PRESENCE OF 1-METHYL-1,2,3,4-TETRAHYDRO-BETA-CARBOLINE-3-CARBOXYLIC ACID, A PRECURSOR OF A MUTAGENIC NITROSO COMPOUND, IN SOY SAUCE
PRESENCE OF 1-METHYL-1,2,3,4-TETRAHYDRO-BETA-CARBOLINE-3-CARBOXYLIC ACID, A PRECURSOR OF A MUTAGENIC NITROSO COMPOUND, IN SOY SAUCE
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DOI：
10.1073/pnas.80.10.2912
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发表时间：
1983-01-01
期刊：
影响因子：
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通讯作者：
SUGIMURA, T
中科院分区：
文献类型：
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作者：
WAKABAYASHI, K;OCHIAI, M;SUGIMURA, T
日本酱料经亚硝酸盐处理后，对不加S9混合物的鼠伤寒沙门氏菌TA 100有较强的致突变性。从日本酱料中分离出诱变剂的两种前体，它们被鉴定为（-）-（1 S，3S）-1-甲基-1，2，3，4-四氢-β-咔啉-3-羧酸[（-）-（1 S，4S）-MTCA]及其立体异构体（-）-（1 R，3S）-MTCA。用亚硝酸盐处理后，在不含S9混合物的情况下，1 mg这些化合物样品分别诱导了17，400和13，000个TA 100回复突变体。日本生产的各种酱油的定量分析表明存在82-678 μ g/ml的MTCA。这些化合物对亚硝酸盐的致突变性占含亚硝酸盐酱料总致突变性的16-61%。美国生产的大多数酱油的诱变性低于日本生产的酱油，在美国生产的酱油中几乎没有发现这两种诱变剂的前体。（-）-（1 S，3S）-MTCA与亚硝酸根的主要反应产物是在N-2位具有亚硝基取代的化合物，但该化合物无致突变性。因此，由（-）-（1 S，3S）-MTCA和亚硝酸盐形成的诱变剂是次要产物，其比诱变活性必须非常高。[This人类的应用[编辑]
After treatment with nitrite, Japanese soy sauce was strongly mutagenic to Salmonella typhimurium TA100 without S9 mixture. Two precursors of the mutagen were isolated from Japanese soy sauce, and these were identified as (-)-(1S,3S)-1-methyl-1,2,3,4-tetrahydro-.beta.-carboline-3-carboxylic acid [(-)-(1S,4S)-MTCA] and its stereoisomer (-)-(1R,3S)-MTCA. After treatment with nitrite, 1-mg samples of these compounds induced 17,400 and 13,000 revertants of TA100, respectively, without S9 mixture. Quantitative analysis of various kinds of soy sauces produced in Japan showed the presence of 82-678 .mu.g of MTCA/ml. The mutagenicities of these compounds with nitrite accounted for 16-61% of the total mutagenicity of soy sauce with nitrite. Most soy sauces produced in the USA were less mutagenic than those produced in Japan and little, if any, of these 2 precursors of the mutagen was found in them. A major reaction product of (-)-(1S,3S)-MTCA and nitrite was a compound having a nitroso substitution at position N-2, but this compound was not mutagenic. Thus, the mutagen(s) formed from (-)-(1S,3S)-MTCA and nitrite was a minor product(s), and its specific mutagenic activity must be very high. [This study has human applications.].