Abstract
In this study, we developed a column-switching high-performance liquid chromatography method with fluorescence detection for the simultaneous analysis of biogenic amines (BAs). This method uses an isocratic solution using acetonitrile with water as the mobile phase. Column-switching is achieved by using a switching valve with a set time program to change flow direction. Using this method, seven BAs (tryptamine, 2-phenylethylamine, putrescine, cadaverine, histamine, tyramine, and spermidine) could be separated and impurities eliminated. Using fluorescence detection, BAs could be identified with high sensitivity. We employed this method to determine the BA contents of fish (mackerel, tuna, and cod) and fermented food (a soybean product and cheese). Our results are in line with previous reports, yielded highly reproducible and quantitative results, and enabled the quick and simultaneous analysis of multiple BAs. Therefore, the method developed here may be useful for the continuous analysis of BAs in different samples to evaluate food quality.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Baixas-Nogueras S, Bover-Cid S, Vidal-Carou MC, Veciana-Nogues MT (2006) Volatile and nonvolatile amines in Mediterranean hake as function of their storage temperature. J Food Sci 66(1):83–88. https://doi.org/10.1111/j.1365-2621.2001.tb15586.x
Barbosa Roberta G, Gonzaga Luciano V, Lodetti E, Olivo G, Costa Ana Carolina O, Aubourg Santiago P, Fett R (2017) Biogenic amines assessment during different stages of the canning process of skipjack tuna (Katsuwonus pelamis). Int J Food Sci Technol 53(5):1236–1245. https://doi.org/10.1111/ijfs.13703
Boffi A, Favero G, Federico R, Macone A, Antiochia R, Tortolini C, Sanzó G, Mazzei F (2015) Amine oxidase-based biosensors for spermine and spermidine determination. Anal Bioanal Chem 407(4):1131–1137. https://doi.org/10.1007/s00216-014-8324-4
Bonaiuto E, Magro M, Baratella D, Jakubec P, Sconcerle E, Terzo M, Miotto G, Macone A, Agostinelli E, Fasolato S, Venerando R, Salviulo G, Malina O, Zboril R, Vianello F (2016) Ternary hybrid γ-Fe2O3/CrVI/amine oxidase nanostructure for electrochemical sensing: application for polyamine detection in tumor tissue. Chem Eur J 22(20):6846–6852. https://doi.org/10.1002/chem.201600156
Chauhan N, Jain U, Gandotra R, Hooda V (2017) Zeolites-AuNPs assembled interface towards amperometric biosensing of spermidine. Electrochim Acta 230:106–115. https://doi.org/10.1016/j.electacta.2017.01.069
Clements RLH, Holt A, Gordon ES, Todd KG, Baker GB (2004) Determination of rat hepatic polyamines by electron-capture gas chromatography. J Pharmacol Toxicol Methods 50(1):35–39. https://doi.org/10.1016/j.vascn.2003.12.001
Elbashir AA, Krieger S, Schmitz OJ (2013) Simultaneous determination of polyamines and acetylpolyamines in human urine by capillary electrophoresis with fluorescence detection. Electrophoresis 35(4):570–576. https://doi.org/10.1002/elps.201300337
Gençcelep H, Kaban G, Aksu Mİ, Öz F, Kaya M (2008) Determination of biogenic amines in sucuk. Food Control 19(9):868–872. https://doi.org/10.1016/j.foodcont.2007.08.013
Gosetti F, Chiuminatto U, Zampieri D, Mazzucco E, Robotti E, Calabrese G, Gennaro MC, Marengo E (2010) Determination of perfluorochemicals in biological, environmental and food samples by an automated on-line solid phase extraction ultra high performance liquid chromatography tandem mass spectrometry method. J Chromatogr A 1217(50):7864–7872. https://doi.org/10.1016/j.chroma.2010.10.049
Hu Y, Huang Z, Li J, Yang H (2012) Concentrations of biogenic amines in fish, squid and octopus and their changes during storage. Food Chem 135(4):2604–2611. https://doi.org/10.1016/j.foodchem.2012.06.121
Hungerford JM (2010) Scombroid poisoning: a review. Toxicon 56(2):231–243. https://doi.org/10.1016/j.toxicon.2010.02.006
Jiang HL, Ying LY, Zhou SC, Ying M, Shen W, Qiu DH (2011) Chromatographic determination of biogenic amines in wines after treatment with ionic liquids as novel media. J Sep Sci 34(9):1055–1062. https://doi.org/10.1002/jssc.201000772
