Synthesis of bidesmosidic dihydrodiosgenin saponins bearing a 3-O-beta-chacotriosyl moiety.
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.
Zhang
Yichun
Y
Marine Drugs and Food Institute, Ocean University of China, Qingdao 266003, China.
Li
Yingxia
Y
Zhu
Shilei
S
Guan
Huashi
H
Lin
Feng
F
Yu
Biao
B
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
D000970:Antineoplastic Agents; D012503:Saponins; D012997:Solvents; C459619:protodioscin; D004144:Diosgenin; D012825:Silicon