10 海洋動物タツナミガイから得られた新規細胞毒性マクロリド配糖体、オーリサイドA、Bと新規シクロデプシペプチド、オーリライドの構造(口頭発表の部)

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Constituents of the Japanese sea hare Dolabella auricularia collected in Mie Prefecture were examined by using bioassay, and novel cytotoxic macrolide glycosides, aurisides A (1) and B (2), and a new cyclodepsipeptide aurilide (4) were isolated. Aurisides A (1) and B (2) exhibited cytotoxicities against HeLa S3 cells with IC50 values of 0.17 and 1.2μg/mL, respectively. Their gross structures were established by spectroscopic analysis including the 2D NMR technique. On the basis of the NOESY spectral analysis and the degradation experiments, their absolute stereostructures were determined to be 14-membered macrolide glycosides that contain a bromine-substituted conjugated diene structure, a cyclic hemiacetal moiety, and a 2,4-di-O-methyl-L-rhamnopyranoside part. Aurilide (4) proved to be a 26-membered cyclodepsipeptide composed of a hexadepsipeptide part and a new dihydroxy acid on the basis of the 2D NMR analysis. The stereochemistry of the hexadepsipeptide moiety was determined by the HPLC analysis of the acid hydrolysate of 4. The stereochemistry of the dihydroxy acid moiety was determined by the enantioselective synthesis of the corresponding fragment 5 obtained by degradation of aurilide (4). Of the four syntheticdiastereomers 5a, 5b, 5c, and 5d, the ^1HNMR and the CD spectra for 5d were identical to those for natural 5, establishing the absolute stereochemistry of 5. On the basis of these findings the complete stereostructure of aurilide was determined as depicted in 4.
天然有機化合物討論会の論文
1996-09-02

10 海洋動物タツナミガイから得られた新規細胞毒性マクロリド配糖体、オーリサイドA、Bと新規シクロデプシペプチド、オーリライドの構造(口頭発表の部)

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