Synthesis and antitumor activity of icogenin and its analogue

Icogenin: R = α- l-rhamnopyranosyl-(1 → 2)-[ β- d-glucopyranosyl(1 → 3)]-β- d-glucopyranosyl ( 1). The designed analogue of icogenin: R = α- l-rhamnopyranosyl-(1 → 2)-[β- d-glucopyranosyl(1 → 3)]-α- d-glucopyranosyl ( 2). Natural saponin icogenin, namely 25( S)-22- O-methyl-furost-5-en-3β,26-dio-3-...

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Bibliographic Details
Published in:	Bioorganic & medicinal chemistry letters Vol. 16; no. 9; pp. 2454 - 2458
Main Authors:	Hou, Shujie, Xu, Peng, Zhou, Liang, Yu, Dequan, Lei, Pingsheng
Format:	Journal Article
Language:	English
Published:	Oxford Elsevier Ltd 01-05-2006 Elsevier
Subjects:	Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Cell Line, Tumor Cell Proliferation - drug effects Cytotoxicity Drug Screening Assays, Antitumor General aspects Glycosylation Humans Icogenin In Vitro Techniques Medical sciences Molecular Conformation Pharmacology. Drug treatments Saponin Saponins - chemical synthesis Saponins - chemistry Saponins - pharmacology Stereoisomerism Steroids - chemical synthesis Steroids - chemistry Steroids - pharmacology Cytotoxicity Glycosylation Icogenin Saponin Antineoplastic agent Pentacyclic compound Steroid Oxygen heterocycle In vitro Biological activity Acetal Cell line Anomer Glycoside Chemical synthesis Tumor cell Trisaccharide
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Summary:	Icogenin: R = α- l-rhamnopyranosyl-(1 → 2)-[ β- d-glucopyranosyl(1 → 3)]-β- d-glucopyranosyl ( 1). The designed analogue of icogenin: R = α- l-rhamnopyranosyl-(1 → 2)-[β- d-glucopyranosyl(1 → 3)]-α- d-glucopyranosyl ( 2). Natural saponin icogenin, namely 25( S)-22- O-methyl-furost-5-en-3β,26-dio-3- O-α- l-rhamnopyranosyl-(1 → 2)-[β- d-glucopyranosyl-(1 → 3)]-β- d-glucopyranoside, and one of its analogues, 25( S)-22- O-methyl-furost-5-en-3β,26-dio-3- O-α- l-rhamnopyranosyl-(1 → 2)-[β- d-glucopyranosyl-(1 → 3)]-α- d-glucopyranoside, were first synthesized via line strategy and convergent approach, respectively. It was observed that icogenin and its analogue show potent antitumor activity in vitro.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2006.01.074