resulted in the isolation of seven known phenolic compounds. Densiflorol B (3) and phoyunnanin E (6) showed the strongest antimalarial activity and a high selectivity index, whereas gigantol (2), batatasin III (5) and phoyunnanin C (7) exhibited moderate activity. Compounds 2 and 5 also showed weak activity against the Herpes simplex virus. This study is the first report on the chemical and biological activities of D. venustum.
Dialyzable Leukocyte Extracts Activate TLR-2 on Monocytes
Authors: García-Hernández Uriel , Robledo-Ávila Frank H. , Álvarez-Jiménez Violeta D. , Rodríguez-Cortés Octavio , Wong-Baeza Isabel , Serafín-López Jeanet , Aguilar-Anguiano Luz M. , Estrada-Parra Sergio , Estrada-García Iris , Pérez-Tapia Sonia M , Chacón-Salinas Rommel
Published: March 2019

Dialyzable leukocyte extracts (DLE) transfer specific cell-mediated immune responses from sensitized donors to non-immune recipients. In addition, DLE have several immunomodulatory effects and are used for the treatment of several infectious and non-infectious diseases. Previous studies showed that human DLE obtained from virus-infected leukocytes and bovine DLE decrease the production of the pro-inflammatory cytokine TNF-α in response to bacterial lipopolysaccharide, in vitro and in vivo. In the present work, we inquire as to whether DLE from uninfected human leukocytes have the ability to regulate cytokine production in peripheral blood mononuclear cells (PBMC) in vitro. We observed that PBMC from healthy individuals were able to produce TNF-α, IL-12 and IL-10 after stimulation with DLE. Moreover, we identified monocytes as the main cell population that produced TNF-α after DLE stimulation. Interestingly, we found that DLE contain unidentified ligands that activate Toll-like receptor (TLR)-2. Finally, we observed that DLE directly activated monocytes through TLR-2. These results reveal a new biological activity of DLE, and suggest that part of the immunomodulatory properties of DLE could be attributed to TLR-2 activation on monocytes and to the induction of a pro-inflammatory environment that is crucial for control of infectious diseases.
Seasonal Variations in the Composition of the Essential Oils of Lavandula angustifolia (Lamiacae)
Authors: Lakušic Branislava , Lakušic Dmitar , Ristic Mihailo , Marčetic Mirjana , Slavkovska Violeta
Published: March 2019

Seasonal variations in the composition of the essential oils obtained from the same individual (of the same genotype) of Lavandula angustifolia cultivated in Belgrade were determined by GC and GC/MS. The main constituents were 1,8-cineole (7.1–48.4%), linalool (0.1–38.7%), borneol (10.9–27.7%), β-phellandrene (0.5–21.2%) and camphor (1.5–15.8%). Cluster analysis showed that the 21 samples collected each month during the vegetation cycle were separable into three main clades with different compositions of essential oils. In the shoots with flowers, inflorescences and fruits of clade I, linalool is dominant, in the young leaves before flowering and old leaves of clade II, 1,8-cineole is dominant. In the young and incompletely developed leaves of clade III, β-phellandrene is dominant. The composition of the essential oils of lavender depended on the plant part and the stage of development.
Cytotoxic Alkaloids from Leaves and Twigs of Dasymaschalon sootepense
Authors: Hongthong Sakchai , Kuhakarn Chutima , Reutrakul Vichai , Jariyawat Surawat , Piyachaturawat Pawinee , Nuntasaen Narong , Jaipetch Thaworn
Published: March 2019

Bioassay-guided fractionation of the cytotoxic ethyl acetate fraction of the sequential methanol extract from the leaves and twigs of Dasymaschalon sootepense led to the isolation of a new 7-hydroxy aporphine alkaloid, 6a,7-dehydrodasymachaline (1) along with the five known compounds (-)-nordicentrine (2), dicentrinone (3), (-)-sinactine (4), aristolactam AII (5) and epiberberine (6). Their structures were elucidated by spectroscopic methods. This is the first report of alkaloids 1–2 and 5–6 from the genus Dasymaschalon. Compounds 1 and 5 showed cytotoxicity against a panel of cancer cell lines.
Spirocyclic Acylphloroglucinol Derivatives from Hypericum pyramidatum
Authors: Force Rebecca , Chen Shui Ling , Fortier Emily , Rowlands Emily , Heneks Jean , Rovnyak David , Henry Geneive E.
Published: March 2019

