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Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain
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SYSNO ASEP 0429932 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain Author(s) Cmoch, P. (PL)
Korda, A. (PL)
Rárová, Lucie (UEB-Q) RID, ORCID
Oklešťková, Jana (UEB-Q) RID, ORCID, SAI
Strnad, Miroslav (UEB-Q) RID, ORCID
Luboradzki, R. (PL)
Pakulski, Z. (PL)Source Title Tetrahedron. - : Elsevier - ISSN 0040-4020
Roč. 70, č. 17 (2014), s. 2717-2730Number of pages 14 s. Language eng - English Country GB - United Kingdom Keywords BETULIN DERIVATIVES ; SECONDARY ALCOHOLS ; ANTITUMOR-ACTIVITY 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 000334132800005 DOI 10.1016/j.tet.2014.03.006 Annotation A concise synthesis of lupane triterpenes with an elongated carbon chain at the C-28 position, as well as saponins containing D-mannose, L-arabinose, and L-rhamnose moieties at the C-3 position is described. The overall synthesis of the new triterpenes involved seven linear steps starting from natural betulin: selective protection of a hydroxyl group, oxidation, elongation of the carbon chain by Grignard reaction, and deoxygenation. O-Glycosides were obtained by glycosylation of triterpenes with classical Schmidt's donors. Additionally, all new compounds were evaluated in vitro for their cytotoxic activities. Several triterpenes and the corresponding saponins exhibited an interesting cytotoxic activity profile against human cancer cell lines. The therapeutical index of active triterpenes is very high, since almost none of them were cytotoxic for normal BJ fibroblasts. These results open the way to the synthesis of various lupane-type saponin derivatives as potentially bioactive compounds. Workplace Institute of Experimental Botany Contact David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469 Year of Publishing 2015
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