P-8 ユリ科Ornithogalum saundersiae鱗茎の化学成分研究 : ヒト末梢血リンパ球幼若化抑制活性を有する新規cholestane配糖体の構造(ポスター発表の部)

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During our search for naturally occurring compounds with medicinal potential, we have studied the fresh bulbs of Ornithogalum saundersiae belonging to the subfamily Scilloideae in Liliaceae. As a result of this, nine novel cholestane glycosides were isolated, the structures of which were established by the concerted use of modern two-dimensional NMR techniques, ^1H-^1H COSY, HOHAHA, HSQC, HMBC and phase-sensitive NOESY spectra. The isolated compounds (1〜9) appeared to have a novel steroidal skeleton with migration of C-24-C-27 to C-22 (22-homo-23-norcholestane skeleton). The comformation of the E-ring part of 1 and 8 were studied through spectroscopic (NMR) analysis and computational chemical methods, molecular mechanics and molecular dynamics calculation studies. The observed proton coupling constants, ^3J_<20-H, 22-H>=11.7Hz and ^3J<22-H, 23-H>=7.3Hz, almost corresponded to those (12.5Hz and 7.4Hz) calculated through the application of the given dihedral angles to the advanced Karplus-type equation proposed by Altona et al. The isolated compounds were evaluated for suppresive effect on in vitro mitogen-induced proliferation of human peripheral blood lymphocytes to identify new immunosuppressive agents. The cholestane glycosides with a saccharide moiety bearing an aromatic acid derivative exhibited almost equl or more potent inhibitory activity than that of cyclosporin A. These compounds are worthy to be evaluated for in vivo immunosuppresive activity.
天然有機化合物討論会の論文
1995-09-01

P-8 ユリ科Ornithogalum saundersiae鱗茎の化学成分研究 : ヒト末梢血リンパ球幼若化抑制活性を有する新規cholestane配糖体の構造(ポスター発表の部)

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