Abstract
The successful determination of mutagenic/carcinogenic heterocyclic amines (HCAs) in trace amounts (ng/g, ppb levels) in commercial foods depends largely on the detection sensitivity and selectivity, as well as the quality of clean-up of complex food matrices. In the present study, UV and fluorescence detection in series with gradient elution HPLC was used for the separation and determination of eight HCAs present in a local delicacy, satay. The identification of peaks was carried out by UV diode-array spectrophotometry. The most common HCA found in all types of satay (chicken, mutton, pork) cooked under Chinese and Malay styles was 2-amino-9H-pyrido[2,3-b]indole (AαC) (1.3-12 ppb) while 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) was found at comparatively high levels (78 ppb) in both Chinese-style pork and Malay-style chicken satay. Other major HCAs included 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1) (non-detectable (ND) to 31 ppb), 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) (ND-12 ppb) and 2-aminodipyrido[1,2-a:3′,2′-d]-imidazole (Glu-P-2) (ND-25 ppb). Comutagen norharman (NH) was also detected at levels up to 84 ppb, while harman (H) was only detected in one sample (Chinese-style pork satay), at a level of 25 ppb. The differences in the type and level of HCAs in satay samples may be attributed to the variation in raw foodstuffs cooked under different styles by Chinese or Malay vendors, and the ingredients added during cooking.
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References
Abu-Shakra, A., Ioannides, C. and Walker, R.: 1988, ‘Comparative mutagenicty studies on fried minced beef, grilled sausage and grilled hamburgers’, J. Sci. Food Agric. 42, 343–354.
Adamson, R.H., Thorgeirsson, U.P., Snyderwine, E.G., Thorgeirsson, S.S., Reeves, J., Dalgard, D.W., Takayama, S. and Sugimura, T.: 1990, ‘Carcinogenecity of 2 amino-3-methylimidazo[4,5-f]quinoline in nonhuman primates. Induction of tumors in three macaques’, Jpn. J. Cancer Res. 81, 10–14.
Ames, B.N.: 1986, ‘Food constituents as a source of mutagens, carcinogens, and anticarcinogens’, Pro. Clin. Biol. Res. 206, 3–32.
Davis, C.D., Schut, H.A.J., Adamson, R.H., Thorgeirsson, U.P., Thorgeirsson, S.S. and Snyderwine, E.G.: 1993, ‘Mutagenic activation of IQ, PhIP, and MeIQx by hepatic microsomes from rat, monkey, and man: low mutagenic activation of MeIQx in cynomolgus monkeys in vitro reflects low DNA adduct levels in vivo’, Carcinogenesis 14, 61–65.
Doll, R. and Peto, R.: 1981, ‘The causes of cancer: quantitative estimates of avoidable risks of cancer in the United States today’, J. Natl. Cancer Inst. 66, 1191–1308.
Eisenbrand, G. and Tang, W.: 1993, ‘Food-borne heterocyclic amines. Chemistry, formation, occurrence and biological activities. A literature review’, Toxicology 84, I-82.
Felton, J.S. and Knize, M.G.: 1990, Heterocyclic-amine mutagens/carcinogens in food. In Cooper, C.S. and Grover, P.L. (eds.), Chemical Carcinogenesis and Mutagenesis I, Springer-Verlag, Berlin, Heideberg, pp. 471.
Gross, G.A., Philippossian, G. and Aeschbacher, H.U.: 1989, ‘An efficient and convenient method for the purification of mutagenic heterocyclic amines in heated meat products’, Carcinogenesis 10, 1175–1182.
Gross, G.A.: 1990, ‘Simple methods for quantifying mutagenic heterocyclic aromatic amines in food products’, Carcinogenesis 11, 1597–1603.
Gross, G.A. and Grüter, A.: 1992, ‘Quantitation of mutagenic/carcinogenic heterocyclic aromatic amines in food products’, J. Chromatogr. 592, 271–278.
Gross, G.A., Grüter, A. and Heyland, S.: 1992, ‘Optimization of the sensitivity of high-performance liquid chromatography in the detection of heterocyclic aromatic amine mutagens’, Fd. Chem. Toxic. 30, 491–498.
Grose, K.R., Grant, J.L., Bjeldanes, L.F., Andersen, B.D., Healy, S.K., Lewis, P.R., Felton, J.S. and Hatch, F.T.: 1986, ‘Isolation of the carcinogen IQ from fried egg patties’, J. Agric. Food Chem. 34, 201–202.
Gry, J., Vahl, M. and Aagaard Nielsen, P.: 1986, ‘Mutagens in fried meat. Influence of frying temperatures. Publ-Levnedsmiddelstyr 139, 42 pp (CA 106: 212686k).
