Isolation and anti-hepatitis B virus activity of dibenzocyclooctadiene lignans from the fruits of Schisandra chinensis

Yongbo Xue; Xifeng Li; Xue Du; Xiaonian Li; Weiguang Wang; Jianhong Yang; Jijun Chen; Jianxin Pu; Handong Sun

doi:10.1016/j.phytochem.2015.03.009

Isolation and anti-hepatitis B virus activity of dibenzocyclooctadiene lignans from the fruits of Schisandra chinensis

Phytochemistry. 2015 Aug:116:253-261. doi: 10.1016/j.phytochem.2015.03.009. Epub 2015 Apr 13.

Authors

Yongbo Xue¹, Xifeng Li², Xue Du³, Xiaonian Li³, Weiguang Wang³, Jianhong Yang³, Jijun Chen³, Jianxin Pu⁴, Handong Sun⁵

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China; Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, PR China.
² Chemical Biology Research Center, Yanbian University, Yanji 133002, PR China.
³ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China.
⁴ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China. Electronic address: pujianxin@mail.kib.ac.cn.
⁵ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China. Electronic address: hdsun@mail.kib.ac.cn.

PMID: 25882501
DOI: 10.1016/j.phytochem.2015.03.009

Abstract

Seven lignans with a dibenzocyclooctadiene skeleton, termed schinlignans A-G, and a 6,7-seco-homolignan, schischinone, together with seven known lignans, were isolated from the fruits of Schisandra chinensis (Turcz.) Baill. Their structures were elucidated by extensive spectroscopic methods, including HRESIMS, IR, UV, and 2D NMR (COSY, HMQC, COSY, and HMBC experiments). The stereochemistry at the chiral centers and the biphenyl moiety, were determined using ROESY, as well as via interpretation of their ECD spectra. Schinlignan G and methylgomisin O exhibited potent anti-hepatitis B virus activity against HBV DNA replication with IC50 values of 5.13 and 5.49μgmL(-1), respectively.

Keywords: 6,7-Seco-homolignan; Dibenzocyclooctadiene lignans; Hepatitis B virus; Schisandra chinensis; Schisandraceae.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antiviral Agents / chemistry
Antiviral Agents / isolation & purification*
Antiviral Agents / pharmacology*
Cyclooctanes / chemistry
Cyclooctanes / isolation & purification*
Cyclooctanes / pharmacology*
Fruit / chemistry
Hepatitis B virus / drug effects*
Humans
Lignans / chemistry
Lignans / isolation & purification*
Lignans / pharmacology*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Schisandra / chemistry*

Substances

Antiviral Agents
Cyclooctanes
Lignans
dibenzocyclooctadiene
dibenzocyclooctadiene lignan