Lignans from Schisandra sphenathera Rehd. et Wils. and semisynthetic schisantherin A analogues: Absolute configuration, and their estrogenic and anti-proliferative activity

被引：28

作者：

Liu, Han-Wei ^{[1
]}

Yu, Xiu-Zhu ^{[1
]}

Padula, Daniele ^{[2
]}

Pescitelli, Gennaro ^{[2
]}

Lin, Zhi-Wei ^{[3
]}

Wang, Fei ^{[3
]}

Ding, Kai ^{[4
]}

Lei, Ming ^{[1
]}

Gao, Jin-Ming ^{[1
]}

机构：

[1] Northwest A&F Univ, Coll Sci, Shaanxi Engn Ctr Bioresource Chem & Sustainable U, Yangling 712100, Shaanxi, Peoples R China

[2] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy

[3] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

[4] Chinese Acad Sci, Shanghai Inst Mat Med, Glycochem & Glycobiol Lab, Shanghai 201203, Peoples R China

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 59卷

基金：

中国博士后科学基金;

关键词：

Natural products; Structure elucidation; Circular dichroism; Estrogenic activity; Antitumor agents; Schisandra sphenathera Rehd. et Wils; SCHIZANDRA-CHINENSIS BAILL; DIBENZOCYCLOOCTADIENE LIGNANS; CHIROPTICAL PROPERTIES; CIRCULAR-DICHROISM; GOMISIN-F; CONSTITUENTS; CONFORMATION; STEMS;

D O I：

10.1016/j.ejmech.2012.11.003

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new dibenzocyclooctene-type lignan, named schisandrin A1 (1), together with nine known lignans (2-10), was isolated from the stems of Schisandra sphenathera. The structure of schisandrin A1, which contains a spirocyclic epoxy unit, was established by means of spectroscopic methods. The absolute configurations of schisandrin A1 (1) and schisantherin A (2) were determined by electronic circular dichroism (CD) and TDDFT calculations, with 2 further confirmed by X-ray crystallographic data. Ten new schisantherin A derivatives (11-20) and 6,7-secoschisantherol A (2b) were synthesized. In addition, natural lignans and semisynthetic schisantherin A derivatives showed the antiproliferative activity on four human cancer cell lines and Id1 (an inhibitor of DNA binding protein) and estrogenic potency. Compounds 5, 7, and 8 exhibited very potent estrogenic activity. (C) 2012 Elsevier Masson SAS. All rights reserved.

引用

页码：265 / 273

页数：9

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