Five spirocyclic acylphloroglucinol derivatives (1–5) have been isolated from a hexanes extract of the leaves of Hypericum pyramidatum. Pyramidatones A-D (1–3, 5) are new, and chipericumin C (4) has been previously reported. The acylphloroglucinols were characterized based on spectroscopic (NMR, IR, UV-VIS) and mass spectrometric data.
A New Cytosporone Derivative from the Endophytic Fungus Cytospora sp
Authors: Takano Tomoya , Koseki Takuya , Koyama Hiromasa , Shiono Yoshihito
Published: March 2019

Japanese oak wilt (JOW) is a tree disease caused by the fungus Raffaelea quercivora, which is vectored by the ambrosia beetle, Platypus quercivorus. In a screening study of the inhibitory active compounds from fungi, a new cytosporone analogue, compound 1, was isolated from the endophytic fungus Cytospora sp. TT-10 isolated from Japanese oak, together with the known compounds, integracin A (2), cytosporones N (3) and A (4). Their structures were determined by extensive 1D– and 2D–NMR spectroscopic and mass spectral analyses. Compound 1 was identified as 4,5-dihydroxy-3-heptylphthalide and named cytosporone E. Compounds 2 and 3 showed antimicrobial activity against Raffaelea quercivora.
2-Acetoxyverecynarmin C, a New Briarane COX Inhibitory Diterpenoid from Pennatula aculeata
Authors: Bahl Anu , Jachak Sanjay M. , Palaniveloo Kishneth , Ramachandram Tulasiramanan , Vairappan Charles S. , Chopra Harish K.
Published: March 2019

A new briarane-type diterpenoid, named 2-acetoxyverecynarmin C, was isolated from the methanolic extract of an octocoral, Pennatula aculeata, that exhibited cyclooxygenase (COX) inhibitory activity. The structure of the compound was elucidated by ESI-HRMS, 1D and 2D NMR spectroscopy and comparison of the measured spectral data with those reported in the literature. The relative stereochemistry at chiral carbons was established from 2D NOESY experiments. 2-Acetoxyverecynarmin C is a tricyclic compound containing a furan ring at C-7,8 of a briarane skeleton. 2-Acetoxyverecynarmin C showed moderate inhibitory activity in in vitro COX-1 and COX-2 assays.
Spiculisporic Acid E, a New Spiculisporic Acid Derivative and Ergosterol Derivatives from the Marine-Sponge Associated Fungus Talaromyces trachyspermus (KUFA 0021)
Authors: Kumla Decha , Dethoup Tida , Buttachon Suradet , Singburaudom Narong , Silva Artur M.S. , Kijjoa Anake
Published: March 2019

A new spiculisporic acid derivative, spiculisporic acid E (2), and a new natural product 3-acetyl ergosterol 5, 8-endoperoxide (1), were isolated, together with ergosta-4, 6, 8 (14), 22-tetraen-3-one, glaucanic acid and glauconic acid, from the culture of the marine-sponge associated fungus Talaromyces trachyspermus (KUFA 0021). All the compounds were inactive against Gram-positive and Gram-negative bacteria, and Candida albicans, as well as multidrug-resistant isolates from the environment. Spiculisporic acid E (2), glaucanic acid and glauconic acid did not show in vitro growth inhibitory activity against the MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A375-C5 (melanoma) cell lines by the protein binding dye SRB method.
Anthranilic Acid Derivatives and Other Components from Ononis pusilla
Authors: Khouni Lyes , Long Christophe , Haba Hamada , Molinier Nicolas , Benkhaled Mohammed
Published: March 2019

