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  • Title: Efficient synthesis of alpha- and beta-chacotriosyl glycosides using appropriate donors, and their cytotoxic activity.
    Author: Miyashita H, Kai Y, Nohara T, Ikeda T.
    Journal: Carbohydr Res; 2008 Jun 09; 343(8):1309-15. PubMed ID: 18440498.
    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.
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