Abstract
Multiple studies have demonstrated the harmful effects of consuming high levels of biogenic amines (BAs) and organic amines (OAs), underscoring the need for precise monitoring techniques. This study presents an innovative precolumn derivatization high-performance liquid chromatography-tandem mass spectrometry approach, utilizing the Hinsberg reaction, which can accurately detect 9 BAs and 2 OAs in fish meat with excellent sensitivity. BAs and OAs in fish meat were extracted using 5% trichloroacetic acid solution. Add dansyl chloride-acetonitrile solution (5 mg mL−1) and react in the dark at 45 °C water bath temperature for 30 min. The derivative products were analyzed on a liquid chromatography-tandem mass spectrometer. The results presented in this study provide excellent RSDs of 0.7–5.4% and great linear relationship (R2 > 0.99) for 9 BAs and 2 OAs; high recoveries were obtained in different fish samples (79.4–101.4%). This study provides new analytical methods for BAs and OAs, providing a solution to the potential hazards of these amines in fish meat.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Data Availability
Availability of data is available upon request from the corresponding author.
Abbreviations
- BAs:
-
Biogenic amines
- OAs:
-
Organic amines
- Dns-Cl:
-
Dansyl chloride
- LC–MS/MS:
-
Liquid chromatography-tandem mass spectrometry
- Npr:
-
n-Propanolamine
- Dnb:
-
Di-n-butylamine
- His:
-
Histamine
- Spd:
-
Spermidine
- Put:
-
Putrescine
- Oct:
-
Octopamine
- Spe:
-
Spermine
- Cad:
-
Cadaverine
- Tyr:
-
Tyramine
- Trp:
-
Tryptamine
- Phe:
-
β-Phenylethylamine
- H-ESI:
-
Heatable electric spray ion source
- MRM:
-
Multireaction monitoring
- LOD:
-
Limit of detection
- LOQ:
-
Limit of quantification
- RSD:
-
Relative standard deviation
References
Bulushi IA, Poole S, Deeth HC, Dykes GA (2009) Biogenic amines in fish: roles in intoxication, spoilage, and nitrosamine formation—a review. Food Sci Nutr 49:369–377. https://doi.org/10.1080/10408390802067514
Chia K-J, Huang S-D (2006) Simultaneous derivatization and extraction of primary amines in river water with dynamic hollow fiber liquid-phase microextraction followed by gas chromatography–mass spectrometric detection. J Chromatogr A 1103:158–161. https://doi.org/10.1016/j.chroma.2005.11.072
Cristiane MG, Silva MB, Glória A (2002) Bioactive amines in chicken breast and thigh after slaughter and during storage at 4±1°C and in chicken-based meat products. Food Chem 78:241–248. https://doi.org/10.1016/s0308-8146(01)00404-6
Dong H, Xiao K-J (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
GB 5009.208–2016 (2016) National standard for food safety - determination of biogenic amines in foods, Beijing, Standards Press of China
Gil RL, Amorim CG, Montenegro MCBSM, Araújo AN (2021) Determination of biogenic amines in tomato by ion-pair chromatography coupled to an amine-selective potentiometric detector. Electrochim Acta 378:9–16. https://doi.org/10.1016/j.electacta.2021.138134
Hinsberg O (1890) Ueber Piazthiole und Piaselenole. II. Chem Ber 23:1393–1397. https://doi.org/10.1002/cber.189002301222
Jia W, Zhang R, Shi L, Zhang F, Chang J, Chu X-G (2020) Effects of spices on the formation of biogenic amines during the fermentation of dry fermented mutton sausage. Food Chem 321:126–135. https://doi.org/10.1016/j.foodchem.2020.126723
Li L-T, Peng Z-L, Zhang Y-H, Wang C (2020) Determination of organic amine in waste water from 1,6-hexanediamine production by pre-column derivatization and ultra-high performance liquid chromatography method. Petrochem Technol 49:93–97. https://doi.org/10.3969/j.issn.1000-8144.2020.01.015
