Abstract
Heterocyclic aromatic amines (HAA) and polycyclic aromatic hydrocarbons (PAH) are mutagens and animal carcinogens sometimes formed when foods are heated or processed. Determining their role in cancer etiology depends on comparing human exposures and determining any significant dose-related effect. Chemical analysis of foods shows that flame-grilling can form both PAH and HAA, and that frying forms predominantly HAA. With detection limits of about 0.1 ng/g, amounts found in commercially processed or restaurant foods range from 0.1 to 14 ng/g for HAA, and levels of PAH up to 1 ng/g in a liquid smoke flavoring. Laboratory fried samples have greater amounts of PAH, up to 38 ng/g in hamburgers, and high levels of HAA, over 300 ng/g, are measured in grilled chicken breast. Understanding the processing conditions that form PAH and HAA can lead to methods to greatly reduce their occurrence in processed foods.
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Abbreviations
- B[a]A:
-
benzo[a]anthracene
- B[a]P:
-
benzo[a]pyrene
- B[b]F:
-
benzo[b]fluoranthene
- B[k]F:
-
benzo[k]fluoranthene
- DBA:
-
dibenzo[a,h]anthracene
- DiMeIQx:
-
2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline
- Indenopyrene:
-
indeno[1,2,3-c,d]pyrene
- MeIQx:
-
2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline
- PhIP:
-
2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine
References
Ames, B. N.; McCann, J.; Yamasaki E. Methods for detecting carcinogens and mutagens with the Salmonella/mammalian microsome mutagenicity test. Mutat.Res. 1975, 31, 347–364.
Badger, G. M.; Kimber, R. W. L. The formation of aromatic hydrocarbons at high temperatures, Part VI. The pyrolysis of tetralin. J. Chem. Soc. 1960, 51,266–270.
Basel, R. M. U.S. patent 1995, 5,439,691.
Chen, B. H.; Wang, C. Y.; Chiu, C. P. Evaluation of analysis of polycyclic aromatic hydrocarbons in meat products by liquid chromatography. J. Agric. Food Chem. 1996, 44, 2244–2251.
Chu, M. M. L.; Chen, C. W. The evaluation and estimation of potential carcinogenic risks of polynuclear aromatic hydrocarbons (PAH). United States Environmental Protection Agency Research and Development 1985, 1–29.
Commoner, B.; Vithayathil, A. J.; Dolara, P.; Nair, S.; Madyastha, P.; Cuca, G. C. Formation of mutagens in beef and beef extract during cooking. Science 1978, 201, 913–916.
Dennis, M. J.; Massey, R. C.; McWeeny, D. J.; Knowles, M. E.; Watson, D. Analysis of polycyclic aromatic hydrocarbons in UK total diets. Food Chem. Toxic. 1983, 21, 569–574.
Dennis, M. J.; Massey, R. C.; McWeeny, D. J.; Larsson, B.; Eriksson, A.; Sahlberg, G. Comparison of a capillary gas chromatographic and a high-performance liquid chromatographic method of analysis for polycyclic aromatic hydrocarbons in food. J. Chromatogr. 1984, 285, 127–133.
Doll, R. Nature and nurture: possibilities for cancer control. Carcinogenesis 1996, 17, 177–184.
El-Bayoumy, K.; Chae, Y-H.; Upadhyaya, P.; Rivenson, A.; Kurtzke, C.; Reddy, B.; Hecht, S. S. Comparative tumorigenicity of benzo[a]pyrene, 1-nitropyrene, and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine administered by gavage to female CD rats. Carcinogenesis 1995, 16, 431–434.
Felton, J. S.; Fultz, E.; Dolbeare, F. A.; Knize, M. G. Reduction of heterocyclic amine mutagens/carcinogens in fried beef patties by microwave pretreatment. Food Chem. Toxic. 1994, 32, 897–903.
GarcÃa Falcón, M. S.; González Amigo, S.; Lage Yusty, M. A.; López de Alda-Villaizán, M. J.; Simal Lozano, J. Enrichment of benzo[a]pyrene in smoked food products and determination by high-performance liquid chromatography-fluorescence detection. J. Chromatogr. A 1996, 753, 207–215.
