Steroidal saponins from Smilax officinalis

Article abstract of DOI:10.1016/0031-9422(96)00274-9

Three new steroidal saponins were isolated from the rhizomes of Smilax officinalis. The structures of these saponins were established by extensive spectral data, hydrolysis and chemical correlation as sarsasapogenin 3-O-β- D-glucopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 6)]-β-D- glucopyranoside, neotigogenin 3-O-β-D-glucopyranosyl-(1 → 4)-[α-L- arabinopyranosyl-(1 → 6)]-β-D-glucopyranoside and 25S-spirostan-6β-ol 3- O-β-D-glucopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 6)]-β-D- glucopyranoside. Acid hydrolysis of the latter compound gave a sapogenin which has a new orientation of an hydroxyl on the steroidal skeleton. A route is proposed for the biogenesis of the latter sapogenin which is an uncommon steroidal aglycone.