Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F14%3A33152497" target="_blank" >RIV/61989592:15310/14:33152497 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61389030:_____/14:00429932

Výsledek na webu

<a href="http://www.sciencedirect.com/science/article/pii/S0040402014003123" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0040402014003123</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tet.2014.03.006" target="_blank" >10.1016/j.tet.2014.03.006</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain

Popis výsledku v původním jazyce

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 compoun

Název v anglickém jazyce

Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain

Popis výsledku anglicky

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 compoun

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

ED - Fyziologie

OECD FORD obor

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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)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2014

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Tetrahedron

ISSN

0040-4020

e-ISSN

—

Svazek periodika

70

Číslo periodika v rámci svazku

17

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

14

Strana od-do

2717-2730

Kód UT WoS článku

000334132800005

EID výsledku v databázi Scopus

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