title: Steroidal saponins from Smilax officinalis.
abstract: 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-beta-D-glucopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->6 )-beta- D-glucopyranoside, neotigogenin 3-O-beta-D-glucopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->6 )]-beta- D-glucopyranoside and 25S-spirostan-6 beta-ol 3-O-beta-D-glucopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->6 )]-beta- 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.
authors.affiliation: Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Brazil.
authors.forename: R R
authors.initials: RR
authors.lastname: Bernardo
authors.forename: A V
authors.initials: AV
authors.lastname: Pinto
authors.forename: J P
authors.initials: JP
authors.lastname: Parente
mesh_terms: D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000032:analysis; D009682:Magnetic Resonance Spectroscopy; D008519:Medicine, Traditional; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010946:Plants, Medicinal; D012503:Saponins / Q000737:chemistry* / Q000302:isolation & purification; D013256:Steroids / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D002241:Carbohydrates; D012503:Saponins; D013256:Steroids