Three new anthranilic acid derivatives: N-( R)-3′-hydroxydocosanoylanthranilic acid (1), N-( R)-3′-hydroxytricosanoylanthranilic acid (2) and N-( R)-3′-hydroxytetracosanoylanthranilic acid (3), in addition to one knownanthranilic acid and six known flavonoids, were isolated from the ethyl acetate extract of Ononis pusilla L. The structures of the isolated compounds were assigned by spectroscopic methods, including 1D and 2D homo and heteronuclear NMR experiments, ESI-MS, chemical transformation and comparison with literature data.
Phenols and Antioxidant Activity in Vitro and in Vivo of Aqueous Extracts Obtained by Ultrasound-Assisted Extraction from Artichoke By-Products
Authors: Punzi Rossana , Paradiso Annalisa , Fasciano Cristina , Trani Antonio , Faccia Michele , de Pinto Maria Concetta , Gambacorta Giuseppe
Published: March 2019

Artichoke by-products are rich in phenolic compounds although they represent a waste for the food industry. This paper examines the application of ultrasound-assisted extraction (UAE) for obtaining organic solvent-free extracts rich in nutraceuticals from artichoke scraps. Application of ultrasounds for 60 minutes on test samples, using water as a solvent, improved recovery of phenolic substances compared with untreated samples. Among the phenols detected by high performance liquid chromatography, 5- O-caffeoylquinic and 1,5-di- O-caffeoylquinic acids were identified. In vivo treatments of tobacco BY-2 cells with ultrasonic extracts consistently enhanced their antioxidant power, making the cells more resistant to heat stress. UAE applied to artichoke by-products, using water as a solvent, appears to be a powerful eco-friendly technique that can provide extracts rich in nutraceuticals and turn waste products into resources. The extracts could be advantageously utilized in the food industry to produce functional foods.
The Effect of Ginkgo biloba and Camellia sinensis Extracts on Psychological State and Glycemic Control in Patients with Type 2 Diabetes Mellitus
Authors: Lasaite Lina , Spadiene Asta , Savickiene Nijole , Skesters Andrejs , Silova Alise
Published: March 2019

Interest in finding natural antioxidants for use in food or medical materials to prevent free radical imbalance has increased considerably over the past years. The aim of this research was to evaluate changes in glycemic control and psychological state of patients with type 2 diabetes mellitus (T2DM) after use of antioxidant plant preparations. Fifty-six patients with T2DM were randomly allocated to receive standardized Ginkgo biloba L. leaves dry extract, green tea dry extract, or placebo capsules. Diabetes glycemic control measured as glycated hemoglobin (HbA1c) level, antioxidant state and psychological data were evaluated at baseline, after 9 and 18 months of using either antioxidant preparations or placebo. The level of perceived stress lowered significantly after 9 months ( p=0.038) and 18 months ( p=0.030), and the psychological aspect of quality of life significantly improved after 18 months ( p=0.019) of use of G. biloba extract. No significant differences were detected after using green tea extract. In patients using placebo, significant lowering of HbA1c level was observed after 18 months ( p=0.017). In conclusion, antioxidant G. biloba leaf extract exhibited a mild effect on psychological state and a trend of improving glycemic control in patients with type 2 diabetes mellitus.
Dissecting Traditional Chinese Medicines by Omics and Bioinformatics
Authors: Quan Yuan , Wang Zhong-Yi , Xiong Min , Xiao Zheng-Tao , Zhang Hong-Yu
Published: March 2019

Traditional Chinese medicines (TCM) are a rich source of potential leads for drug development. However, there are fundamental differences between traditional Chinese medical concepts and modern pharmacology, which greatly hinder the modern development of TCM. To address this challenge, new techniques associated with genomics, transcriptomics, proteomics, metabolomics and bioinformatics have been used to dissect the pharmacological mechanisms of TCM. This review article provides an overview of the current research in this area, and illustrates the potential of omic and bioinformatic methods in TCM-based drug discovery.
Anti-obesity Effect of (8-E)-Nüzhenide, a Secoiridoid from Ligustrum lucidum, in High-fat Diet-induced Obese Mice
Authors: Liu Qing , Kim Sang Hyun , Kim Seon Beom , Jo Yang Hee , Kim Eun Sil , Hwang Bang Yeon , Oh Kyunghee , Lee Mi Kyeong
Published: March 2019

