Synthesis and biological activity of new homolupanes and homolupane saponins
Identifikátory výsledku
Kód výsledku v 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>
Nalezeny alternativní kódy
RIV/61389030:_____/15:00446691
Výsledek na webu
<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>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Synthesis and biological activity of new homolupanes and homolupane saponins
Popis výsledku v původním jazyce
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
Název v anglickém jazyce
Synthesis and biological activity of new homolupanes and homolupane saponins
Popis výsledku anglicky
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
Klasifikace
Druh
J<sub>x</sub> - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)
CEP obor
CE - Biochemie
OECD FORD obor
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Návaznosti výsledku
Projekt
<a href="/cs/project/LO1204" target="_blank" >LO1204: Udržitelný rozvoj výzkumu v Centru regionu Haná</a><br>
Návaznosti
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Ostatní
Rok uplatnění
2015
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Tetrahedron
ISSN
0040-4020
e-ISSN
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Svazek periodika
71
Číslo periodika v rámci svazku
13
Stát vydavatele periodika
GB - Spojené království Velké Británie a Severního Irska
Počet stran výsledku
9
Strana od-do
2004-2012
Kód UT WoS článku
000352747900015
EID výsledku v databázi Scopus
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