Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer

被引：14

作者：

Ren, Li ^{[1
]}

Liu, Yong-Xiang ^{[1
]}

Lv, Dan ^{[1
]}

Yan, Mao-Cai ^{[1
]}

Nie, Han ^{[1
]}

Liu, Yang ^{[1
]}

Cheng, Mao-Sheng ^{[1
]}

机构：

[1] Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, Shenyang 110016, Peoples R China

来源：

MOLECULES | 2013年 / 18卷 / 12期

基金：

中国国家自然科学基金;

关键词：

oleanolic acid saponin; stepwise glycosylation; tumor cytotoxicity; chair conformational fluctuation; DISACCHARIDE MOIETY; BETA-HEDERIN; URSOLIC ACID; BEARING; CELLS; OLIGOSACCHARIDES; DERIVATIVES; A(1);

D O I：

10.3390/molecules181215193

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The first chemical synthesis of the natural triterpenoid saponin Patrinia-glycoside B-II, namely oleanolic acid 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[beta-D-gluco-pyranosyl( 1 -> 3)]-alpha-L-arabinopyranoside, has been accomplished in a linear 11-step sequence 11 with 9.4% overall yield. The abnormal C-1(4) conformation of the arabinose residue was found to occur via conformational fluctuation during preparation of the intermediates. Molecular mechanism and quantum chemistry calculations showed that Patrinia-glycoside B-II and its conformer 1 cannot interconvert under normal conditions. Preliminary structure-activity relationships studies indicated that the C-4(1) chair conformation of the arabinose residue in the unique alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl disaccharide moiety is one of the chief positive factors responsible for its cytotoxic activity against tumors.

引用

页码：15193 / 15206

页数：14

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