The effect of the extract of Ligustrum lucidum fruits (LFE) and its major secoiridoid (LFS), (8- E)-nüzhenide, on obesity was investigated using high fat-diet (HFD)-induced C58BL/6J obese mice. LFE and LFS were administered at the doses of 300 mg/kg and 30 mg/kg, respectively, for 6 weeks. The anti-obesity activity was evaluated by measuring body weight, epididymal fat and metabolic plasma parameters. On Day 42, the body weight of the LFS-treated group was significantly lower compared with the HFD-treated group. Body weight gain was also reduced by 23.2% and 32.0% in the LFE- and LFS-treated groups, respectively, compared with the HFD group. In addition, the weight of the epididymal fat in the mice was significantly decreased in the HFD+LFS group. The food efficiency ratios (FERs) of the HFD+LFE and HFD+LFS groups were also lower compared with the HFD group with the same food intake. Metabolic parameters that had increased in the HFD group were decreased in the HFD+LFE and HFD+LFS groups. In particular, the increased triglyceride values were significantly reduced in the HFD+LFS group. These results show that treatment with LFE and LFS decreased HFD-induced obesity, mainly by improving metabolic parameters, such as fats and triglycerides. Therefore, LFE and LFS have potential benefits in regulation of obesity.
Variations of Carnosic acid and Carnosol Concentrations in Ethanol Extracts of Wild Lepechinia salviae in Spring (2008–2011)
Authors: Labbé Cecilia , Faini Francesca , Calderón Daniela , Molina Juanita , Arredondo Susana
Published: March 2019

Ethanol extracts from dried leaves of wild Lepechinia salvia (Lindl) Epling, collected during the flowering period (September-November), contained 15% to 25% carnosic acid and 2 to 8% carnosol, depending on the month of collection. The highest concentration of carnosic acid in extracts was in October, while carnosol concentration had a peak in September, which suggests that it is not a product of carnosic acid oxidation. A comparison of extracts obtained in September 2008 to 2011 shows that the production of both abietanes increased in years with less winter rainfall and higher temperatures, which induced an early blooming. EC50values in DPPH radical scavenging and antiproliferative (CCRF-CEM tumor cells) bioassays confirm that the high bioactivity of the extracts of rosemary, sage and L. salviae does not arise only from carnosol and carnosic acid. The cytotoxic activity was significantly higher in extracts of L. salviae, probably due to water stress differences between the cultivars and the wild species. These results correlate well with the close phylogenetic relationship between the three species, and their similar medicinal uses.
Triterpene Glycosides from the Sea Cucumber Cladolabes schmeltzii. II. Structure and Biological Action of Cladolosides A1-A6
Authors: Silchenko Alexandra S. , Kalinovsky Anatoly I. , Avilov Sergey A. , Andryjaschenko Pelageya V. , Dmitrenok Pavel S. , Yurchenko Ekaterina A. , Dolmatov Igor Yu. , Savchenko Alexander M. , Kalinin Vladimir I.
Published: March 2019

