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Determination of Heterocyclic Amines in Roasted Fish and Shellfish by Liquid Chromatography-Electrospray Ionization/Mass Spectrometry  

Lee, Jae-Hwan (Department of Food Science and Technology and Institute of Lotus Functional Food Ingredient, Dongguk University)
Back, Yoo-Mi (Department of Food Science and Technology and Institute of Lotus Functional Food Ingredient, Dongguk University)
Lee, Kwang-Geun (Department of Food Science and Technology and Institute of Lotus Functional Food Ingredient, Dongguk University)
Shin, Han-Seung (Department of Food Science and Technology and Institute of Lotus Functional Food Ingredient, Dongguk University)
Publication Information
Korean Journal of Food Science and Technology / v.41, no.3, 2009 , pp. 326-333 More about this Journal
Abstract
Heterocyclic aromatic amines (HCAs) are mutagenic and carcinogenic substances that are formed during the heating of protein-rich foods. HCAs are generally found at low amounts in a complex matrix, which requires sophisticated analysis. In this study, HCAs were extracted from lyophilized fish and shellfish samples using solid-phase extraction (SPE) and determined by liquid chromatography-electrospray ionization/mass spectrometry (LC-ESI-MS). The HCA recoveries in the fish and shellfish ranged from 15.7 to 74.7% with standard deviations from 0.2 to 7.63%. And HCA concentrations ranged from 0.8 to 1,117.7 $ng/g^{-1}$ in cooked food samples. 1-methyl-9H-pyrido[3,4-b]indole (Harman), 9H-pyrido[3,4-b]indole (Norharman), and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) were the most abundant HCAs formed in the muscle of fried mackerel, at levels of 1,117.7, 926.6, and 133.7 ng/g, respectively. 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2), 2-aminodipiryrido[1,2-a:3,2-d]imidazole(Glu-P-2), 2-amino-9H-pyrido[2,3-b]indole(A${\alpha}$C), 2-amino-3methyl-9H-pyrido [1,2-a:3,2-d]imidazole(MeA${\alpha}$C), 2-amino-3,4,7,8-tetramethylimidazo[4,5-f]quinoxaline (TriMeIQx), 2-amino-3,7,8-trimethylimidazo [4,5-f]quinoxaline(7,8-DiMeIQx), and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) were only detected by small quantities ranged from 1.5 to 98.6 ng/g. Overall, this study provides useful information on HCA levels in fish and shellfish products consumed in Korea.
Keywords
heterocyclic aromatic amine; fish; shellfish; solid-phase extraction; LC/MS;
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1 Becher G, Knize MG, Nes IF, Felton JS. Isolation and identification of mutagens from a fried Norwegian meat product. Carcinogenesis 9: 247-1253 (1988)   DOI   ScienceOn
2 Sugimura T, Wakabayashi K, Nakagama H, Nagao M. Heterocyclic amines: Mutagens/carcinogens produced during cooking of meat and fish. Cancer Sci. 95: 290-299 (2004)   DOI   ScienceOn
3 Matsukura N, Kawachi T, Morino K, Ohgaki H, Sugimura T, Takayama S. Carcinogenicity in mice of mutagenic compounds from a tryptophan pyrolysate. Science 213: 346-347 (1981)   DOI   PUBMED
4 Sugimura T, Wakabayashi K. Mutagens and carcinogens in food. Prog. Clin. Biol. Res. 347: 1-18 (1990)
5 Rohrmann S, Becker N. Development of a short questionnaire to assess the dietary intake of heterocyclic aromatic amines. Public Health Nutr. 5: 699-705 (2002)   PUBMED   ScienceOn
6 Felton JS, Knize MG. New mutagens from cooked food. Prog. Clin. Biol. Res. 347: 19-38 (1990)
7 Ha YL, Grimm NK, Pariza MW. Anticarcinogens from fried ground beef: heat-altered derivatives of linoleic acid. Carcinogenesis 8: 1881-1887 (1987)   DOI   ScienceOn
8 Yamashita K, Umemoto A, Grivas S, Kato S, Sato S, Sugimura T. Heterocyclic amines -DNA adducts analysed by 32 P-postlabeling method. Nucleic Acids Res. Symp. Ser. 14: 111-114 (1988)
9 Skog K. Cooking procedures and food mutagens: A literature review. Food Chem. Toxicol. 31: 655-675 (1993)   DOI   ScienceOn
10 Aoyama S, Yamamoto Y. Antioxidant activity and flavonoid content of Welsh onion (Allium fistulosum) and the effect of thermal treatment. Food Sci. Technol. Res. 13: 67-72 (2007)   DOI   ScienceOn
