Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
New Cholestane Bisdesmosides from the Bulbs of Ornithogalum thyrsoides
Satoshi KuboYoshihiro MimakiYutaka SashidaTamotsu NikaidoTaichi Ohmoto
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1992 Volume 65 Issue 4 Pages 1120-1124

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Abstract

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.

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© 1992 The Chemical Society of Japan
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