36 食品汚染菌Aspergillus fumigatusより得られた痙攣性代謝産物の化学構造と薬理活性

概要

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In the course of our survey investigation of the toxigenic fungi found growing in foods and foodstuffs, some strains of Aspergillus fumigatus having a tremorgenic property have been found. By intraperitoneal administration of ethyl acetate extract of the fungus, experimental animals such as mice, rats or rabbits exhibited a sustained trembling with an intermittent convulsion. From the extract of the mycelia, four new indole compounds (FTA, B, C and D) were isolated. FTA and B were found to cause tremor to the animals but C and D were not. On the structure of fumitremorgin B (FTB), the presence of the 6-methoxy indole ring as a basic skeletone was first estimated and the structure was finally proposed as I from the spectral studies. The relative stereo-structure was subsequently determined by the X-ray analysis of FTB itself and the absolute configuration was determined based on that of proline obtained by hydrolysis of FTB. Fumitremorgin A (FTA) showed a closely resembled property to that of FTB in the spectral data and the structure was established as IV from the results of chemical and spectral studies on FTA and its derivatives. The structures of FTC and D were shown as XI and XIII, and they were named isotryptoquivaline and norisotryptoquivaline, respectively.
天然有機化合物討論会の論文
1975-10-01