11 Holder CL, Preece SW, Conway SC, Pu YM, Doerge DR. Quantification of heterocyclic amine carcinogens in cooked meats using isotope dilution liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry. Rapid Commun. Mass Sp. 11: 1667-1672 (1997)   DOI   ScienceOn
12 Richling E, Decker C, Haring D, Herderich M, Schreier P. Analysis of heterocyclic aromatic amines in wine by high-performance liquid chromatography-electrospray tandem mass spectrometry. J. Chromatogr. A 791: 71-77 (1997)
13 Tai CY, Lee KH, Chen BH. Effects of various additives on the formation of heterocyclic amines in fried fish fibre. Food Chem. 75: 309-316 (2001)   DOI   ScienceOn
14 Harris DC. Quantitative Chemical Analysis. 7th ed. W. H. Freeman and Company, New York, NY, USA. pp. 78-95 (2006)
15 Hatch FT, Felton JS, Knize MG. Mutagens Formed in Foods During Cooking. ICI Atlas of Science: Pharmacology. ISI Press, Philadelphia, PA, USA. pp. 222-228 (1988)
16 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)   DOI   PUBMED   ScienceOn
17 Gross GA, Gruter A. Quantitation of mutagenic/carcinogenic heterocyclic amines in food products. J. Chromatogr. 592: 271-278 (1992)   DOI   PUBMED   ScienceOn
18 Augustsson K, Skog K, Jagerstad M, Steineck G. Assessment of the human exposure to heterocyclic amines. Carcinogenesis 18: 1931-1935 (1997)   DOI   ScienceOn
19 Ohgaki H, Takayama S, Sugimura T. Carcinogenicities of heterocyclic amines. Mutat. Res. 259: 399-410 (1991)   DOI   ScienceOn
20 Jagerstad M, Reutersward 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: 239-44 (1983)
21 Sentellas S, Moyano E, Puignou L, Galceran MT. 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. Chromatogr. A 1032: 193-201 (2004)   DOI   PUBMED   ScienceOn
22 Knize MG, Hopmans E, Happe JA. The identification of a new heterocyclic amine mutagen from a heated mixture of creatine, glutamic acid, and glucose. Mutat. Res. 260: 313-319 (1991)   DOI   PUBMED   ScienceOn
23 Pais P, Knize MG. Chromatographic and related techniques for the determination of aromatic heterocyclic amines in foods. J. Chromatogr. B 747: 139-169 (2000)   DOI   ScienceOn
24 Abdulkarim BG, Smith JS. Heterocyclic amines in fresh and processed meat products. J. Agr. Food Chem. 46: 4680-4687 (1998)   DOI   ScienceOn
25 Totsuka T, Ushiyama H, Ishihara J, Sinha R, Goto S, Sugimura T, Wakabayashi K. Quantification of the co-mutagenic ${\beta}-carbolines$, norharman and harman, in cigarette smoke condensates and cooked foods. Cancer Lett. 143: 139-143 (1999)   DOI   ScienceOn
26 Vollenbroker M, Eichner K. A new quick solid-phase extraction method for the quantification of heterocyclic aromatic amines. Eur. Food Res. Technol. 212: 122-125 (2000)   DOI   ScienceOn
27 Lee JH, Shin HS. Influence of genotoxic heterocyclic aromatic amine formation and overall mutagenicity in ground beef patties using korean bramble (Rubus coreanum Miquel). Food Sci. Biotechnol. 16: 576-579 (2007)   ScienceOn
28 Sugimura T, Kawachi T, Nagao M, Yahagi T, Seino Y, Okamato T, Shudo K, Kosuge T, Tsuji K, Wakabayashi K, Iitaka Y, Itai A. Mutagenic principle(s) in tryptophan and phenylalanine pyrolysis products. P. Jpn. Acad. 53: 58-61 (1977)
29 Arimoto S, Hayatsu H. Role of hemin in the inhibition of mutagenic activity of 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) and other aminoazaarenes. Mutat. Res. 213: 217-226 (1989)   DOI   PUBMED   ScienceOn
30 Balogh Z, Gray JI, Gomaa EA, Booren AM. Formation and inhibition of heterocyclic aromatic amines in fried ground beef patties. Food Chem. Toxicol. 38: 395-401 (2000)   DOI   ScienceOn
31 Shin HS, Lee YS. Influence of commercial marinades on heterocyclic aromatic amine formation and overall mutagenicity in fried beef steaks. Food Sci. Biotechnol. 14: 323-327 (2005)   ScienceOn
32 Gibis M. Effect of oil marinades with garlic, onion, and lemon juice on the Formation of heterocyclic aromatic amines in fried beef patties. J. Agr. Food Chem. 55: 10240–10247 (2007)   DOI   PUBMED   ScienceOn
33 Lan CM, Chen BH. Effects of soy sauce and sugar on the formation of heterocyclic amines in marinated foods. Food Chem. Toxicol. 40: 989-1000 (2002)   DOI   ScienceOn
34 Sugimura T. Food and cancer. Toxicology 182: 17-21 (2002)   DOI   PUBMED   ScienceOn