Synthesis and cytotoxicities of icogenin analogues with disaccharide residues.

Abstract

For further structure-activity relationships (SAR) research of furostan saponin, two icogenin analogues: (25R)-22-O-methyl-furost-5-en-3beta,26-diol-3-O-alpha-l-rhamnopyranosyl-(1-->2)-beta-d-glucopyranoside 1 and (25R)-22-O-methyl-furost-5-en-3beta,26-diol-3-O-alpha-l-rhamnopyranosyl-(1-->2)-alpha-d-glucopyranoside 2, with valuable disaccharide moieties, were synthesized from diosgenin through eight steps. Both of the analogues behaved the similar cytotoxic activities with icogenin, towards nine types of human tumor cells herein.

• Authors: Haixing Wang, Fuqin Su, Liang Zhou, Xiaoguang Chen, Pingsheng Lei
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 19 Issue 10 Pg. 2796-800 (May 15 2009) ISSN: 1464-3405 [Electronic] England
• PMID: 19362474 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• (25R)-22-O-methyl-furost-5-en-3beta,26-diol-3-O-alpha-L-rhamnopyranosyl-(1-2)-beta-D-glucopyranoside
• Disaccharides
• Icogenin
• Saponins
• Steroids
• Sterols

Topics

• Cell Line, Tumor
• Disaccharides (chemical synthesis, chemistry)
• Drug Screening Assays, Antitumor
• Humans
• Saponins (chemical synthesis, chemistry, toxicity)
• Steroids (chemical synthesis, chemistry, toxicity)
• Sterols (chemical synthesis, chemistry, toxicity)
• Structure-Activity Relationship