Nuphar alkaloids with immediately apoptosis-inducing activity from Nuphar pumilum and their structural requirements for the activity

被引：48

作者：

Matsuda, H ^{[1
]}

Yoshida, K ^{[1
]}

Miyagawa, K ^{[1
]}

Nemoto, Y ^{[1
]}

Asao, Y ^{[1
]}

Yoshikawa, M ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Yamashima Ku, Kyoto 6078412, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2006年 / 16卷 / 06期

关键词：

Nuphar alkaloids; 6-hydroxythiobinupharidine; apoptosis-inducing activity; cytotoxic effect; caspases; U937; B16F10; HT1080;

D O I：

10.1016/j.bmcl.2005.12.032

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The methanolic extract and its alkaloid fraction from the rhizomes of Nuphar pumilum showed cytotoxic effects on human leukemia cell (U937), mouse melanoma cell (B16F10), and human fibroblast (HT 1080). Dimeric sesquiterpene thioalkaloids with the 6-hydroxyl group (6-hydroxythiobinupharidine, 6,6'-dihydroxythiobinupharidine, 6-hydroxythionuphlutine B) showed substantial cytotoxic activity at a concentration of 10 mu M, but dimeric sesquiterpene thioalkaloids lacking the 6-hydroxyl group (thiobinupharidine, thionuphlutine B, 6'-hydroxythionuphlutine B, neothiobinupharidine, thionuphlutine B beta-sulfoxide, and neothiobinupharidine beta-sulfoxide) and monomeric sesquiterpene alkaloids (nupharidine, 7-epideoxynupharidine, and nupharolutine) showed weak activity. Next, apoptosis-inducing activity of a principal active constituent, 6-hydroxythiobinupharidine, on U937 was examined using morphological observation and DNA fragmentation assay (TUNEL method). Apoptosis of U937 was immediately observed within 1 h after treatment of 6-hydroxythiobinupharidine at 2.5-10 mu M. (C) 2006 Published by Elsevier Ltd.

引用

页码：1567 / 1573

页数：7

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