Premium
Two food‐borne heterocyclic amines: Metabolism and DNA adduct formation of amino‐α‐carbolines
Author(s) -
Frederiksen Hanne
Publication year - 2005
Publication title -
molecular nutrition and food research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.495
H-Index - 131
eISSN - 1613-4133
pISSN - 1613-4125
DOI - 10.1002/mnfr.200400061
Subject(s) - amino acid , carcinogen , chemistry , indole test , tryptophan , metabolism , adduct , microsome , mutagen , biochemistry , dna adduct , heterocyclic compound , in vivo , stereochemistry , in vitro , organic chemistry , biology , microbiology and biotechnology
The amino‐α‐carbolines 2‐amino‐9 H ‐pyrido[2,3‐ b ]indole (AαC) and 2‐amino‐3‐methyl‐9 H ‐pyrido‐[2,3‐ b ]indole (MeAαC) are two mutagenic and carcinogenic heterocyclic amines formed during ordinary cooking. Amino‐α‐carbolines can be formed in model systems by pyrolyzing tryptophan or proteins of animal or vegetable origin, furthermore they are found in many cooked foods, such as fish, meat, and chicken. The specific mutagenicity of the amino‐α‐carbolines are lower in the Ames Salmonella assay than other heterocyclic amines, but in rodent studies the carcinogenicity of the amino‐α‐carbolines are comparable to other heterocyclic amines. The metabolic pathways of the amino‐α‐carbolines have been studied in vitro and in vivo , and the detoxified phase I and phase II metabolites characterized and quantified. The metabolic activation of the amino‐α‐carbolines and the formation of DNA‐adducts have also been studied. Characteristic for the amino‐α‐carbolines are that relatively large amounts of these compounds in rat and human hepatic microsomes are activated to potent carcinogenic compounds compared with other heterocyclic amines, but further in vivo studies of the amino‐α‐carbolines are needed to highlight these indications. In this review, the main characteristics with focus on the metabolism and the DNA‐adduct formation of the amino‐α‐carbolines are described and compared with other heterocyclic amines.