Number of the records: 1
Synthesis and Cytotoxicity of 28a-Homothiolupanes and 28a-Homothiolupane Saponins
- 1.
SYSNO ASEP 0457676 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis and Cytotoxicity of 28a-Homothiolupanes and 28a-Homothiolupane Saponins Author(s) Sidoryk, K. (PL)
Korda, A. (PL)
Rárová, Lucie (UEB-Q) RID, ORCID
Oklešťková, Jana (UEB-Q) RID, ORCID, SAI
Pakulski, Z. (PL)
Strnad, Miroslav (UEB-Q) RID, ORCID
Cmoch, P. (PL)
Gwardiak, K. (PL)
Karczewski, R. (PL)Source Title European Journal of Organic Chemistry - ISSN 1434-193X
-, č. 2 (2016), s. 373-383Number of pages 11 s. Language eng - English Country DE - Germany Keywords Natural products ; Saponins ; Terpenoids Subject RIV EB - Genetics ; Molecular Biology R&D Projects LO1204 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Institutional support UEB-Q - RVO:61389030 UT WOS 000368814900020 DOI 10.1002/ejoc.201501147 Annotation A concise synthesis of 28a-homo-28a-thiolupane triterpenes and the corresponding saponins containing D-mannose, D-idose, L-arabinose and L-rhamnose moieties was elaborated. New triterpenes were obtained from readily available 3-O-allylbetulinal by elongation of the carbon chain by Wittig reaction, followed by hydrolysis of the enol ether, reduction of the elongated aldehyde and nucleophilic substitution of the corresponding mesylate with thiocyanate ion. Saponins were obtained by glycosylation of triterpenes with classical Schmidt donors. The cytotoxic activities of the new homothiolupane compounds were evaluated in vitro, revealing that some triterpenes and the corresponding saponins exhibited interesting cytotoxic activity profiles against human cancer cell lines. An unexpected influence of the allyl protecting group on the cytotoxicity of homothiobetulin derivatives was revealed. These results open the way to the synthesis of various lupane-type derivatives containing sulfur in the lupane side chain as potential anticancer compounds. Workplace Institute of Experimental Botany Contact David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469 Year of Publishing 2016
Number of the records: 1