Formation of the mutagenic/carcinogenic imidazoquinoxaline-type heterocyclic amines through the unstable free radical Maillard intermediates and its inhibition by phenolic antioxidants

Carcinogenesis

Volumn 17, Issue 11, 1996, Pages 2469-2476

  Kato, Tetsuta ^a   Harashima, Takehiro ^a   Moriya, Natsumi ^a   Kikugawa, Kiyomi ^a   Hiramoto, Kazuyuki ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; ANTIOXIDANT; BUTYLATED HYDROXYANISOLE; CARBON; CATION; CREATININE; EPIGALLOCATECHIN GALLATE; ESCULETIN; FREE RADICAL; GALLIC ACID PROPYL ESTER; GLUCOSE; GLYCINE; HETEROCYCLIC AMINE; IMIDAZOLE DERIVATIVE; MUTAGENIC AGENT; N TERT BUTYL ALPHA PHENYLNITRONE; PHENOL DERIVATIVE; PYRAZINE; QUINOXALINE DERIVATIVE;

ARTICLE; CARCINOGENESIS; DOSE RESPONSE; ELECTRON SPIN RESONANCE; GLYCATION; HEATING; MEAT; MODEL; MUTAGENESIS; NONHUMAN; PRIORITY JOURNAL; TEA;

EID: 0029801149     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/17.11.2469     Document Type: Article

References (34)

