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Development and application of microwave-assisted extraction and advanced low density microextraction technique coupled with high-performance liquid chromatography for the successful determination of heterocyclic aromatic amines in barbecued meat sample and method optimization using response surface methodology

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Abstract

Heterocyclic aromatic amines (HAAs) produced during heat processing in meat samples are introduced as chemical toxicants with hazardous effect on human body. In this study, we applied an advanced, simple, efficient and sensitive analytical procedure based on microwave-assisted extraction and low density solvent/dispersive liquid–liquid microextraction coupled with high-performance liquid chromatography for the determination of four kinds of HAAs (2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), 2-amino-1-methyl-6-phenyl-imidazo[4,5-b]pyridine (PhIP) and 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)) in barbecued meat samples for the first time. The parameters affected on microextraction method including type and volume of extraction and disperser solvents, salt percent and PH were optimized using response surface design. The dynamic linear range was 1–1000 ng g−1. The coefficient of determination was higher than 0.982, relative standard deviations were between 3.7 and 8.1%. The recoveries in tree levels (10, 50 and 100 ng g−1) were obtained 89–101.5%. Detection limits were between 0.25 and 0.71 ng g−1. Offered technique is sensitive, selective‚ quick and precise. The most concentration of HAAs determined in barbecued meat samples was for IQ 1250 ng g−1 and the lowest amount is also related to IQ type 25 ng g−1. This proposed method presents proper concentration factors and detection limits for determination of HAAs in different barbecued meat samples.

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References

  1. T. Lafarga, M. Hayes, Bioactive peptides from meat muscle and by-products: generation, functionality and application as functional ingredients. Meat Sci. 98, 227–239 (2014)

    Article  CAS  Google Scholar 

  2. K. Arihara, Strategies for designing novel functional meat products. Meat Sci. 74, 219–229 (2006)

    Article  CAS  Google Scholar 

  3. W. Zhang, B.M. Naveena, C. Jo, R. Sakata, G. Zhou, R. Banerjee, T. Nishiumi, Technological demands of meat processing–an Asian perspective. Meat Sci. 132, 35–44 (2017)

    Article  Google Scholar 

  4. S. Jinap, M.S. Mohd-Mokhtar, A. Farhadian, N.D.S. Hasnol, S.N. Jaafar, P. Hajeb, Effects of varying degrees of doneness on the formation of heterocyclic aromatic amines in chicken and beef satay. Meat Sci. 94, 202–207 (2013)

    Article  CAS  Google Scholar 

  5. F. Toribio, R. Busquets, L. Puignou, M.T. Galceran, Heterocyclic amines in griddled beef steak analysed using a single extract clean-up procedure. Food Chem. Toxicol. 45, 667–675 (2007)

    Article  CAS  Google Scholar 

  6. A. Dundar, C. Sarıçoban, M.T. Yılmaz, Response surface optimization of effects of some processing variables on carcinogenic/mutagenic heterocyclic aromatic amine (HAA) content in cooked patties. Meat Sci. 91, 325–333 (2012)

    Article  CAS  Google Scholar 

  7. R. Gonzalo-Lumbreras, N. Rosales-Conrado, M.E. León-González, L.V. Pérez-Arribas, L. M. Polo-Díez, Capillary liquid chromatography with diode array and mass spectrometry detection for heterocyclic aromatic amine determination in ready-to-eat food treated with electron-beam irradiation. J. Chromatogr. A 1217, 6778–6784 (2010)

    Article  CAS  Google Scholar 

  8. F. Oz, G. Kotan, Effects of different cooking methods and fat levels on the formation of heterocyclic aromatic amines in various fishes. Food Control 67, 216–224 (2016)

    Article  CAS  Google Scholar 

  9. R. Zaidi, S. Kumar, P.R. Rawat, Rapid detection and quantification of dietary mutagens in food using mass spectrometry and ultra performance liquid chromatography. Food Chem. 135, 2897–2903 (2012)

    Article  CAS  Google Scholar 

  10. M. Raman, U. Nilsson, K. Skog, M. Lawther, B. Nair, M. Nyman, Physicochemical characterisation of dietary fibre components and their ability to bind some process-induced mutagenic heterocyclic amines, Trp-P-1, Trp-P-2, AαC and MeAαC. Food Chem. 138, 2219–2224 (2013)

    Article  CAS  Google Scholar 

  11. R. Busquets, M. Bordas, F. Toribio, L. Puignou, M. Galceran, Occurrence of heterocyclic amines in several home-cooked meat dishes of the Spanish diet. J. Chromatogr. B 802, 79–86 (2004)

