Abstract
An effective ion-pair-based surfactant-assisted dispersive liquid-liquid microextraction combined with high-performance liquid chromatography (HPLC) has been evaluated for the extraction and preconcentration of four heterocyclic aromatic amines (i.e., 2-amino-3,4-dimethyl-3H-imidazo[4,5-f]quinoline (MeIQ); 2-amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline (4,8-DiMeIQx); 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP); and 1-methyl-9H-pyrido[3,4-B]indole (Harmane)). In the extraction method, sodium dodecyl sulfate (SDS) was used as both ion-pairing and disperser agent and 1-octanol was selected as extraction solvent. The effects of various parameters on the extraction efficiency such as kind and concentration of surfactant, kind and volume of extraction, salt addition, vortex extraction, and centrifugation time were investigated. Under the selected condition, the method provided high enrichment factor in the ranged of 124–145. Good linearity was 0.01–1000 μg kg−1 with the correlation coefficient (R 2) > 0.999. The limit of detection was 0.01 μg kg−1 for all compounds. The matrix match calibration was used for quantitation of the target analytes in grilled pork samples. The proposed method was successfully applied to analysis of heterocyclic aromatic amines in grilled pork samples where good recoveries were obtained in the range of 90 and 106 %.
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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
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 25:380–388
Busquets R, Bordas M, Toribio F, Puignou L, Galceran MT (2004) Occurrence of heterocyclic amines in several home-cooked meat dishes of the Spanish diet. J Chromatogr B 802:79–86
Cooper KM, Jankhaikhot N, Cuskelly G (2014) Optimised extraction of heterocyclic aromatic amines from blood using hollow fibre membrane liquid-phase microextraction and triple quadrupole mass spectrometry. J Chromatogr A 1358:20–28
Donthuan J, Yunchalard S, Srijaranai S (2014a) Ultrasound-assisted dispersive liquid–liquid microextraction combined with high performance liquid chromatography for sensitive determination of five biogenic amines in fermented fish samples. Anal Methods 6:1128–1134
Donthuan J, Yunchalard S, Srijaranai S (2014b) Vortex-assisted surfactant-enhanced-emulsification liquid–liquid microextraction of biogenic amines in fermented foods before their simultaneous analysis by high-performance liquid chromatography. J Sep Sci 37:3164–3173
Fei X-Q, Li C, Yu X-D, Chen H-Y (2007) Determination of heterocyclic amines by capillary electrophoresis with UV-DAD detection using on-line preconcentration. J Chromatogr B 854:224–229
Haskaraca G, Demirok E, Kolsarıcı N, Öz F, Özsaraç N (2014) Effect of green tea extract and microwave pre-cooking on the formation of heterocyclic aromatic amines in fried chicken meat products. Food Res Int 63:373–381
Janoszka B, Błaszczyk U, Damasiewicz-Bodzek A, Sajewicz M (2009) Analysis of heterocyclic amines (HAs) in pan-fried pork meat and its gravy by liquid chromatography with diode array detection. Food Chem 113:1188–1196
Leng G, Lui G, Chen Y, Yin H, Dan D (2012) Vortex-assisted extraction combined with dispersive liquid-liquid microextraction for the determination of polycyclic aromatic hydrocarbons in sediment by high performance liquid chromatography. J Sep Sci 35:2796–2804
Li Y, Chen P-S, Huang S-D (2013) Water with low concentration of surfactant in dispersed solvent-assisted emulsion dispersive liquid–liquid microextraction for the determination of organochlorine pesticides in aqueous samples. J Chromatogr A 1300:51–57
Lynch A, Murray S, Gooderham N, Boobis A (1995) Exposure to and activation of dietary heterocyclic amines in humans. Crit Rev Oncol 21:19–31
Martín-Calero A, Ayala JH, González V, Afonso AM (2007) Determination of less polar heterocyclic amines in meat extracts: Fast sample preparation method using solid-phase microextraction prior to high-performance liquid chromatography-fluorescence quantification. Anal Chim Acta 582:259–266
Mesa LBA, Padró JM, Reta M (2013) 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
Moradi M, Yamini Y (2012) Surfactant roles in modern sample preparation techniques: a review. J Sep Sci 35:2319–2340
Moradi M, Yamini Y, Esrafili A, Seidi S (2010) Application of surfactant assisted dispersive liquid–liquid microextraction for sample preparation of chlorophenols in water samples. Talanta 82:1864–1869
