Presence of 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, a precursor of a mutagenic nitroso compound, in soy sauce.

Wakabayashi, Keiji; Ochiai, Masako; Saitô, Hazime; Tsuda, Mitsuhiro; Suwa, Yoshihide; Nagao, Minako; Sügimura, Takashi

doi:10.1073/pnas.80.10.2912

Cited by 77 publications

(46 citation statements)

References 23 publications

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“…Two isomers of 1-methyl-1,2,3,4-tetrahydro-p-carboline-3-carboxylic acids which can be produced by condensation of L-tryptophan and acetaldehyde were found to be mutagen precursors in soy sauce by Wakabayashi et al (68). Tyramine is also found in soy sauce and a mutagenic diazo-oxide compound was produced after nitrite treatment (69).…”

Section: Mutagen Precursors Found In Fermented Foods and Vegetablesmentioning

confidence: 99%

Past, present, and future of mutagens in cooked foods.

Sügimura¹

1986

Environ Health Perspect

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Mutation assay with Salmonella typhimurium enabled us to detect various types of mutagens in cooked foods. A series of mutagenic heterocyclic amines has been isolated and identified in broiled fish and meat and in pyrolyzates of amino acids and proteins. Feeding experiments showed these mutagens to be carcinogenic in mice and rats. The mechanism of formation and pathway of metabolic activation of these heterocyclic amines have been elucidated. Their contents in various cooked foods have been determined. The presence of mutagenic nitropyrenes (some of which were confirmed as carcinogens) in grilled chicken was also established. Roasted coffee beans also yield mutagens such as methylglyoxal. The formation of mutagen precursors, including ,B-carboline derivatives and tyramine which become mutagens with nitrite treatment, was found during food processing. Oncogene activation in animal tumors induced by some of these food mutagens/carcinogens has been confirmed. The role of mutagens/carcinogens in cooked foods in human cancer development has not yet been exactly evaluated. In order to do this, more information on their carcinogenic potency, human intake, metabolism in the human body, and the effects of combined administration with other initiators, promoters and other modifying factors in food is required.

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Section: Mutagen Precursors Found In Fermented Foods and Vegetablesmentioning

confidence: 99%

Past, present, and future of mutagens in cooked foods.

Sügimura¹

1986

Environ Health Perspect

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“…Both the (1S,3S) and (1R,3S) diastereoisomers are obtained in the reaction, which are easily separated and isolated in the pure form. Of the two, the SS isomer has been seen to be present in amounts four times higher than the RS isomer (7,18).…”

Section: Synthesis Of IIImentioning

confidence: 99%

“…␤-Carbolines formed between hexulose, xylose, furan-2-carboxaldehyde, acetaldehyde, and glucose on the one hand and amino acids such as lysine, glycine, proline, arginine, histidine, and tryptophan on the other have been reported (5)(6)(7)(8)(9)(10). They are formed endogenously in plants and animals (for example, harmane, structure I in Fig.…”

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confidence: 99%

β-Carbolines That Accumulate in Human Tissues May Serve a Protective Role against Oxidative Stress

Pari¹,

Sundari²,

Chandani³

et al. 2000

Journal of Biological Chemistry

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␤-Carbolines are tricyclic nitrogen heterocycles formed in plants and animals as Maillard reaction products between amino acids and reducing sugars or aldehydes. They are being detected increasingly in human tissues, and their physiological roles need to be understood. Two ␤-carboline carboxylates have been reported to accumulate in the human eye lens. We report here on the identification of another ␤-carboline, namely 1-methyl-1-vinyl -2,3,4-trihydro-␤-carboline-3-carboxylic acid, in the lenses of some cataract patients from India. Analysis of these three lenticular ␤-carbolines using photodynamic and antioxidant assays shows all of them to be inert as sensitizers and effective as antioxidants; they quench singlet oxygen, superoxide and hydroxyl radicals and inhibit the oxidative formation of higher molecular weight aggregates of the test protein, eye lens ␥-crystallin. Such antioxidative ability of ␤-carbolines is of particular relevance to the lens, which faces continual photic and oxidative stress. The ␤-carboline diacid IV is also seen to display an unexpected ability of inhibiting the thermal coagulation of ␥-crystallin and the dithiothreitol-induced precipitation of insulin. These results offer experimental support to earlier suggestions that one of the roles that the ␤-carbolines have is to offer protection against oxidative stress to the human tissues where they accumulate.

