title: Synthesis of bidesmosidic dihydrodiosgenin saponins bearing a 3-O-beta-chacotriosyl moiety.
abstract: 3-O-beta-Chacotriosyl-26-O-beta-D-glucopyranosyl-(25R)-furost-5-en (1), a mimic of the antitumor active proto-dioscin, was concisely synthesized from diosgenin in a linear nine steps and in 17% overall yield. Its congeners with a alpha-l-rhamnopyranosyl, beta-lactosyl, or without a substituent at the 26-OH (13-15) were also prepared. Compound 1, as well as 13-15, did not show any inhibition against tumor cells, implying that proto-dioscin might be also inactive, but readily converted into the antitumor active dioscin.
authors.affiliation: Marine Drugs and Food Institute, Ocean University of China, Qingdao 266003, China.
authors.forename: Yichun
authors.initials: Y
authors.lastname: Zhang
authors.forename: Yingxia
authors.initials: Y
authors.lastname: Li
authors.forename: Shilei
authors.initials: S
authors.lastname: Zhu
authors.forename: Huashi
authors.initials: H
authors.lastname: Guan
authors.forename: Feng
authors.initials: F
authors.lastname: Lin
authors.forename: Biao
authors.initials: B
authors.lastname: Yu
mesh_terms: D000970:Antineoplastic Agents / Q000494:pharmacology*; D002855:Chromatography, Thin Layer; D004144:Diosgenin / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D012503:Saponins / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D012825:Silicon; D012997:Solvents / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D012503:Saponins; D012997:Solvents; C459619:protodioscin; D004144:Diosgenin; D012825:Silicon