Synthesis and cytotoxicities of icogenin analogues with disaccharide residues

Haixing Wang; Fuqin Su; Liang Zhou; Xiaoguang Chen; Pingsheng Lei

doi:10.1016/j.bmcl.2009.03.092

Synthesis and cytotoxicities of icogenin analogues with disaccharide residues

Bioorg Med Chem Lett. 2009 May 15;19(10):2796-800. doi: 10.1016/j.bmcl.2009.03.092. Epub 2009 Mar 26.

Authors

Haixing Wang¹, Fuqin Su, Liang Zhou, Xiaoguang Chen, Pingsheng Lei

Affiliation

¹ Ministry of Education, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing, PR China.

PMID: 19362474
DOI: 10.1016/j.bmcl.2009.03.092

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

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

Substances

(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