Abstract
In this work, a new methodology for the determination of biogenic amines in cheese is presented, which includes an innovative sample preparation approach based on salting-out assisted liquid-liquid extraction (SALLE). The method features a pre-extraction of the soluble biogenic amines with hydrochloric acid, a derivatization with dansyl chloride, the use of the salting-out effect, and the analysis of the derivatized biogenic amines using high-performance liquid chromatography with fluorescence detection. Several extraction parameters were studied and optimized, such as the HCl extraction time, concentration of the derivatization reagent and influence of the medium’s pH, among others. For the considered biogenic amines, the developed method exhibits adequate limits of detection (0.015 to 1.77 mg L−1) and quantification (0.050 to 5.91 mg L−1) and average recoveries between 94 and 110%, with the highest determined amounts found for putrescine, dimethylamine and histamine. Furthermore, mass spectrometry studies identified and confirmed the presence of several biogenic amines in the samples. SALLE stands as a good alternative to existing methods, since it simplifies the sample preparation step, while improving the overall selectivity of the process. It may also be adopted for the determination of biogenic amines in different solid samples besides cheese, such as meat, fish or other food products.
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Abdali S, Daneshfar A, Ghaedi M, Khezeli T (2016) Development of an indirectly suspended droplet for the extraction of hazardous phenols from environmental aqueous samples. Anal Methods 8:6074–6081. https://doi.org/10.1039/c6ay01598k
Alizadeh N, Kamalabadi M, Mohammadi A (2017) Determination of histamine and tyramine in canned fish samples by headspace solid-phase microextraction based on a nanostructured polypyrrole fiber followed by ion mobility spectrometry. Food Anal Methods 10:3001–3008. https://doi.org/10.1007/s12161-017-0860-z
Atlabachew M, Chandravanshi BS, Redi-Abshiro M (2017) Preparative HPLC for large scale isolation, and salting-out assisted liquid-liquid extraction based method for HPLC-DAD determination of khat (Catha edulis Forsk) alkaloids. Chem Cent J 11:107. https://doi.org/10.1186/s13065-017-0337-6
Awan MA, Fleet I, Thomas CLP (2008) Determination of biogenic diamines with a vaporisation derivatisation approach using solid-phase microextraction gas chromatography-mass spectrometry. Food Chem 111:462–468. https://doi.org/10.1016/j.foodchem.2008.03.068
Benkerroum N (2016) Biogenic amines in dairy products: origin, incidence, and control means. Compr Rev Food Sci Food Saf 15:801–826. https://doi.org/10.1111/1541-4337.12212
Brandão PF, Ramos RM, Almeida PJ, Rodrigues JA (2017) Determination of carbonyl compounds in Cork agglomerates by GDME-HPLC-UV: identification of the extracted compounds by HPLC-MS/MS. J Agric Food Chem 65:1037–1042. https://doi.org/10.1021/acs.jafc.6b05370
Brito C, Cid N, Muñoz O, Báez A, Horzella M (2014) Biogenic amine content in Chilean Gauda cheese: Physico-chemical and microbiological factors that may influence this content. Int J Dairy Technol 67:554–561. https://doi.org/10.1111/1471-0307.12148
Bunkova L, Adamcova G, Hudcova K, Velichova H, Pachlova V, Lorencova E, Bunka F (2013) Monitoring of biogenic amines in cheeses manufactured at small-scale farms and in fermented dairy products in the Czech Republic. Food Chem 141:548–551. https://doi.org/10.1016/j.foodchem.2013.03.036
Casal S, Oliveira M, Ferreira MA (2002) Determination of biogenic amines in coffee by an optimized liquid chromatographic method. J Liq Chromatogr Relat Technol 25:2535–2549. https://doi.org/10.1081/jlc-120014273
