Food Science and Biotechnology

, Volume 20, Issue 1, pp 159–165 | Cite as

Influence of extra virgin olive oil on the formation of heterocyclic amines in roasted beef steak

  • Jiyeong Lee
  • Ahyoung Dong
  • Kyunghee Jung
  • Han-Seung ShinEmail author
Research Article


In this study, heterocyclic anime (HCA) contents were monitored in commonly consumed pan-fried beefsteak based on the highest level of human exposure. Effect of addition of extra virgin olive oil (EVOO) on HCAs formation in fried beef steaks was evaluated. After EVOO was spread on the meat surface, the raw beef was cooked at 200°C for 5 min on each side. The HCAs were extracted from the meat samples and purified using a solid-phase extraction method and then analyzed by liquid chromatography-mass spectrometry (LC-MS). 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), 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-methyl-9H-pyrido [2,3-b]indole (MeAαC), 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 beefsteaks. HCAs formation was significantly reduced (p<0.05) when the EVOO was added to the beef prior to cooking. The addition of 2 and 4 g of EVOO considerably inhibited HCAs formation in the fried beefsteak. However, adding excess amounts of EVOO promoted some HCAs formation.


heterocyclic amine extra virgin olive oil roasted beef pathy cooking 


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  1. 1.
    Follmann W, Birkner S. The use of cultured primary bovine epithelial cells as a screening model to detect genotoxic effects of heterocyclic aromatic amines in the comet assay. J. Toxicol. Env. Heal. A 71: 947–953 (2008)CrossRefGoogle Scholar
  2. 2.
    Knize MG, Felton JS. Formation and human risk of carcinogenic heterocyclic amines formed from natural precursors in meat. Mol. Nutr. Food Res. 63: 158–165 (2005)Google Scholar
  3. 3.
    Lang NP, Butler MA, Massengill JP, Lawson M, Stotts RC, Hauer JM, Kadlubar FF. Rapid metabolic phenotypes for acetyltransferase and cytochrome P4501A2 and putative exposure to food-borne heterocyclic amines increase the risk for colorectal cancer or polyps. Cancer Epidem. Biomar. 3: 675–682 (1994)Google Scholar
  4. 4.
    Guan Y, Louis ED, Zheng W. Toxicokinetics of tremorogenic natural products harmane and harmine, in male Sprague-dawley rats. J. Toxicol. Env. Heal. A 64: 645–660 (2001)CrossRefGoogle Scholar
  5. 5.
    Sugimura T. Nutrition and dietary carcinogens. Carcinogenesis 21: 387–395 (2000)CrossRefGoogle Scholar
  6. 6.
    Exon JH. A review of the toxicology of acrylamide. J. Toxicol. Env. Heal. B 9: 397–412 (2006)CrossRefGoogle Scholar
  7. 7.
    Jagerstad M, Laser reutersward A, Olsson R, Grivas S, Nyhammar T, Olsson K, Dahlqyist A. Creatin(in)e and Maillard reaction products as precursors of mutagenic compounds: Effects of various amino acids. Food Chem. 12: 239–244 (1983)CrossRefGoogle Scholar
  8. 8.
    Felton JS, Knize MG. Heterocyclic amine mutagens /carcinogens in foods. pp. 471–502. In: Handbook of Experimental Pharmacology. Copper CS, Grover PL (eds). Springer-Verlag, Berlin, Germany (1990)Google Scholar
  9. 9.
    Jagerstad M, Skog K, Arvidsson P, Solyakov A. Chemistry, formation, and occurrence of genetoxic heterocyclic amines identified in model systems and cooked foods. Z. Lebensm. Unters. For. A 207: 419–427 (1998)CrossRefGoogle Scholar
  10. 10.
    Louis ED, Zheng W, Jiang W, Bogen KT, Keating GA. Quantification of the neurotoxic β-carboline harmane in barbecued/grilled meat samples and correlation with level of doneness. J. Toxicol. Env. Heal. B 70: 1014–1019 (2007)CrossRefGoogle Scholar
  11. 11.
    Abdulkarim BG, Smith JS. Heterocyclic amines in fresh and processed meat products. J. Agr. Food Chem. 44: 4680–4687 (1998)CrossRefGoogle Scholar
  12. 12.
    Solyakov A, Skog K. Screening for heterocyclic amines in chicken cooked in various ways. Food Chem. Toxicol. 40: 1205–1211 (2002)CrossRefGoogle Scholar
  13. 13.
    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)CrossRefGoogle Scholar
  14. 14.
    Jägerstad M, Skog K, Arvidsson P, Solyakov A. Chemistry, formation, and occurrence of genotoxic heterocyclic amines identified in model systems and cooked foods. Z. Lebensm. Unters. For. A 207: 419–427 (1998)CrossRefGoogle Scholar
  15. 15.
    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)CrossRefGoogle Scholar
  16. 16.
    Britt C, Gomaa EA, Gray JI, Booren AM. Influence of cherry tissue on lipid oxidation and heterocylic aromatic amine formation in ground beef patties. J. Agr. Food Chem. 46: 4891–4897 (1998)CrossRefGoogle Scholar
  17. 17.
    Murkovic M, Steinberger D, Pfannhauser W. Antioxidant spices reduce the formation of heterocyclic amines in fried meat. Food Res. Technol. 207: 477–480 (1998)Google Scholar
