从云南风车子中分离并合成一种新的生物活性鞣花酸衍生物。

Isolation and synthesis of a new bioactive ellagic acid derivative from Combretum yunnanensis.

作者信息

Asami Yukihiro, Ogura Takashi, Otake Noboru, Nishimura Toshio, Xinsheng Yao, Sakurai Takashi, Nagasawa Hiromichi, Sakuda Shohei, Tatsuta Kuniaki

机构信息

Department of Biosciences, School of Science and Technology, Teikyo University, 1-1 Toyosatodai, Utsunomiya 320-8551, Japan.

出版信息

J Nat Prod. 2003 May;66(5):729-31. doi: 10.1021/np030041j.

DOI:10.1021/np030041j

PMID:12762821

Abstract

A new ellagic acid derivative (1) was isolated from the branches of Combretum yunnanensis, and its structure was assigned as 4-(4' '-O-acetyl-alpha-rhamnopyranosyl)ellagic acid by analysis of its spectral data. Total synthesis of 1 was achieved by the glycosylation of 3,3'-di-O-benzylellagic acid (5) with 4-O-acetyl-2,3-di-O-benzyl-l-rhamnose (4) as a key reaction, and the absolute configuration of 1 was determined. Compound 1 showed weak inhibitory activity against the growth of various tumor cells and inhibited HIV-1 protease.

摘要

从云南风车子的树枝中分离出一种新的鞣花酸衍生物（1），通过光谱数据分析，其结构被确定为4-（4''-O-乙酰基-α-鼠李糖基）鞣花酸。以3,3'-二-O-苄基鞣花酸（5）与4-O-乙酰基-2,3-二-O-苄基-L-鼠李糖（4）的糖基化反应为关键反应，实现了1的全合成，并确定了1的绝对构型。化合物1对多种肿瘤细胞的生长显示出微弱的抑制活性，并能抑制HIV-1蛋白酶。