88(P-93) 繊毛虫Climacostomum virensの自己防御物質クリマコストールの構造と合成(ポスター発表の部)

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The heterotrich ciliates, Stentor coeruleus and Blepharisma japonicum, have pigment granules which contain blue pigment stentorin and red pigment blepharismin, respectively. We recently reported that the pigment granules and the pigments act as defense against the predatory ciliate, Dileptus margaritifer. Although Climacostomum virens, another heterotrich ciliate, is colorless, it has cortical vesicles, which are morphologically similar to the pigment granules in the red species of Blepharisma. The retreating behavior of D. margaritifer observed when it attacks C. virens suggests that C. virens also has the defense toxin against the predator. Indeed, we found a potent toxin against D. margaritifer in 70% ethanol extract of C. virens. The active fraction obtained by repeated chromatography on silica gel contained a new compound climacostol (1) (LD_<50> 1.8μg/ml), whose molecular formula was estimated to be C_<15>H_<22>O_2 by HRMS and ^1H and ^<13>C NMR. The presence of two phenolic OH protons and the close resemblance of the chemical shifts of the aromatic protons and the carbons of 1 to that of olivetol (1,3-dihydoxy-5-pentylbenzene) suggested that 1 is a derivative of 5-alkenyl resorcinol. The ^1H-^1H COSY, HMBC, and HMQC spectra of 1 indicated the presence of Ar-CH_2-CH=CH-CH_2, from which is deduced the presence of the 2-nonenyl group as the side chain attached to resorcinol at the 5-position. The Z-configuration of △2,3-olefin was determined by the observation of NOE between the 1'- and 4'-methylene protons. Thus, the structure of 1 was established to be 1,3-dihydoxy-5-[(Z)-2-nonenyl]benzene. The structure and biological activity of climacostol were confirmed by the total synthesis of 1.
天然有機化合物討論会の論文
2000-10-01

88(P-93) 繊毛虫Climacostomum virensの自己防御物質クリマコストールの構造と合成(ポスター発表の部)

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