Food-borne heterocyclic amines. Chemistry, formation, occurrence and biological activities. A literature review

Eisenbrand, Gerhard; Tang, Weici

doi:10.1016/0300-483x(93)90109-6

Cited by 142 publications

(61 citation statements)

References 346 publications

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“…Over the past two decades, a series of aminoimidazoazaarenes (AIAs) has been isolated from cooked foods, determined to be mutagenic in bacterial and mammalian test systems, and shown to be carcinogenic in rodents and monkeys Hatch et al, 1992;Overik and Gustafsson, 1990;Skog, 1993;Wakabayashi et al, 1993;Eisenbrand and Tang, 1993;Munro et al, 19931. Some of these chemicals are among the most potent known bacterial mutagens, and related congeners have been synthesized for research [Hatch et al, 19911.…”

Section: Introductionmentioning

confidence: 99%

Structural and quantum chemical factors affecting mutagenic potency of aminoimidazo-azaarenes

Hatch

Colvin

Seidl

1996

Environ. Mol. Mutagen.

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Section: Introductionmentioning

confidence: 99%

Structural and quantum chemical factors affecting mutagenic potency of aminoimidazo-azaarenes

Hatch

Colvin

Seidl

1996

Environ. Mol. Mutagen.

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“…Detoxified compounds are often ring-hydroxylated, followed by phase II conjugation. Activated compounds are hydroxylated in their characteristic exocyclic amino group, usually followed by O-esterification catalyzed by acetyltransferase or sulfotransferase (Eisenbrand and Tang, 1993). Enzymes from the CYP1A family are especially involved in the phase I metabolism of ␣-carbolines to their corresponding N 2 -OH-derivates (Niwa et al, 1982;Sugimura, 1985).…”

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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“…The heterocyclic amine PhIP is considered to be the most abundant HCA responsible for inducing various types of tumours in rats (Felton et al, 2004). More than 600 individual compounds and complex dietary mixtures have been studied for protective effects towards HCA (Schwab et al, 2000) and numerous articles have been published regarding mammalian enzymes involved in the bioactivation and detoxification of these compounds (Eisenbrand and Tang, 1993). The genotoxicity of HCA originates from their activation by a series of reactions involving cytochrome P450 when the parent compound is converted to an electrophilic derivative such as a nitrenium ion that covalently binds to DNA resulting in DNA adducts and subsequently in nucleotide alterations and chromosomal aberrations (Goldman and Shields, 2003;Hatch et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

The Effect of Flavonoids in Soybean Products in Lymphocytes from IBD and Colon Cancer Patients After Treatment with Food Mutagens and Hydrogen Peroxide

Najafzadeh¹,

Kurzawa-Zegota²,

Baumgartner³

et al. 2011

Soybean and Health

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Food-borne heterocyclic amines. Chemistry, formation, occurrence and biological activities. A literature review

Cited by 142 publications

References 346 publications

Structural and quantum chemical factors affecting mutagenic potency of aminoimidazo-azaarenes

Structural and quantum chemical factors affecting mutagenic potency of aminoimidazo-azaarenes

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)

The Effect of Flavonoids in Soybean Products in Lymphocytes from IBD and Colon Cancer Patients After Treatment with Food Mutagens and Hydrogen Peroxide

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