title: Synthesis of neosaponins and neoglycolipids containing a chacotriosyl moiety.
abstract: Alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranose (chacotriose) is the oligosaccharide moiety of dioscin. Chacotriosyl trichloroacetimidate was synthesized from d-glucose and l-rhamnose, and glycosylated to mevalonate (diosgenin, cholesterol, and glycyrrhetic acid) to yield dioscin and neosaponins. In order to simplify the structure of the aglycone part, the mevalonate moiety was replaced with double-chain neoglycolipids that mimicked glycosyl ceramides. A cytotoxicity test revealed the importance of the glycosidic linkage of the naturally occurring beta-form and that dioscin and the neoglycolipid with the longest chain showed a moderate activity.
authors.affiliation: Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Miyashita
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Ikeda
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Nohara
mesh_terms: D000818:Animals; D002236:Carbohydrate Conformation; D002784:Cholesterol / Q000737:chemistry; D004144:Diosgenin / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry*; D006034:Glycyrrhetinic Acid / Q000737:chemistry; D006801:Humans; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D016716:PC12 Cells; D011714:Pyrans / Q000737:chemistry; D051381:Rats; D012210:Rhamnose / Q000737:chemistry; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry*; D014326:Tropanes / Q000737:chemistry
chemical_list: D006017:Glycolipids; D011714:Pyrans; D012503:Saponins; D014326:Tropanes; C433845:chacotriose; D002784:Cholesterol; D005947:Glucose; D004144:Diosgenin; D006034:Glycyrrhetinic Acid; D012210:Rhamnose