title: 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.affiliation: Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Miyashita
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Kai
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Nohara
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Ikeda
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000633:toxicity*; D002240:Carbohydrate Sequence; D045744:Cell Line, Tumor; D004144:Diosgenin / Q000138:chemical synthesis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D018197:Hepatoblastoma / Q000188:drug therapy / Q000473:pathology; D006801:Humans; D008175:Lung Neoplasms / Q000188:drug therapy / Q000473:pathology; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D014326:Tropanes / Q000138:chemical synthesis*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D006027:Glycosides; D014326:Tropanes; C433845:chacotriose; D004144:Diosgenin