Liu F-X, Bi X-H, Ren Z-F, Zhang G-H, Wang X-M, Peng P-A, Sheng G-Y (2017) Determination of amines in particulate matter by gas chromatography-mass spectrometry. Chin J Anal Chem 45:477–482. https://doi.org/10.11895/j.issn.0253-3820.170086
Luo J-Y, Zheng Y-N, Liu T-T, Guo Y-H, Cao J, Sun S-S (2021) Determination of 9 kinds of biogenic amines in salmon by precolumn derivatization-ultra performance liquid chromatography-tandem mass spectrometry. J Food Safety and Quality 12:6909–6917. https://doi.org/10.19812/j.cnki.jfsq11-5956/ts.2021.17.029
Malec PA, Oteri M, Inferrera V, Cacciola F, Mondello L, Kennedy RT (2017) Determination of amines and phenolic acids in wine with benzoyl chloride derivatization and liquid chromatography–mass spectrometry. J Chromatogr A 1523:248–256. https://doi.org/10.1016/j.chroma.2017.07.061
Maráková K, Piešt’ansky J, Zelinková Z, Mikuš P (2020) Simultaneous determination of twelve biogenic amines in human urine as potential biomarkers of inflflammatory bowel diseases by capillary electrophoresis – tandem mass spectrometry. J Pharmaceut Biomed 186:113294. https://doi.org/10.1016/j.jpba.2020.113294
Maraschiello C, Miranda E, Millán E, Floriano P, Vilageliu J (2003) henylisothiocyanate and dansyl chloride precolumn derivatizations for the high-performance liquid chromatography analysis of the antitumoral agent ES-285 in dog plasma. J Chromatogr B 791:1–11. https://doi.org/10.1016/S1570-0232(03)00161-2
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. TrAC-Trend Anal Chem 47:84–94. https://doi.org/10.1016/j.trac.2016.02.007
Molognoni L, Daguer H, de SáPloêncio LA, DeLindner JD (2018) A multi-purpose tool for food inspection: simultaneous determination of various classes of preservatives and biogenic amines in meat and fish products by LC-MS. Talanta 178:1053–1066. https://doi.org/10.1016/j.Talanta.2017.08.081
Ning W, Chen J, Zhang C-Y, Sun R, Tian Z-Y, Li Y-X (2020) Simultaneous determination of 9 biogenic amines in rice wine by direct dilution-UPLC-MS/MS. Mod Prev Med 47:4335–4339+4407
Ochi N (2019) Simultaneous determination of eight underivatized biogenic amines in salted mackerel fillet by ion-pair solid-phase extraction and volatile ion-pair reversed-phase liquid chromatography-tandem mass spectrometry. J Chromatogr A 1601:115–120. https://doi.org/10.1016/j.chroma.2019.06.027
Paleologos EK, Kontominas MG (2004) On-line solid-phase extraction with surfactant accelerated on-column derivatization and micellar liquid chromatographic separation as a tool for the determination of biogenic amines in various food substrates. Anal Chem 76:1289–1294. https://doi.org/10.1021/ac030355b
Shalaby AR (1999) Simple, rapid and valid thin layer chromatographic method for determining biogenic amines in foods. Food Chem 65:117–121. https://doi.org/10.1016/s0308-8146(98)00113-7
Song W-D, Xu M-L, Gao Y-H, Lin L-H, Du L-J, Zhang C-J (2020) Simultaneous determination of twenty organic amine, biogenic amines and cations in fruit juice by ion chromatography. Chinese J Anal Lab 39:590–595. https://doi.org/10.13595/j.cnki.issn1000-0720.2019.081101
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 affffecting their presence and concentration. Food Chem 101:704–716. https://doi.org/10.1016/j.foodchem.2006.02.028
Tsiasioti A, Tzanavaras PD (2021) Selective post-column derivatization coupled to cation exchange chromatography for the determination of histamine and its precursor histidine in fish and Oriental sauce samples. Food Chem 351:7–14. https://doi.org/10.1016/j.foodchem.2021.129351
