Synthesis of β-hederin and Hederacolchiside A1:: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety

被引：47

作者：

Cheng, MS ^{[1
]}

Yan, MC ^{[1
]}

Liu, Y ^{[1
]}

Zheng, LG ^{[1
]}

Liu, J ^{[1
]}

机构：

[1] Shenyang Pharmaceut Univ, Key Lab New Drugs Design, Sch Pharmaceut Engn, Shenyang 110016, Peoples R China

来源：

CARBOHYDRATE RESEARCH | 2006年 / 341卷 / 01期

关键词：

beta-hederin; Hederacolchiside A(1); alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside; cytotoxicity-inducing oligosaccharide; triterpenoid saponin; stepwise glycosylation;

D O I：

10.1016/j.carres.2005.10.015

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 [生物化学与分子生物学]; 081704 [应用化学];

摘要：

A facile synthetic approach toward oleanolic acid glycoside bearing alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl moiety, a unique oligosaccharide that strongly induces antitumor activity of oleanane-type triterpenoid saponins, was developed. Based on this approach P-hederin (oleanolic acid 3-0-Gt-L-rhamnopyranosyl-(1 -> 2)-alpha- L-arabinopyrano side) was efficiently prepared from oleanolic acid through stepwise glycosylation in linear eight steps with 52% overall yield, while Hederacolchiside A, (oleanolic acid 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[beta-D-glucopyranosyl-(1 -> 4)]-alpha-L-arabinopyranoside) in linear 13 steps with 20% overall yield. (c) 2005 Published by Elsevier Ltd.

引用

页码：60 / 67

页数：8

共 32 条

[1]

Inhibition of HUVEC tubulogenesis by hederacolchiside-A1 is associated with plasma membrane cholesterol sequestration and activation of the Ha-Ras/MEK/ERK cascade [J].