Cherkashina K, Vakh C, Lebedinets S, Pochivalov A, Moskvin L, Lezov A, Bulatov A (2018) An automated salting-out assisted liquid-liquid microextraction approach using 1-octylamine: on-line separation of tetracycline in urine samples followed by HPLC-UV determination. Talanta 184:122–127. https://doi.org/10.1016/j.talanta.2018.02.112
Cortacero-Ramirez S, Arraez-Roman D, Segura-Carretero A, Fernandez-Gutierrez A (2007) Determination of biogenic amines in beers and brewing-process samples by capillary electrophoresis coupled to laser-induced fluorescence detection. Food Chem 100:383–389. https://doi.org/10.1016/j.foodchem.2005.09.037
Creveling CR, Daly JW (1971) The use of dansyl derivatives for the identification and quantitation of amines. Clin Chem 17:302–309. https://doi.org/10.1016/0076-6879(71)17151-0
Dong H, Xiao K (2017) Modified QuEChERS combined with ultra high performance liquid chromatography tandem mass spectrometry to determine seven biogenic amines in Chinese traditional condiment soy sauce. Food Chem 229:502–508. https://doi.org/10.1016/j.foodchem.2017.02.120
Dong H, Xiao K, Xian Y, Wu Y, Zhu L (2019) A novel approach for simultaneous analysis of perchlorate (ClO 4 − ) and bromate (BrO 3 − ) in fruits and vegetables using modified QuEChERS combined with ultrahigh performance liquid chromatography-tandem mass spectrometry. Food Chem 270:196–203. https://doi.org/10.1016/j.foodchem.2018.07.091
Douny C, Benmedjadi S, Brose F, Afé OHI, Igout A, Hounhouigan DJ, Anihouvi VB, Scippo ML (2019) Development of an analytical method for the simultaneous measurement of 10 biogenic amines in meat: application to Beninese grilled pork samples. Food Anal Methods 12:2392–2400. https://doi.org/10.1007/s12161-019-01587-4
EFSA (2011) Scientific opinion on risk based control of biogenic amine formation in fermented foods. EFSA J 9:2393. https://doi.org/10.2903/j.efsa.2011.2393
Fernández M, Linares DM, Del Río B, Ladero V, Alvarez MA (2007) HPLC quantification of biogenic amines in cheeses: correlation with PCR-detection of tyramine-producing microorganisms. J Dairy Res 74:276–282. https://doi.org/10.1017/S0022029907002488
García-Villar N, Saurina J, Hernández-Cassou S (2006) High-performance liquid chromatographic determination of biogenic amines in wines with an experimental design optimization procedure. Anal Chim Acta 575:97–105
Gosetti F, Mazzucco E, Gianotti V, Polati S, Gennaro MC (2007) High performance liquid chromatography/tandem mass spectrometry determination of biogenic amines in typical Piedmont cheeses. J Chromatogr A 1149:151–157. https://doi.org/10.1016/j.chroma.2007.02.097
Gure A, Lara FJ, Moreno-González D, Megersa N, Del Olmo-Iruela M, García-Campaña AM (2014) Salting-out assisted liquid-liquid extraction combined with capillary HPLC for the determination of sulfonylurea herbicides in environmental water and banana juice samples. Talanta 127:51–58. https://doi.org/10.1016/j.talanta.2014.03.070
Halász A, Baráth Á, Holzapfel WH (1999) The influence of starter culture selection on sauerkraut fermentation. Eur Food Res Technol 208:434–438
He Y, Zhao XE, Wang R, Wei N, Sun J, Dang J, Chen G, Liu Z, Zhu S, You J (2016) Simultaneous determination of food-related biogenic amines and precursor amino acids using in situ derivatization ultrasound-assisted dispersive liquid-liquid microextraction by ultra-high-performance liquid chromatography tandem mass spectrometry. J Agric Food Chem 64:8225–8234. https://doi.org/10.1021/acs.jafc.6b03536
Huang J, Gan N, Lv F, Cao Y, Ou C, Tang H (2016) Environmentally friendly solid-phase microextraction coupled with gas chromatography and mass spectrometry for the determination of biogenic amines in fish samples. J Sep Sci 39:4384–4390. https://doi.org/10.1002/jssc.201600893
