Journal
CHEMICO-BIOLOGICAL INTERACTIONS
Volume 185, Issue 2, Pages 128-136Publisher
ELSEVIER IRELAND LTD
DOI: 10.1016/j.cbi.2010.02.038
Keywords
Betulinic acid; Betulin; Cytotoxicity; Apoptosis; Caspase
Funding
- BMBF [Fla 01GU0609]
- BioSolutions Halle GmbH
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Four derivatives of betulin containing a D-glucopyranosyl moiety at C3 position were synthesized and characterized by H-1 and C-13 NMR spectroscopy as well as mass spectrometry. The crystal structure of 28-O-acetylbetulin-3-yl-beta-D-(2',3',4',6'-tetra-O-acetyl)glucopyranoside was determined. The compounds were tested against fifteen tumor cell lines of different histogenic origins. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside, exerted a dose dependent antiproliferative action towards the tumor cell lines. Treatment of HCT-116 cells for 24 h induced apoptosis, which was confirmed by the appearance of a typical ladder pattern in the DNA fragmentation assay and cell cycle analysis. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside seem to induce apoptosis by activation of different upstream caspases on colon cancer HCT-116 cell line. (C) 2010 Elsevier Ireland Ltd. All rights reserved.
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