Mutagenic products are promoted in the nitrosation of tyramine

Food Chemistry

Volumn 216, Issue , 2017, Pages 60-65

  González Jiménez, Mario ^a,b   Arenas Valgañón, Jorge ^a   García Santos, María del Pilar ^a   Calle, Emilio ^a   Casado, Julio ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

Monoamines; Nitrosation reactions; Nitroso compounds; Tyramine

Indexed keywords

ABSORPTION SPECTROSCOPY; AMINO ACIDS; CARBOXYLATION; CHEMICAL COMPOUNDS; CHEMICAL REACTIONS; NITROGEN COMPOUNDS;

AMINO ACID TYROSINE; BIOGENIC COMPOUNDS; C-NITROSO COMPOUNDS; MONOAMINES; NITROSATION; NITROSO COMPOUNDS; TYRAMINE; VISIBLE ABSORPTION SPECTROSCOPY;

AMINES;

DEUTERIUM; ETHYLBENZENE; HYDROGEN; PHENETHYLAMINE; TYRAMINE; BENZENE DERIVATIVE; MUTAGENIC AGENT; NITRITE; NITROSO DERIVATIVE; PHENETHYLAMINE DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; ENTHALPY; MUTAGENICITY; NITROSATION; PROTON TRANSPORT; ULTRAVIOLET SPECTROSCOPY; CHEMISTRY; DRUG EFFECTS; HUMAN; STOMACH; THEORETICAL MODEL;

BENZENE DERIVATIVES; HUMANS; MODELS, THEORETICAL; MUTAGENS; NITRITES; NITROSATION; NITROSO COMPOUNDS; PHENETHYLAMINES; STOMACH; TYRAMINE;

EID: 84981262527     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2016.08.006     Document Type: Article

References (40)

