The Dangers of Heterocyclic Aromatic Amines

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“Heterocyclic amines are a group of 20 chemical compounds formed during cooking. They are found in meats that are cooked to the well done stage, in pan drippings, and in meat surfaces that show a crispy brown crust. Epidemiological studies show associations between intakes of heterocyclic amines and cancers of the colon, rectum, breast, prostate, pancreas, lung, stomach, and esophagus, and animal feeding experiments support a causal relationship. The U.S. Department of Health and Human Services Public Health Service labeled several heterocyclic amines as likely to be carcinogenic to humans in its most recent Report on Carcinogens.”

(Source: Wikipedia.org)

The most common types of Heterocyclic Aromatic Amines (HAA’s) include:

  • 4,8-DiMelQx 2-Amino-3,4,8-Trimethylimidazo [4,5-f]Quinoxaline
  • 8-MelQx 2-Amino-3,8-Dimethylimidazo [4,5-f]Quinoxaline
  • IQ 2-Amino-3-Methylimidazo [4,5-f]Quinoline
  • MelQ 2-Amino-3,4-Dimethylimidazo [4,5-f]Quinoline
  • PhIP 2-Amino-1-Methyl-6-Phenylimidazo [4,5,b]Pyridine
  • TMIP 2-Amino-N,N,N-Trimethylimidazopyridine

HAAs form when Amino Acids and Creatine present in muscle Meats react at high temperatures (above 100° C). Temperature is the most important factor in formation of HAAs. Frying, Grilling, and Barbecuing produce the largest amounts of HAAs because the Meats are cooked at very high temperatures. Roasting and Baking are done at lower temperatures, so lower levels of HAAs are likely. Microwaving, Stewing, Boiling, or Poaching are done at or below 100° and cooking at this low temperature creates negligible amounts of HAAs.

The following substances have been studied and research for their ability to counteract the toxic effects of HAA’s:

Indole-3-Carbinol

Guo, D., et al. Protection by chlorophyllin and indole-3-carbinol against 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-induced DNA adducts and colonic aberrant crypts in the F344 rat. Carcinogenesis. 16(12):2931-2937, 1995

Caffeic Acid

Mitchell, T. Barbequer beware. Life Extension. 6(11), 2000

Curcumin

Shishu, et al. Inhibitory effect of curcumin and its natural analogues on genotoxicity of heterocyclic amines from cooked food. Indian J Exp Biol. 40(12):1365-1372, 2003

Epigallo-Catechin-Gallate (EGCG)

Dashwood, R. H., et al. Cancer chemopreventive mechanisms of tea against heterocyclic amine mutagens from cooked meat. Proc Soc Exp Biol Med. 220(4):239-243, 1999

Luteolin

Mitchell, T. Barbequer beware. Life Extension. 6(11), 2000

Quercetin

Ciolino, H. P., et al. Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially. Biochem J. 340(Part 3):715-722, 1999

Chlorophyll

Ziegler, J. It’s not easy being green: Chlorophyll being tested Journal of the National Cancer Institute. 87(1):11, 1995

Guo, D., et al. Protection by chlorophyllin and indole-3-carbinol against 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-induced DNA adducts and colonic aberrant crypts in the F344 rat. Carcinogenesis. 16(12):2931-2937, 1995

Natto

Rajendran, R., et al. Binding activity of natto (a fermented food) and Bacillus natto isolates to mutagenic-carcinogenic heterocyclic amines. Can J Microbiol. 47(10):935-942, 2001

Rosemary

Puangsombat, K., et al. Inhibition of heterocyclic amine formation in beef patties by ethanolic extracts of rosemary. J Food Sci. 75(2):T40-T47, 2010

Broccoli

Walters, D. G., et al. Cruciferous vegetable consumption alters the metabolism of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in humans. Carcinogenesis. 2004

Brussels Sprouts

Hoelzl, C., et al. Consumption of Brussels sprouts protects peripheral human lymphocytes against 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and oxidative DNA-damage: results of a controlled human intervention trial. Mol Nutr Food Res. 2008


References:

Knize, M. G., et al. Analysis of cooked muscle meats for heterocyclic aromatic amine carcinogens. Mutation Research. 376(1-2):129-134, 1997

Sugimura,T.(1997). Overview of carcinogenic heterocyclic amines. Mutation Research, 376, 211-219

Chemicals in Meat Cooked at High Temperatures and Cancer Risk

A Review on the Formation of Carcinogenic/Mutagenic Heterocyclic Aromatic Amines


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