Terpenoids from Flueggea virosa and their anti-hepatitis C virus activity

Phytochemical study of the methanolic root extract of Flueggea virosa allowed for the characterization of 18 non-alkaloid terpenoids. Their structures have skeletons composed of six rearranged ent-podocarpanes, 11 ent-podocarpanes, and a 3,4-seco-30-nor-friedelane. These were characterized based on...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2016-08, Vol.128, p.60-70
Main Authors: Chao, Chih-Hua, Cheng, Ju-Chien, Shen, De-Yang, Huang, Hui-Chi, Wu, Yang-Chang, Wu, Tian-Shung
Format: Article
Language:English
Subjects:
3,4-seco-30-nor-Friedelane
Anti-hepatitis C virus
Antiviral Agents - chemistry
Antiviral Agents - isolation & purification
Antiviral Agents - pharmacology
Carcinoma, Hepatocellular - drug therapy
ent-Podocarpane
Euphorbiaceae
Euphorbiaceae - chemistry
Flueggea virosa
Hepacivirus - drug effects
Hepatitis C virus
Humans
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Roots - chemistry
Triterpenes - analysis
Triterpenes - isolation & purification
Triterpenes - pharmacology
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Summary:Phytochemical study of the methanolic root extract of Flueggea virosa allowed for the characterization of 18 non-alkaloid terpenoids. Their structures have skeletons composed of six rearranged ent-podocarpanes, 11 ent-podocarpanes, and a 3,4-seco-30-nor-friedelane. These were characterized based on 2D NMR, IR, UV, and MS spectroscopic analysis and their absolute configurations were determined by single-crystal X-ray studies, as well as by 1H NMR spectroscopic analysis for the corresponding chiral derivatives. The isolates were evaluated for therapeutic potential against hepatitis C virus (HCV) infection to human hepatoma Huh7.5 cells. Terpenoids with anti-HCV activity were identified from Flueggea virosa. The 9(10 → 20)-abeo-ent-podocarpanes were reported from this genus for the first time. The amide coupling reaction on 3,4-seco-30-nor-friedelane yielded unexpected compounds. [Display omitted] •18 terpenoids with anti-HCV activity were identified from Flueggea virosa.•Their structures were elucidated by 2D NMR, IR, UV, and MS spectroscopic analysis.•9(10 → 20)-abeo-ent-podocarpane was reported from this genus.•The amide coupling reaction on 3,4-seco-30-nor-friedelane yielded unexpected compounds.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2016.04.003