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113. Koskinas, J. (2002). Acetaldehyde adducts: role in ethanol-induced liver disease. Ethanol Liver, 130 149. 114. Quertemont, E., Tambour, S. (2004). Is ethanol a pro-drug The role of acetaldehyde in the central effects of ethanol. Trends Pharmacol. Sci., 25, 130 134. 115. Salaspuro, M.P. (2004). Alcohol, acetaldehyde, and digestive tract cancer, in Nutrition and Alcohol, CRC Press, Boca Raton, pp. 393 411. 116. Quertemont, E., Grant, K.A., Correa, M., Arizzi, M.N., Salamone, J.D., Tambour, S., Aragon, C.M.G., McBride, W.J., Rodd, Z.A., Goldstein, A., Zaffaroni, A., Li, T.-K., Pisano, M., Diana, M. (2005). The role of acetaldehyde in the central effects of ethanol. Clin. Exp. Res., 29, 221 234. 117. Brooks, P.J., Theruvathu, J.A. (2005). DNA adducts from acetaldehyde: implications for alcohol related carcinogenesis. Alcohol, 35, 187 193.
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HETEROCYCLIC AROMATIC AMINES
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INTRODUCTION
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Heterocyclic aromatic amines (HAAs) are a class of hazardous chemicals in the diet that are receiving attention as a risk factor for human cancer. These chemicals were discovered 30 years ago by Professor Sugimura and colleagues in Japan (1), who showed that the charred parts and smoke generated from broiled sh and beef contained potent activity in Salmonella typhimuriumbased mutagenicity assays. Since that discovery, more than 20 HAAs have been identi ed in cooked meats, sh, and poultry (2 5). Several HAAs have also been identi ed in cigarette smoke condensate and diesel exhaust (6, 7). Many HAAs are potent mutagens in bacteria, genotoxic to mammalian cells, and carcinogenic in experimental laboratory animals (4). The recent Report on Carcinogens, Eleventh Edition, of the National Toxicology Program, concluded that several prevalent HAAs are reasonably anticipated to be human carcinogens (8). Therefore, questions have been raised about the safety of foods containing HAAs and much research has been devoted to the biochemical toxicology of HAAs and their potential role in the etiology of human cancer.
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Process-Induced Food Toxicants: Occurrence, Formation, Mitigation, and Health Risks, Edited by Richard H. Stadler and David R. Lineback Copyright 2009 by John Wiley & Sons, Inc.
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Heterocyclic Aromatic Amines (HAAs): At a Glance
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HAAs were described some 30 years ago as potent in vitro mutagens present in smoke generated from broiled sh and beef. Since that discovery, >20 HAAs have been identi ed in cooked meats, sh, and poultry. Tandem SPE coupled with LC/MS provides a robust and selective method to detect and quantify HAAs in complex food matrices. Formed in many types of foods (meats, sh) and under diverse cooking conditions. Two major classes of HAAs can be distinguished, namely, the pyrolytic HAAs and the aminoimidazoarenes. The former are formed at elevated temperatures (>250 C) during the pyrolysis of individual amino acids (e.g., tryptophan, glutamic acid, phenylalanine, and ornithine). The latter compounds occur in meats cooked at temperatures as commonly encountered in domestic practices (150 250 C), and the Maillard reaction is thought to play an important role in their formation (creatine, amino acids, and hexoses). Lower pan temperatures to cook meat and frequent turns as the meat cooks. However, it is critical to attain an internal temperature of 70 C in the cooked meat to ensure microbial inactivation. Addition of ingredients that may react with the precursors/intermediates could also reduce the amounts of HAAs. For thermal process avors, optimization of the reaction conditions and the use of high-quality ingredients will minimize formation. The major source of human exposure to HAAs is through consumption of household-cooked meats and sh. The range of HAAs detected in foods is highly variable and dependent on cooking preferences, i.e., pan-frying or barbecuing of meats at high temperature produce the greatest amounts of HAAs. Many HAAs are potent bacterial mutagens, genotoxic to mammalian cells, and carcinogenic in experimental laboratory animals, inducing tumors in rodents in multiple organs (e.g., oral cavity, liver, stomach, lung, colorectum, mammary glands, and prostate). Human cancer risk factor estimates range widely. An upper limit is proposed at 1 cancer case per 1000 individuals, and a lower limit as 50 cases per million individuals. The European Commission has proposed regulations for maximum levels of PhIP and 4,8-DiMeIQx of 50 g/kg in thermal process avorings. Sensitive quantitative methods are needed to measure human biomarkers of ideally multiple HAA exposure (urinary, protein, and DNA adducts), as the extent of exposure to various HAAs can vary in the diet. With better analytical techniques, it may be feasible to more reliably assess the exposure to HAAs, and to determine the biologically effective dose of each HAA and the resultant potential genetic damage. Another uncertainty in the risk assessment is the bioavailability of HAAs in cooked foods. http://eur-lex.europa.eu/LexUriServ/site/en/com/2006/com2006_ 0427en01.pdf Avoiding eating pan residues and scrapings of fried meat and sh. Fry/barbecue foods to the appropriate doneness.
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