Two Spirostan Steroid Glycoside Fatty Esters from Dioscorea cayenensis

Abstract

Two new fatty acid-spirostan steroid glycoside esters, progenin III palmitate (1) and progenin III linoleate (2), were isolated from the MeOH extract of Dioscorea cayenensis rhizomes. The extract also yielded seven previously known spirostan and furostan steroid glycosides (3-9). The structures of the new compounds were established as (25R)-spirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-[6-O-palmitoyl]-O-β-D-glucopyranoside (1) and (25R)-spirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-[6-O-linoleoyl]-O-β-D-glucopyranoside (2) by chemical and spectroscopic methods, including 1D and 2D NMR. The known compounds were identified as progenin III (3), dioscin (4), deltonin (5), asperin (6), gracillin (7), protodioscin (8)], and methyl protodioscin (9).