  18. 18.
    Weisburger JH, Veliath E, Larios E, Pittman B, Zang E, Hara Y. Tea polyphenols inhibit the formation of mutagens during the cooking of meat. Mutat. Res. 516: 19–22 (2002)Google Scholar
  19. 19.
    Ryan D, Robarts K. Phenolic compounds in olives. Analyst 123: 31R–44R (1998)CrossRefGoogle Scholar
  20. 20.
    Keys A. Mediterranean diet and public health: Personal reflections. Am. J. Clin. Nutr. 61: 1321S–1323S (1995)Google Scholar
  21. 21.
    de Lorgeril M, Salen P. The Mediterranean-style diet for the prevention of cardiovascular diseases. Public Health Nutr. 9: 118–123 (2006)Google Scholar
  22. 22.
    Solfrizzi V, Panza F, Torres F, Mastroianni F, Del Parigi A, Venezia A, Capurso A. High monounsaturated fatty acids intake protects against age-related cognitive decline. Neurology 52: 1563–1569 (1999)Google Scholar
  23. 23.
    Owen RW, Giacosa A, Hull WE, Haubner R, Spiegelhalder B, Bartsch H. The antioxidant/anticancer potential of phenolic compounds isolated from olive oil. Eur. J. Cancer 36: 1235–1247 (2000)CrossRefGoogle Scholar
  24. 24.
    Owen RW, Haubner R, Wurtele G, Hull E, Spiegelhalder B, Bartsc H. Olives and olive oil in cancer prevention. Eur. J. Cancer. Prev. 13: 319–326 (2004)CrossRefGoogle Scholar
  25. 25.
    Fernandez E, Gallus S, La Vecchia C. Nutrition and cancer risk: An overview. J. Br. Menopause. Soc. 12: 139–142 (2006)CrossRefGoogle Scholar
  26. 26.
    Braga C, La Vecchia C, Franceschi S, Negri E, Parpinel M, Decarli A, Giacosa A, Trichopoulos D. Olive oil, other seasoning fats and the risk of colorectal carcinoma. Cancer 82: 448–453 (1998)CrossRefGoogle Scholar
  27. 27.
    Stoneham M, Goldacre M, Seagroatt V, Gill L. Olive oil, diet, and colorectal cancer: An ecological study and a hypothesis. J. Epidemiol. Commun. H. 54: 756–760 (2000)CrossRefGoogle Scholar
  28. 28.
    Hashim YZ, Eng M, Gill CI, McGlynn H, Rowland IR. Components of olive oil and chemoprevention of colorectal cancer. Mol. Nutr. Food Res. 63: 374–386 (2005)Google Scholar
  29. 29.
    Galeone C, Talamini R, Levi F, Pelucchi C, Negri E, Giacosa A, Montella M, Franceschi S, La Vecchia. Fried foods, olive oil, and colorectal cancer. Ann Oncol. 18: 36–39 (2007)CrossRefGoogle Scholar
  30. 30.
    Gross GA, Gruter A. Quantitation of mutagenic/carcinogenic heterocyclic amines in food products. J. Chromatogr. A 592: 271–278 (1992)CrossRefGoogle Scholar
  31. 31.
    Kinze 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)CrossRefGoogle Scholar
  32. 32.
    Bordas M, Moyano E, Puignou L, Galceran MT. Formation and stability of heterocyclic amines in a meat flavor model system. Effect of temperature, time, and precursors. J. Chromatogr. B 802: 11–17 (2004)CrossRefGoogle Scholar
  33. 33.
    Arnoldi A, Arnoldi C, Baldi O, Ghizzoni C. Effect of lipids in the Maillard reaction. pp. 133–138. In: The Maillard Reaction. Advances in Life Sciences. Finot PA, Aeschbacher HU, Hurrell RF, Liardon R (eds). Birkhäuser Verlag, Basel, Switzerland (1990)Google Scholar
  34. 34.
    Jägerstad M, Skog K, Grivas S, Olsson K. Formation of heterocyclic amines using model systems. Mutat. Res. 259: 219–223 (1991)CrossRefGoogle Scholar
  35. 35.
    Satue MT, Huang SW, Frankel EN. Effect of natural antioxidants in virgin olive oil on oxidative stability of refined, bleached, and deodorized olive oil. J. Am. Oil Chem. Soc. 72: 1131–1137 (1995)CrossRefGoogle Scholar
  36. 36.
    Pearson AM, Chen C, Gray JI, Aust SD. Mechanism(s) involved in meat mutagen formation and inhibition. Free Radical Bio. Med. 13: 161–167 (1992)CrossRefGoogle Scholar
  37. 37.
    Monti SM, Ritieni A, Sacchi R, Skog K, Borgen E, Fogliano V. Characterization of phenolic compounds in virgin olive oil and their effect on the formation of carcinogenic/mutagenic heterocyclic amines in a model system. J. Agr. Food Chem. 49: 3969–3975 (2001)CrossRefGoogle Scholar
  38. 38.
    Johansson MA, Fredholm L, Bjerne I, Jagerstad M. Influence of frying fat on the formation of heterocyclic amines in fried beefburgers and pan residues. Food Chem. Toxicol. 33: 993–1004 (1995)CrossRefGoogle Scholar
  39. 39.
    Vitaglione P, Monti SM, Ambrosino P, Skog K, Fogliano V. Carotenoids from tomatoes inhibit heterocyclic amine formation. Eur. Food Res. Technol. 215: 108–113 (2002)CrossRefGoogle Scholar

Copyright information

© The Korean Society of Food Science and Technology and Springer Netherlands 2011

Authors and Affiliations

  • Jiyeong Lee
    • 1
  • Ahyoung Dong
    • 1
  • Kyunghee Jung
    • 1
  • Han-Seung Shin
    • 1
    Email author
  1. 1.Department of Food Science and Biotechnology and Institute of Lotus Functional Food IngredientsDongguk University-SeoulSeoulKorea

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