Research SectionFormation and inhibition of heterocyclic aromatic amines in fried ground beef patties
Introduction
A number of mutagenic and/or carcinogenic heterocyclic aromatic amines (HAAs) have been found in meat and fish cooked at temperatures over 150°C. The most common HAAs identified in fried ground beef are 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (DiMeIQx) and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). Several of these compounds are multi-potential carcinogens in rodent bioassays (Ohgaki, Takayama and Sugimura, 1991, Skog, Steineck, Augustsson and Jagerstad, 1995, Sugimura and Wakabayashi, 1990, Tanaka, Barnes, Weisburger and Williams, 1985) and PhIP, the most abundant HAA in cooked meats, has been shown to induce colon and mammary carcinomas in rats (Ito, Hasegawa, Sano, Tarnano, Esumi, Takayarna and Sugimura, 1991, Ochiai, Ogawa, Wakabayashi, Sugimura, Nagase, Esumi and Nagao, 1991).
Epidemiological studies suggest that the consumption of well-done red meat is associated with the high risk of colon and other cancers (Schiffman and Felton, 1990, Willet, Stampfer, Colditz, Rosner and Speizer, 1990). Recent estimates of potential human cancer potency are consistent with an upper-bound cancer risk between 10−3 and 10−4 for an average lifetime cooked-beef intake of 3.3 g/kg body weight/day (or approx. 0.5 lb/day) (Bogen, 1994).
Precursors of these mutagenic/carcinogenic compounds in beef are creatine/creatinine, amino acids and sugars (Jägerstad et al.., 1983a). However, HAAs can also be formed in dry-heated mixtures of amino acids and creatine (Felton and Knize, 1990, Overvik, Kleman, Berg and Gustafsson, 1989, Taylor, Flutz, Knize and Felton. 1987). Cooking time and temperature are important factors in the formation of these compounds (Knize et al.., 1994). HAA formation has been suggested to follow the Maillard reaction through vinylpyrazine, vinylpyridine and aldehyde formation (Jägerstad et al.., 1983b). However, the formation of the free radical, N,N-disubstituted pyrazine cation, by early carbon fragmentation prior to the Amadori product was demonstrated by Namiki and Hayashi (1981). Further evidence of free radical involvement in HAA formation was provided by Milic et al.. (1993).
Concentrations of HAAs in fried ground beef patties can be reduced by the addition of compounds which possess antioxidative activity. Soy protein concentrate and defatted glandless cottonseed flour, both of which contain antioxidant compounds, reduced the overall mutagenicity in cooked beef (Rhee, Donnelly and Ziprin, 1987, Wang, Vuolo, Spingarn and Weisburger, 1982). Polyphenolic compounds in tea were effective inhibitors of HAA formation in model systems (Weisburger, Nagao, Wakabayashi and Oguri, 1994, Yen and Chen, 1995). Faulkner (1994) demonstrated the inhibition of PhIP formation by vitamin E using both the Salmonella typhimurium overall mutagenicity test and an analytical procedure to quantitate the extent of inhibition. Recently, Britt et al.. (1998) reported the effectiveness of tart cherry tissue as an inhibitor of HAA formation in fried ground beef patties, while Kato et al.. (1998) determined that the mutagenicity of cooked hamburger is reduced by the addition of onion to ground beef.
The objectives of the present study were to investigate the formation of HAAs in ground beef patties fried at various time/temperature combinations, and to evaluate their inhibition through the addition of vitamin E and oleoresin rosemary to patties before frying.
Section snippets
Safety
Heterocyclic aromatic amines are mutagenic/carcinogenic and must be handled with appropriate safety precautions including the use of goggles, latex gloves and efficient fume hoods.
Reagents
HAA standards (IQ, MeIQ, MeIQx, DiMeIQx and PhIP) were purchased from Toronto Research Chemicals (Toronto, Canada). The HAA standard (FEMA—Flavor and Extracts Manufacturers' Association) and the internal standard, caffeine, were gifts from Dr Mark Knize, Lawrence Livermore National Laboratory, Livermore, CA, USA. The
RESULTS AND DISCUSSION
Recoveries for the five HAAs were as follows: IQ 58.2–84.8% (av. 71.5%), MeIQ 51.7–78.2% (av. 64.95%), MeIQx 66.7–88.5% (av. 7–7.6%), DiMeIQx 72.1–92.4% (av. 82.25%) and PhIP 32.1–61.9% (av. 47.0%). These recoveries matched the upper range of published results (Johansson and Jagerstad, 1994, Johansson, Fredholm, Bjerne and Jagerstad, 1995, Skog, Augustsson, Steineck, Stenburg and Jagerstad, 1997, Thiebaud, Knize, Kuzmicky, Felton and Hsieh, 1994). Salmon et al.. (1997) reported recoveries
Acknowledgements
This research is a contribution from the Michigan Agricultural Experimental Station.
References (42)
Cancer potencies of heterocyclic amines found in cooked foods
Food and Chemical Toxicology
(1994)- et al.
Reduction of heterocyclic aromatic amine mutagens/carcinogens in fried patties by microwave pretreatment
Food and Chemical Toxicology
(1994) - et al.
Quantitation of mutagenic/carcinogenic heterocyclic aromatic amines in food products
Journal of Chromatography
(1992) - et al.
Creatin(in)e and Maillard reaction products as precursors of mutagenic compounds: effects of various amino acids
Food Chemistry
(1983) - et al.
Influence of frying fat on the formation of heterocyclic amines in fried beefburgers and pan residues
Food and Chemical Toxicology
(1995) - et al.
l-tryptophan inhibits formation of mutagens during cooking of meat in laboratory animals
Mutation Research
(1988) - et al.
Mutagenicity of cooked hamburger is reduced by addition of onion to ground beef
Mutation Research
(1998) - et al.
Effects of cooking time and temperature on the heterocyclic amine content of fried beef patties
Food and Chemical Toxicology
(1994) - et al.
Heterocyclic amine content in fast-food meat products
Food and Chemical Toxicology
(1995) - et al.
Analysis of foods for heterocyclic aromatic amine carcinogens by solid-phase extraction and high-performance liquid chromatography
Journal of Chromatography
(1997)
Synthesis of some heterocyclic amino-imidazoazarenes
Food Chemistry
Inhibitory effects of antioxidants on formation of heterocyclic amines
Mutation Research
Carcinogenicities of heterocyclic amines in cooked food
Mutation Research
Effect of marinating on heterocyclic amine carcinogen formation in grilled chicken
Food and Chemical Toxicology
Cooking procedures and food mutagens: a literature review
Food and Chemical Toxicology
Polar and non-polar heterocyclic amines in cooked fish and meat products and their corresponding pan residues
Food and Chemical Toxicology
Inhibitory effect of carbohydrates on the formation of mutagens in fried beef patties
Food and Chemical Toxicology
Formation of mutagens in cooked foods I. Beef
Cancer Letters
Formation of mutagens in cooked foods V. the mutagen reducing effect of soy protein concentrates and antioxidants during frying of beef
Cancer Letters
Prevention of heterocyclic amine formation by tea and tea polyphenols
Cancer Letters
Cited by (153)
Effect of Different Roasting Conditions and Coreopsis Extract on Heterocyclic Amine Formation in Roast Lamb Products
2022, Journal of Food Protection