A New Nortriterpenoid, a Sesquiterpene and Hepatoprotective Lignans Isolated from the Fruit of Schisandra chinensis

Fenghua Li; Ting Zhang; Hua Sun; Haifeng Gu; Hongqing Wang; Xianming Su; Changkang Li; Baoming Li; Ruoyun Chen; Jie Kang

doi:10.3390/molecules22111931

A New Nortriterpenoid, a Sesquiterpene and Hepatoprotective Lignans Isolated from the Fruit of Schisandra chinensis

Molecules. 2017 Nov 10;22(11):1931. doi: 10.3390/molecules22111931.

Authors

Fenghua Li¹, Ting Zhang², Hua Sun³, Haifeng Gu⁴, Hongqing Wang⁵, Xianming Su⁶, Changkang Li⁷, Baoming Li⁸, Ruoyun Chen⁹, Jie Kang¹⁰

Affiliations

¹ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1 Xiannongtan Street, Beijing 100050, China. lifenghua@imm.ac.cn.
² Institute of Medical Information & Library, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 3 Yabao Street, Beijing 100020, China. brendatingting@126.com.
³ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1 Xiannongtan Street, Beijing 100050, China. sunhua@imm.ac.cn.
⁴ Beijing Institute for Drug Control, 25 Science Park Road, Changping District, Beijing 102206, China. ryan-ku@139.com.
⁵ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1 Xiannongtan Street, Beijing 100050, China. wanghongqing@imm.ac.cn.
⁶ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1 Xiannongtan Street, Beijing 100050, China. suxianming@imm.ac.cn.
⁷ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1 Xiannongtan Street, Beijing 100050, China. lichangkang@imm.ac.cn.
⁸ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1 Xiannongtan Street, Beijing 100050, China. libaoming@imm.ac.cn.
⁹ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1 Xiannongtan Street, Beijing 100050, China. rych@imm.ac.cn.
¹⁰ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1 Xiannongtan Street, Beijing 100050, China. jiekang@imm.ac.cn.

Abstract

A new nortriterpenoid, 19(R)-hydroxyl-wuweizidilactone H (1), and a sesquiterpene, (6R)-β-chamigrenic acid (2), together with one known nortriterpenoid, wuweizidilactone H (3), and three known hepatoprotective lignans, micrantherin A (4), gomisin M₂ (5) and schizandrin (6) were isolated from the fruit of Schisandra chinensis. Their structures were elucidated by UV, IR, HRESIMS, NMR spectra and X-ray analysis. Among them, the absolute configuration of 2 was confirmed for the first time. In vitro assays, compounds 4-6 (10 μM) exhibited hepatoprotective activities (survival rate: 44%, 43% and 44%) against damage induced by N-acetyl-p-aminophenol (APAP) in human liver carcinoma (HepG2) cells.

Keywords: Schisandra chinensis; absolute configuration; hepatoprotective activity; lignan; nortriterpenoid; sesquiterpene.

MeSH terms

Cell Survival / drug effects
Crystallography, X-Ray
Fruit / chemistry*
Hep G2 Cells
Humans
Lignans / isolation & purification*
Protective Agents / chemistry
Protective Agents / pharmacology*
Schisandra / chemistry*
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification*
Sesquiterpenes / pharmacology*
Triterpenes / chemistry
Triterpenes / isolation & purification*
Triterpenes / pharmacology*

Substances

Lignans
Protective Agents
Sesquiterpenes
Triterpenes