New Cholestane Bisdesmosides from the Bulbs of Ornithogalum thyrsoides

• Published in: Bulletin of the Chemical Society of Japan Vol. 65; no. 4; pp. 1120 - 1124
• Main Authors: Kubo, Satoshi, Mimaki, Yoshihiro, Sashida, Yutaka, Nikaido, Tamotsu, Ohmoto, Taichi
• Format: Journal Article
• Language: English
• Published: Tokyo The Chemical Society of Japan 01.04.1992; Chemical Society of Japan
• Subjects: Analytical, structural and metabolic biochemistry; Biological and medical sciences; Fundamental and applied biological sciences. Psychology; Other biological molecules; Terpenes, steroids. Hormones; Steroid; Molecular structure; Enzyme inhibitor; Isolation; Glycoside; NMR spectrum; Biological activity
• ISSN: 0009-2673; 1348-0634
• DOI: 10.1246/bcsj.65.1120

Four new cholestane bisdesmosides have been isolated from the fresh bulbs of Ornithogalum thyrsoides. Their structures were determined by spectroscopic analysis and chemical evidence to be (22S)-5α-cholestane-1β,3β,16β,22-tetrol 1-O-α-L-rhamnopyranoside 16-O-β-D-glucopyranoside (1), (22S)-5α-cholestane-1β,3β,16β,22-tetrol 1-O-α-L-rhamnopyranoside 16-O-(6-O-acetyl-β-D-glucopyranoside) (2), (22S)-5α-cholest-24-ene-1β,3β,16β,22-tetrol 1-O-α-L-rhamnopyranoside 16-O-β-D-glucopyranoside (3), and (22S)-5α-cholest-24-ene-1β,3β,16β,22-tetrol 1-O-α-L-rhamnopyranoside 16-O-(6-O-acetyl-β-D-glucopyranoside) (4), respectively. An advanced Mosher’s method was applied to determine the C-22 absolute configuration. Compound 4 showed inhibitory activity on cyclic AMP phosphodiesterase.