Influence of intramolecular hydrogen bonds on regioselectivity of glycosylation. Synthesis of lupane-type saponins bearing the OSW-1 saponin disaccharide unit and its isomers

0459173 - ÚEB 2017 RIV NL eng J - Journal Article
Kuczynska, K. - Cmoch, P. - Rárová, L. - Oklešťková, Jana - Korda, A. - Pakulski, Z. - Strnad, Miroslav
Influence of intramolecular hydrogen bonds on regioselectivity of glycosylation. Synthesis of lupane-type saponins bearing the OSW-1 saponin disaccharide unit and its isomers.
Carbohydrate Research. Roč. 423, MAR 24 (2016), s. 49-69. ISSN 0008-6215. E-ISSN 1873-426X
R&D Projects: GA MŠMT(CZ) LO1204; GA ČR GA14-19590S
Institutional support: RVO:61389030
Keywords : OSW-1 disaccharide * Glycosylation * Lupane saponins
Subject RIV: EB - Genetics ; Molecular Biology
Impact factor: 2.096, year: 2016

A series of lupane-type saponins bearing OSW-1 disaccharide unit as well as its regio- and stereoisomers were prepared and used for the structure-activity relationships (SAR) study. Unexpected preference for 1 -> 4-linked regioisomers and an unusual inversion of the conformation of the sugar rings were noted. Cytotoxic activity of new lupane compounds was evaluated in vitro and revealed that some saponins exhibited an interesting bioactivity profile against human cancer cell lines. Influence of the protecting groups on the cytotoxicity 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/11104/0259411