Six new triterpene glycosides, cladolosides A1–A6(1–6), have been isolated from the Vietnamese sea cucumber Cladolabes schmeltzii (Cladolabinae, Sclerodactylidae, Dendrochirotida). Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. All the glycosides have nonsulfated tetrasaccharide linear carbohydrate moieties. Glycoside 6 has a glucose residue as the third monosaccharide unit, while the rest of the compounds comprise a xylose in this postion of the carbohydrate chain. Glycosides 1–6 differ from each other in the structures of their holostane aglycones. Cytotoxic activities of glycosides 1–6 were studied against mouse spleenocytes, along with hemolytic activities against mouse erythrocytes. All the compounds, except cladoloside A5(5) posessing a hydroxy-group in the aglycone side chain, demonstrated rather strong cytotoxic and hemolytic effects. The most active glycosides were cladolosides A1(1) and A2(2) having two O-acetic groups and the xylose residue in the third position of the sugar chain.
Flavone Induces Cell Death in Human Hepatoma HepG2 Cells
Authors: Valdameri Glaucio , Kenski Juliana C. N. , Moure Vivian R. , Trombetta-Lima Marina , Martinez Glaucia R. , Sogayar Mari C. , Winnischofer Sheila M. B. , Rocha Maria E. M.
Published: March 2019

Flavones have received considerable attention because of their antiproliferative properties and selective effects on cancer cells, making them good candidates for use in cancer therapy. In contrast to other flavones, little is known about the effects of the flavone core structure (2-phenyl-4H-1-benzopyran-4one) on cancer cells. Here, we report that flavone induces cell death in human hepatoma HepG2 cells. Furthermore, annexin-V+/PI- and SubG1 populations of HepG2 cells increased after flavone treatment. Exposure of HepG2 to flavone did not result in either cytochrome c release into the cytosol or changes in the mitochondrial membrane potential. Treatment of HepG2 cells with flavone for 24 h reduced the accumulation of intracellular ROS, which correlated with upregulation of Gred, CuZnSOD and MnSOD mRNA levels. Taken together, our results provided useful insights into the mechanism of cell death caused by flavones, in order to evaluate their future application in hepatocarcinoma therapy.
Isolation of (–)–Avenaciolide as the Antifungal and Antimycobacterial Constituent of a Seimatosporium sp. Endophyte from the Medicinal Plant Hypericum perforatum
Authors: Clark Trevor N. , Bishop Amanda I. , McLaughlin Mark , Calhoun Larry A. , Johnson John A. , Gray Christopher A.
Published: March 2019

An extract of Seimatosporium sp., an endophyte from the Canadian medicinal plant Hypericum perforatum, exhibited significant antifungal and antimycobacterial activity against Candida albicans and Mycobacterium tuberculosis H37Ra. Bioassay guided fractionation led to the isolation of (-)–avenaciolide as the only bioactive constituent of the extract. This is the first report of both the antimycobacterial activity of avenaciolide and its isolation from a Seimatosporium sp. fungus.
Compositional Variability and Antifungal Potentials of Ocimum basilicum, O. tenuiflorum, O. gratissimum and O. kilimandscharicum Essential Oils against Rhizoctonia solani and Choanephora cucurbitarum
Authors: Padalia Rajendra C. , Verma Ram S. , Chauhan Amit , Goswami Prakash , Chanotiya Chandan S. , Saroj Arvind , Samad Abdul , Khaliq Abdul
Published: March 2019

The composition of hydrodistilled essential oils of Ocimum basilicum L. (four chemovariants), O. tenuiflorum L., O. gratissimum L., and O. kilimandscharicum Guerke were analyzed and compared by using capillary gas chromatography (GC/FID) and GC-mass spectrometry (GC/MS). Phenyl propanoids (upto 87.0%) and monoterpenoids (upto 83.3%) were prevalent constituents distributed in the studied Ocimum taxa. The major constituents of the four distinct chemovariants of O. basilicum were methyl chavicol (86.3%), methyl chavicol (61.5%)/linalool (28.6%), citral (65.9%); and linalool (36.1%)/citral (28.8%). Eugenol (66.5% and 78.0%) was the major constituent of O. tenuiflorum and O. gratissimum. Eugenol (34.0%), β-bisabolene (15.4%), ( E)-α-bisabolene (10.9%), methyl chavicol (10.2%) and 1,8-cineole (8.2%) were the major constituents of O. kilimandscharicum. In order to explore the potential for industrial use, the extracted essential oils were assessed for their antifungal potential through poison food technique against two phytopathogens, Rhizoctonia solani and Choanephora cucurbitarum, which cause root and wet rot diseases in various crops. O. tenuiflorum, O. gratissimum, and O. kilimandscharicum exhibited complete growth inhibition against R. solani and C. cucurbitarum after 24 and 48 h of treatment. O. basilicum chemotypes showed variable levels of growth inhibition (63.0%–100%) against these two phytopathogens.
Non-Competitive Inhibition of Acetylcholinesterase by Bromotyrosine Alkaloids
Authors: Olatunji Opeyemi J. , Ogundajo Akintayo L. , Oladosu Ibrahim A. , Changwichit Kanokwan , Ingkaninan Kornkanok , Yuenyongsawad Supreeya , Plubrukarn Anuchit
Published: March 2019

