88 焼魚に存在する新突然変異原物質の単離,構造決定および合成

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Two potent mutagens (compound 1 and 2) on Salmonella typhimurium TA98 were isolated from a methanol extract of sardines broiled under normal domestic cooking conditions. The methanol extract of broiled sardines (10kg) was fractionated by acid-base partitioning, column chromatographies of Diaion HP-20,Sephadex LH-20 and silica-gel and the two pure mutagens (200μg each) were finally isolated by high pressure liquid chromatography using reverse phase column. The structures of compound 1 and 2 were determined as 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ) and 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (Me-IQ), respectively, based on 270MHz ^1H-NMR, mass and FTIR spectra, UV absorption, pK_a values, and chemical synthesis. IQ and Me-IQ were synthesized from 5,6-diamino-quinoline and 5,6-diamino-7-methylquinoline, respectively, by two step reactions. Synthetic IQ and Me-IQ showed strong mutagenic activities towards S. typhimurium TA98. These mutagens require metabolic activation by microsomal enzymes (S-9). Specific activities of these compounds towards TA98 and TA100 were determined to be 433,000 and 7,000 revertants/μg for IQ and 661,000 and 30,000 revertants/μg for Me-IQ. The mutagen IQ was also isolated from heated beef extract and hamburger, suggesting that these mutagens are commonly present in ordinary cooked foods. Carcinogenic tests are in progress for evaluation of these mutagens on humans.
天然有機化合物討論会の論文
1980-09-10