Abstract
Microwave-assisted extraction and dispersive liquid–liquid microextraction followed by gas chromatography–mass spectrometry as a sensitive and efficient method was applied to extract and determine four biogenic amines (BAs) in Iranian Lighvan cheese samples. Carrez solutions were used for the sedimentation of proteins. Effective factors on the performance of microextraction were studied and optimized. The proposed method showed good linear ranges from 5 to 500 ng mL−1, with the coefficients of determination higher than 0.9929. Average recoveries were between 97 and 103%. Limits of detection for all analyzed BAs ranged from 5.9 to 14.0 ng g−1, and limits of quantitation ranged between 19.7 and 46.2 ng g−1. Compared with previous methods, the proposed method is simple, fast, accurate, and precise and gives low detection limits for investigating trace amounts of BAs in Iranian Lighvan cheese samples. The levels of four BAs were determined in five Lighvan cheese samples. Cadaverine was found as prevailing amine in the cheese samples. Putrescine, tyramine, and histamine were present at the second, third, and fourth highest levels, respectively.
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Mayer H, Fiechter G, Fischer E (2010) A new ultra-pressure liquid chromatography method for the determination of biogenic amines in cheese. J Chromatogr A 1217(19):3251–3257
Innocente N, Biasutti M, Padovese M, Moret S (2007) Determination of biogenic amines in cheese using HPLC technique and direct derivatization of acid extract. Food Chem 101(3):1285–1289
Martuscelli M, Gardini F, Torriani S, Mastrocola D, Serio A, Chaves-López C, Schirone M, Suzzi G (2005) Production of biogenic amines during the ripening of Pecorino Abruzzese cheese. Int Dairy J 15(6):571–578
Kao YY, Liu KT, Huang MF, Chiu TC, Chang HT (2010) Analysis of amino acids and biogenic amines in breast cancer cells by capillary electrophoresis using polymer solutions containing sodium dodecyl sulfate. J Chromatogr A 22(4):582–587
Saaid M, Saad B, Hashim NH, Mohamed Ali AS, Saleh MI (2009) Determination of biogenic amines in selected Malaysian food. Food Chem 113(4):1356–1362
Rauscher-Gabernig E, Gabernig R, Brueller W, Grossgut R, Bauer F, Paulsen P (2012) Dietary exposure assessment of putrescine and cadaverine and derivation of tolerable levels in selected foods consumed in Austria. Eur Food Res Technol 235(2):209–220
Önal A (2007) A review: current analytical methods for the determination of biogenic amines in foods. Food Chem 103(4):1475–1486
Gosetti F, Mazzucco E, Gianotti V, Polati S, Gennaro M (2007) High performance liquid chromatography/tandem mass spectrometry determination of biogenic amines in typical Piedmont cheeses. J Chromatogr A 1149(2):151–157
Jeya Shakila R, Vasundhara TS, Kumudavally KV (2001) A comparison of the TLC-densitometry and HPLC method for the determination of biogenic amines in fish and fishery products. Food Chem 75(2):255–259
Li W, Pan Y, Liu Y, Zhang X, Ye J, Chu Q (2014) Simultaneous determination of eight typical biogenic amines by CZE with capacitively coupled contactless conductivity detection. Chromatographia 77(3–4):287–292
Ali Awan M, Fleet I, Paul Thomas CL (2008) Determination of biogenic diamines with a vaporisation derivatisation approach using solid-phase microextraction gas chromatography–mass spectrometry. Food Chem 111(2):462–468
Almeida C, Fernandes JO, Cunha SC (2012) A novel dispersive liquid-liquid microextraction (DLLME) gas chromatography-mass spectrometry (GC–MS) method for the determination of eighteen biogenic amines in beer. Food Control 25(1):380–388
Ghasemzadeh-Mohammadi V, Mohammadi A, Hashemi M, Khaksar R, Haratian P (2012) 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
Ramezani H, Hosseini H, Kamankesh M, Ghasemzadeh-Mohammadi V, Mohammadi A (2015) 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(2):441–450
Aeenehvand S, Toudehrousta Z, Kamankesh M, Mashayekh M, Tavakoli HR, Mohammadi A (2016) Evaluation and application of microwave-assisted extraction and dispersive liquid–liquid microextraction followed by high-performance liquid chromatography for the determination of polar heterocyclic aromatic amines in hamburger patties. Food Chem 190:429–435
Guo L, Lee HK (2013) Microwave assisted extraction combined with solvent bar microextraction for one-step solvent-minimized extraction, cleanup and preconcentration of polycyclic aromatic hydrocarbons in soil samples. J Chromatogr A 19:9–15
