Abstract
The effects of fructooligosaccharide (FOS) and garlic on the formation of 15 heterocyclic amines (HCAs) were evaluated in fried beef patties. The HCAs were extracted from the fried meat samples and purified using a solid-phase extraction method and then analyzed on a liquid chromatography-mass spectrometry. Among the 15 HCAs, 3-amino-1, 4-dimethyl-5H-pyrido-[4,3-b]indole (Trp-P-1), 3-amino-1-methyl-5H-pyrido [4,3-b]indole (Trp-P-2), 2-amino-6-methyldipyrido [1,2-a:3′,2′-d]imidazole (Glu-P-1), 2-aminodipyrido [1,2-a:3′,2′-d]imidazole (Glu-P-2), 9H-pyrido [3,4-b]indole (norharman), 1-methyl-9H-pyrido [3,4-b]indole (harman), 2-amino-9H-pyrido [2,3-b]indole (AαC), 2-amino-3,8 dimethylimidazo [4,5-f]-quinoxaline (MeIQx), and 2-amino-1-methyl-6-phenylimidazo [4,5-b]-pyridine (PhIP) were detected in all of the cooked beef patties. Analysis of variance revealed that the addition of 1 or 3 g of FOS significantly reduced the formation of total amino-carboline type HCAs in the cooked beef patties, and adding the 1 or 3 g of FOS to ground beef patties reduced levels of PhIP and MeIQx (amino-imidazo-azaarenes; AIAs) in the patties. When it is compared with the HCA formation in control, additions of minced garlic (5.0, 10.0, and 15.0 g) to the ground beef patties (100 g) reduced HCA formation in the range of 14 to 100%.
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References
Skog KI, Johansson MAE, Jägerstad MI. Carcinogenic heterocyclic amines in model systems and cooked foods: A review on formation, occurrence, and intake. Food Chem. Toxicol. 36: 879–896 (1998)
Zimmerli B, Rhyn P, Zoller O, Schlatter J. Occurrence of heterocyclic aromatic amines in the Swiss diet: Analytical method, exposure estimation, and risk assessment. Food Addit. Contam. 18: 533–551 (2001)
Salmon CP, Knize MG, Felton JS, Zhao B, Seow A. Heterocyclic aromatic amines in domestically prepared chicken and fish from singapore chinese households. Food Chem. Toxicol. 44: 484–492 (2006)
Busquets R, Mitjans D, Puignou L, Galceran MT. Quantification of heterocyclic amines from thermally processed meats selected from a small-scale population-based study. Mol. Nutr. Food Res. 52: 1408–1420 (2008)
Knize MG, Salmon CP, Pais P, Felton JS. Food heating and the formation of heterocyclic aromatic amine and polycyclic aromatic hydrocarbon mutagens/carcinogens. Vol. 459, pp. 179–193. In: Impact of Processing on Food Safety. Jackson LS, Knize MG, Morgan JN (eds). Kluwer Academic/Plenum Publishers, New York, NY, USA (1999)
Felton JS, Knize MG, Shen NH, Andresen BD, Bjeldanes LF, Hatch FT. Identification of the mutagens in cooked beef. Environ. Health Persp. 67: 17–24 (1986)
IARC. IARC Monographs on the evaluation of carcinogenic risks to humans. International Agency for Research on Cancer. Res. Cancer. Vol. 56, pp. 165–242 (1993)
Jaegerstad M, Reuterswaerd AL, Olsson R, Grivas S, Nyhammar T, Olsson K, Dahlqvist A. Creatin(in)e and Maillard reaction products as precursors of mutagenic compounds: Effects of various amino acids. Food Chem. 12: 255–264 (1983)
Yoshida D, Matsumoto T, Okamoto H, Mizusaki S, Kushi A, Fukuhara Y. Formation of mutagens by heating foods and model systems. Environ. Health Persp. 67: 55–58 (1986)
Sugimura T, Kawachi T, Nagao M, Yahagi T, Seino Y, Okamoto T, Shudo K, Kosuge T, Tsuji K, Wakabayashi K, Iitaka Y. Mutagenic principle(s) in tryptophan and phenylalanine pyrolysis products. Proc. Jpn. Acad. 53: 58–61 (1977)
Sugimura T. Overview of carcinogenic heterocyclic amines. Mutat. Res. 376: 211–219 (1997)
Yamamoto T, Tsuji K, Kosuge T, Okamoto T, Shudo K, Takeda K, Iitaka Y, Yamaguchi K, Seino Y, Yahagi T, Nagao M, Sugimura T. Isolation and structure determination of mutagenic substances in l glutamic acid pyrolysate. Proc. Jpn. Acad. 54: 248–250 (1978)
Ohgaki H, Hasegawa H, Kato T, Suenaga M, Ubukata M, Sato S, Takayama S, Sugimura T. Carcinogenicity in mice and rats of heterocyclic amines in cooked foods. Eviron. Health Persp. 67: 129–134 (1986)
Totsuka Y, Hada N, Matsumoto K, Kawahara N, Murakami Y, Yokoyama Y, Sugimura T, Wakabayashi K. Structural determination of a mutagenic aminophenylnorharman produced by the co-mutagen norharman with aniline. Carcinogenesis 19: 1995–2000 (1998)
