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Influence of intramolecular hydrogen bonds on regioselectivity of glycosylation. Synthesis of lupane-type saponins bearing the OSW-1 saponin disaccharide unit and its isomers
K. Kuczynska, P. Cmoch, L. Rárová, J. Oklešťková, A. Korda, Z. Pakulski, M. Strnad,
Carbohydrate research.
2016 ;
423 (-) :
49-69.
[pub] 20160126
Jazyk angličtina Země Nizozemsko
Typ dokumentu časopisecké články, práce podpořená grantem
Perzistentní odkaz
https://www.medvik.cz/link/bmc17000468
- MeSH
- antitumorózní látky chemická syntéza chemie farmakologie MeSH
- arabinosa chemie MeSH
- disacharidy chemická syntéza chemie farmakologie MeSH
- glykosylace MeSH
- lidé MeSH
- nádorové buněčné linie MeSH
- saponiny chemie MeSH
- stereoizomerie MeSH
- techniky syntetické chemie MeSH
- triterpeny chemie MeSH
- vodíková vazba MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
A series of lupane-type saponins bearing OSW-1 disaccharide unit as well as its regio- and stereoisomers were prepared and used for the structure-activity relationships (SAR) study. Unexpected preference for 1→4-linked regioisomers and an unusual inversion of the conformation of the sugar rings were noted. Cytotoxic activity of new lupane compounds was evaluated in vitro and revealed that some saponins exhibited an interesting bioactivity profile against human cancer cell lines. Influence of the protecting groups on the cytotoxicity was investigated. These results open the way to the synthesis of various lupane-type triterpene and saponin derivatives as potential anticancer compounds.
Citace poskytuje Crossref.org
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