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 101:1285–1289. https://doi.org/10.1016/j.foodchem.2005.12.026
Ishimaru M, Muto Y, Nakayama A, Hatate H, Tanaka R (2019) Determination of biogenic amines in fish meat and fermented foods using column-switching high-performance liquid chromatography with fluorescence detection. Food Anal Methods 12:166–175. https://doi.org/10.1007/s12161-018-1349-0
Kole PL, Venkatesh G, Kotecha J, Sheshala R (2011) Recent advances in sample preparation techniques for effective bioanalytical methods. Biomed Chromatogr 25:199–217. https://doi.org/10.1002/bmc.1560
Lange J, Thomas K, Wittmann C (2002) Comparison of a capillary electrophoresis method with high-performance liquid chromatography for the determination of biogenic amines in various food samples. J Chromatogr B 779:229–239. https://doi.org/10.1016/S1570-0232(02)00372-0
Loizzo MR, Menichini F, Picci N, Puoci F, Spizzirri UG, Restuccia D (2013) Technological aspects and analytical determination of biogenic amines in cheese. Trends Food Sci Technol 30:38–55. https://doi.org/10.1016/j.tifs.2012.11.005
Mayer HK, Fiechter G, Fischer E (2010) A new ultra-pressure liquid chromatography method for the determination of biogenic amines in cheese. J Chromatogr A 1217:3251–3257. https://doi.org/10.1016/j.chroma.2009.09.027
Mietz JL, Karmas E (1977) Chemical quality index of tuna as determined by high-pressure liquid chromatography. J Food Sci 42:155–158. https://doi.org/10.1111/j.1365-2621.1977.tb01240.x
Miller JN, Miller JC (2010) Statistics and Chemometrics for analytical chemistry. 6th edn. Pearson Education Limited
Mohammadi M, Kamankesh M, Hadian Z, Mortazavian AM, Mohammadi A (2017) Determination of biogenic amines in cheese using simultaneous derivatization and microextraction method followed by gas chromatography–mass spectrometry. Chromatographia 80:119–126. https://doi.org/10.1007/s10337-016-3217-7
Palermo C, Muscarella M, Nardiello D, Iammarino M, Centonze D (2013) A multiresidual method based on ion-exchange chromatography with conductivity detection for the determination of biogenic amines in food and beverages. Anal Bioanal Chem 405:1015–1023. https://doi.org/10.1007/s00216-012-6439-z
Papageorgiou M, Lambropoulou D, Morrison C, Kłodzińska E, Namieśnik J, Płotka-Wasylka J (2018) Literature update of analytical methods for biogenic amines determination in food and beverages. TrAC Trends Anal Chem 98:128–142. https://doi.org/10.1016/j.trac.2017.11.001
Ramos RM, Valente IM, Rodrigues JA (2014) Analysis of biogenic amines in wines by salting-out assisted liquid-liquid extraction and high-performance liquid chromatography with fluorimetric detection. Talanta 124:146–151. https://doi.org/10.1016/j.talanta.2014.02.026
Rice NM, Irving HMNH, Leonard MA (1993) Nomenclature for liquid-liquid distribution (solvent extraction). Pure Appl Chem 65:2373–2396. https://doi.org/10.1351/pac199365112373
Rodriguez MBR, Carneiro CS, Feijó MBDS, Júnior CAC, Mano SB (2014) Bioactive amines: aspects of quality and safety in food. Food Nutr Sci 5:138–146. https://doi.org/10.4236/fns.2014.52018
Saaid M, Saad B, Rahman IA, Ali ASM, Saleh MI (2010) Extraction of biogenic amines using sorbent materials containing immobilized crown ethers. Talanta 80:1183–1190. https://doi.org/10.1016/j.talanta.2009.09.006
Shi Z, Fu H, Xu D, Huai Q, Zhang H (2017) Salting-out assisted liquid/liquid extraction coupled with low-temperature purification for analysis of endocrine-disrupting chemicals in milk and infant formula by ultra high performance liquid chromatography-tandem mass spectrometry. Food Anal Methods 10:1523–1534. https://doi.org/10.1007/s12161-016-0684-2
