Et ve Et Ürünlerinde Heterosiklik Aromatik Aminlerin Belirlenmesi

Yıl 2006, Cilt: 37 Sayı: 2, 243 - 248, 10.01.2011

Fatih Öz , Mükerrem Kaya

Öz

Yüksek sıcaklıklarda et pişirmenin, mutajenik ve karsinojenik oldukları tespit edilen heterosiklik aromatik aminleri (HAA)
oluşturduğu bilinmektedir. Son yıllarda gıdalarda HAA oluşumu, HAA’ların kimyası, mutajenik ve karsinojenik aktiviteleri ile
ilgili literatürde pek çok çalışma yer almaktadır. Ayrıca, farklı gıdalarda HAA’ların güvenilir bir şekilde belirlenmesi için analitik
metotlar geliştirilmeye çalışılmaktadır. HAA’ların analizi oldukça zordur, çünkü gıdalarda oldukça düşük konsantrasyonlarda
bulunurlar. Bu derlemede HAA’ların belirleme metotları verilmiştir.

Anahtar Kelimeler

Et, Et Ürünleri, Heterosiklik Aromatik Aminler

Kaynakça

• Barnes, W. S., Maher, J.C., Weisburger, J. H., 1983. High- Pressure Liquid Chromatographic Method for the Analysis of 2-Amino-3-methylimidazo[4,5-f]quinoline, a Mutagen Formed during the Cooking of Food. J. Agric. Food Chem., 31: 883-886.
• Barceló-Barrachina, E., Moyano, E., Puignou, L., Galceran, M. T., 2004. Evaluation of Reversed-phase Columns for the Analysis of Heterocyclic Aromatic Amines by Liquid Chromatography-Electrospray Mass Spectrometry. J. of Chrom. B, 802: 45–59.
• Bång, J., Nukaya, H., Skog, K., 2002. Blue Chitin Columns for the Extraction of Heterocyclic Amines from Cooked Meat. J. of Chrom. A, 977: 97–105.
• Bianchi, F., Careri, M., Corradini, C., Elviri, L., Mangia, A., Zagnoni, I., 2005. Investigation of the Separation of Heterocyclic Aromatic Amines by Reversed Phase Ion-pair Liquid Chromatography Coupled with Tandem Mass Spectrometry: The Role of Ion Pair Reagents on LC-MS/MS Sensitivity. J. of Chrom. B, 825 (2): 193-200.
• Cárdenes, L., Ayala, J. H., Afonso, A. M., González, V., 2004. Solid-Phase Microextraction Coupled with High- Performance Liquid Chromatography for the Analysis of Heterocyclic Aromatic Amines. J. of Chrom. A, 1030: 87– 93.
• Chen, B. H., Meng, C. N., 1999. Formation of Heterocyclic Amines in a Model System during Heating. J. Food Prot., 62 (12): 1445-1450. Nishimura, S., McCloskey, J. A., 1986. Analysis of Mutagens from Cooked Foods by Directly Combined Liquid Chromatography-Mass Spectrometry. Environ. Health Persp., 67: 35-40.
• Felton, J. S., Knize, M. G., Shen, N. H., Lewis, P. R., Andresen, B. D., Happe, J., Hatch, P. R., 1986a. The Isolation and Identification of a New Mutagen from Fried Ground Beef: 2- Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). Carcinogenesis, 7 (7): 1081–1086.
• Felton, J. S., Knize, M. G., Shen, N. H., Andresen, B. D., Bjeldanes, L. F., Hatch, F. T., 1986b. Identification of the Mutagens in Cooked Beef. Environ. Health Persp., 67: 17- 24.
• Felton, J. S., Malfatti, M. A., Knize, M. G., Salmon, C. P., Hopmans, E. C., Wu, R. W., 1997. Health Risks of Heterocyclic Amines. Mutation Research, 376: 37–41.
• Friesen, M. D., Garren, L., Béréziat, J.-C., Kadlubar, F., Lin, D., 1993. Gas Chromatography-Mass Spectrometry Analysis of 2-Amino-1-methyl-6-phenyl-imidazo[4,5-b]pyridine in Urine and Feces. Environ. Health Persp., 99: 179-181.
• Galceran, M. T., Pais, P., Puignou, L., 1996a. Isolation by Solid- Phase Extraction and Liquid Chromatographic Determination of Mutagenic Amines in Beef Extracts. J. of Chrom. A, 719: 203–212.