Gold, L. S.; Manley, N. B.; Slone, T. H.; Garfinked, B. G.; Rohlbach, L.; Ames, B. N. The fifth plot of the carcinogenic potency database: results in animal bioassays published in the general literature through 1988 and by the National Toxicology Program through 1989. Environ. Health Perpec. 1993, 100, 65–135.
Gross, G. A. Simple methods for quantifying mutagenic heterocyclic amines in food products. Carcinogenesis 1990, 11, 1597–1603.
Gross, G. A.; Grüter, A. Quantitation of mutagen i c/carcinogenic heterocyclic aromatic amines in food products. J. Chromatogr. 1992, 592, 271–278.
Gross, G. A.; Turesky, R. J.; Fay, L. B.; Stillwell, W. G.; Skipper, P. L.; Tannenbaum, S. R. Heterocyclic amine formation in grilled bacon, beef, and fish, and in grill scrapings. Carcinogenesis 1993, 14, 2313–2318.
Hatch, F. T.; Knize, M. G.; Moore, D. H.; Felton, J. S. Quantitative correlation of mutagenic and carcinogenic potencies for heterocyclic amine from cooked foods and additional aromatic amines. Mutat. Res. 1992, 271, 269–287.
Howard, J. W.; Fazio, T. Review of polycyclic aromatic hydrocarbons in foods: analytical methodology and reported findings of polycyclic aromatic hydrocarbons in foods. J. Assoc. Off. Anal. Chem. 1980, 63, 1077–1104.
Johansson, M. A. E.; Knize, M. G.; Jägerstad, M.; Felton, J. S. Characterization of mutagenic activity in instant hot beverage powders. Environ. Molec. Mutag. 1995, 25, 154–161.
Knize M. G.; Andresen, B. D.; Healy, S. K.; Shen, N. H.; Lewis, P. R.; Bjeldanes, L. F.; Hatch, F. T.; Felton, J. S. Effect of temperature, patty thickness and fat content on the production of mutagens in fried ground beef. Food Chem. Toxic. 1985, 23, 1035–1040
Knize M. G.; Dolbeare F. A.; Carroll K. L.; Moore II, D. H.; Felton J. S. Effect of cooking time and temperature on the heterocyclic amine content of fried-beef patties. Food Chem. Toxic. 1994, 32, 595–603.
Knize, M. G.; Cunningham, P. L.; Jones, A. L.; Griffin, E. A.; Felton, J. S. Mutagenic activity and heterocyclic amine content in cooked grain food products. Food Chem. Toxic. 1993, 32, 15–21.
Knize, M. G.; Shen, N. H.; Healy, S. K.; Hatch, F. T.; Felton, J. S. The use of bacterial mutation tests to monitor chemical isolation of the mutagens in cooked beef. Devel, Ind. Microbiol. 1987, 28, 171–180.
Knize, M. G.; Sinha, R.; Rothman, N.; Brown, E. D.; Salmon, C. P.; Levander, O. A.; Cunningham P. L.; Felton J. S. Fast-food meat products have relatively low heterocyclic amine content. Food Chem. Toxic. 1995, 33, 545–551.
Larsson, B. K.; Shalberg, G. P.; Eriksson, A. T.; Busk, L. Å. Polycyclic aromatic hydrocarbons in grilled food. J. Agric. Food Chem. 1983, 31, 867–873.
Lawrence, J. F. Determination of nanogram/kilogram of polycyclic aromatic hydrocarbons in foods by HPLC with fluorescence detection. Intern. J. Environ. Anal. Chem. 1986, 24, 113–131.
Lawrence, J. F.; Weber, D. F. Determination of polycyclic aromatic hydrocarbons in Canadian samples of processed vegetable and dairy products by liquid chromatography with fluorescence detection. J. Agric. Food Chem. 1984, 32, 794–797.
Lawrence, J. F.; Weber, D. F. Determination of polycyclic aromatic hydrocarbons in some Canadian commercial fish, shellfish, and meat products by liquid chromatography with confirmation by capillary gas chromatography-mass spectrometry. J. Agric. Food Chem. 1984, 32, 789–793.
Layton, D. W.; Bogen, K. T.; Knize, M. G.; Hatch, F. T.; Johnson, V. M.; Felton, J. S. Cancer risk of heterocyclic amines in cooked foods: An analysis and implications for research. Carcinogenesis. 1995, 16, 39–52.
