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Published on: September 25, 2017
Occurrence, identification, and bacterial mutagenicity of heterocyclic amines in cooked food
1Biomedical Sciences Division, Lawrence Livermore National Laboratory, University of California, Livermore 94550.
Abstract:
Potent mutagenic activity in Salmonella bacteria has been reported in cooked foods in numerous laboratories worldwide. Determining the human risk from exposure to these biologically active compounds in our diet requires genotoxic and carcinogenic evaluation of the chemicals coupled with determination of the dose consumed. Thus, knowledge of the exact structure of the mutagens present in the food and enough synthesized material for biological assessment are essential for this evaluation. To reach this goal, isolation of these compounds requires the Ames/Salmonella assay to guide the purification and identification process. Mass and NMR spectrometry are used to identify the isolated compounds. Finally, these findings are followed by synthesis of the exact isomer. The predominant class of mutagens found in cooked foods of the western diet are amino-imidazo-quinoxalines, amino-imidazo-pyridines and amino-imidazo-quinolines, collectively called amino-imidazoazaarenes (AIAs). Mass amounts of these specific compounds range from less than 1 to 70 ng/g of meat. The mutagens are formed from the heating of natural precursors (creatinine, amino acids, and possibly sugars) in the food. These AIAs are some of the most potent mutagens ever tested in Salmonella bacteria with the number and position of methyl groups having an important influence on the mutagenic activity.
Insights
Cooked foods contain potent mutagens called amino-imidazoazaarenes (AIAs). Understanding their structure and human health risks requires isolation, identification, and synthesis for further toxicological evaluation.
Area of Science:
- Food chemistry
- Toxicology
- Organic chemistry
Background:
- Cooked foods worldwide exhibit potent mutagenic activity in Salmonella bacteria.
- Assessing human health risks necessitates genotoxic and carcinogenic evaluations of dietary mutagens.
- Identifying the precise structure and quantity of these mutagens is crucial for risk assessment.
Purpose of the Study:
- To outline the essential steps for isolating, identifying, and synthesizing dietary mutagens.
- To highlight the importance of the Ames/Salmonella assay in guiding the purification and identification process.
- To emphasize the need for synthesized compounds for comprehensive biological assessment.
Main Methods:
- Utilizing the Ames/Salmonella assay to guide the purification of mutagens.
- Employing Mass and NMR spectrometry for structural identification of isolated compounds.
- Synthesizing the exact isomer of identified mutagens for further testing.
Main Results:
- The predominant mutagens in cooked Western diets are amino-imidazoazaarenes (AIAs).
- AIAs are found in concentrations ranging from less than 1 to 70 ng/g of meat.
- These compounds are formed from heating natural precursors like creatinine and amino acids.
- AIAs are highly potent mutagens, with methyl group configuration significantly impacting activity.
Conclusions:
- Amino-imidazoazaarenes (AIAs) are potent mutagens found in cooked foods.
- Structure elucidation and synthesis are critical for evaluating the human health risks of AIAs.
- Further research is needed to fully understand the toxicological impact of these dietary mutagens.
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