Cooked foods amines

R. Edenharder, 1. von Petersdorff, and R. Rauscher, Antimutagenic effects of flavonoids, chalcones and structurally related compounds on the activity of 2-amino-3-methylimidazo(4,5-f quinoline (IQ) and other heterocyclic amine mutagens from cooked food. Mutat Res. 287 261 (1993). 

Jiigerstad, M., Skog, K., Arvidsson, P. and Solyakov, A. (1998). Chemistry, formation and occurrence of genotoxic heterocyclic amines identified in model systems and cooked foods, Z. Lebensm. Unters. Forsch A, 207, 419—427. 

Sugimura, T. Nagao, M. Wakabayashi, K. Mutagenic heterocyclic amines in cooked food. Environ. Carcinog. Sel. Methods Anal. 1981, 4, 251-67. 

Whether any one of the contaminants or mixture of contaminants of food introduced by cooking, if any, is responsible for some cancers is not currently known and awaits further research. What is clear is that cooking food in certain ways will introduce known carcinogens, such as polycyclic aromatic hydrocarbons, heterocyclic amines, and acrylamide into our diet. By avoiding this style of cooking any risk can be minimized. 

Problems associated with the determination of HAs in cooked foods and with human exposure have been reported. The estimated daily intake of HAs, in different studies, ranges from 0-15 pg/person/day (230). In a study that looked at the heterologous expression of human N-acetyltransferases 1 and 2 and sulfotransferase lAl in Salmonella typhimurium for the mutagenicity testing of heterocyclic amines, it was found that both 0-acetylation and 0-sulfonation were important determinants for HA genotoxicity in humans (231). 

Felton, J- S., Knize, M. G., Roper, M., Fultz, E., Shen, N-, and Turteltaub, K. W. (1992). Chemical analysis, prevention, and low-level dosimetiy of heterocyclic amines from cooked food- ConecJ Rfs. 52, 2103S-21D7S-... 

Heterocyclic aromatic amines (HAA) are carcinogenic compounds that may occur in food. They are probably formed during cooking processes by the pyrolysis of amino acids and proteins. Since the mid 1990s, LC-MS plays a role in the analysis and characterization of these HAA. Both ESI-MS and APCl-MS are applied. A recent special issne of Journal of Chromatography B [82] emphasizes the analytical challenges related to HAA. The stractnres of the most abundant HAA in cooked food are shown in Figure 14.10. 

The Maillard reaction and the oxidation of lipids are two of the most important reactions for the formation of aromas in cooked foods. Interactions between lipid oxidation and the Maillard reaction have received less attention, despite the fact that lipids, sugars, and amino acids exist in close proximity in most foods. Lipids, upon exposure to heat and oxygen, are known to decompose into secondary products, including alcohols, aldehydes, ketones, carboxylic acids, and hydrocarbons. Aldehydes and ketones produce heterocyclic flavor compounds reacting with amines and... 

Edenharder, E. et al., Antimutagenic effects and possible mechanisms of action of vitamins and related compounds against genotoxic heterocyclic amines from cooked food, Mutat. Res., 444, 235, 1999. 

Robbana-Bamat, S. et al., Heterocyclic amines occurrence and prevention in cooked food, Environ. Health Perspect., 104, 280, 1996. 

Skog K.I., Johansson A.E. and Jagerstad M.I. Carcinogenic heterocyclic amines in model, systems and cooked foods a review on formation, occurrence and intake. Food and Chemical Toxicology. 36,879.1998. 

During toe 1980s research on roasted meat and other types of heated protein containing foods indicated the presence of Polycyclic Heterocyclic Amines (PHA). These materials were shown to be mutagenic and major carcinogens. Cooked foods contained these materials so it was reasoned toat "process flavors" would also contain them. Foods and their metoods of cooking are not regulated except for... 

Ohgaki, H., Hasegawa, H., Kato, T., Suenaga, M., Ubukata, M., Sato, S., Takayama, S., and Sugimura, T. Carcinogenicity in mice and rats of heterocyclic amines in cooked foods, Environ. Health Persp., 67, 129, 1986. 

Table XVn.E-2 hsts, with appropriate citations, the chronology of the studies pertinent to the aza-arenes and other polycyclic nitrogen compounds in tobacco smoke. A similar chronology of studies pertinent to the A-heterocyclic amines, the cooked food mutagens, is presented in a subsequent section.

Unlike the PAHs and the A-nitrosamines, nontobacco smoke exposure to the acridines/benzacridines does not include foods. However, exposures other than tobacco smoke to polycyclic nitrogen compounds include exposures to the A-heterocyclic amines, the so-called cooked food mutagens, in a variety of foods. 

In the late 1970s, Japanese investigators, in their detailed studies of components of various cooked foods, isolated and identified the first of a series of Af-heterocyclic amines as pyrolysis products of several amino acids. Sugimura et al. (3829) reported the isolation and identification of 3 -am ino-1,4-dimethyl-5//-py rido[4,3 -fcjindole (designated as Trp-P-1) IV and 3-amino-l-methyl-5//-pyrido[4,3-fc] indole (Trp-P-2) V (Figure XVII.F-2) from tryptophan pyrolysates. 

FIGURE XVII.F-2 MHeterocyclic amines, the cooked food mutagens. 

J UPLC-MS/MS Analysis of Heterocyclic Amines in Cooked Food... 

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