17 Theonella属海綿の産生する二量体マクロリド類の化学構造と抗腫瘍活性(口頭発表の部)

概要

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In search of new bioactive substances from marine organisms, we have investigated the chemical constituent of the Okinawan marine sponge Theonella sp. and isolated a potent cytotoxic dimeric macrolide, swinholide A (3). The absolute stereostructure of 3, having a dimeric dilactone structure with a 44-membered ring, has been determined on the basis of its chemical behavior and an X-ray crystallographic analysis of its derivative (12). Following the characterization of 3, three new congeneric dimeric macrolides, named swinholide B (14), swinholide C (15), and isoswinholide A (18), have been isolated. The absolute stereo-structures of these dimeric macrolides (14, 15, and 18) together with misakinolide A (19), which was previously isolated from another Okinawan marine sponge of Theonella sp., have been elucidated. These dimeric macrolides (3, 14, and 15) exhibited potent cytotoxic activities for KB cell lines (IC_<50> 0.04, 0.04, and 0.05 μg/ml, respectively) while 18 showed a weaker cytotoxicity (IC_<50> 1.1μg/ml). These results suggest that the size and conformation of the lactone-ring are essential for exhibiting cytotoxic activities.
天然有機化合物討論会の論文
1990-09-25