Synthesis and biological activity of new homolupanes and homolupane saponins

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F15%3A33157597" target="_blank" >RIV/61989592:15310/15:33157597 - isvavai.cz</a>
Alternative codes found
RIV/61389030:_____/15:00446691
Result on the web
<a href="http://www.sciencedirect.com/science/article/pii/S0040402015001428" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0040402015001428</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tet.2015.02.008" target="_blank" >10.1016/j.tet.2015.02.008</a>

Result language
angličtina
Original language name
Synthesis and biological activity of new homolupanes and homolupane saponins
Original language description
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 com
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CE - Biochemistry
OECD FORD branch
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Project
<a href="/en/project/LO1204" target="_blank" >LO1204: Sustainable development of research in the Centre of the Region Haná</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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