Effect of food reductones on the generation of the pyrazine cation radical and on the formation of the mutagens in the reaction of glucose, glycine and creatinine

Mutation Research - Genetic Toxicology and Environmental Mutagenesis

Volumn 465, Issue 1-2, 2000, Pages 183-190

  Kikugawa, Kiyomi ^a   Hiramoto, Kazuyuki ^a   Kato, Tetsuta ^a   Yanagawa, Hirokazu ^a  

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

Author keywords

2,5 Dimethyl 4 hydroxy 3(2H) furanone (DMHF); 4 Hydroxy 2(or 5) ethyl 5(or 2) methyl 3(2H) furanone (HEMF); Ascorbic acid; Erythorbic acid; Maillard reaction; Mutagen; Pyrazine cation radical

Indexed keywords

ASCORBIC ACID; CREATININE; FURANONE DERIVATIVE; GLUCOSE; GLYCINE; ISOASCORBIC ACID; PYRAZINE; RADICAL;

ARTICLE; ELECTRON SPIN RESONANCE; FOOD PROCESSING; GLYCATION; IN VITRO STUDY; MUTAGENIC ACTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS;

ANIMALS; ANTIOXIDANTS; ASCORBIC ACID; CATIONS; CREATININE; ELECTRON SPIN RESONANCE SPECTROSCOPY; FOOD ANALYSIS; FOOD CONTAMINATION; FREE RADICALS; GLUCOSE; GLYCINE; MAILLARD REACTION; MICROSOMES, LIVER; MUTAGENICITY TESTS; MUTAGENS; PYRAZINES; RATS; SALMONELLA TYPHIMURIUM;

EID: 0034673238     PISSN: 13835718     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1383-5718(99)00227-2     Document Type: Article

References (31)

