Počet záznamů: 1
Synthesis and Cytotoxicity of 28a-Homothiolupanes and 28a-Homothiolupane Saponins
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SYSNO ASEP 0457676 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Synthesis and Cytotoxicity of 28a-Homothiolupanes and 28a-Homothiolupane Saponins Tvůrce(i) 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)Zdroj.dok. European Journal of Organic Chemistry - ISSN 1434-193X
-, č. 2 (2016), s. 373-383Poč.str. 11 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova Natural products ; Saponins ; Terpenoids Vědní obor RIV EB - Genetika a molekulární biologie CEP LO1204 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy Institucionální podpora UEB-Q - RVO:61389030 UT WOS 000368814900020 DOI 10.1002/ejoc.201501147 Anotace 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. Pracoviště Ústav experimentální botaniky Kontakt David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469 Rok sběru 2016
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