Clintoniosides A-C, new polyhydroxylated spirostanol glycosides from the rhizomes of Clintonia udensis

Abstract

Phytochemical analyses were carried out on the rhizomes of Clintonia udensis (Liliaceae) with particular attention paid to the steroidal glycoside constituents, resulting in the isolation of three new polyhydroxylated spirostanol glycosides, named clintonioside A (1), B (2), and C (3). On the basis of their spectroscopic data, including 2D-NMR spectroscopy, in combination with acetylation and hydrolytic cleavage, the structures of 1 - 3 were determined to be (1β,3β,23S,24S,25R)-1,23,24-trihydroxyspirost-5-en-3- yl O-β-D-glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)] -β-D-glucopyranoside (1), (1β,3β,23S,24S)-3,21,23,24- tetrahydroxyspirosta-5,25(27)-dien-1-yl O-α-L-rhamnopyranosyl-(1→2)- O-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranoside (2), and (1β,3β,23S,24S)-21-(acetyloxy)-24-[(6-deoxy-β-D-gulopyranosyl) oxy]-3,23-dihydroxyspirosta-5,25(27)-dien-1-yl O-α-L-rhamnopyranosyl- (1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranoside (3). © 2008 Verlag Helvetica Chimica Acta AG.