• Galceran, M. T., Moyano, E., Puignou, L., Pais, P., 1996b. Determination of Heterocyclic Amines by Pneumatically Assisted Electrospray Liquid Chromatography-Mass Spectrometry. J. of Chrom. A, 730: 185–194.
• Grose, K. R., Grant, J. L., Bjeldanes, L., F., Andresen, B. D., Healy, S. K., Lewis, P. R., Felton, J. S., Hatch, F. T., 1986. Isolation of the Carcinogen IQ from Fried Egg Patties. J. Agric. Food Chem., 34: 201-202.
• Gross, G. A., Philippossian, G., Aeschbacher, H. U., 1989. An Efficient and Convenient Method for the Purification of Mutagenic Heterocyclic Amines in Heated Meat Products. Carcinogenesis, 10 (7): 1175–1182.
• Gross, G. A., 1990. Simple Methods for Quantifying Mutagenic Heterocyclic Aromatic Amines in Food Products. Carcinogenesis, 11 (9): 1597–1603.
• Gross, G. A., Grüter, A., 1992. Quantitation of Mutagenic/Carcinogenic Heterocyclic Aromatic Amines in Food Products. J. Chrom., 592: 271-278.
• Gross, G. A., Grüter, A., Heyland, S., 1992. Optimization of the Sensitivity of High-Performance Liquid Chromatography in the Detection of Heterocyclic Aromatic Amine Mutagens. Food and Chem. Toxic., 30 (6): 491-498.
• Janoszka, B., Blaszcyk, U., Warzecha, L., Strόzyk, M., Damasiewicz-Bodzek, A., Bodzek, D., 2001. Clean-up Procedures for the Analysis of Heterocyclic Aromatic Amines (Aminoazaarenes) from Heat-Treated Meat Samples. J. of Chrom. A, 938: 155–165.
• Jägerstad, M., Skog, K., Arvidsson, P., Solyakov, A., 1998. Chemistry, Formation and Occurence of Genetoxic Heterocyclic Amines Identified in Model Systems and Cooked Foods. Z. Lebensm. Unters Forsch. A, 207: 419– 427.
• Kataoka, H., Kijima, K., 1997. Analysis of Heterocyclic Amines as their N-dimethylaminomethylene Derivatives by Gas Chromatography with Nitrogen-Phosphorus Selective Detection. J. of Chrom. A, 767: 187–194.
• Knize, M. G., Felton, J. S., Gross, G. A., 1992. Chromatographic Methods for the Analysis of Heterocyclic Amine Food Mutagens/Carcinogens. J. of Chrom., 624: 253-265.
• Lee, H., Tsai, S.-J., 1991. Detection of IQ-Type Mutagens in Canned Roasted Eel. Food and Chem. Toxic., 29 (8): 517- 522.
• Manabe, S., Yanagisawa, H., Ishikawa, S., Kitagawa, Y., Kanai, Y., Wada, O., 1987. Accumulation of 2-Amino-6- methyldipyrido[1,2-a:3ı,2ı-d]imidazole and 2- Aminodipyrido[1,2-a:3ı,2ı-d]imidazole, Carcinogenic Glutamic Acid Pyrolysis Products, in Plasma of Patients with Uremia. Cancer Research, 47: 6150–6155.
• Messner, C., Murkovic, M., 2003a. Formation of Heterocyclic Amines in Model Systems. 2nd International Workshop on Analytical, Chemical, and Biological Relevance of Heterocyclic Aromatic Amines from 7.- 9. May 2003 in Graz, University of Technology.
• Messner, C., Murkovic, M., 2003b. Formation of Heterocyclic Amines in Chicken Meat. 2nd International Workshop on Analytical, Chemical, and Biological Relevance of Heterocyclic Aromatic Amines from 7.- 9. May 2003 in Graz, University of Technology.
• Murray, S., Lynch, A. M., Knize, M. G., Gooderham, N. J., 1993. Quantification of the Carcinogens 2-Amino-3,8-dimethyl- and 2-Amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline and 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Food using A Combined Assay based on Gas Chromatography- Negative Ion Mass Spectrometry. J. of Chromatography, 616: 211–219.
