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Statements

Subject Item
n2:RIV%2F61389030%3A_____%2F14%3A00429932%21RIV15-AV0-61389030
rdf:type
skos:Concept n16:Vysledek
dcterms:description
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 compounds. 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 compounds.
dcterms:title
Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain
skos:prefLabel
Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain
skos:notation
RIV/61389030:_____/14:00429932!RIV15-AV0-61389030
n3:aktivita
n4:P n4:I n4:S
n3:aktivity
I, P(LO1204), S
n3:cisloPeriodika
17
n3:dodaniDat
n9:2015
n3:domaciTvurceVysledku
n11:4712048 n11:6978932 n11:4952340
n3:druhVysledku
n5:J
n3:duvernostUdaju
n15:S
n3:entitaPredkladatele
n8:predkladatel
n3:idSjednocenehoVysledku
48992
n3:idVysledku
RIV/61389030:_____/14:00429932
n3:jazykVysledku
n6:eng
n3:klicovaSlova
BETULIN DERIVATIVES; SECONDARY ALCOHOLS; ANTITUMOR-ACTIVITY
n3:klicoveSlovo
n10:SECONDARY%20ALCOHOLS n10:ANTITUMOR-ACTIVITY n10:BETULIN%20DERIVATIVES
n3:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n3:kontrolniKodProRIV
[59FD196C83E4]
n3:nazevZdroje
Tetrahedron
n3:obor
n18:EB
n3:pocetDomacichTvurcuVysledku
3
n3:pocetTvurcuVysledku
7
n3:projekt
n12:LO1204
n3:rokUplatneniVysledku
n9:2014
n3:svazekPeriodika
70
n3:tvurceVysledku
Pakulski, Z. Korda, A. Luboradzki, R. Cmoch, P. Oklešťková, Jana Strnad, Miroslav Rárová, Lucie
n3:wos
000334132800005
s:issn
0040-4020
s:numberOfPages
14
n7:doi
10.1016/j.tet.2014.03.006