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Phi T.D.,Institute of Marine biochemistry | Pham V.C.,Institute of Marine biochemistry | Thi Mai H.D.,Institute of Marine biochemistry | Litaudon M.,CNRS Natural Product Chemistry Institute | And 3 more authors.
Journal of Natural Products | Year: 2011

Four new steroids, 3-epi-gitingensine (1), N-acetylgitingensine (6), kibalaurifoline (7) and kibalaurifenone (8), along with the known para-allarine (2), 7α-hydroxypara-allarine (3), gitingensine (4), and N-methylgitingensine (5) were isolated from the lea-es of Kibatalia laurifolia. Their structures were determined primarily from mass spectrometry and 2D NMR analyses. On the basis of the known absolute configurations of 2 and 4, the absolute configurations of the new compounds were proposed. Due to the structural relationships of compounds 1-8, a biosynthetic pathway was suggested. Compound 2 was cytotoxic to KB cells (IC 50 12.8 μM), followed by 1 with IC 50 21.2 μM. (Chemical Equation Presented). © 2011 The American Chemical Society and American Society of Pharmacognosy.


Hanh N.P.,Vietnam Academy of Science and Technology | Phan N.H.T.,Tay Nguyen Institute for Scientific Research | Thuan N.T.D.,Tay Nguyen Institute for Scientific Research | Hanh T.T.H.,Institute of Marine Biochemistry | And 9 more authors.
Natural Product Research | Year: 2016

Six iridoid derivatives (1–6), including two new compounds myrmecodoides A and B (1 and 2), were isolated from the ant-plant Myrmecodia tuberosa. Their structures were determined on the basis of spectroscopic data (1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, NOESY and HR-ESI-MS) and by comparison with the literature values. Among isolates, 3 and 4 exhibit weak antibacterial effect against Staphylococcus aureus subsp. aureus with MIC value of 100.0 μg/mL. © 2015 Taylor & Francis.


Tai B.H.,Chungnam National University | Tai B.H.,Institute of Natural Products Chemistry | Nhiem N.X.,Chungnam National University | Nhiem N.X.,Institute of Marine Biochemistry | And 8 more authors.
Bioorganic and Medicinal Chemistry Letters | Year: 2011

A new iridoid, named methylscutelloside (1) together with 19 known compounds belonging to the iridoids (2-4), monoterpenoids (5), flavonoids (6-8), triterpenoids (9-14), and phenylethanoids (15-20) were isolated from the flowers of Buddleja officinalis. Their chemical structures were elucidated on the basis of physicochemical properties, and by spectroscopic methods including 1D, 2D NMR, and MS. All isolated compounds were tested in vitro for their effects on the proliferation of rat aortic vascular smooth muscle cells (VSMCs). Among them, iridoids were the main active components and showed significant inhibitory effects on PDGF-BB-induced proliferation in rat aortic VSMCs. © 2011 Elsevier Ltd. All rights reserved. © 2011 Elsevier Ltd. All rights reserved.


Ho D.V.,Hue University | Kodama T.,University of Toyama | Le H.T.B.,Hue University | Phan K.V.,Institute of Marine Biochemistry | And 8 more authors.
Bioorganic and Medicinal Chemistry Letters | Year: 2015

Abstract A new polyoxygenated cyclohexene, (-)-3-O-debenzoylzeylenone (1), and a new megastigmane glycoside, grandionoside A (2), were isolated from the aerial parts of Uvaria grandiflora collected in Vietnam, together with ten known compounds including polyoxygenated cyclohexenes (3-6), a triterpenoid (7), an alkaloid (8), a long chain alcohol (9), hexenyl glycopyranoside (10), and saponins (11-12). Their chemical structures were elucidated by a combination of extensive NMR spectroscopy with X-ray crystallographic analysis for 1, and chemical conversion for 2. Compound 1 exhibited significant cytotoxicity against the LU-1 and SK-Mel-2 cell lines with IC50 values of 4.68 and 3.63 μM, respectively. Remarkably, the cytotoxicity of 12 against the LU-1, KB, Hep-G2, MKN-7, and SW-480 cell lines was comparable to that of ellipticine, the positive control, with IC50 values ranging from 1.24 to 1.60 μM. © 2015 Elsevier Ltd.


PubMed | Institute of Biotechnology, Tokushima Bunri University, University of Toyama, Institute of Marine Biochemistry and 3 more.
Type: Journal Article | Journal: Bioorganic & medicinal chemistry letters | Year: 2015

A new polyoxygenated cyclohexene, (-)-3-O-debenzoylzeylenone (1), and a new megastigmane glycoside, grandionoside A (2), were isolated from the aerial parts of Uvaria grandiflora collected in Vietnam, together with ten known compounds including polyoxygenated cyclohexenes (3-6), a triterpenoid (7), an alkaloid (8), a long chain alcohol (9), hexenyl glycopyranoside (10), and saponins (11-12). Their chemical structures were elucidated by a combination of extensive NMR spectroscopy with X-ray crystallographic analysis for 1, and chemical conversion for 2. Compound 1 exhibited significant cytotoxicity against the LU-1 and SK-Mel-2 cell lines with IC50 values of 4.68 and 3.63 M, respectively. Remarkably, the cytotoxicity of 12 against the LU-1, KB, Hep-G2, MKN-7, and SW-480 cell lines was comparable to that of ellipticine, the positive control, with IC50 values ranging from 1.24 to 1.60 M.