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“…In most of these studies the experimental conditions during nitrosation were modifications of the so-called nitrosation assay procedure which is the test protocol adopted by the World Health Organization to investigate the occurrence of compounds susceptible to nitrosation in drugs. After nitrite treatment sauerkraut, pickled vegetables, Chinese cabbage (Brassica pekinensis) and fava beans (Vicia faba) contained direct mutagenic activity (Piacek-Llanes & Tannenbaum, 1982;Wakabayashi et al 1983Wakabayashi et al , 1984Wakabayashi et al , 1985van der Hoeven et al 1984;Jongen et al 1987;Groenen & Bussink, 1988). Further work showed that I3A, 4-methoxyindole-3-acetonitrile and 4-methoxyindole-3-aldehyde could act as precursors of NOC in Chinese cabbage (Wakabayashi et al 1985(Wakabayashi et al , 1986.…”

Section: Nitrosation Of Glucosinolatesmentioning

confidence: 99%

Glucosinolates in Brassica: Occurrence and significance as cancer-modulating agents

Jongen

1996

Proc. Nutr. Soc.

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Les glycosinolates R E S U M ELes legumes brassicas comprennent toutes sortes de choux, choux de Bruxelles, broccolis, choux-fleurs, choux-raves, navets et rutabagas. 11s appartiennent a famille des crucifkres et sont connus en botannique sous le nom de Brussica. Les brassicas sont frkquemment consommes par les hommes des cultures occidentales et orientales aussi bien que par les animaux. Aux Pays-Bas. on ne connaft pas prkcisement les quantitts consummkes par les hommes, mais plus de 36 g brassicas y sont disponibles par personne et par jour. La saveur typique des brassicas est en grande partie due i des molecules volatiles dCrivCes du glycosinolate. I1 semble que la presence de glycosinolates dans les plantes pour la consommation humaine est limitee aux cruciferes. La composition chimique et la presence de glycosinolates et de leurs produits de degradation ont CtC Ctudikes. I1 est possible que les niveaux de glycosinolates totaux dans les plantes dependent de la variCtC, des conditions de culture, du climat et des pratiques agronomiques, alors que les niveaux dans une plante particulikre varient selon les parties de la plante. Dans les plantes, les glycosinolates et leurs produits d'hydrolyse agissent comme des allilochimiques, qui sont des composes qui affectent les comportement, la santC et la croissance d'autres espkces.Du point de vue de la toxicologie, tous les produits volatiles d'hydrolyse des glucosinolates sont intkressants. Parmi les problkmes lies a la consommation de ces composes, ceux affectant la thyroi'de ont etk CtudiCs de faSon plus approfondie. Dans la plupart des etudes sur les animaux rkalisees dans le passe, la goitrogknicite induite par les produits derives des glycosinolates s'est rCvClCe &re limitCe A des situations de dkficience en iode. Dans une etude sur la fonction thyroldienne aucun effet des glycosinolates n'a pu &tre retrouve (McMillan et al. 1986).On a suggere que les produits derives des glycosinolates deviennent mutagenes et candrigknes aprks nitrosation. Dans une etude approfondie, on a recherche dans plusieurs brassicas hollandais leur potentiel a former directement des composes mutagknes de nitrosyl en reponse ii un traitement de nitrite. Ce potentiel a etC compare avec les niveaux des glycosinolates. On a Ctudie la formation de produits nitroses d'indole-3-acetonitrile, indole-3-carbinol et indole, en portant une attention particulikre i la stabilitk de ces produits. Ces etudes ont rCvelC que les composes indoliques presents dans les brassicas peuvent Ctre nitroses et devenir mutagknes a la nitrosation. Cependant les produits nitroses ne sont stables qu'en presence de grandes quantites de nitrite libre. La nitrosation des glucosinolates et de leurs produits derives ne constitue pas un danger significatif pour la sant6.https://www.cambridge.org/core/terms. https://doi

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Presence of 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, a precursor of a mutagenic nitroso compound, in soy sauce.

Cited by 77 publications

References 23 publications

Past, present, and future of mutagens in cooked foods.

Past, present, and future of mutagens in cooked foods.

β-Carbolines That Accumulate in Human Tissues May Serve a Protective Role against Oxidative Stress

Glucosinolates in Brassica: Occurrence and significance as cancer-modulating agents

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