1. Andersen, A.M., The crystal and molecular structure of tyramine hemihydrate. Acta Chemica Scandinavica B 31 (1977), 162–166.
2. Arenas-Valgañón, J., Gómez Bombarelli, R., González-Pérez, M., González-Jiménez, M., Calle, E., Casado, J., Taurine-nitrite interaction as a precursor of alkylation mechanisms. Food Chemistry 134 (2012), 986–991.
3. Arenas-Valgañón, J., González-Pérez, M., Gómez Bombarelli, R., González-Jiménez, M., Calle, E., Casado, J., Interference by nitrous acid decomposition in the kinetic study of nitrosation reactions. International Journal of Chemical Kinetics 46 (2014), 321–327.
4. Bayram, M., Biogenic amines in wines. Food Reviews International 25:1 (2008), 86–102.
5. Casado, J., Nitrosation reactions. Fast reactions in solution, 1994, Universidad de Burgos: Royal Society of Chemistry Annual Meeting.
6. 3 as a nitrosating agent. Monatshefte fur Chemie 114 (1983), 639–646.
7. Challis, B.C., Higgins, R.J., The chemistry of nitroso-compounds. Part VII. The first ‘fast’ proton transfer for an aromatic nitrosation. Journal of the Chemical Society, Perkin Transactions 2 (1973), 1597–1604.
8. Challis, B.C., Lawson, A.J., The chemistry of nitroso-compounds. Part II. The nitrosation of phenol and anisole. Journal of the Chemical Society B, 1971, 770–775.
9. Challis, B.C., Ridd, J.H., Nitrosation, diazotisation, and deamination. Part XI. The influence of neutral salts on the kinetics of diazotisation. Journal of the Chemical Society, 1962, 5197–5203.
10. Connors, Chemical kinetics. The study of reaction rates in solution. 1990, VHC, New York.
11. Dix, L.R., Moodie, R.B., Nitrosation and nitrous acid-catalysed nitration of anisole and 2, 6-dimethylanisole. Journal of the Chemical Society, Perkin Transactions 2:6 (1986), 1097–1101.
12. Espenson, J.H., Chemical kinetics and reaction mechanisms. 1995, McGraw-Hill, New York.
13. Exner, O., Correlation analysis of chemical data. 1988, Plenum, New York.
14. Fernández-Liencres, M.P., Calle, E., González-Mancebo, S., Casado, J., Quintero, B., Nitrosation kinetics of phenolic components of foods and beverages. International Journal of Chemical Kinetics 29 (1997), 119–125.
15. García-Santos, M.P., González-Mancebo, S., Hernández-Benito, J., Calle, E., Casado, J., Reactivity of amino acids in nitrosation reactions and its relation to the alkylating potential of their products. Journal of the American Chemical Society 124 (2002), 2177–2182.
16. González-Jiménez, M., Arenas-Valgañón, J., Calle, E., Casado, J., Aromatic C-nitrosation of a bioactive molecule. Nitrosation of minoxidil. Organic & Biomolecular Chemistry 9:22 (2011), 7680–7684.
17. González-Mancebo, S., García-Santos, M.P., Hernández-Benito, J., Calle, E., Casado, J., Nitrosation of phenolic compounds: inhibition and enhancement. Journal of Agricultural and Food Chemistry 47:6 (1999), 2235–2240.
18. 2 absorption from (293 to 353) K. Journal of Chemical Engineering Data 52 (2007), 2491–2502.
19. Laires, A., Gaspar, J., Borba, H., Proença, M., Monteiro, M., Rueff, J., Genotoxicity of nitrosated red wine and of the nitrosatable phenolic compounds present in wine: tyramine, quercetin and malvidine-3-glucoside. Food and Chemical Toxicology 31:2 (1993), 989–994.
20. Leffler, J.E., Grunwald, E., Rates and equilibria of organic reactions. 1989, Dover, New York.
21. Lijinsky, W., Chemistry and biology of N-nitroso compounds. 2011, Cambridge University Press, Cambridge.
22. Linares, D.M., Martín, M., Ladero, V., Álvarez, M.A., Fernández, M., Biogenic amines in dairy products. Critical Reviews in Food Science and Nutrition 51:7 (2011), 691–703.
23. Marcobal, A., De las Rivas, B., Landete, J.M., Tabera, L., Muñoz, R., Tyramine and phenethylamine biosynthesis by food bacteria. Critical Reviews in Food Science and Nutrition 52:5 (2012), 448–467.
24. Markovits, G.Y., Schwartz, S.E., Newman, L., Hydrolysis equilibrium of dinitrogen trioxide in dilute acid solution. Inorganic Chemistry 20 (1981), 445–450.
25. Masoud, M.S., Haggag, S.S., Ramadan, A.M., Mahmoud, S.A., Nitrosophenol complexes of transition metal salts. Transition Metal Chemistry 23:4 (1998), 343–347.
26. Mirvish, S.S., Role of N-nitroso compounds (NOC) and N-nitrosation in etiology of gastric, esophageal, nasopharyngeal and bladder cancer and contribution to cancer of known exposures to NOC. Cancer Letters 93 (1995), 17–48.
27. Morrison, D.A., Turney, T.A., The nitrosation of phenol in aqueous perchloric acid. Journal of the Chemical Society, 1960, 4827–4828.
28. Mysliwy, T.S., Wick, E.L., Archer, M.C., Shank, R.C., Newberne, P.M., Formation of N-nitrosopyrrolidine in a dog's stomach. British Journal of Cancer 30 (1974), 279–283.
29. Ochiai, M., Wakabayashi, K., Nagao, M., Sugimura, T., Tyramine is a major mutagen precursor in soy sauce, being convertible to a mutagen by nitrite. Gann 75:1 (1984), 1–3.
30. Prester, L., Biogenic amines in fish, fish products and shellfish: a review. Food Additives & Contaminants: Part A 28:11 (2011), 1547–1560.
31. Ridd, J.H., Diffusion control and pre-association in nitrosation, nitration and halogenation. Gold, V., Bethell, D., (eds.) Advances in physical organic chemistry, vol. 16, 1978, Academic Press, 1–49.
32. Senent, S., Cinética química. 1986, UNED, Madrid.
33. Stratton, J.E., Hutkins, R.W., Taylor, S.L., Biogenic-amines in cheese and other fermented foods – A review. Journal of Food Protection 54:6 (1991), 460–470.
34. Tuckerman, M.M., Mayer, J.R., Nachod, F.C., Anomalous pKa values of some substituted phenylethylamines. Journal of the American Chemical Society 81:1 (1959), 92–94.
35. Tummavouri, J., Lumme, P., Protolysis of nitrous acid in aqueous sodium nitrate and sodium nitrite solutions at different temperatures. Acta Chemica Scandinavica 22:6 (1968), 2003–2011.
36. Turney, T., Wright, G., Nitrous acid equilibria in perchloric acid. Journal of the Chemical Society, 1958, 2415–2418.
37. Wakabayashi, K., Nagao, M., Chung, T.H., Yin, M.Q., Karai, I., Ochiai, M., Sugimura, T., Appearance of direct-acting mutagenicity of various foodstuffs produced in Japan and Shoutheast Asia on nitrite treatment. Mutation Research 158:3 (1985), 119–124.
38. Ward, M.H., Pan, W.H., Cheng, Y.J., Li, F.H., Brinton, L.A., Chen, C.J., Hildesheim, A., Dietary exposure to nitrite and nitrosamines and risk of nasopharyngeal carcinoma in Taiwan. International Journal of Cancer 86:5 (2000), 603–609.
39. Williams, D.H.L., Nitrosation reactions and chemistry of the nitric oxide. 2004, Elsevier, Amsterdam.
40. Wishnok, J.S., Formation of nitrosamines in food and in the digestive system. Journal of Chemical Education 54:7 (1977), 440–442.