Pregnane steroidal glycosides and their cytostatic activities.

Abstract

Four new steroidal glycosides such as 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1 → 4)-β-D-oleandropyranosyl-(1 → 4)-β-D-cymaropyranosyl-(1 → 4)-β-D-cymaropyranoside-12-β-tigloyl-14-β-hydroxy-17-β-pregnane (1), 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1 → 4)-β-D-oleandropyranosyl-(1 → 4)-β-D-cymaropyranosyl-(1 → 4)-β-D-cymaropyranoside-12-β-(2'-amino)-benzoyl-14-β-hydroxy-17-β-pregnane (2), 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1 → 4)-β-D-oleandropyranosyl-(1 → 4)-β-D-cymaropyranosyl-(1 → 4)-β-D-cymaropyranoside-12-β-14-β-dihydroxy-17-α-pregnane (3) and 3-O-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1 → 4)-β-D-oleandropyranosyl-(1 → 4)-β-D-cymaropyranosyl-(1 → 4)-β-D-cymaropyranoside-12-β-14-β-dihydroxy-17-β-pregnane (4) were isolated from the aerial parts of Ceropegia fusca Bolle (Asclepiadaceae), a crassulacean acid metabolism plant, an endemic species to the Canary Islands that has been used in traditional medicine as a cicatrizant, vulnerary and disinfectant. The dichloromethane extract exhibited significant cytostatic activity against HL-60, A-431 and SK-MEL-1 cells, human leukemic, epidermoid carcinoma and melanoma cells, respectively. As shown in Table I, compounds 1 and 2 showed very similar IC(50) values. The acetylation of 1 to give the diacetate 5 increases 5-fold the cytotoxicity against HL-60 cells. Compounds 3 and 4 did not show cytotoxicity at the assayed concentrations. With respect to the compounds containing only the steroid ring (6-8), the presence of a charged O-amino-benzoyl but not a tigloyl group improved the cytotoxicity.

• Authors: Víctor P García, Jaime Bermejo, Sara Rubio, José Quintana, Francisco Estévez
• Journal: Glycobiology (Glycobiology) Vol. 21 Issue 5 Pg. 619-24 (May 2011) ISSN: 1460-2423 [Electronic] England
• PMID: 21147757 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Cytostatic Agents
• Glycosides
• Plant Extracts
• Pregnanes

Topics

• Antineoplastic Agents (isolation & purification, pharmacology)
• Apoptosis (drug effects)
• Cell Cycle (drug effects)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Cell Shape (drug effects)
• Cell Survival (drug effects)
• Cytostatic Agents (isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Gentiana (chemistry, metabolism)
• Glycosides (isolation & purification, pharmacology)
• Humans
• Inhibitory Concentration 50
• Molecular Structure
• Plant Components, Aerial (chemistry, metabolism)
• Plant Extracts (isolation & purification, pharmacology)
• Pregnanes (isolation & purification, pharmacology)
• Structure-Activity Relationship