Lijinsky, W. The formation and occurrence of food-associated polycyclic aromatic hydrocarbons associated withfood. Mutat. Res. 1991, 259, 251–261.
Lijinsky, W.; Raha, C. R. The pyrolysis of 2-methyl-naphthalene. J. Org. Chem. 1961, 26, 3566–3567.
Makamura, T.; Ysuji, K. Japanese patent 1986, 61–25345.
Manabe, S.; Kurihara, N.; Wada, O.; Izumikawa, S.; Asakuna, K.; Morita, M. Detection of a carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, in airborne particles and diesel-exhaust particles. Environ. Pollut. 1993, 80, 281–286.
Manabe, S.; Tohyama, K.; Wada, O.; Aramaki, T. Detection of a carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5–b]pyridine (PhIP), in cigarette smoke condensate. Carcinogenesis 1991, 12, 1945–1947.
Nadon, L.; Siemiatycki, J.; Dewar, R.; Krewski, D.; Gerin, M. Cancer risk due to occupational exposure to polycyclic aromatic hydrocarbons. Am. J. Ind. Med. 1995, 28, 303–324.
Nagao, M.; Honda, M.; Seino, Y; Yahagi, T.; Sugimura, T. Mutagenicities of smoke condensates and the charred surface of fish and meat. Cancer Lett. 1977, 2, 221–226.
Ohgaki, H.; Takayama, S.; Sugumura, T. Carcinogenicities of heterocyclic amines in cooked food. Mutat. Res. 1991, 259, 399–410.
Övervik, E.; Kleman, M.; Berg, I.; Gustafsson J-Å. Influence of creatine, amino acids and water on the formation of the mutagenic heterocyclic amines found in cooked meat. Carcinogenesis 1989, 10, 2293–2301.
Rivera, L.; Curto, M. J. C.; Pais, P.; Galceran, M. T.; Puignou, L. Solid-phase extraction for the selective isolation of polycyclic aromatic hydrocarbons, azaarenes, and heterocyclic amines in charcoal-grilled meat. J. Chromatogr. A 1996, 719, 85–94.
Robbana-Barnat, S.; Rabache, M.; Rialland E.; Fradin, J. Heterocyclic amines: Occurrence and prevention in cooked food. Environ. Health Persp. 1996, 104, 280–288.
Salmon, C. P.; Knize, M. G.; Felton, J. S. Effects of marinating on heterocyclic amine carcinogen production in grilled chicken (Food Chem. Toxic. 1997, 35, 433–441).
Sheilds, P. G.; Xu, G. X.; Blot, W. J.; Fraumeni Jr., J. F.; Trivers, G. E.; Pellizzari, E. D.; Qu, Y. H.; Gao, Y. T.; Harris, C. C. Mutagens from heated Chinese and U.S. cooking oils. J. Natl. Cancer Inst. 1995, 87, 836–841.
Shirai, T.; Sano, M.; Tamano, S.; Takahashi, S.; Hirose, M.; Futakuchi, M.; Hasegawa, R.; Imaida, K; Matsumoto, K-I.; Wakabayashi, K.; Sugimura, T.; Ito, N. The prostate: A target for the carcinogenicity of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine derived from cooked foods. Cancer Res. 1997, 57, 195–198.
Sinha, R.; Rothman, N.; Brown, E.; Levander, O.; Salmon, C. P.; Knize, M. G.; Felton, J. S. High concentrations of the carcinogen 2-amino-1-methyl-6-imidazo[4,5-b]pyridine (PhIP) occur in chicken but are dependent on the cooking method. Cancer Res. 1995, 55, 4516–4519.
Skog, K. Cooking procedures and food mutagens: A literature review. Food Chem. Toxic. 1993, 31, 655–675.
Skog, K.; Jägerstad, M.; Laser Reuterswärd, A. Inhibitory effect of carbohydrates on the formation of mutagens in fried beef patties. Food Chem. Toxic. 1992, 30, 681–688.
Skog, K.; Steineck, G.; Augustsson, K.; Jägerstad, M. Effect of cooking temperature on the formation of heterocyclic amines in fried meat products and pan residues. Carcinogenesis 1995, 16, 861–867.
