79(P67) 沖縄産海綿Hippospongia sp.由来の新規アセチレン化合物Taurospongin Aの構造(ポスター発表の部)

概要

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During our studies on bioactive substances from Okinawan marine organisms, we recently examined extracts of the sponge Hippospongia sp., and isolated a novel acetylenic compound, taurospongin A (1). The monomethyl ester derivative (2), C_<41>H_<73>O_9NS, derived from 1, was revealed to be an acetylenic compound consisting of a taurine and two (trihydroxyl and unsaturated) fatty acids on the basis of analysis of the spectral data including several types of 2D NMR spectra (^1H-^1H gradient COSY, HMQC, decoupling HMBC, and gradient HMBC). Amino acid analysis of hydrolysis products of 1 showed the presence of taurine. Two fragments, trihydroxylamide (3) and unsaturated fatty acid methyl ester (4), were obtained by methanolysis of 2 to elucidate the lengths of the methylene chains contained in 3 and 4, respectively. Relative stereochemistry of 1,3-diol moiety of 3 was shown as syn from the ^<13>C NMR data of the acetonide (5) prepared from 3 by applying the Rychnovsky rule. Studies for determining the absolute stereochemistry of 1 are currently in progress by preparation of two possible diasteromers of 5. Taurospongin A (1) showed inhibitory activity against c-erbB-2 Kinase (IC_<50> 28μg/mL), and exibited no cytotoxicity.
天然有機化合物討論会の論文
1996-09-02