Fifteen bromotyrosine-derived alkaloids were isolated from the sponge Pseudoceratina cf. purpurea. The acetylcholinesterase-inhibiting activity of all the isolated compounds were examined; to purealidin Q, isoanomoian A, aplyzanzine A, and aplysamine 2 were active with IC50 values of 1.2, 70, 104, and 1.3 μM, respectively. On the other hand, antiproliferative activity against MCF-7 cells of aerophobin 1 gave an IC50 value of 0.8 μM. The Michaelis-Menten plots of the active alkaloids indicated that all the four compounds inhibited acetylcholinesterase in a non-competitive manner. The structures of the active compounds suggested that the N, N-dimethylaminopropyloxydibromotyramine moiety may play an important role in the enzyme-inhibiting activity, presumably on the anionic and hydrophobic binding sites.
Phytochemical Analysis, Antioxidant and Anti-Inflammatory Activity of Calyces from Physalis peruviana
Authors: Toro Reina M. , Aragón Diana M. , Ospina Luis F. , Ramos Freddy A. , Castellanos Leonardo
Published: March 2019

Physalis peruviana calyces are used extensively in folk medicine. The crude ethanolic extract and some fractions of calyces were evaluated in order to explore antioxidant and anti-inflammatory activities. The anti-inflammatory activity was evaluated by the TPA-induced ear edema model. The antioxidant in vitro activity was measured by means of the superoxide and nitric oxide scavenging activity of the extracts and fractions. The butanolic fraction was found to be promising due to its anti-inflammatory and antioxidant activities. Therefore, a bio-assay guided approach was employed to isolate and identify rutin (1) and nicotoflorin (2) from their NMR spectroscopic and MS data. The identification of rutin in calyces of P. peruviana supports the possible use of this waste material for phytotherapeutic, nutraceutical and cosmetic preparations.
Phenolic Derivatives from Radix Astragali and their Anti-inflammatory Activities
Authors: Chen Wei , Zhang Ying-Ying , Wang Zhuo , Luo Xiao-Hua , Sun Wan-Chun , Wang Hong-Bing
Published: March 2019

Two new (3, 4) and two known phenolic derivatives (1, 2) were isolated from Radix Astragali. The structures of 1–4 were elucidated by extensive spectroscopic analysis. The anti-inflammatory activities of the isolated compounds were evaluated in LPS-induced mouse peritoneal macrophages. All four compounds exhibited potent inhibitory effects on TNF-α production and TNF-α, COX-2, IL-1β, IL-6 and iNOS mRNA expression at 50 μM.
Composition of Headspace Volatiles and Essential Oils of Three Thymus Species
Authors: Stojanović Gordana , Jovanović Olga , Petrović Goran , Mitić Violeta , Jovanović Vesna Stankov , Jovanović Snežana
Published: March 2019