Shishov A, Chromá R, Vakh C, Kuchár J, Simon A, Andruch V, Bulatov A (2019) In situ decomposition of deep eutectic solvent as a novel approach in liquid-liquid microextraction. Anal Chim Acta 1065:49–55. https://doi.org/10.1016/j.aca.2019.03.038
Silla Santos MH (1996) Biogenic amines: their importance in foods. Int J Food Microbiol 29:213–231
Spizzirri UG, Restuccia D, Curcio M, Parisi OI, Iemma F, Picci N (2013) Determination of biogenic amines in different cheese samples by LC with evaporative light scattering detector. J Food Compos Anal 29:43–51. https://doi.org/10.1016/j.jfca.2012.09.005
Stadnik J, Dolatowski ZJ (2010) Biogenic amines in meat and fermented meat products. Acta Sci Pol Technol Aliment 9:251–263
ten Brink B, Damink C, Joosten HMLJ, Huis in’tVeld JHJ (1990) Occurrence and formation of biologically active amines in foods. Int J Food Microbiol 11:73–84. https://doi.org/10.1016/0168-1605(90)90040-C
European Union (2005) Commission regulation (EC) no 2073/2005 of 15 November 2005 on microbiological criteria for foodstuffs. vol L 338/1-L 338/26. Off J Eur Union
Valente IM, Gonçalves LM, Rodrigues JA (2013) Another glimpse over the salting-out assisted liquid–liquid extraction in acetonitrile/water mixtures. J Chromatogr A 1308:58–62. https://doi.org/10.1016/j.chroma.2013.08.014
Valente IM, Ramos RM, Gonçalves LM, Rodrigues JA (2014) Determination of ethyl carbamate in spirits using salting-out assisted liquid-liquid extraction and high performance liquid chromatography with fluorimetric detection. Anal Methods 6:9136–9141. https://doi.org/10.1039/c4ay02075h
Veciana-Nogués MT, Mariné-Font A, Vidal-Carou MC (1997) Biogenic amines as hygienic quality indicators of tuna. Relationships with microbial counts, ATP-related compounds, volatile amines, and organoleptic changes. J Agric Food Chem 45:2036–2041. https://doi.org/10.1021/jf960911l
Woźniakiewicz M, Woźniakiewicz A, Nowak PM, Kłodzińska E, Namieśnik J, Płotka-Wasylka J (2018) CE-MS and GC-MS as “green” and complementary methods for the analysis of biogenic amines in wine. Food Anal Methods 11:2614–2627. https://doi.org/10.1007/s12161-018-1219-9
Zhang J, Wu H, Kim E, El-Shourbagy TA (2009) Salting-out assisted liquid/liquid extraction with acetonitrile: a new high throughput sample preparation technique for good laboratory practice bioanalysis using liquid chromatography-mass spectrometry. Biomed Chromatogr 23:419–425. https://doi.org/10.1002/bmc.1135
Acknowledgement
The authors acknowledge Dra. Zélia Azevedo for the valuable technical assistance in the HPLC-DAD-MS/MS analysis.
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This work received financial support from the European Union (FEDER funds POCI/01/0145/FEDER/007265) and from FCT/MEC through national funds and cofinanced by FEDER (UID/QUI/50006/2013 – NORTE-01-0145-FEDER-00011) under the Partnership Agreement PT2020, which includes a postdoc grant to RMR and a studentship to PFB.
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Rui Miguel Ramos declares that he has no conflict of interest. Pedro Francisco Brandão declares that he has no conflict of interest. José António Rodrigues declares that he has no conflict of interest.
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Ramos, R.M., Brandão, P.F. & Rodrigues, J.A. Development of a SALLE-HPLC-FLD Analytical Method for the Simultaneous Determination of Ten Biogenic Amines in Cheese. Food Anal. Methods 13, 1088–1098 (2020). https://doi.org/10.1007/s12161-020-01730-6
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DOI: https://doi.org/10.1007/s12161-020-01730-6