Vandenabeele O, Garrelly L, Ghelfenstein M, Commeyras A, Mion L (1998) Use of 2-chloroethylnitrosourea, a new type of pre-column derivatizing agent for the measurement of biogenic amines, by high-performance liquid chromatography with ultraviolet detection. J Chromatogr A 795:239–250. https://doi.org/10.1016/s0021-9673(97)00992-8
Wang G-D (1989) Hinsberg Reaction. Univ Chem 4:45–47
Wang F, Luo M, Tao W-B, Xu L (2018) GC determination of 5 bioamines in bacon with solid phase extraction. Part B: Chem Anal 54:512–515. https://doi.org/10.11973/lhjy-hx201805004
Wang L, Sun X-J, Geng Y, Shi X-M, He P-Q, Xu Y-P, Liu X-W (2023) Rapid determination of 9 kinds of biogenic amines in fish by non-derivatization-QuEChERS-ultra performance liquid chromatography-tandem mass spectrometry. J Food Safety and Quality 14:269–276. https://doi.org/10.19812/j.cnki.jfsq11-5956/ts.2023.03.034
Zhang H-F, Ren S-Y, Yu J-W, Yang M (2012) Occurrence of selected aliphatic amines in source water of major cities in China. J Environ Sci-China 24:1885–1890. https://doi.org/10.1016/S1001-0742(11)61055-3
Zhang Y-J, Zhang Y, Zhou Y, Li G-H, Yang W-Z, Feng X-S (2019) A review of pretreatment and analytical methods of biogenic amines in food and biological samples since 2010. J Chromatogr A 16:8–16. https://doi.org/10.1016/j.chroma.2019.07.015
Zhang Y-M, Yu J-S, Lai S-Y, Song J, Wu X-M, Wang D-N, Pang L-J, Chai T-T (2021) Rapid determination of histamine level in seafood using read-out strips based on high-performance thin layer chromatography modified with self-visualization nanomaterials. Food Control 122:8–15. https://doi.org/10.1016/j.foodcont.2020.107816
Zou Y-C, Li W-F, Liu L-Y (2022) Simultaneous determination of 6 organic amines in soil by gas chromatography-mass spectrometry after headspace. Part B: Chem Anal 58:836–840. https://doi.org/10.11973/lhjy-hx202207017
Acknowledgements
The authors would like to thank the Thermo Fisher Scientific for providing technical support and optimization schemes.
Funding
The authors would like to thank the Shaanxi Qinyun Agricultural Science Research Institute for the financial support.
Author information
Authors and Affiliations
Contributions
All authors contributed to the study conception and design. Xiwen He: investigation, methodology, validation, data collation, resources, writing—original draft, review and editing. Hao Lei: investigation, project management, methodology, review and editing. Juan Zhao: investigation, methodology, validation, review and editing. Junming Wang: investigation, methodology, validation, review and editing. Songli Li: investigation, methodology, validation, review and editing. Hong Li: investigation, methodology, validation, review and editing. Caihui Zhao: investigation, methodology, validation, review and editing.
Corresponding author
Ethics declarations
Conflict of Interest
Xiwen He declares that he has no conflict of interest. Hao Lei declares that he has no conflict of interest. Juan Zhao declares that he has no conflict of interest. Junming Wang declares that he has no conflict of interest. Songli Li declares that he has no conflict of interest. Hong Li declares that he has no conflict of interest. Caihui Zhao declares that he has no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
He, X., Lei, H., Zhao, J. et al. Determination of 9 Biological Amines and 2 Organic Amines in Fish Meat by Precolumn Derivatization Liquid Chromatography-Tandem Mass Spectrometry Based on Hinsberg Reaction. Food Anal. Methods 16, 1381–1391 (2023). https://doi.org/10.1007/s12161-023-02515-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12161-023-02515-3