Determination of mutagens, amino-α-carbolines in grilled foods and cigarette smoke condensate

Matsumoto, Takashi; Yoshida, Daisuke; Tomita, Hideo

doi:10.1016/0304-3835(81)90045-8

Cited by 137 publications

(79 citation statements)

References 10 publications

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“…Development of liver and blood vessel tumors was 10 to 20 weeks later in groups treated with Glu-P-2 than in the groups treated with Glu-P-1 in both sexes. Tumor development was about 20 weeks later for liver and blood vessel tumors in mice given AaC than in mice of both sexes given MeAaC. Thus the carcinogenic potency of Glu-P-1 was slightly higher than that of Glu-P-2, and MeAc-C showed slightly more potent carcinogenicity than AaC.…”

Section: Carcinogenicity Of Heterocyclic Amines In Micementioning

confidence: 87%

Carcinogenicity in mice and rats of heterocyclic amines in cooked foods.

Ohgaki¹,

Hasegawa²,

Kato³

et al. 1986

Environ Health Perspect

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Carcinogenicities of mutagenic heterocyclic amines in cooked foods have been tested in CDF, mice and F344 rats of both sexes. Eight heterocyclic amines-Trp-P-1, Trp-P-2, Glu-P-1, Glu-P-2, MeAaC, AaC, IQ, and MeIQ-were given to mice and/or rats at 0.02 to 0.08% in the diet continuously. In mice, all heterocyclic amines tested were demonstrated to be carcinogenic. Hepatocellular carcinomas were induced in a high incidence in all groups treated with heterocyclic amines. Hemangioendothelial sarcomas were also induced by Glu-P-1, Glu-P-2, MeAaC, and AaC. Most hemangioendothelial sarcomas were located in the interscapular brown adipose tissue. In mice given IQ, forestomach and lung tumors were also observed in a high incidence. Carcinogenicity tests on MeIQ are ongoing, and interim data by week 83 show that MeIQ also induces forestomach tumors in addition to liver tumors.In rats, hepatocellular carcinomas were induced by Trp-P-1, Glu-P-1, Glu-P-2, and IQ. In rats given Glu-P-1, Glu-P-2, and IQ, adenocarcinomas in the small and large intestines, squamous cell carcinomas in the Zymbal gland and clitoral gland were also observed in a high incidence.

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Section: Carcinogenicity Of Heterocyclic Amines In Micementioning

confidence: 87%

Carcinogenicity in mice and rats of heterocyclic amines in cooked foods.

Ohgaki¹,

Hasegawa²,

Kato³

et al. 1986

Environ Health Perspect

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“…Aminox-carboline (AaC) and methylamino-a-carboline (MeA(xC) were isolated from a pyrolyzate of soybean globulin by Yoshida et al (29). The presence of Glu-P-2 (30), Trp-P-1 and Trp-P-2 (31), and AaxC and MeAaC in broiled foods (32) and of AcLC and MeAaC in cigarette smoke condensates (32,33) has been reported. These heterocyclic amines also possess a fairly high mutagenic activity toward S. typhimurium TA 98 with S9 mix as shown in Table 3.…”

Section: Mutagens Found In Cooked Foods and Heated Amino Acids And Amentioning

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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“…␣-Carbolines are formed as pyrolysis products of either tryptophan or proteins of animal or vegetable origin (e.g., albumin, casein, or soybean globulin) (Yoshida et al, 1978;Sugimura, 1997). ␣-Carbolines are found in cooked food such as fried meat, chicken, fish, mushroom, and bouillon concentrates (Matsumoto et al, 1981;Gross and Gruter, 1992;Layton et al, 1995;Knize et al, 1997;Skog et al, 1998;Solyakov et al, 1999) and cigarette smoke condensates (Yoshida and Matsumoto, 1980;Matsumoto et al, 1981;Manabe et al, 1990;Wakabayashi et al, 1993). Finally, MeA␣C is also found in wine (Richling et al, 1997).…”

mentioning

confidence: 99%

IDENTIFICATION OF METABOLITES IN URINE AND FECES FROM RATS DOSED WITH THE HETEROCYCLIC AMINE, 2-AMINO-3-METHYL-9H-PYRIDO[2,3-b]INDOLE (MeAαC)