1. T. Sugimura, S. Sato, Mutagens-carcinogens in food, Cancer Res. 43 (1983) 2415s-2421s, Suppl.
2. J.S. Felton, M.G. Knize, Occurrence, identification and bacterial mutagenicity of heterocyclic amines in cooked foods, Mutat. Res. 259 (1991) 205-217.
3. K. Skog, Cooking procedures and food mutagens: a literature review, Food Chem. Toxicol. 31 (1993) 655-675.
4. H. Ohgaki, S. Takayama, T. Sugimura, Carcinogenesis of heterocyclic amines in cooked food, Mutat. Res. 259 (1991) 399-412.
5. D.W. Layton, K.T. Bogen, M.G. Knize, F.T. Hatch, V.M. Johnson, J.S. Feiton, Cancer risk of heterocyclic amines in cooked foods: an analysis and implications for research, Carcinogenesis 16 (1995) 39-52.
6. M. Jägerstad, K. Olsson, S. Grivas, C. Negishi, K. Wakabayashi, M. Tsuda, S. Sato, T. Sugimura, Formation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in a model system by heating creatinine, glycine and glucose, Mutat. Res. 126 (1984) 239-244.
7. C. Negishi, K. Wakabayashi, M. Tsuda, S. Sato, T. Sugimura, H. Saito, M. Maeda, M. Jägerstad, 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 (1984) 55-59.
8. A.L. Reutersward, K. Skog, M. Jägerstad, Effects of creatine and creatinine content on the mutagenic activity of meat extracts, bouillons and gravies from different sources, Food Chem. Toxicol. 25 (1987) 747-754.
9. J.S. Felton, M.G. Knize, Mutagen precursors in food: mutagen formation in muscle meats and model heating systems, in: H. Hayatsu (Ed.), Mutagens in Food: Detection and Prevention, CRC Press, Boston, 1991, pp. 57-66.
10. J.H. Weisburger, Prevention of mutagen formation: prevention of heterocyclic amine formation in relation to carcinogenesis, in: H. Hayatsu (Ed.), Mutagens in Food: Detection and Prevention, CRC Press, Boston, 1991, pp. 193-203.
11. M. Jägerstad, R.A. Kaser, R. Oste, A. Dahlqvist, S. Grivas, K. Olsson, T. Nyhammar, Creatinine and Maillard reaction products as precursors of mutagenic compounds formed in fried beef, in: G.R. Waller, M.S. Feather (Eds.), The Maillard Reaction in Foods and Nutrition, ACS Symposium Series 215, American Chemical Society, Washington, DC, 1983, pp. 507-520.
12. K. Skog, M. Jägerstad, Effects of monosaccharides and disaccharides on the formation of food mutagens in model systems, Mutat. Res. 230 (1990) 263-272.
13. M. Johansson, K. Skog, M. Jägerstad, Effects of edible oils and fatty acids on the formation of mutagenic heterocyclic amines in a model system, Carcinogenesis 14 (1993) 89-94.
14. A.M. Pearson, C. Chen, J.I. Gray, S.D. Aust, Mechanism(s) involved in meat mutagen formation and inhibition, Free Rad. Biol. Med. 13 (1992) 161-167, Hypothesis paper.
15. T. Kato, T. Harashima, N. Moriya, K. Kikugawa, K. Hiramoto, Formation of the mutagenic/carcinogenic imidazoquinoxaline-type heterocyclic amines through the unstable free radical Maillard intermediates and its inhibition by phenolic antioxidants, Carcinogenesis 17 (1996) 2469-2476.
16. B.Lj. Millic, S.M. Djilas, M.C.-B. Jasna, Synthesis of some heterocyclic amino imidazoazarenes, Food Chem. 46 (1993) 273-276.
17. M.A.E. Johansson, S.M. Jägerstad, Influence of pro- and antioxidants on the formation of mutagenic-carcinogenic heterocyclic amines in a model system, Food Chem. 56 (1996) 69-75.
18. K.I. Skog, M.A.E. Johansson, M.I. Jägerstad, Carcinogenic heterocyclic amines in model systems and cooked foods: a review on formation, occurrence and intake, Food Chem. Toxicol. 36 (1998) 879-896.
19. K. Kikugawa, T. Kato, K. Hiramoto, C. Takada, M. Tanaka, Y. Maeda, T. Ishihara, Participation of the pyrazine cation radical in the formation of mutagens in the reaction of glucose/glycine/creatinine, Mutat. Res. 444 (1999) 133-144.
20. W.H. Weisburger, M. Nagao, K. Wakabayashi, A. Oguri, Prevention of heterocyclic amine formation by tea and tea polyphenols, Cancer Lett. 83 (1994) 143-147.
21. A. Oguri, M. Suda, Y. Totsuka, T. Sugimura, K. Wakabayashi, Inhibitory effects of antioxidants of formation of heterocyclic amines, Mutat. Res. 402 (1998) 237-245.
22. T. Kato, K. Kikugawa, Attempt to decrease the mutagenicity of smoked-and-dried bonito (katsuobushi) by boiling of bonito meat in green tea extract, J. Health Sci. 45 (1999) 130-132.
23. K. Kikugawa, K. Hiramoto, T. Kato, Generation of oxygen-derived radicals in the Maillard reaction that induce DNA strand cleavage, Recent Dev. Agric. Food Chem. 2 (1998) 237-257.
24. H. Hayatsu, 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. Chromatogr. 597 (1992) 37-56.
25. T. Yahagi, M. Nagao, Y. Seino, T. Matsushima, T. Sugimura, M. Okada, Mutagenicities of N-nitrosamines on salmonella, Mutat. Res. 48 (1977) 121-136.
26. B.N. Ames, J. McCann, E. Yamazaki, Methods for detecting carcinogens and mutagens with the salmonella/mammalian microsome mutagenicity test, Mutat. Res. 31 (1975) 364-374.
27. T. Kato, R. Michikoshi, Y. Minowa, Y. Maeda, K. Kikugawa, Mutagenicity of cooked hamburger is reduced by addition of onion to ground beef, Mutat. Res. 420 (1998) 109-113.
28. K. Hiramoto, K. Sekiguchi, R. Aso-o, K. Ayuha, H. Ni-iyama, K. Kato, K. Kikugawa, DNA strand breaks induced through active oxygen radicals by fragrant component 4-hydroxy-2-hydroxymethyl-5-methyl-3(2H)-furanone in Maillard reaction of hexose/amino acid, Food Chem. Toxicol. 33 (1995) 803-814.
29. K. Hiramoto, A. Nasuhara, K. Michikoshi, T. Kato, K. Kikugawa, DNA strand-breaking activity and mutagenicity of 2,3-dihydro-6-methyl-4H-pyran-4-one (DDMP), a Maillard reaction product of glucose and glycine, Mutat. Res. 395 (1997) 47-56.
30. H. Oubrahim, J.-M. Richard, D. Cantin-Esnault, Peroxidase-mediated oxidation, a possible pathway for activation of the fungal nephrotoxin orellanine and related compounds, ESR and spin-trapping studies, Free Radical Res. 28 (1998) 497-505.
31. Y. Wang, L.L. Vuoki, N.E. Spingarn, J.H. Weisburger, Formation of mutagens in cooked foods: V. The mutagen reducing effect of soy protein concentrates and antioxidants during frying of beef, Cancer Lett. 16 (1982) 179-189.