Efficient synthesis of alpha- and beta-chacotriosyl glycosides using appropriate donors, and their cytotoxic activity.

Abstract

Natural steroidal glycosides containing alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranose (chacotriose) at the oligosaccharide moiety exhibit anti-cancer and anti-herpes activities. To investigate the structure-activity relationships of the aglycone parts of chacotriosides, we developed a synthesis method for chacotriosyl glycosides having various aglycones. In the process, it was revealed that alpha-chacotriosyl glycosides could be obtained mainly by using a trichloroacetimidate donor, while beta-chacotriosyl glycosides were afforded by using phosphite and phosphate donors. In cytotoxicity tests using the A549 and HepG2 cell lines, naturally occurring beta-chacotriosyl diosgenin and cholestanol exhibited higher activities than the corresponding alpha-chacotriosyl glycosides.

• Authors: Hiroyuki Miyashita, Yuuki Kai, Toshihiro Nohara, Tsuyoshi Ikeda
• Journal: Carbohydrate research (Carbohydr Res) Vol. 343 Issue 8 Pg. 1309-15 (Jun 09 2008) ISSN: 0008-6215 [Print] Netherlands
• PMID: 18440498 (Publication Type: Journal Article)

Chemical References

• Antineoplastic Agents, Phytogenic
• Glycosides
• Tropanes
• chacotriose
• Diosgenin

Topics

• Antineoplastic Agents, Phytogenic (chemical synthesis, toxicity)
• Carbohydrate Sequence
• Cell Line, Tumor
• Diosgenin (chemical synthesis)
• Glycosides (chemical synthesis, chemistry, toxicity)
• Hepatoblastoma (drug therapy, pathology)
• Humans
• Lung Neoplasms (drug therapy, pathology)
• Magnetic Resonance Spectroscopy
• Molecular Sequence Data
• Tropanes (chemical synthesis)