Analysis of head space volatiles (HSV) and hydrodistilled essential oils (EO) of the above-ground parts of Thymus glabrescens Willd., T. praecox Opiz subsp. jankae (Celak.) Jalas (from two localities) and T. pulegoides L. was made by GC-FID and GC-MS. This is the first report on the headspace volatiles composition of T. glabrescens and T. pulegoides. The most abundant compound of T. glabrescens HSV was p-cymene (27.8%) followed by γ-terpinene (18.4%), while thymol (55.4%) and geraniol (10.5%) were the most abundant in the corresponding EO. T. praecox subsp. jankae EO from Serbia was characterized by ( E)-caryophyllene (14.6%) and thymol (10.7%), which is substantially different from that of Bulgarian T. praecox subsp. jankae, which contained α-terpinyl acetate (20.1%) and linalool (17.7%) as its main components. The dominating components of the Serbian and Bulgarian T. praecox subsp. jankae HSV were α-pinene (29.4% and 18.6%, respectively), myrcene (12.1% and 23.2%, respectively), limonene (7.5% and 17.8%, respectively) and β-pinene (11.7% and 7.6%, respectively). Linalyl acetate predominated in T. pulegoides EO and HSV, representing 40.0% and 42.4% (respectively) of the total peak area. The chemical composition of the essential oils of the examined Thymus species could not be attributed to any particular recorded chemotype of T. glabrescens, T praecox and T. pulegoides.
Biobased Lactams as Novel Arthropod Repellents
Authors: Chauhan Kamlesh R. , Khanna Hemant , Bathini Nagendra Babu , Le Thanh C. , Grieco John
Published: March 2019

Enanatiomerically pure 4a S,7 S,7a R and 4a S,7 S,7a S-nepetalactams and their analogs have been prepared in just two steps from 4a S,7 S,7a R and 4a S,7 S,7a S-nepetalactones, major components of catnip oil. Lactams or cyclic amides from iridoid monoterpenes are generated and being evaluated as a new class of compounds as arthropod deterrents against disease vectors.
Two New Aromadendrane Sesquiterpenes from the Stem Bark of Alafia multiflora
Authors: Tchinda Alembert T. , Tsala David E. , Nga Nnanga , Cieckiewicz Ewa , Kiss Robert , Connolly Joseph D. , Frédérich Michel
Published: March 2019

Two new aromadendrane sesquiterpenoids (1β,4β,5β,6α,7α,11 S)-aromadendr-9-en-13,14-dioic acid (1) and (1β,4β,5β,6α,7α,11 S)-13-oxoaromadendr-9-en-14-oic acid (2) have been isolated from the stem bark of Alafia multiflora along with β-sitosterol and β-sitosterol glucoside. Their structures were established on the basis of spectroscopic analyses, including 1D and 2D NMR experiments (1H-1H COSY, NOESY, HSQC, HMBC). Compound 1 showed a weak growth inhibitory activity against the murine melanoma line B16F10 MTT.
Isolation and Structural Characterization of a New Minor Diterpene Glycoside from Stevia rebaudiana
Authors: Chaturvedula Venkata Sai Prakash , Zamora Julian
Published: March 2019

From the commercial extract of the leaves of the sweet plant Stevia rebaudiana Bertoni obtained from Sinochem Qingdao Co. Ltd., a new diterpene glycoside having three β-D-glucopyranosyl units of which two of them were connected in a relatively rare linkage of 3-β-D-glucobiosyl substitution at C-19 position of the aglycone steviol. The structure of the new compound has been characterized as 13-β-D-glucopyranosyloxy ent-kaur-16-en-19-oic acid-[(3-O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester (1) on the basis of extensive 1D (1H and 13C) and 2D NMR (TOCSY, HMQC, and HMBC), and High Resolution mass spectroscopic data as well as hydrolysis studies.
ent-Kaurane Diterpenes from Annona glabra and Their Cytotoxic Activities
Authors: Le Tuan Anh Hoang , Hien Nguyen Thi Thu , Hang Dan Thi Thuy , Ha Tran Minh , Nhiem Nguyen Xuan , Hien Truong Thi Thu , Thu Vu Kim , Thao Do Thi , Minh Chau Van , Kiem Phan Van
Published: March 2019