Moradi M, Yamini Y, Kakehmam J, Esrafili A, Ghambarian M (2011) A new strategy to simultaneous microextraction of acidic and basic compounds. J Chromatogr A 1218:3945–3951
Murkovic M (2007) Analysis of heterocyclic aromatic amines. Anal Bioanal Chem 389:139–146
Ni W, McNaughton L, LeMaster DM, Sinha R, Turesky RJ (2008) Quantitation of 13 heterocyclic aromatic amines in cooked beef, pork, and chicken by liquidchromatography-electrospray ionization/tandem mass spectrometry. J Agric Food Chem 56:68–78
Persson E, Graziani G, Ferracane R, Fogliano V, Skog K (2003) Influence of antioxidants in virgin olive oil on the formation of heterocyclic amines in fried beefburgers. Food Chem Toxicol 41:1587–1597
Rezaee M, Assadi Y, Hosseini M-R M, Aghaee E, Ahmadi F, Berijani S (2006) Determination of organic compounds in water using dispersive liquid–liquid microextraction. J Chromatogr A 1106:1–9
Rezaee M, Yamini Y, Faraji M (2010) Evolution of dispersive liquid-liquid microextraction method. J Chromatogr A 1217:2342–2357
Saraji M, Bidgoli AAH (2010) Dispersive liquid-liquid microextraction using a surfactant as disperser agent. Anal Bioanal Chem 397:3107–3115
Seebunrueng K, Santaladchaiyakit Y, Srijaranai S (2014) Vortex-assisted low density solvent based demulsified dispersive liquid–liquid microextraction and high-performance liquid chromatography for the determination of organophosphorus pesticides in water samples. Chemosphere 103:51–58
Sentellas S, Moyano E, Puignou L, Galceran MT (2004) 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
Vichapong J, Burakham R, Srijaranai S (2015) In-coupled syringe assisted octanol–water partition microextraction coupled with high-performance liquid chromatography for simultaneous determination of neonicotinoid insecticide residues in honey. Talanta 139:21–26
Yamini Y, Moradi M, Tahmasebi E (2012) High-throughput quantification of palladium in water samples by ion pair based-surfactant assisted microextraction. Anal Chim Acta 728:26–30
Yao Y, Peng ZQ, Wan KH, Shao B, Shi JM, Zhang YW, Wang FL, Hui T (2013) Determination of heterocyclic amines in braised sauce beef. Food Chem 141:1847–1853
Yiantzi E, Psillakis E, Tyrovola K, Kalogerakis N (2010) Vortex-assisted liquid–liquid microextraction of octylphenol, nonylphenol and bisphenol-A. Talanta 80:2057–2062
Yousefi SM, Shemirani F (2013) Selective and sensitive speciation analysis of Cr(VI) and Cr(III) in water samples by fiber optic-linear array detection spectrophotometry after ion pair based-surfactant assisted dispersive liquid–liquid microextraction. J Hazard Mater 254–255:134–140
Zhang J-W, Wang Y-K, Du X, Lei X, Ma J-J, Li J-C (2011) Ultrasound-assisted emulsification solidified floating organic drop microextraction for the determination of trace cadmium in water samples by flame atomic absorption spectrometry. J Braz Chem Soc 22:446–453
Zhang Y, Yu C, Mei J, Wang S (2013) Formation and mitigation of heterocyclic aromatic amines in fried pork. Food Addit Contam, A Chem Anal Control Expo Risk Assess 30:1501–1507
Zhang Q, Li G, Xiao X (2015) Acrylamide-modified graphene for online micro-solid-phase extraction coupled to high-performance liquid chromatography for sensitive analysis of heterocyclic amines in food samples. Talanta 131:127–135
Acknowledgments
This article is dedicated to Professor Dr. Kate Grudpan (Chiang Mai University, Thailand) in celebration of his 60th birthday. The authors gratefully acknowledge the financial supports of this research by the Center of Excellence for Innovation in Chemistry, the Commission on Higher Education (CHE), and Mahasarakham University.
Conflict of Interest
Jitlada Vichapong declares that she has no conflict of interest. Supalax Srijaranai declares that she has no conflict of interest. Yanawath Santaladchaiyakit declares that he has no conflict of interest. Wanna Kanchanamayoon declares that she has no conflict of interest. Rodjana Burakham declares that she has no conflict of interest. This article does not contain any studies with human or animal subjects.
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Vichapong, J., Srijaranai, S., Santaladchaiyakit, Y. et al. Preconcentration and Simultaneous Determination of Heterocyclic Aromatic Amines in Grilled Pork Samples by Ion-Pair-Based Surfactant-Assisted Dispersive Liquid-Liquid Microextraction and High-Performance Liquid Chromatography. Food Anal. Methods 9, 1120–1127 (2016). https://doi.org/10.1007/s12161-015-0291-7
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DOI: https://doi.org/10.1007/s12161-015-0291-7