Le H.T.,National Institute of Medicinal Materials | Ha D.T.,National Institute of Medicinal Materials | Minh C.T.A.,Yeungnam University | Kim T.H.,Yeungnam University | And 3 more authors.
Archives of Pharmacal Research | Year: 2012

Phytochemical investigation of the stem barks of Canarium bengalense (Burseraceace) resulted in the isolation of a new flavone glycoside (5) together with six known compounds (1-4, 6, and 7). The chemical structure of the new compound was elucidated as 3′-hydroxy-7,4′-dimethoxyflavone-5-O- α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside by means of 1D and 2D NMR ( 1H- 1H COSY, HMQC, and HMBC) and MS analyses. To evaluate the in vitro cytoprotective effect, the isolates (1-7) were tested against hydrogen peroxide (H 2O 2)-induced damage in primary cultured hepatocytes. The viability of hepatocytes was increased by treatment with each compound, except compound 1. Compounds 3, 4, and 7 exerted cytoprotective effects comparable to curcumin, the positive control. Our results suggest that the cytoprotective constituents of C. bengalense may contribute to its traditional use in the treatment of tumor and liver damage. © 2012 The Pharmaceutical Society of Korea and Springer Netherlands.


Nhiem N.X.,Chungnam National University | Nhiem N.X.,Institute of Marine Biochemistry | Kim K.C.,Jeju National University | Kim A.-D.,Jeju National University | And 9 more authors.
Journal of Asian Natural Products Research | Year: 2011

By various chromatographic methods, one new phenylpropanoid, acanthopanic acid (1), and three known compounds, 1,2-O-dicaffeoylcyclopenta-3-ol (2), (4S)-α- terpineol 8-O-β- D-glucopyranoside (3), and rutin (4), were isolated from the methanol extract of the Acanthopanax koreanum leaves. Their structures were elucidated on the basis of spectroscopic analyses, and their antioxidant activities were evaluated by the intracellular reactive oxygen species (ROS) radical scavenging 2',7'-dichlorofluorescein diacetate assay. Among them, compounds 1, 2, and 4 showed significant scavenging capacity with IC50 values of 3.8, 2.6, and 2.9μM, respectively, and compound 3 showed weak scavenging capacity with the inhibition rate of 37% at 40μM. © 2011 Taylor & Francis.


Van N.T.H.,Vietnam Academy of Science and Technology | Vien T.A.,Industrial University of Ho Chi Minh City | Nhiem N.X.,Institute of Marine Biochemistry | Van Kiem P.,Institute of Marine Biochemistry | And 9 more authors.
Natural Product Communications | Year: 2014

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.


Van Nguyen H.,Institute of Marine Biochemistry | Van Pham C.,Institute of Marine Biochemistry | Do T.T.,Institute of Biotechnology | Mai H.D.T.,Institute of Marine Biochemistry | And 6 more authors.
Natural Product Communications | Year: 2014

New oseltamivir analogues were designed and synthesized, starting from shikimic acid. Biological evaluation against three human cancer cell lines (KB, MCF7 and Lu-1) showed that many of them exhibited cytotoxic activity. Azides 5 are more active than the corresponding amines 6. Thus, the reduction of the azide group into amine led to the loss of cytotoxicity. The compounds with a cyclohexanemethyloxy group at C-3 were more active than the other investigated compounds belonging to the same series. This cyclohexanemethyloxy group seems to be critical for the cytotoxic activity of this class of compounds. The synthetic oseltamivir analogues 6a-e had no inhibition activity, even at the concentration of 50 μM when they were evaluated for their in vitro influenza A neuraminidase inhibitory activity by an enzymatic assay.


Phan N.H.T.,Vietnam Academy of Science and Technology | Thuan N.T.D.,Vietnam Academy of Science and Technology | Ngoc N.T.,Institute of Marine Biochemistry | Huong P.T.M.,Institute of Marine Biochemistry | And 6 more authors.
Phytochemistry Letters | Year: 2014

Various chromatographic separations of the methanolic extract of Paramignya scandens stem and leaves resulted in the isolation of two new tirucallane derivatives, paramignyols A and B (1 and 2). Their structures were established by HR-ESI-MS, 1D and 2D NMR experiments, as well as, comparison with literature data. Compounds 1 and 2 showed significant cytotoxic activity (IC50s ∼ 3.55-10.50 μM) on four tested human cancer cell lines: KB (epidermoid carcinoma), SK-Mel-2 (melanoma), LU-1 (lung adenocarcinoma), and MCF7 (breast cancer). This is the first report on chemical constituents and biological activities of P. scandens. © 2014 Phytochemical Society of Europe.

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