A new ent-kaurane glycoside, annoglabasin H (1), and three known ent-kauranes, annoglabasin E (2), annoglabasin B (3), and 19-nor- ent-kaurent-4-ol-17-oic acid (4) were isolated from the fruits of Annona glabra. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, as well as by comparison with the NMR data reported in the literature. The cytotoxic activities of these compounds were evaluated on four human cancer cell lines, LU-1, MCF-7, SK-Mel2, and KB. Compound 1 exhibited significant cytotoxic activity on all tested human cancer cell lines with IC50 values ranging from 3.7 to 4.6 μM.
Synthesis and Biological Evaluation of Febrifugine Analogues
Authors: Mai Huong Doan Thi , Thanh Giang Vo , Tran Van Hieu , Vu Van Nam , Vu Van Loi , Le Cong Vinh , Nguyen Thuy Linh , Phi Thi Dao , Truong Bich Ngan , Chau Van Minh , Pham Van Cuong
Published: March 2019

A series of febrifugine analogues were designed and synthesized. Antimalarial activity evaluation of the synthetic compounds indicated that these derivatives had a strong inhibition against both chloroquine-sensitive and -resistant Plasmodium falciparum parasites. Many of them were found to be more active than febrifugine hydrochloride. The tested analogues had also a significant cytotoxicity against four cancer cell lines (KB, MCF7, LU1 and HepG2). Among the synthetic analogues, two compounds 17b and 17h displayed a moderate cytotoxicity while they exhibited a remarkable antimalarial activity.
Flavonoids from Twigs of Millettia pubinervis
Authors: Na Zhi , Song Qi-Shi , Hu Hua-Bin
Published: March 2019

A new flavone, 3-methoxy-5-hydroxy-[2”,3”:7,8] furanoflavone, pubinerone (1), was isolated from the twigs of Millettia pubinervis Kurz, together with ten known flavonoids, karanjin (2), kanjone (3), 3,6-dimethoxy-[2”,3”:7,8] furanoflavone (4), pongaglabrone (5), pongapin (6), pongaflavone (7), 3,6-dimethoxy-6”,6”-dimethylchromene-[2”,3”:7,8] flavone (8), pongachromene (9), 3,6-dimethoxy-3′,4′-methylenedioxy-6”,6”-dimethylchromene-[2”,3”:7,8] flavone (10) and demethoxykanugin (11). This is the first phytochemical investigation of this plant. The structure of compound 1 was elucidated on the basis of spectroscopic data interpretation, including 1D and 2D NMR and HREIMS analysis. The cytotoxicity of 1 against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7 and SW480, was evaluated, but it was inactive (IC50>40μM).
Effect of Osajin and Pomiferin on Antidiabetic Effects from Normal and Streptozotocin-induced Diabetic Rats
Authors: Moon Hyung-In
Published: March 2019

The present study evaluated the antidiabetic effect of osajin and pomiferin from the osajin orange in normal and streptozotocin-induced diabetic rats. Pomiferin in the streptozotocin-induced diabetic effects showed significant hypoglycemic activity for 14 days significantly decreased the serum glucose, triglyceride while it increased the serum insulin in diabetic rats but not in normal rats (p < 0.05; at doses of 100 and 300mg/kg for 14 days). Pomiferin showed potential in anti-diabetic effects compared to osajin. It also has no effects on C-peptide (ECLIA). Further structure-activity relationships of aromatic position 3 on ring B from osajin and pomiferin will be reported in due course.
Two New Homoisoflavonoids from the Bulbs of Bessera elegans
Authors: Matsuo Yukiko , Kurihara Risa , Akagi Nana , Mimaki Yoshihiro
Published: March 2019

A further chemical investigation of the bulbs of Bessera elegans (Liliaceae) led to the isolation of a new homoisoflavonoid (1), a new scillascillin-type homoisoflavonoid (2), three known flavonoids (3–5), and two known norlignans (6 and 7). The structures of the new homoisoflavonoids (1 and 2) were determined based on the results of extensive spectroscopic analysis, including two-dimensional NMR data. The isolated compounds (1–7) were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells and TIG-3 normal human diploid fibroblasts. Compound 1 exhibited potent tumor-selective cytotoxic activity against HL-60 cells.