    Article  CAS  Google Scholar 

  12. T. Sugimura, K. Wakabayashi, H. Nakagama, M. Nagao, Heterocyclic amines: mutagens/carcinogens produced during cooking of meat and fish. Cancer Sci. 95, 9–290 (2004)

    Article  Google Scholar 

  13. G.A. Gross, Simple methods for quantifying mutagenic heterocyclic aromatic amines in food products. Carcinogenesis 11, 1597–1603 (1990)

    Article  CAS  Google Scholar 

  14. F. Oz, Quantitation of heterocyclic aromatic amines in ready to eat meatballs by ultra fast liquid chromatography. Food Chem. 126, 2010–2016 (2011)

    Article  CAS  Google Scholar 

  15. O. Viegas, P. Novo, E. Pinto, O. Pinho, I.M.P.L.V.O. Ferreira, Effect of charcoal types and grilling conditions on formation of heterocyclic aromatic amines (HAs) and polycyclic aromatic hydrocarbons (PAHs) in grilled muscle foods. Food Chem. Toxicol. 50, 2128–2134 (2012)

    Article  CAS  Google Scholar 

  16. M.R. Khan, R. Busquets, F.J. Santos, L. Puignou, New method for the analysis of heterocyclic amines in meat extracts using pressurised liquid extraction and liquid chromatography–tandem mass spectrometry. J. Chromatogr. A 1194, 155–160 (2008)

    Article  CAS  Google Scholar 

  17. K. Puangsombat, P. Gadgil, T.A. Houser, M.C. Hunt, J.S. Smith, Heterocyclic amine content in commercial ready to eat meat products. Meat Sci. 88, 227–233 (2011)

    Article  CAS  Google Scholar 

  18. C. Krach, G. Sontag, Determination of some heterocyclic aromatic amines in soup cubes by ion-pair chromatography with coulometric electrode array detection. Anal. Chim. Acta 417, 77–83 (2000)

    Article  CAS  Google Scholar 

  19. L.B. Agudelo Mesa, J.M. Padró, M. Reta, Analysis of non-polar heterocyclic aromatic amines in beefburguers by using microwave-assisted extraction and dispersive liquid–ionic liquid microextraction. Food Chem. 141, 1694–1701 (2013)

    Article  CAS  Google Scholar 

  20. U. Jautz, G. Morlock, Validation of a new planar chromatographic method for quantification of the heterocyclic aromatic amines most frequently found in meat. Anal. Bioanal. Chem. 387, 1083–1093 (2007)

    Article  CAS  Google Scholar 

  21. C.-C. Chang, T.-H. Kao, D. Zhang, Z. Wang, B.S. Inbaraj, K.-Y. Hsu, B.H. Chen, Application of QuEChERS coupled with HPLC-DAD-ESI-MS/MS for determination of heterocyclic amines in commercial meat products. Food Anal. Methods 11, 3243–3256 (2018)

    Article  Google Scholar 

  22. E. Barceló-Barrachina, F.J. Santos, L. Puignou, M.T. Galceran, Comparison of dimethylformamide dialkylacetal derivatization reagents for the analysis of heterocyclic amines in meat extracts by gas chromatography–mass spectrometry. Anal. Chim. Acta 545, 209–217 (2005)

    Article  Google Scholar 

  23. V. Ghasemzadeh-mohammadi, A. Mohammadi, M. Hashemi, Microwave-assisted extraction and dispersive liquid –liquid microextraction followed by gas chromatography–mass spectrometry for isolation and determination of polycyclic aromatic hydrocarbons in smoked fish. J. Chromatogr. A 1237, 30–36 (2012)

    Article  CAS  Google Scholar 

  24. H. Ramezani, H. Hosseini, M. Kamankesh, Rapid determination of nitrosamines in sausage and salami using microwave-assisted extraction and dispersive liquid–liquid microextraction followed by gas chromatography–mass spectrometry. Eur. Food Res. Technol. 240, 441–450 (2014)

    Article  Google Scholar 

  25. T.S. Ballard, P. Mallikarjunan, K. Zhou, S. O’Keefe, Microwave-assisted extraction of phenolic antioxidant compounds from peanut skins. Food Chem. 120, 1185–1192 (2010)

    Article  CAS  Google Scholar 

  26. M.T. Galceran, P. Pais, L. Puignou, Isolation by solid-phase extraction and liquid chromatographic determination of mutagenic amines in beef extracts. J. Chromatogr. A 719, 203–212 (1996)