Sinha R, Rothman N, Salmon CP, Knize MG, Brown ED, Swanson CA, Rhodes D, Rossi S, Felton JS, Levander OA. Heterocyclic amine content in beef cooked by different methods to varying degrees of doneness and gravy made from meat drippings. Food Chem. Toxicol. 36: 279–287 (1998)
Salmon CP, Knize MG, Panteleakos FN, Wu RW, Nelson DO, Felton JS. Minimization of heterocyclic amines and thermal inactivation of Escherichia coli in fried ground beef. J. Natl. Cancer I. 92: 1773–1778 (2000)
Ahn J, Grün IU. Heterocyclic amines: 1. Kinetics of formation of polar and nonpolar heterocyclic amines as a function of time and temperature. Food Chem. Toxicol. 70: 173–179 (2005)
Ahn J, Grün IU. Heterocyclic amines: 2. Inhibitory effects of natural extracts on the formation of polar and nonpolar heterocyclic amines in cooked beef. Food Chem. Toxicol. 70: 263–268 (2005)
Cheng KW, Wu Q, Zheng ZP, Peng X, Simon JE, Chen F, Wang M. Inhibitory effect of fruit extracts on the formation of heterocyclic amines. J. Agr. Food Chem. 55: 10359–10365 (2007)
Shin HS, Ustunol Z. Influence of honey-containing marinades on heterocyclic aromatic amine formation and overall mutagenicity in fried beef steak and chicken breast. Food Chem. Toxicol. 69: 147–153 (2004)
Tai CY, Lee KH, Chen BH. Effects of various additives of the formation of heterocyclic amines in fried fish fibre. Food Chem. 75: 309–316 (2001)
Shin HS, Rodgers WJ, Strasburg GM, Gray JI. Reduction of heterocyclic aromatic amine formation and overall mutagenicity in fried ground beef patties by organosulfur compounds. Food Chem. Toxicol. 67: 3304–3308 (2002)
Shin HS, Park H, Park D. Influence of different oligosaccharides and inulin on heterocylic aromatic amine formation and overall mutagenicity in fried ground beef patties. J. Agr. Food Chem. 51: 6726–6730 (2003)
Gross GA, Grüter A. Quantitation of mutagegnic/carcinogenic heterocyclic aromatic amines in food products. J. Chromatogr. A 592: 271–278 (1992)
Knize MG, Salmon CP, Hopmans EC, Felton JS. Analysis of foods for heterocyclic aromatic amine carcinogens by solid-phase extraction and high-performance liquid chromatography. J. Chromatogr. A 763: 179–185 (1997)
Abdulkarim BG, Smith JS. Heterocyclic amines in fresh and processed meat products. J Agr. Food Chem. 46: 4680–4687 (1998)
Harris DC. Exploring Chemical Analysis. 3rd ed. WH Freeman, NY, USA. pp. 91–98 (2001)
Bordas M, Moyano E, Puignou L, Galceran MT. Formation and stability of heterocyclic amines in a meat flavour model system: Effect of temperature, time, and precursors. J. Chromatogr. B 802: 11–17 (2004)
Messner C, Murkovic M. Evaluation of a new model system for studying the formation of heterocyclic amines. J. Chromatogr. A 802: 19–26 (2004)
Skog K, Jägerstad M. Effects of monosaccharides and disaccharides on the formation of food mutagens in model systems. Mutat. Res. 230: 263–272 (1990)
Cheng KW, Chen F, Wang M. Heterocyclic amines: Chemistry and health. Mol. Nutr. Food Res. 50: 1150–1170 (2006)
Tsai SJ, Jenq SN, Lee H. Naturally occurring diallyl disulfide inhibits the formation of carcinogenic heterocyclic aromatic amines in boiled pork juice. Mutagenesis 11: 235–240 (1996)
Kato T, Michikoshi K, Minowa Y, Maeda Y, Kikugawa K. Mutagenicity of cooked hamburger is reduced by addition of onion to ground beef. Mutat. Res. 420: 109–114 (1998)
Shin HS, Strasburg GM, Gray JI. A model system study of the inhibition of heterocyclic aromatic amine formation by organosulfur compounds. J. Agr. Food Chem. 50: 7684–7690 (2002)
Friedman M, Molnar-Perl I. Inhibition of browning by sulfur amino acids: 1. Heated amino acid-glucose systems. J. Agr. Food Chem. 38: 1642–1647 (1990)
Skog K, Solyakov A. Heterocyclic amines in poultry products: A literature review. Food Chem. Toxicol. 40: 1213–1221 (2002)
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Jung, K., Lee, K., Park, J. et al. Influence of fructooligosaccharides and garlic on formation of heterocyclic amines in fried ground beef patties. Food Sci Biotechnol 19, 1159–1164 (2010). https://doi.org/10.1007/s10068-010-0165-0
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DOI: https://doi.org/10.1007/s10068-010-0165-0