Synthesis and biological activity of new homolupanes and homolupane saponins

0446691 - ÚEB 2016 RIV GB eng J - Journal Article
Sidoryk, K. - Korda, A. - Rárová, Lucie - Oklešťková, Jana - Strnad, Miroslav - Cmoch, P. - Pakulski, Z. - Gwardiak, K. - Karczewski, R. - Luboradzki, R.
Synthesis and biological activity of new homolupanes and homolupane saponins.
Tetrahedron. Roč. 71, č. 13 (2015), s. 2004-2012. ISSN 0040-4020. E-ISSN 1464-5416
R&D Projects: GA MŠMT(CZ) LO1204
Institutional support: RVO:61389030
Keywords : Homobetulin * Homobetulinic acid * Glycosylation
Subject RIV: EB - Genetics ; Molecular Biology
Impact factor: 2.645, year: 2015

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.
Permanent Link: http://hdl.handle.net/11104/0248670