    Article  CAS  Google Scholar 

  27. F. Rezaei, Y. Yamini, M. Moradi, B. Ebrahimpour, Solid phase extraction as a cleanup step before microextraction of diclofenac and mefenamic acid using nanostructured solvent. Talanta 105, 173–178 (2013)

    Article  CAS  Google Scholar 

  28. Y.S. Gu, I.S. Kim, J.K. Ahn, D.C. Park, D.M. Yeum, C. Ji, S.B. Kim, Mutagenic and carcinogenic heterocyclic amines as affected by muscle types/skin and cooking in pan-roasted mackerel. Mutat. Res. 515, 95–189 (2002)

    Google Scholar 

  29. B.H. Chen, D.J. Yang, An improved analytical method for determination of heterocyclic amines in chicken legs. Chromatographia 48, 223–230 (1998)

    Article  CAS  Google Scholar 

  30. M. Rezaee, Y. Assadi, M.-R. Milani Hosseini, E. Aghaee, F. Ahmadi, S. Berijani, Determination of organic compounds in water using dispersive liquid–liquid microextraction. J. Chromatogr. A 1116, 1–9 (2006)

    Article  CAS  Google Scholar 

  31. M. Kamankesh, A. Mohammadi, Z. Modarres Tehrani, R. Ferdowsi, H. Hosseini, Dispersive liquid–liquid microextraction followed by high-performance liquid chromatography for determination of benzoate and sorbate in yogurt drinks and method optimization by central composite design. Talanta 109, 46–51 (2013)

    Article  CAS  Google Scholar 

  32. M. Madani-Tonekaboni, M. Kamankesh, A. Mohammadi, Determination of furfural and hydroxymethyl furfural from baby formula using dispersive liquid–liquid microextraction coupled with high performance liquid chromatography and method optimization by response surface methodology. J. Food Compos. Anal. 40, 1–7 (2015)

    Article  CAS  Google Scholar 

  33. A. Mohammadi, V. Ghasemzadeh-Mohammadi, P. Haratian, R. Khaksar, M. Chaichi, Determination of polycyclic aromatic hydrocarbons in smoked fish samples by a new microextraction technique and method optimisation using response surface methodology. Food Chem. 141, 2459–2465 (2013)

    Article  CAS  Google Scholar 

  34. M. Kamankesh, A. Mohammadi, H. Hosseini, Z.M. Tehrani, Rapid determination of polycyclic aromatic hydrocarbons in grilled meat using microwave-assisted extraction and dispersive liquid-liquid microextraction coupled to gas chromatography-mass spectrometry. Meat Sci. 103, 61–67 (2015)

    Article  CAS  Google Scholar 

  35. L. Cárdenes, J.H. Ayala, A.M. Afonso, V. González, Solid-phase microextraction coupled with high-performance liquid chromatography for the analysis of heterocyclic aromatic amines. J. Chromatogr. A 1030, 87–93 (2004)

    Article  Google Scholar 

Download references

Acknowledgements

This study was conducted in laboratory of Department of Food Science and Technology, Faculty of Nutrition Science, Food Science and Technology/National Nutrition and Food Technology Research Institute, Shahid Beheshti University of Medical Sciences, Iran. We gratefully acknowledges for their assistance.

Funding

Dr. Mohammadi has received research grants from National Nutrition and Food Technology Research Institute, Faculty of Nutrition Sciences and Food Technology.

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Authors and Affiliations

  1. Department of Food Science and Technology, Faculty of Nutrition Science, Food Science and Technology/National Nutrition and Food Technology Research Institute, Shahid Beheshti University of Medical Sciences, Tehran, Iran

    Fatemeh Barzegar, Marzieh Kamankesh & Abdorreza Mohammadi

  2. Research Laboratory of Spectroscopy & Micro and Nano Extraction, Department of Chemistry, Iran University of Science and Technology, Tehran, Iran

    Marzieh Kamankesh

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  1. Fatemeh Barzegar
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  2. Marzieh Kamankesh
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  3. Abdorreza Mohammadi
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Correspondence to Abdorreza Mohammadi.

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Barzegar, F., Kamankesh, M. & Mohammadi, A. Development and application of microwave-assisted extraction and advanced low density microextraction technique coupled with high-performance liquid chromatography for the successful determination of heterocyclic aromatic amines in barbecued meat sample and method optimization using response surface methodology. Food Measure 13, 1755–1764 (2019). https://doi.org/10.1007/s11694-019-00093-9

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  • DOI: https://doi.org/10.1007/s11694-019-00093-9

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