Hashemi-Moghaddam H, Hagigatgoo M (2015) Nonderivatized sarcosine analysis by gas chromatography after solid-phase microextraction by newly synthesized monolithic molecularly imprinted polymer. Chromatographia 78(19–20):1263–1270
Feng X-F, Jing N, Li Z-G, Wei D, Lee M-R (2014) Ultrasound-microwave hybrid-assisted extraction coupled to headspace solid-phase microextraction for fast analysis of essential oil in dry traditional Chinese medicine by GC-MS. Chromatographia 77(7–8):619–628
Jabbari M, Razmi H, Farrokhzadeh S (2016) Application of magnetic graphene nanoparticles for determination of organophosphorus pesticides using solid-phase microextraction. Chromatographia 79(15–16):985–993
Mohammadi A, Ghasemzadeh-Mohammadi V, Haratian P, Khaksar R, Chaichi M (2013) Determination of polycyclic aromatic hydrocarbons in smoked fish samples by a new microextraction technique and method optimisation using response surface methodology. Food Chem 141(3):2459–2465
Nojavan Y, Kamankesh M, Shahraz F, Hashemi M, Mohammadi A (2015) Ion pair-based dispersive liquid–liquid microextraction followed by high performance liquid chromatography as a new method for determining five folate derivatives in foodstuffs. Talanta 137:31–37
Pena-Pereira F, Duarte RBO, Duarte A (2012) Considerations on the application of miniaturized sample preparation approaches for the analysis of organic compounds in environmental matrices. Centeurjchem 10(3):433–449
Rezaee M, Assadi Y, Milani Hosseini M-R, Aghaee E, Ahmadi F, Berijani S (2006) Determination of organic compounds in water using dispersive liquid–liquid microextraction. J Chromatogr A 1116(1–2):1–9
Kamankesh M, Mohammadi A, Tehrani ZM, Ferdowsi R, Hosseini H (2013) 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
Mohammadi A, Tavakoli R, Kamankesh M, Rashedi H, Attaran A, Delavar M (2013) Enzyme-assisted extraction and ionic liquid-based dispersive liquid–liquid microextraction followed by high-performance liquid chromatography for determination of patulin in apple juice and method optimization using central composite design. Anal Chim Acta 804:104–110
Haddadi H, Rezaee M, Semnani A, Mashayekhi HA, Hosseinian A (2014) Application of solid-phase extraction coupled with dispersive liquid–liquid microextraction for the determination of benzaldehyde in injectable formulation solutions. Chromatographia 77(13–14):951–955
Abedi A-S, Mohammadi A, Azadniya E, Mortazavian AM, Khaksar R (2013) Simultaneous determination of sorbic and benzoic acids in milk products using an optimised microextraction technique followed by gas chromatography. Food Addit Contamin Part A 31(1):21–28
Kamankesh M, Mohammadi A, Hosseini H, Modarres Tehrani Z (2015) 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
Madani-Tonekaboni M, Kamankesh M, Mohammadi A (2015) 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 Comp Anal 40:1–7
Navidghasemizad S, Hesari J, Saris PER, Nahaei MR (2009) Isolation of lactic acid bacteria from Lighvan cheese, a semihard cheese made from raw sheep milk in Iran. Int J Dairy Technol 62(2):260–264
Buňková L, Buňka F, Dráb V, Kráčmar S, Kubáň V (2012) Effects of NaCl, lactose and availability of oxygen on tyramine production by the Enterococcus durans CCDM 53. Eur Food Res Technol 234(6):973–979
Psillakis E, Kalogerakis N (2002) Developments in single-drop microextraction. Trends Anal Chem 21(1):54–64
Lundh T, Akesson B (1993) Gas chromatographic determination of primary and secondary low-molecular-mass aliphatic amines in urine using derivatization with isobutyl chloroformate. J Chromatogr B 617(2):191–196
Fiechter G, Sivec G, Mayer HK (2013) Application of UHPLC for the simultaneous analysis of free amino acids and biogenic amines in ripened acid-curd cheeses. J Chromatogr B 927:191–200
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The authors gratefully acknowledge the financial support of the National Nutrition and Food Technology Research Institute of Iran in conducting this study.
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Mansoureh Mohammadi, Marzieh Kamankesh and Amir Mohammad Mortazavian declare that they have no conflict of interest. Abdorreza Mohammadi has received research grants from National Nutrition and Food Technology Research Institute.
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Mohammadi, M., Kamankesh, M., Hadian, Z. et al. Determination of Biogenic Amines in Cheese Using Simultaneous Derivatization and Microextraction Method Followed by Gas Chromatography–Mass Spectrometry. Chromatographia 80, 119–126 (2017). https://doi.org/10.1007/s10337-016-3217-7
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DOI: https://doi.org/10.1007/s10337-016-3217-7