• Olsson, J. C., Dyremark, A., Karlberg, B., 1997. Determination of Heterocyclic Aromatic Amines by Micellar Electrokinetic Chromatography with Amperometric Detection. J. of Chrom. A, 765: 329–335.
• Öz, F., 2006. Farklı Sıcaklıklarda Pişirilen Taze Et Ürünlerinde Çeşitli Baharatların Heterosiklik Aromatik Aminlerin Oluşumu Üzerine Etkileri. Atatürk Üniversitesi Fen Bilimleri Ens., Doktora Tezi, Erzurum.
• Öz, F., Kaya, M., 2006a. Heterosiklik Aromatik Aminlerin Mutajenliği ve Karsinojenliği. Atatürk Üniv. Zir. Fak. Derg. (yayına sunuldu).
• Öz, F., Kaya, M., 2006b. Et ve Et Ürünlerinde Heterosiklik Aromatik Amin Oluşumunun Engellenmesi. Atatürk Üniv. Zir. Fak. Derg. (yayına sunuldu).
• Öz, F., Kaya, M., 2006c. The Effects of Different Spices on Formation of Heterocyclic Amines in Beef Chops Fried at Different Temperatures. Submitted for Publication.
• Öz, F., Kaya, M., 2006d. The Effects of Different Spices and Fat Levels on Formation of Heterocyclic Amines in Kofte Fried at Different Temperatures. Submitted for Publication.
• Öz, F., Kaban, G., Kaya, M., 2007. Effects of Cooking Methods on the Formation of Heterocyclic Aromatic Amines of Two Different Species Trout. Food Chemistry, in press.
• Pais, P., Moyano, E., Puignou, L., Galceran, M. T., 1997a. Liquid Chromatography-Electrospray Mass Spectrometry with in- source Fragmentation for the Identification and Quantification of Fourteen Mutagenic Amines in Beef Extracts. J. of Chrom. A., 775: 125-136.
• Pais, P., Moyano, E., Puignou, L., Galceran, M. T., 1997b. Liquid Chromatography-Atmospheric-Pressure Chemical Ionization Mass Spectrometry as a Routine Method for the Analysis of Mutagenic Amines in Beef Extracts. J. of Chrom. A, 778: 207–218.
• Pais, P., Tanga, M. J., Salmon, C. P., Knize, M. G., 2000. Formation of the Mutagen IFP in Model Systems and Detection in Restaurant Meats. J. of Agric. and Food Chem., 48: 1721-1726.
• Perfetti, G. A., 1996. Determination of Heterocyclic Aromatic Amines in Process Flavors by a Modified Liquid Chromatographic Method. J. of AOAC International, 79: 813–816.
• Richling, E., Herderich, M., Schreier, P., 1996. High Performance Liquid Chromatography-Electrospray Tandem Mass Spectrometry (HPLC-ESI-MS-MS) for the Analysis of Heterocyclic Aromatic Amines (HAA). Chromatographia, 42 (1/2): 7–11.
• Richling, E., Decker, C., Häring, D., Herderich, M., Schreier, P., 1997. Analysis of Heterocyclic Aromatic Amines in Wine by High-Performance Liquid Chromatography-Electrospray Tandem Mass Spectrometry. J. of Chrom. A, 791: 71–77.
• Ristic, A., Cichna, M., Sontag, G., 2004. Determination of Less Polar Heterocyclic Aromatic Amines in Standardised Beef Extracts and Cooked Meat Consumed in Austria by Liquid Chromatography and Fluorescence Detection. J. of Chromatograhy B, 802: 87–94.
• Salmon, C. P., Knize, M. G., Panteleakos, F. N., Wu, R. W., Nelson, D. O., Felton, J. S., 2000. Minimization of Heterocyclic Amines and Thermal Inactivation of Escherichia coli in Fried Ground Beef. J. of National Cancer Inst., 92 (21): 1773-1778.
• Santos, F. J., Barceló-Barrachina, E., Toribio, F., Puignou, L., Galceran, M. T., Persson, E., Skog, K., Messner, C., Murkovic, M., Nabinger, U., Ristic, A., 2004. Analysis of Heterocyclic Amines in Food Products: Interlaboratory Studies. J. of Chrom. B, 802: 69–78.