Khuhawar MY, Memon AA, Jaipal PD, Bhanger MI (1999) Capillary gas chromatographic determination of putrescine and cadaverine in serum of cancer patients using trifluoroacetylacetone as derivatizing reagent. J Chromatogr B 723(1):17–24. https://doi.org/10.1016/S0378-4347(98)00478-2
Kim B, Byun BY, Mah J-H (2012) Biogenic amine formation and bacterial contribution in natto products. Food Chem 135(3):2005–2011. https://doi.org/10.1016/j.foodchem.2012.06.091
Křížek M, Vácha F, Pelikánová T (2011) Biogenic amines in carp roe (Cyprinus carpio) preserved by four different methods. Food Chem 126(3):1493–1497. https://doi.org/10.1016/j.foodchem.2010.12.040
Křížek M, Matějková K, Vácha F, Dadáková E (2014) Biogenic amines formation in high-pressure processed pike flesh (Esox lucius) during storage. Food Chem 151:466–471. https://doi.org/10.1016/j.foodchem.2013.11.094
Loukou Z, Zotou A (2003) Determination of biogenic amines as dansyl derivatives in alcoholic beverages by high-performance liquid chromatography with fluorimetric detection and characterization of the dansylated amines by liquid chromatography–atmospheric pressure chemical ionization mass spectrometry. J Chromatogr A 996(1):103–113. https://doi.org/10.1016/S0021-9673(03)00558-2
Martuscelli M, Pittia P, Casamassima LM, Manetta AC, Lupieri L, Neri L (2009) Effect of intensity of smoking treatment on the free amino acids and biogenic amines occurrence in dry cured ham. Food Chem 116(4):955–962. https://doi.org/10.1016/j.foodchem.2009.03.061
Mohammed GI, Bashammakh AS, Alsibaai AA, Alwael H, El-Shahawi MS (2016) A critical overview on the chemistry, clean-up and recent advances in analysis of biogenic amines in foodstuffs. Trends Anal Chem 78:84–94. https://doi.org/10.1016/j.trac.2016.02.007
Moret S, Smela D, Populin T, Conte LS (2005) A survey on free biogenic amine content of fresh and preserved vegetables. Food Chem 89(3):355–361. https://doi.org/10.1016/j.foodchem.2004.02.050
Naccarato A, Elliani R, Cavaliere B, Sindona G, Tagarelli A (2018) Development of a fast and simple gas chromatographic protocol based on the combined use of alkyl chloroformate and solid phase microextraction for the assay of polyamines in human urine. J Chromatogr A 1549:1–13. https://doi.org/10.1016/j.chroma.2018.03.034
Novella-Rodríguez S, Veciana-Nogués MT, Izquierdo-Pulido M, Vidal-Carou MC (2003) Distribution of biogenic amines and polyamines in cheese. J Food Sci 68(3):750–756. https://doi.org/10.1111/j.1365-2621.2003.tb08236.x
Önal A, Tekkeli SEK, Önal C (2013) A review of the liquid chromatographic methods for the determination of biogenic amines in foods. Food Chem 138(1):509–515. https://doi.org/10.1016/j.foodchem.2012.10.056
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. Trends Anal Chem 98:128–142. https://doi.org/10.1016/j.trac.2017.11.001
Parrilla Vázquez P, Gil García MD, Barranco Martínez D, Martínez Galera M (2005) Application of coupled-column liquid chromatography combined with post-column photochemically induced fluorimetry derivatization and fluorescence detection to the determination of pyrethroid insecticides in vegetable samples. Anal Bioanal Chem 381(6):1217–1225. https://doi.org/10.1007/s00216-004-3043-x
Petrarca MH, Fernandes JO, Godoy HT, Cunha SC (2017) Determination of polyamines in baby food by gas chromatography-mass spectrometry: optimization of extraction and microwave-assisted derivatization using response surface methodology. Food Anal Methods 10(11):3548–3557. https://doi.org/10.1007/s12161-017-0918-y
Pineda A, Carrasco J, Peña-Farfal C, Henríquez-Aedo K, Aranda M (2012) Preliminary evaluation of biogenic amines content in Chilean young varietal wines by HPLC. Food Control 23(1):251–257. https://doi.org/10.1016/j.foodcont.2011.07.025
Pleva P, Buňková L, Theimrová E, Bartošáková V, Buňka F, Purevdorj K (2014) Biogenic amines in smear and mould-ripened cheeses. Potravinarstvo 8(1):321–327. https://doi.org/10.5219/408
