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

Chih-Hua Chao; Ju-Chien Cheng; De-Yang Shen; Hui-Chi Huang; Yang-Chang Wu; Tian-Shung Wu

doi:10.1016/j.phytochem.2016.04.003

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

Phytochemistry. 2016 Aug:128:60-70. doi: 10.1016/j.phytochem.2016.04.003. Epub 2016 Apr 21.

Authors

Chih-Hua Chao¹, Ju-Chien Cheng², De-Yang Shen³, Hui-Chi Huang⁴, Yang-Chang Wu⁵, Tian-Shung Wu⁶

Affiliations

¹ School of Pharmacy, China Medical University, Taichung 40402, Taiwan; Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 40447, Taiwan. Electronic address: chaochihhua@hotmail.com.
² Department of Medical Laboratory Science and Biotechnology, China Medical University, Taichung 40402, Taiwan.
³ Department of Pharmacy, National Cheng Kung University, Tainan 70101, Taiwan.
⁴ Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 40402, Taiwan.
⁵ School of Pharmacy, China Medical University, Taichung 40402, Taiwan; Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 40447, Taiwan; Center for Molecular Medicine, China Medical University Hospital, Taichung 40447, Taiwan; Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
⁶ Department of Pharmacy, National Cheng Kung University, Tainan 70101, Taiwan; Department of Pharmacy and Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 90741, Taiwan. Electronic address: tswu@mail.ncku.edu.tw.

PMID: 27112277
DOI: 10.1016/j.phytochem.2016.04.003

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.

Keywords: 3,4-seco-30-nor-Friedelane; Anti-hepatitis C virus; Euphorbiaceae; Flueggea virosa; ent-Podocarpane.

MeSH terms

Antiviral Agents / chemistry
Antiviral Agents / isolation & purification*
Antiviral Agents / pharmacology*
Carcinoma, Hepatocellular / drug therapy
Euphorbiaceae / chemistry*
Hepacivirus / drug effects*
Humans
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Roots / chemistry
Triterpenes / analysis
Triterpenes / isolation & purification*
Triterpenes / pharmacology*

Substances

Antiviral Agents
Triterpenes