Terpenoids from Flueggea virosa and their anti-hepatitis C virus activity. (August 2016)

• Record Type: Journal Article
• Authors: Chao, Chih-Hua; Cheng, Ju-Chien; Shen, De-Yang; Huang, Hui-Chi; Wu, Yang-Chang; Wu, Tian-Shung
• Is Part Of: Phytochemistry. Volume 128(2016:Aug.)
• Page Start: 60
• Page End: 70
• Publication Date: 2016-08
• Subjects: Flueggea virosa -- Euphorbiaceae -- Anti-hepatitis C virus -- ent-Podocarpane -- 3, 4-seco-30-nor-Friedelane; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2016.04.003
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: 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 1 H 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. Graphical abstract: 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. Highlights: 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.