Skip to main content
Log in

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

  • Research Article
  • Published:
Food Science and Biotechnology Aims and scope Submit manuscript

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  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)

    Article  Google Scholar 

  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. 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)

    CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  5. Sugimura T. Nutrition and dietary carcinogens. Carcinogenesis 21: 387–395 (2000)

    Article  CAS  Google Scholar 

  6. Exon JH. A review of the toxicology of acrylamide. J. Toxicol. Env. Heal. B 9: 397–412 (2006)

    Article  CAS  Google Scholar 

  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)

    Article  Google Scholar 

  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. 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)

    Article  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  11. Abdulkarim BG, Smith JS. Heterocyclic amines in fresh and processed meat products. J. Agr. Food Chem. 44: 4680–4687 (1998)

    Article  Google Scholar 

  12. Solyakov A, Skog K. Screening for heterocyclic amines in chicken cooked in various ways. Food Chem. Toxicol. 40: 1205–1211 (2002)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    CAS  Google Scholar 

  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)

    CAS  Google Scholar 

  19. Ryan D, Robarts K. Phenolic compounds in olives. Analyst 123: 31R–44R (1998)

    Article  CAS  Google Scholar 

  20. Keys A. Mediterranean diet and public health: Personal reflections. Am. J. Clin. Nutr. 61: 1321S–1323S (1995)

    CAS  Google Scholar 

  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. 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)

    CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  25. Fernandez E, Gallus S, La Vecchia C. Nutrition and cancer risk: An overview. J. Br. Menopause. Soc. 12: 139–142 (2006)

    Article  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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. 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)

    Article  CAS  Google Scholar 

  30. Gross GA, Gruter A. Quantitation of mutagenic/carcinogenic heterocyclic amines in food products. J. Chromatogr. A 592: 271–278 (1992)

    Article  CAS  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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. Jägerstad M, Skog K, Grivas S, Olsson K. Formation of heterocyclic amines using model systems. Mutat. Res. 259: 219–223 (1991)

    Article  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Han-Seung Shin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lee, J., Dong, A., Jung, K. et al. Influence of extra virgin olive oil on the formation of heterocyclic amines in roasted beef steak. Food Sci Biotechnol 20, 159–165 (2011). https://doi.org/10.1007/s10068-011-0022-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10068-011-0022-9

Keywords

Navigation