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Title: Effect of C-ring modifications on the cytotoxicity of spirostan saponins and related glycosides
Authors: Pérez-Labrada, Karell
Brouard Martín,Ignacio 
Estévez, Sara 
Marrero, María Teresa
Estevez, Francisco 
Rivera, Daniel G.
UNESCO Clasification: 32 Ciencias médicas
2302 Bioquímica
Keywords: Human Leukemia-Cells
Issue Date: 2012
Project: Evaluación de Potenciales Compuestos Antileucémicos. 
Journal: Bioorganic and Medicinal Chemistry 
Abstract: Twelve C-ring modified spirostanyl glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). With the aim of assessing the influence of the hydrophobic character, the conformational flexibility and the stereochemistry of the C-ring functionalities on the cytotoxic activity, a variety of spirostanic aglycones incorporating methylene, methoxyl, alpha,beta-unsaturated ketone and lactone groups were subjected to a linear glycosylation strategy leading to glycosides derived from the 3,6-dipivaloylated beta-D-glucoside and the beta-chacotrioside moieties. The 3,6-dipivaloylated spirostanyl beta-D-glucosides showed moderate to good cytotoxic activity against HL-60, but no significant cytotoxicity against benign blood cells. However, the cytotoxicity of spirostanyl beta-chacotriosides was highly dependent on the nature of the C-ring functional groups of the steroidal aglycones. Actually, the chacotrioside-based saponins either with no functionality or bearing a hydrophobic methylene group at C-12 were the most cytotoxic ones against both HL-60 and benign blood cells. On the other hand, the incorporation of very polar functionalities and the opening of the ring C with the consequent loss of rigidity led to a significant drop in the cytotoxicity against HL-60. These results confirm that spirostanyl beta-chacotriosides including very lipophilic aglycones are the most cytotoxic ones among their congeners.
ISSN: 0968-0896
DOI: 10.1016/j.bmc.2012.05.018
Source: Bioorganic & Medicinal Chemistry[ISSN 0968-0896],v. 20 (14), p. 4522-4531
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