Frederiksen¹

2004

Drug Metab Dispos

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ABSTRACT:2-Amino-3-methyl-9H-pyrido[2,3-b]indole (MeA␣C) is a proximate mutagenic and carcinogenic heterocyclic amine formed during ordinary cooking. In model systems, MeA␣C can be formed by pyrolyses of either tryptophan or proteins of animal or vegetable origin. In the present study, the in vivo metabolism of MeA␣C in rats was investigated. Rats were dosed with tritium-labeled MeA␣C, and urine and feces were collected over 3 days. The metabolites of MeA␣C were identified by high performance liquid chromatography-mass spectrometry and quantified by liquid scintillation counting. Conjugated metabolites were characterized by enzymatic hydrolyzes with ␤-glucuronidase or arylsulfatase. The data showed that the metabolic pattern of MeA␣C was similar in all rats. About 65% of the dose was excreted in urine and feces, and the major amount of MeA␣C-metabolites was excreted during the first 24 h. Thirty-four percent of the dose was found in the rat urine samples collected to 24 h. In addition to unmetabolized MeA␣C and two phase I metabolites, 6-OH-MeA␣C and 7-OH-MeA␣C, the following conjugated metabolites were identified: MeA␣C-N 2 -glucuronide, A␣C-3-CH 2 O-glucuronide, 3-carboxy-A␣C and 3-carboxy-A␣C-glucuronide, and sulfate and glucuronide conjugates of 6-OH-MeA␣C and 7-OH-MeA␣C. Also, a large amount of a rather unstable compound proposed to be of MeA␣C-N1-glucuronide was found. About 21% of the dose was excreted in feces during the first 24 h, and MeA␣C and 7-OH-MeA␣C were the only compounds identified in feces. Any activated metabolites of MeA␣C were not detected in rat urine or feces.2-Amino-9H-pyrido[2,3-b]indole (A␣C 1 ) and its methyl homolog 2-amino-3-methyl-9H-pyrido[2,3-b]indole (MeA␣C) are two foodborne mutagenic and carcinogenic heterocyclic amines (Wakabayashi et al., 1992). A␣C and MeA␣C are often referred to as ␣-carbolines and are classified as unpolar heterocyclic aromatic amines. ␣-Carbolines are formed as pyrolysis products of either tryptophan or proteins of animal or vegetable origin (e.g., albumin, casein, or soybean globulin) (Yoshida et al., 1978;Sugimura, 1997). ␣-Carbolines are found in cooked food such as fried meat, chicken, fish, mushroom, and bouillon concentrates (Matsumoto et al., 1981;Gross and Gruter, 1992;Layton et al., 1995;Knize et al., 1997;Skog et al., 1998;Solyakov et al., 1999) and cigarette smoke condensates (Yoshida and Matsumoto, 1980;Matsumoto et al., 1981;Manabe et al., 1990;Wakabayashi et al., 1993). Finally, MeA␣C is also found in wine (Richling et al., 1997). ␣-Carbolines are mutagenic in bacterial test systems (Matsumoto et al., 1977;Nagao et al., 1983). Dietary administration of ␣-carbolines to rodents has shown that they are moderately potent carcinogens (Ohgaki et al., 1984;Tamano et al., 1994;Snyderwine et al., 1998).Like other heterocyclic amines, the metabolism of ␣-carbolines usually follows two different pathways, detoxification and activation. The first step in the metabolism of heterocyclic amines is a phase I hydroxylation catalyzed by cytochrome P450 enzym...

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Determination of mutagens, amino-α-carbolines in grilled foods and cigarette smoke condensate

Cited by 137 publications

References 10 publications

Carcinogenicity in mice and rats of heterocyclic amines in cooked foods.

Carcinogenicity in mice and rats of heterocyclic amines in cooked foods.

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

IDENTIFICATION OF METABOLITES IN URINE AND FECES FROM RATS DOSED WITH THE HETEROCYCLIC AMINE, 2-AMINO-3-METHYL-9H-PYRIDO[2,3-b]INDOLE (MeAαC)

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