• Sentellas, S., Moyano, E., Puignou, L., Galceran, M. T., 2004. Optimization of a Clean–up Procedure for the Determination of Heterocyclic Aromatic Amines in Urine by Field- amplified Sample Injection-Capillary Electrophoresis-Mass Spectrometry. J. of Chrom. A, 1032: 193–201.
• Skog, K., 2002. Problems Associated with the Determination of Heterocyclic Amines in Cooked Foods and Human Exposure. Food and Chem. Toxic., 40: 1197-1203.
• Skog, K., Solyakov, A., 2002. Heterocyclic Amines in Poultry Products: A Literatue Review. Food and Chem. Toxic., 40: 1213-1221.
• Solbeck., P. A. M., Martos, P. A., Wainman, B. C., Josephy, P. D., 2003. Analysis of Human Milk for the Mammaly Carcinogen PhIP. 2nd International Workshop on Analytical, Chemical, and Biological Relevance of Heterocyclic Aromatic Amines from 7.- 9. May 2003 in Graz, University of Technology.
• Sugimura, T., Adamson, R. H., 2000. Introduction. Baffins Lane, Chichester, West Sussex, 373, England.
• Takahashi, M., Wakabayashi, K., Nagao, M., Yamaizumi, Z., Sato, S., Kinae, N., Tomita, I., Sugimura, T., 1985. Identification and Quantificaiton of 2-Amino-3,4,8-trimethylimidazo[4,5- f]quinoxaline (4,8-DiMeIQx) in Beef Extract. Carcinogenesis, 6 (10): 1537–1539.
• Tikkanen, L. M., Latva-Kala, K. J., Heiniö, R.-L., 1996. Effect of Commercial Marinades on the Mutagenic Activity, Sensory Quality and Amount of Heterocyclic Amines in Chicken Grilled under Different Conditions. Food and Chem. Toxic., 34: 725-730.
• Thiébaud, H. P., Knize, M. G., Kuzmicky, P. A., Hsieh, D. P., Felton, J. S, 1995. Airborne Mutagens Produced by Frying Beef, Pork and Soy-based Food. Food and Chem. Toxic., 33 (10): 821-828.
• Toribio, F., Moyano, E., Puignou, L., Galceran, M. T., 2002. Ion- Trap Tandem Mass Spectrometry for the Determination of Heterocyclic Amines in Food. J. of Chrom. A, 948: 267–281.
• Tran, N. L., Salmon, C. P., Knize, M. G., Colvin, M. E., 2002. Experimental and Simulation Studies of Heat Flow and Heterocyclic Amine Mutagen/Carcinogen Formation in Pan- Fried Meat Patties. Food and Chem. Toxic., 40: 673-684.
• Turesky, R. J., Bur, H., Huynh-Ba, T., Aeschbacher, H. U., Milon, H., 1988. Analysis of Mutagenic Heterocyclic Amines in Cooked Beef Products by High-Performance Liquid Chromatography in Combination with Mass Spectrometry. Food and Chem. Toxic., 26 (6): 501-509.
• Turesky, R. J., Forster, C. M., Aeschbacher, H. U., Würzner, H. P., Skipper, P. L., Trudel, L. J., Tannenbaum, S. R., 1989. Purification of the Food-borne Carcinogens 2-Amino-3- methylimidazo[4,5-f]quinoline and 2-Amino-3,8- dimethylimidazo[4,5-f]quinoxaline in Heated Meat Products by Immunoaffinity Chromatography. Carcinogenesis, 10 (1): 151–156.
• Turesky, R. J., Taylor, J., Schnackenberg, L., Freeman, J. P., Holland, R. D., 2005. Quantitation of Carcinogenic Heterocyclic Aromatic Amines and Detection of Novel Heterocyclic Aromatic Amines in Cooked Meats and Grill Scrapings by HPLC/ESI-MS. J. Agric. Food Chem., 53: 3248-3258.
• Vanderlaan, M., Watkins, B. E., Hwang, M., Knize, M. G., Felton, J. S., 1988. Monoclonal Antibodies for the Immunoassay of Mutagenic Compounds Produced by Cooking Beef. Carcinogenesis, 9 (1): 153–160.
• Vollenbröker, M., Eichner, K., 2000. A New Quick Solid-Phase Extraction Method for the Quantification of Heterocyclic Aromatic Amines. Eur. Food Res. Tech., 212: 122-125.