1. Sugimura, T. and Sato, S. (1983) Mutagens-carcinogens in food. Cancer Res., 43 (Suppl.), 2415s-2421s.
2. Felton, J.S. and Knize, M.G. (1991) Occurrence, identification and bacterial mutagenicity of heterocyclic amines in cooked foods. Mutat. Res., 259, 205-217.
3. Skog, K. (1993) Cooking procedures and food mutagens: a literature review. Food Chem. Toxicol., 31, 655-675.
4. Ohgaki, H., Takayama, S. and Sugimura, T. (1991) Carcinogenesis of heterocyclic amines in cooked food. Mutat. Res., 259, 399-412.
5. Layton, D.W., Bogen, K.T., Knize, M.G., Hatch, F.T., Johnson, V.M. and Felton, J.S. (1995) Cancer risk of heterocyclic amines in cooked foods: an analysis and implications for research. Carcinogenesis, 16, 39-52.
6. Wang, Y., Vuolo, L.L., Spingarn, N.E. and Weisburger, J.H. (1982) Formation of mutagens in cooked foods V. The mutagen reducing effect of soy protein concentrates and antioxidants during frying of beef. Cancer Lett., 16, 179-189.
7. Barnes, W.S. and Weisburger, J.H. (1984) Formation of mutagens in cooked foods. VI. Modulation of mutagen formation by iron and ethylenediaminetetracetic acid (EDTA) in fried beef. Cancer Lett., 24, 221-226.
8. Jägerstad, M., Olsson, K., Grivas, S., Negishi, C., Wakabayashi, K., Tsuda, M., Sato, S. and Sugimura, T. (1984) Formation of 2-amino-3,8-dimethyl-imidazo[4,5-f]quinoxaline in a model system by heating creatinine, glycine and glucose. Mutat. Res., 126, 239-244.
9. Negishi, C., Wakabayashi, K., Tsuda, M., Sato, S., Sugimura, T., Saito, H., Maeda, M. and Jägerstad, M. (1984) Formation of 2-amino-3,7,8-trimethylimidazo[4,5-f]quinoxaline, a new mutagen, by heating a mixture of creatinine, glucose and glycine. Mutat. Res., 140, 55-59.
10. Reutersward, A.L., Skog, K. and Järgestad, M. (1987) Effects of creatine and creatinine content on the mutagenic activity of meat extracts, bouilons and gravies from different sources. Food Chem. Toxicol., 25, 747-754.
11. Felton, J.S. and Knize, M.G. (1991) Mutagen precursors in food: mutagen formation in muscle meats and model heating systems. In Hayatsu, H. (ed.) Mutagens in Food: detection and prevention. CRC Press, Boston, pp 57-66.
12. Weisburger, J.H. (1991) Prevention of mutagen formation: prevention of heterocyclic amine formation in relation to carcinogenesis. In Hayatsu, H. (ed.) Mutagens in Food: detection and prevention. CRC Press, Boston, pp. 193-203.
13. Jägerstad, M., Kaser, R.A., Oste, R., Dahlqvist, A., Grivas, S., Olsson, K. and Nyhammar, T. (1983) Creatinine and Maillard reaction products as precursors of mutagenic compounds formed in fried beef. In Waller, G.R. and Feather, M.S. (eds), The Maillard Reaction in Foods and Nutrition. ACS Symposium Series 215. American Chemical Society, Washington, D.C., pp. 507-520.
14. Jones, R.C. and Weisburger, J.H. (1988) L-Tryptophan inhibits formation of mutagens during cooking meat and in laboratory models. Mutat. Res., 206, 343-349.
15. Jones, R.C. and Weisburger, J.H. (1988) Inhibition of amino-imidazoquinoxaline-type and aminoimidazol-4-one-type mutagen formation in liquid reflux models by L-tryptophan and other selected indoles. Jpn. J. Cancer Res., 79, 222-230.
16. Jones, R.C. and Weisburger, J.H. (1988) Inhibition of amino-imidazoquinoxaline-type and aminoimidazol-4-one type mutagen formation on liquid-reflux models by the amino acids L-proline and/or L-tryptophan. Environ. Mol. Mutagenesis, 11, 509-514.
17. Skog, K. and Jägerstad, M. (1990) Effects of monosaccharides and disaccharides on the formation of food mutagens in model systems. Mutat. Res., 230, 263-272.
18. Skog, K. and Jägerstad, M. (1991) Effects of glucose on the formation of PhIP in a model system. Carcinogenesis, 12, 2297-2300.
19. Skog, K., Jägerstad, M. and Reutersward, A.L. (1992) Inhibitory effect of carbohydrates on the formation of mutagens in fried beef patties. Food Chem. Toxicol., 30, 681-688.
20. Taylor, R.T., Fultz, E. and Knize, M.G. (1986) Mutagen formation in a model beef supernatant fraction. Elucidation of the role of water in fried ground beef mutagenicity. Environ. Mutagen., 8 (Suppl. 6), 65.
21. Kikugawa, K. and Kato, T. (1987) Effect of water content on the generation of mutagenicity in heated fish meats. Eisei Kagaku, 33, 62-65.
22. Knize, M.G., Andersen, B.D., Healy, K., Shen, N.H., Lewis, P.R., Bjeldanes, L.F., Hatch, F.T. and Felton, J.S. (1985) Effects of temperature, patty thickness and fat content on the production of mutagens in fried ground beef. Food Chem. Toxicol., 23, 1035-1040.
23. Pearson, A.M., Chen, C., Gray, J.I. and Aust, S.D. (1992) Mechanism(s) involved in meat mutagen formation and inhibition (Hypothesis paper). Free Rad. Biol. Med., 13, 161-167.
24. Milic, B.Lj., Djilas, S.M. and Jasna, M.C.-B. (1993) Synthesis of some heterocyclic amino-imidazoazarenes. Food Chem., 46, 273-276.
25. Johansson, M., Skog ,K. and Jägerstad, M. (1993) Effects of edible oils and fatty acids on the formation of mutagenic heterocyclic amines in a model system. Carcinogenesis, 14, 89-94.
26. Kikugawa, K., Kato, T. and Hayatsu, H. (1986) The presence of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in smoked dry bonito (Katsuobushi). Jpn. J Cancer Res., 77, 99-102.
27. Kikugawa, K. and Kato, T. (1987) Formation of mutagens, 2-amino-3,8-dimethylimicazo[4,5-f]quinoxaline (MeIQx) and 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (4,8-DiMeIQx), in heated fish meats. Mutat. Res., 179, 5-14.
28. Yahagi, T., Nagao, M., Seino, Y., Matsushima, T., Sugimura, T. and Okada, M. (1977) Mutagenicities of N-nitrosamines on Salmonella. Mutat. Res., 48, 121-136.
29. Ames, B.N., McCann, J. and Yamazaki, E. (1975) Methods for detecting carcinogens and mutagens with the Salmonella/mammalian microsome mutagenicity test. Mutat. Kes., 31, 347-364.
30. Hayatsu, H. (1992) Cellulose bearing covalently linked copper phthalocyanine trisulphonate as an adsorbent selective for polycyclic compounds and its use in studies of environmental mutagens and carcinogens. J. Chromatog., 597, 37-56.
31. Mitsuda, H., Yasumoto, K. and Yokoyama, K. (1965) Studies on the free radical in amino-carbonyl reaction. Agric. Biol. Chem., 29, 751-756.
32. Namiki, M. and Hayashi, T. (1975) Development of novel free radicals during the amino-carbonyl reaction of sugars with amino acids. J. Agric. Food Chem., 23, 487-491.
33. Hayashi, T., Ohta, Y. and Namiki, M. (1977) Electron spin resonance spectral study on the structure of the novel free radical products formed by the reaction of sugars with amino acids or amines. J. Agric. Food Chem., 25, 1282-1287.
34. Buettner, G.R. (1987) Spin trapping: ESR parameters of spin adducts. Free Rad. Biol. Med., 3, 259-303.