Synthesis and biological activity of new homolupanes and homolupane saponins

被引：21

作者：

Sidoryk, Katarzyna ^{[1
,2
]}

Korda, Anna ^{[1
]}

Rarova, Lucie ^{[3
,4
,5
]}

Oklestkova, Jana ^{[3
,4
,5
]}

Strnad, Miroslav ^{[3
,4
,5
]}

Cmoch, Piotr ^{[1
]}

Pakulski, Zbigniew ^{[1
]}

Gwardiak, Katarzyna ^{[1
]}

Karczewski, Romuald ^{[1
]}

Luboradzki, Roman ^{[6
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

[2] Pharmaceut Res Inst, PL-01793 Warsaw, Poland

[3] ASCR, Inst Expt Bot, Ctr Reg Hand Biotechnol & Agr Res, Lab Growth Regulators, Olomouc 78371, Czech Republic

[4] ASCR, Inst Expt Bot, Ctr Reg Hand Biotechnol & Agr Res, Dept Chem Biol & Genet, Olomouc 78371, Czech Republic

[5] Palacky Univ, Olomouc 78371, Czech Republic

[6] Polish Acad Sci, Inst Phys Chem, PL-01224 Warsaw, Poland

来源：

TETRAHEDRON | 2015年 / 71卷 / 13期

关键词：

Homobetulin; Homobetulinic acid; Glycosylation; Lupane saponins; Homolupane saponins; SAR study; BETULINIC ACID-DERIVATIVES; 3-BETA-O-MONODESMOSIDIC SAPONINS; ANTITUMOR-ACTIVITY; HEMOLYTIC-ACTIVITY; GERMANICANE-TYPE; AGENTS; CYTOTOXICITY;

D O I：

10.1016/j.tet.2015.02.008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of 28a-homolupane triterpenes and the corresponding saponins containing D-mannose, D-idose, D-arabinose, and L-rhamnose moieties was elaborated. The overall synthesis of the new triterpenes involved three linear steps starting from readily available 3-O-acetyl-betulinal: elongation of the carbon chain by Wittig reaction followed by enol ether hydrolysis and reduction (or oxidation) of the elongated aldehyde. Saponins were obtained by glycosylation of triterpenes with classical Schmidt donors. Cytotoxic activities of new lupane and homolupane compounds were evaluated in vitro. Several triterpenes and the corresponding saponins exhibited an interesting cytotoxic activity profile against human cancer cell lines. Influence of the side-chain structure and substituents on the cytotoxicity of betulin and homobetulin derivatives was investigated. These results open the way to the synthesis of various lupane-type triterpene and saponin derivatives as potential anticancer compounds. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2004 / 2012

页数：9

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