Dibenzocyclooctadiene lignans from the fruits of Schisandra chinensis and their cytotoxicity on human cancer cell lines

Sung-Kyu Choi,Hyoung-Geun Kim,Dae Young Lee,Dahye Yoon,Nam-In Baek,Rong Bo Wang,Yeon-Ju Kim,Yeong-Geun Lee

doi:10.1186/s13765-020-00524-y

Abstract

Repeated chromatographic separations of the EtOAc fraction of Schisandra chinensis fruits on silica gel, octadecyl silica gel, and Sephadex LH-20 led to the isolation and identification of seven dibenzocyclooctadiene lignans (1–7). The NMR data reported in the literature for angeloyl gomisin H (5) were shown to be incorrect. We unambiguously identified the compounds based on detailed analysis of the 1D and 2D NMR data, especially from HMBC and NOESY experiments. In addition, MTT assays and cell viability experiments verified the cytotoxicity of the isolated dibenzocyclooctadiene lignans against the human cancer cell lines AGS, HeLa, and HT-29.

Highlights

Schisandra chinensis is a deciduous woody vine native to Far East Asia
Phytochemical studies of S. chinensis fruits have led to the isolation of lignans, triterpenoids, monoterpenes, sesquiterpenes, organic acids, and sterols, [3, 4] among which dibenzocyclooctadiene lignans are overwhelmingly the major components [5]
This paper describes the isolation for seven dibenzocyclooctadiene lignans from the fruits of S. chinensis, structure determination of the isolation ones, especially angeloyl gomisin H (5)

Summary

Introduction

Schisandra chinensis is a deciduous woody vine native to Far East Asia. The fruits, red berries called “Omija” in South Korea, have been used as food as well as a traditional medicine with hepaprotective, cardiovascular, and antibacterial benefits [1, 2]. S. chinensis extracts and some dibenzocyclooctadiene lignans from this plant have been reported to be cytotoxic to certain cancer cell lines [6,7,8,9]. This paper describes the isolation for seven dibenzocyclooctadiene lignans from the fruits of S. chinensis, structure determination of the isolation ones, especially angeloyl gomisin H (5). Their cytotoxicities were evaluated against several human cancer cell lines (AGS, HeLa, and HT-29), and the relationship of their structure to their activity

Materials and methods

R4 eq ax OCH3

Results and discussion