Stavric, B. Biological significance of trace levels of mutagenic heterocyclic aromatic amines (HAAs) in the human diet: a critical review. Food Chem. Toxic. 1994, 32, 977–994.
Sugimura, T.; Nagao, M.; Kawachi, T.; Honda, M.; Yahagi, T.; Seino, Y; Sato, S.; Matsukura, N.; Matsushima, T.; Shirai, A.; Sawamura, M.; Matsumoto, H. Mutagen-carcinogens in foods with special reference to highly mutagenic pyrolytic products in broiled foods. In Origins of Human Cancer, Hiatt, H.H.; Watson, J.D.; Winsten, J.A., Eds.; Cold Spring Harbor, New York, 1977, 1561–1577.
Thiebaud, H. P.; Knize, M. G.; Kuzmicky, P. A.; Felton, J. S.; Hsieh, D. P. Mutagenicity and chemical analysis of fumes from cooking meat. J. Agric. Food Chem. 1994, 42, 1502–1510.
Tikkanen, L. M.; Sauri, T. M.; Latva-Kala, K. J. Screening of heat-processed Finnish foods for the mutagens 2-amino-3,4,8-dimethylimidazo[4,5-f]quinoxaline, 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, and 2-amino-1-methyl-6-phenylimidazo[4,5-f]pyridine. Food Chem. Toxic. 1993, 31, 717–721.
Vaessen, H. A. M. G.; Schuller, P. L.; Jekel, A. A.; Wilbers, A. M. M. A. Polycyclic aromatic hydrocarbons in selected foods; analysis and occurrence. Toxicol Environ. Chem. 1984, 7, 297–324.
Vainiotalo, S.; Matveinen, K.; Reunamen, A. GC/MS Determination of the mutagenic heterocyclic amines MeIQx and DiMeIQx in cooking fumes. Fresenius J. Anal. Chem. 1993, 345, 462–466.
Vikse, R.; Joner, P. E. Mutagenicity, creatine, and nutrient contents of pan fried meat from various animal species. Acta Vet. Scand. 1993, 34, 1–7.
Vogelstein, B.; Kinzler, W. W. Carcinogens leave fingerprints. Nature 1992, 355, 209–210.
Wakabayashi, K.; Kim, I-S.; Kurosaka, R.; Yamaizumi, Z.; Ushiyams, H.; Takahashi, M.; Koyota, A.; Tada, A.; Nukaya. H.; Goto, S.; Sugimura, T.; Nagao, M. In Heterocyclic amines in cooked foods: possible human carcinogens; Adamson, R.H.: Gustafsson, J-A.: Ito, N.: Nagao, M.; Sugimura, T.; Wakabayashi, K.; Yamazoe, Y., Eds.; Princeton Scientific Publishing, Princeton, NJ, USA, 1995, p. 39.
Wakabayashi, K.; Nagao, M.; Esumi, H.; Sugimura T. Food-derived mutagens and carcinogens. Cancer Res. 1992, 52 (suppl.), 2092s-2098s.
Wang, Y. Y.; Vuolo, L. L.; Springarn, N. E.; Weisburger, J. H. Formation of mutagens in cooked foods, V. The mutagen reducing effect of soy protein concentrates and antioxidants during frying of beef. Cancer Lett. 1982, 16, 179–186.
Wynder, E. L.; Gori, G. B. Contribution of the environment to cancer incidence: an epidemiologic exercise. J. Nat. Cancer Inst. 1977, 58, 825–832.
Yabiky, H. Y.; Martins, M. S.; Takahashi, M. Y Levels of benzo[a]pyrene and other polycyclic aromatic hydrocarbons in liquid smoke flavour and some smoked foods. Food Addit. Contamin. 1993, 10, 399–405.
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Knize, M.G., Salmon, C.P., Pais, P., Felton, J.S. (1999). Food Heating and the Formation of Heterocyclic Aromatic Amine and Polycyclic Aromatic Hydrocarbon Mutagens/Carcinogens. In: Jackson, L.S., Knize, M.G., Morgan, J.N. (eds) Impact of Processing on Food Safety. Advances in Experimental Medicine and Biology, vol 459. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4853-9_12
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