Kasai, H., Yamaizumi, Z., Nishimura, S., Wakabayashi, K., Nagao, M., Sugimura, T., Spingarn, N.E., Weisburger, J.II., Yokoyama, S. and Miyazawa, T.: 1981, ‘A potent mutagen in broiled fish’, J. Chem. Soc. Perkin Trans. 1, 2290–2293.
Lee, H., Lin, M.Y. and Chan, S.C.: 1994, ‘Formation and identification of carcinogenic heterocyclic aromatic amines in boiled pork juice’, Mutat. Res. 308, 77–88.
Li, J.Y., Lee, H. and Huang, H.I.: 1982, ‘Formation of mutagens in boiled pork extracts’, Food Chem. Toxicol. 20, 531–533.
Lynch, A.M., Knize, M.G., Boobis, A.R., Gooderham, N.J., Davies, D.S. and Murray, S.: 1992, ‘Intro-and interindividual variability in systematic exposure in humans to 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline and 2-amino-1-methyl-6-phenyl-imidazo[4,5-b]pyridine, carcinogens present in cooked beef’, Cancer Res. 52, 6216–6223.
Manabc, S., Kanai, Y., Yanagisawa, II., Tohyama, K., Ishikawa, S., Kitagawa, Y. and Wada, O.: 1988, ‘Detection of carcinogenic glutamic acid pyrolysis products in Worcestershire sauce by high performance liquid chromatography’, Environ. Mol. Mutagen. 11, 379–388.
Manabe, S., Wada, O. and Kanai, Y.: 1991, ‘Pharmaco-toxicological aspects of carcinogenic tryptophan pyrolysis products in the environment’, J. Environ. Sci. Health A26, 1449–1458.
Murray, S., Gooderham, N.J., Boobis, A.R. and Davies, D.S.: 1988, ‘Measurement of Me and DiMeIQx in fried beef by capillary column gas chromatography electron capture negative ion chemical ionization mass spectrometry’, Carcinogenesis 9, 321–325.
National Research Council: 1982, Diet, Nutrition, and Cancer, Washington, DC: National Academy Press.
Ohgaki, H., Takayama, S. and Sugimura, T. (1991) Short review of the carcinogenicities of mutagens in food pyrolysates. In Hayatsu H. (ed.), Mutagens in Food. Detection and Prevention. CRC Press, Boca Raton, FL pp. 219.
Turesky, R.T., Bur, H., Huynh-Ba, T., Aeschbacher, H.U. and Milon, H.: 1988, ‘Analysis of mutagenic heterocyclic amines in cooked beef products by high performance liquid chromatography in combination with mass spectrometry. Food Chem. Toxicol. 26, 501–509.
Turesky, R.T., Forster, C.M., Aeschbacher, H.U., Wuerzner, H.P., Skipper, L.P., Trudel, L.J. and Tannenbaum, S.R.: 1989, ‘Purification of the food-borne carcinogens 2-amino-3-methylimidazo[4,5-f]quinoline and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in heated meat products by immunoaffinity chromatography’, Carcinogenesis 10, 151–156.
Turesky, R.J., Lang, N.P., Butler, M.A., Teitel, C.H. and Kadlubar, F.F.:1991, ‘Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon’, Carcinogenesis 12, 1839–1845.
Wakabayashi, K., Nagao, M., Esumi, H. and Sugimura, T.: 1992, ‘Food-derived mutagens and carcinogens’, Cancer Res. 52 (Suppl.), 2092s–2098s.
Wu, J., Wong, M.K., Lee, H.K., Lee, B.L., Shi, C.Y. and Ong, C.N.: 1995 a, ‘Determination of heterocyclic amines in flame-grilled fish patty by capillary electrophoresis’, Food Addit. Contam. (in press).
Wu, J., Wong, M.K., Lee, H.K., Shi, C.Y. and Ong, C.N.: 1995 b, ‘Determination of polycyclic aromatic hydrocarbons in rougan, a traditional Chinese barbecued food, by capillary gas chromatography’, presented in The Fifth Symposium on Our Environment.
Yamaguchi, K., Zenda, H., Shudo, K., Kosuge, T., Okamoto, T. and Sugimura, T.: 1979, ‘Presence of 2-aminodipyrido[1,2-a:3′,2′-d]imidazole in casein pyrolysate’, Jpn. J. Cancer Res. (GANN), 70, 849–850.
Yamaizumi, Z., Kasai, H., Nishimura, S., Edmonds, C.G. and McCloskey, J.A.: 1986, ‘Stable isotope dilution quantification of mutagens in cooked foods by combined liquid chromatography thermospray mass spectrometry’, Mutat. Res. 173, 1–7.
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Wu, J., Lee, H., Wong, M. et al. Determination of Carcinogenic Heterocyclic Amines in Satay by Liquid Chromatography. Environ Monit Assess 44, 405–412 (1997). https://doi.org/10.1023/A:1005760102062
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DOI: https://doi.org/10.1023/A:1005760102062