Steroidal saponins from the rhizomes of Smilax sieboldii

• Published in: Phytochemistry (Oxford) Vol. 31; no. 7; pp. 2445 - 2450
• Main Authors: Nikaido, Tamotsu, Ohmoto, Taichi, Kubo, Satoshi, Mimaki, Yoshihiro, Sashida, Yutaka
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01.07.1992; Elsevier
• Subjects: 3',5'-Cyclic-AMP Phosphodiesterases; 3',5'-Cyclic-AMP Phosphodiesterases - antagonists & inhibitors; antagonists & inhibitors; Biological and medical sciences; cAMP phosphodiesterase; Carbohydrate Sequence; chemical constituents of plants; Chemical constitution; chemical structure; chemistry; enzyme inhibitors; Fundamental and applied biological sciences. Psychology; furostanol glycosides; glycosides; Hydrolysis; inhibitory activity; isolation & purification; Japan; laxogenin glycosides; Liliaceae; Magnetic Resonance Spectroscopy; medicinal plants; molecular conformation; Molecular Sequence Data; Molecular Structure; pharmacology; phosphodiesterase I; Phytosterols; Phytosterols - chemistry; Phytosterols - isolation & purification; Phytosterols - pharmacology; Plant physiology and development; Plants; Plants - chemistry; rhizomes; Saponins; Saponins - chemistry; Saponins - isolation & purification; Saponins - pharmacology; Smilax; Smilax sieboldii; spectral analysis; spirostanol glycosides; steroid saponins; steroidal saponins; tigogenin glycoside; Japan; cAMP phosphodiesterase; Liliaceae; laxogenin glycosides; steroidal saponins; Smilax sieboldii; spirostanol glycosides; inhibitory activity; tigogenin glycoside; furostanol glycosides; Steroid; Monocotyledones; Enzymatic activity; Molecular structure; Enzyme; Angiospermae; Rhizome; Isolation; Spermatophyta; Inhibition; Saponin
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/0031-9422(92)83296-B

Six new steroidal saponins were isolated from the rhizomes of Smilax sieboldii. Their structures were determined by spectroscopic analysis and hydrolysis to be 3β-hydroxy-(25 R)-5α-spirostan-6-one (laxogenin)3- O-β- d-glucopyranosyl-(1 → 4)- O-[α- l-arabinopyranosyl-(1 → 6)]-β- d-glucopyranoside, laxogenin 3- O-α- l-arabinopyranosyl (1 → 6) -β- d-glucopyranoside,3β,27-dihydroxy-(25 S)-5α-spirostan-6-one 3- O-β- d-glucopyranosyl-(1 →4 - O-[α- l-arabinopyranosyl-( 1 → 6) )-α- d-glucopyranoside, 26- O-β- d-glucopyranosyl-3β,22ξ,26-trihydroxy-(25 R)-5α-furostan-6-one 3- O-α- l-arabinopyranosyl-(1 ar 6)-β- d-glucopyranoside, 26- O-β- d-glucopyranosyl-3β,22ξ,26-trihydroxy-(25 R-5α-furostan-6-one 3- O-β- d-glucopyranosyl-(1 → 4)- O-[α- l-arabinopyranosyl-(1 ar 6)]-β- d-glucopyranoside and (25 R)-5α-spirostan-3β-ol (tigogenin) 3- O-β- d-glucopyranosyl-(1 → 4)- O-[α- l-arabinopyranosyl-(1 → 6)]-β- d-glucopyranoside. The inhibition of cAMP phosphodiesterase by the saponins was evaluated.