Rabie MA, Siliha HI, El-Saidy SM, El-Badawy AA, Xavier Malcata F (2011) Effect of γ-irradiation upon biogenic amine formation in blue cheese during storage. Int Dairy J 21(5):373–376. https://doi.org/10.1016/j.idairyj.2010.11.009
Rosier J, Van Peteghem C (1988) A screening method for the simultaneous determination of putrescine, cadaverine, histamine, spermidine and spermine in fish by means of high pressure liquid chromatography of their 5-dimethylaminonaphthalene-l-sulphonyl derivatives. Z Lebensm Unters Forsch 186(1):25–28. https://doi.org/10.1007/BF01027175
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. https://doi.org/10.1016/j.foodchem.2008.08.070
Santos MHS (1996) Biogenic amines: their importance in foods. Int J Food Microbiol 29(2):213–231. https://doi.org/10.1016/0168-1605(95)00032-1
Shalaby AR (1996) Significance of biogenic amines to food safety and human health. Food Res Int 29(7):675–690. https://doi.org/10.1016/S0963-9969(96)00066-X
Šimat V, Dalgaard P (2011) Use of small diameter column particles to enhance HPLC determination of histamine and other biogenic amines in seafood. LWT Food Sci Technol 44(2):399–406. https://doi.org/10.1016/j.lwt.2010.08.011
Simó C, Moreno-Arribas MV, Cifuentes A (2008) Ion-trap versus time-of-flight mass spectrometry coupled to capillary electrophoresis to analyze biogenic amines in wine. J Chromatogr A 1195(1):150–156. https://doi.org/10.1016/j.chroma.2008.05.004
Soufleros EH, Bouloumpasi E, Zotou A, Loukou Z (2007) Determination of biogenic amines in Greek wines by HPLC and ultraviolet detection after dansylation and examination of factors affecting their presence and concentration. Food Chem 101(2):704–716. https://doi.org/10.1016/j.foodchem.2006.02.028
Tameem AA, Saad B, Makahleh A, Salhin A, Saleh MI (2010) A 4-hydroxy-N′-[(E)-(2-hydroxyphenyl)methylidene]benzohydrazide-based sorbent material for the extraction-HPLC determination of biogenic amines in food samples. Talanta 82(4):1385–1391. https://doi.org/10.1016/j.talanta.2010.07.004
Teti D, Visalli M, McNair H (2002) Analysis of polyamines as markers of (patho)physiological conditions. J Chromatogr B 781(1):107–149. https://doi.org/10.1016/S1570-0232(02)00669-4
Tsai Y-H, Chang S-C, Kung H-F (2007) Histamine contents and histamine-forming bacteria in natto products in Taiwan. Food Control 18(9):1026–1030. https://doi.org/10.1016/j.foodcont.2006.06.007
Yamanaka H, Matsumoto M (1989) Simultaneous determination of polyamines in red meat fishes by high performance liquid chromatography and evaluation of freshness. Food Hyg Saf Sci (Shokuhin Eiseigaku Zasshi) 30(5):396–400. https://doi.org/10.3358/shokueishi.30.396
Zhai H, Yang X, Li L, Xia G, Cen J, Huang H, Hao S (2012) Biogenic amines in commercial fish and fish products sold in southern China. Food Control 25(1):303–308. https://doi.org/10.1016/j.foodcont.2011.10.057
Zhang L-Y, Tang X-C, Sun M-X (2005) Simultaneous determination of histamine and polyamines by capillary zone electrophoresis with 4-fluor-7-nitro-2,1,3-benzoxadiazole derivatization and fluorescence detection. J Chromatogr B 820(2):211–219. https://doi.org/10.1016/j.jchromb.2005.03.033
Funding
This work was supported by the Grant-in-Aid for JSPS Research Fellow Grant Number 17J01852.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of Interest
Mami Ishimaru declares that she has no conflict of interest. Yuma Muto declares that he has no conflict of interest. Akari Nakayama declares that she has no conflict of interest. Hideo Hatate declares that he has no conflict of interest. Ryusuke Tanaka declares that he has no conflict of interest.
Ethical Approval
Not applicable.
Informed Consent
Not applicable.
Rights and permissions
About this article
Cite this article
Ishimaru, M., Muto, Y., Nakayama, A. et al. 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 (2019). https://doi.org/10.1007/s12161-018-1349-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12161-018-1349-0