Research Section
Formation and inhibition of heterocyclic aromatic amines in fried ground beef patties

https://doi.org/10.1016/S0278-6915(00)00010-7Get rights and content

Abstract

The effect of vitamin E and oleoresin rosemary on heterocyclic aromatic amine (HAA) formation in fried ground beef patties was studied. Patties were fried at three temperatures (175°C, 200°C, 225°C) for 6 and 10 min/side to determine the conditions for optimum HAA formation. HAAs were isolated by solid phase extraction and quantitated by HPLC. Greatest concentrations were generated when patties were fried at 225°C for 10 min/side, 31.4 ng/g 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and 5.8 ng/g 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx). Vitamin E, when used at two concentrations (1% and 10% based on fat content) and added directly to the ground beef patties, reduced PhIP concentrations in the cooked patties by 69% and 72%, respectively. Smaller but more variable reductions were achieved for MeIQx. Comparable inhibition of HAA formation was achieved by the direct addition of vitamin E (1% based on fat content) to the surface of the patties before frying. Concentrations of five HAAs studied were all significantly reduced (P<0.006), with average reductions ranging from 45% to 75%. Oleoresin rosemary, when used at two concentrations (1% and 10% based on fat content), reduced PhIP formation by 44%.

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.

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