107(P-48) 繊毛虫Spirostomum teresの自己防御物質Spirostominの構造と合成研究(ポスター発表の部)

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In the continuing study on predator-prey interaction between ciliates, we reported the isolation and structural determination of a defense toxin climacostol from a heterotrich ciliate Climacostomum virens. On the preliminary study of the predator-prey interaction between ciliates Dileptus margaritifer as a predator and Spirostomum teres an another heterotrich ciliate as a prey, we observed elusive behavior of S. teres from the predator and the presence of the cortical vesicle in S. teres just beneath the cell membrane, which suggested that S. teres had some toxic substance against the predator. We report the isolation and structural determination of a toxic substance spirortomin from S. teres. The whole cells of S. teres were dipped in aqueous 70% EtOH. After removal of the cells by filtration and concentration of the solvent, the residue was partitioned between ethyl acetate and water. From the organic layer, an active fraction based on lethal toxicity against a ciliate Paramecium caudatum was obtained by chromatography on silica gel eluted with 1.5% Me0H/CH2Cl2 (Rf value=0.44). The fraction contained a new compound spirostomin (1),4 whose molecular formula was estimated to be C16H14O5 by HREIMS and 1H and 13C NMR. Based on 1H, 13C NMR and UV spectrum, the structure of spirostomin was established as spiro[(2,5-dimethyl-5,6,7,8-tetrahydronaphtalene-1,4-dione)-8,6'-(pyrane-2',5'-dione)], a spiro compound having a carbon framework hitherto unknown.
天然有機化合物討論会の論文
2004-10-01

107(P-48) 繊毛虫Spirostomum teresの自己防御物質Spirostominの構造と合成研究(ポスター発表の部)

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