7-Oxodioscin, a new spirostan steroid glycoside from the rhizomes of Dioscorea nipponica

Abstract

Nine glycosides of spirostan (1-7) and furostan (8 and 9) type steroids including a new compound, 7-oxodioscin (1), were isolated from the rhizomes of Dioscorea nipponica. The structure of 1 was established as (25R)-3beta-O-[(alpha-L-rhamnopyranosyl-(1 --> 4)-O-[alpha-L-rhamnopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl)oxy]spirost-5-en-7-one by extensive spectroscopic techniques including HRESI-TOFMS, 1D and 2D NMR, and chemical methods. Known compounds were elucidated as dioseptemloside G (2), (25R)-dracaenoside G (3), orbiculatoside B (4), dioscin (5), progenin III (6), gracillin (7), (3beta3,22alpha,25R)-26-(beta-D-glucopyranosyloxy)-22-methoxyfurost-5-en-3-yl O-[alpha-L-rhamnopyranosyl-(1 --4)]-beta-D-glucopyranoside (8), and methylprotodioscin (9).