Mutagenic activity of amino acid pyrolyzates in Salmonella typhimurium TA 98

Matsumoto, Takashi; Yoshida, Daisuke; Mizusaki, Shigenobu; Okamoto, Hitoshi

doi:10.1016/0027-5107(77)90170-1

Cited by 111 publications

(18 citation statements)

References 7 publications

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“…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).…”

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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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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“…We demonstrated previously that the pyrolysis products of amino acids and proteins in model systems are mutagenic (1,2). The mutagenic principles in the pyrolyzates of amino acids have been isolated and identified by Sugimura et al (3,4).…”

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confidence: 93%

Formation of mutagens by heating foods and model systems.

Yoshida¹,

Matsumoto²,

Okamoto³

et al. 1986

Environ Health Perspect

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We have demonstrated that the pyrolysis products of amino acids and proteins in model systems are mutagenic. The mutagenic principles in the pyrolyzates of amino acids have been isolated and identified by Sugimura et al. We have isolated and identified amino-a-carbolines from pyrolyzed soybean globulin as mutagens. The yield of mutagens by the heating of food constituents is changed by the heating method. Effects of heating methods on the yield of amino-a-carbolines were studied in a series of experiments, and the results are shown in this paper. Additionally, it has been shown that by the heating of creatinesugar mixtures imidazoquinoline or quinoxaline mutagens are formed.We demonstrated previously that the pyrolysis products of amino acids and proteins in model systems are mutagenic (1,2). The mutagenic principles in the pyrolyzates of amino acids have been isolated and identified by Sugimura et al. (3,4). We have isolated and identified amino-a-carbolines from pyrolyzed soybean globulin as mutagens (5). The yield of mutagens by the heating of food constituents is changed by the heating method. Formation of Amino-oL-carbolines It was supposed that amino-ot-carbolines (I) and amino-y-carbolines as well as Trp-P-1 or Trp-P-2 would be formed from the tryptophan moiety of protein. Therefore, a relationship between tryptophan content in the protein and the pyrolytic formation of mutagens was studied (6). Zein, gluten, globulin, casein, and albumin as well as chicken meat and horse mackerel were pyrolyzed at 5500C and the yield of mutagens was determined. The content of tryptophan in these materials was determined by an amino acid analyzer. The yield of amino-a-carboline correlated positively with the content of tryptophan in the protein, and it was 60 to 850 times that of Trp-P-2.Yield of amino-ca-carboline and Trp-P-2 per gram of tryptophan in the protein was calculated (Table 1). The yield of amino-ot-carboline per gram of tryptophan in the protein was higher than that of free tryptophan, especially for albumin and chicken meat. Although proteins and proteinaceous materials tested in this experiment showed appreciably higher yield of amino-a-carboline than that expected from the tryptophan content, *Central Research Institute, The Japan Tobacco & Salt Public Corporation, 6-2 Umegaoka, Midori-ku, Yokohama 227 Japan. the yield of Trp-P-2 per gram of tryptophan in the protein was lower than that of free tryptophan and indicated little difference among the proteins tested. The reason for the formation of higher amounts of amino-acarboline than expected from the tryptophan contents remains obscure.The effect of heating temperature on the yield of amino-a-carboline was determined using albumin. Amino-a-carboline was formed when albumin was heated to a temperature of 200°C, and the concentration increased with increasing temperature. The maximum yield of the carboline was obtained at 600 to 700°C, and the ratio of amino-a-carboline to mutagenic activity of whole heated product was approximately constant among the heati...

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“…[1][2][3][4][5] Heterocyclic amines are well-known mutagenic compounds (carcinogens), [6][7][8][9][10][11][12] and we are exposed to such risky compounds every day. The effects of various antimutagenic materials, including chlorophyllin, 13) dietary fiber, 14,15) and bacterial cells, [16][17][18][19][20][21] have been reported to help us from the risk of such food-borne mutagens.…”

Section: Introductionmentioning

confidence: 99%

Ability of lactic acid bacteria isolated from Japanese fermented plant products to bind heterocyclic amines.

Hatakeyama

Tanaka

Satoh

et al. 2011

Jpn. J. Lactic Acid Bact.

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Lactobacillus plantarum SNJ81 (SNJ81), Lb. fermentum SNA41 (SNA41), Lb. parabuchneri SNC91 (SNC91), Lb. delbrueckii SNK64(SNK64), and Leuconostoc mesenteroides subsp. mesenteroides 10D-2 (10D-2), originally isolated from fermented vegetables: Sunki and Kaburazushi, were examined for their ability to bind heterocyclic amines contained in cooked foods. The tested bacteria boundand 2-amino-3,4-dimethylimidazo [4,5-f] quinoline (MeIQ). One of the heterocyclic amines used here, Trp-P-1 was highly bound by all the LAB strains. Dead LAB cells retained their ability to bind these heterocyclic amines, and the binding ability remained even in the presence of artificial digestive enzymes. These results indicate that LAB strains contained in Japanese traditional fermented vegetables have a high potent ability to bind heterocyclic amines.

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Mutagenic activity of amino acid pyrolyzates in Salmonella typhimurium TA 98

Cited by 111 publications

References 7 publications

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)

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)

Formation of mutagens by heating foods and model systems.

Ability of lactic acid bacteria isolated from Japanese fermented plant products to bind heterocyclic amines.

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