Food Analytical Methods

, Volume 12, Issue 1, pp 1–11 | Cite as

Use of Functionalized Covalent Organic Framework as Sorbent for the Solid-Phase Extraction of Biogenic Amines from Meat Samples Followed by High-Performance Liquid Chromatography

  • Qingyun Chang
  • Xiaohuan Zang
  • Tong Wu
  • Mengting Wang
  • Yachao Pang
  • Chun Wang
  • Zhi Wang


A functionalized covalent organic framework (COF) was synthesized via room-temperature solvent-free mechano-chemical grinding method and used as a solid-phase extraction adsorbent for the extraction of eight biogenic amines (tryptamine, n-butylamine, phenylethylamine, cadaverine, putrescine, tyramine, spermine, and spermidine) in diverse meat samples. The target biogenic amines were derived with dansyl chloride to form stable fluorogenic derivatives for their high-performance liquid chromatography–fluorescence detection. The main important experimental parameters were investigated and optimized by both one-factor-at-a-time and response surface methodologies. Under the optimum conditions, a linear response for the biogenic amines was observed in the concentration range of 5.0–800.0 μg L−1 with the coefficients of determination (r2) ranging from 0.9944 to 0.9981. The limits of detection of this method (at a signal-to-noise ratio of 3) for the analytes ranged from 0.92 to 2.57 μg L−1. The method recoveries of the target biogenic amines for five meat samples ranged from 80.3 to 115%, with relative standard deviations lower than 12%. The results indicate that the prepared COF is an effective adsorbent for the enrichment of biogenic amines.


Covalent organic frameworks Sold phase extraction High-performance liquid chromatography Biogenic amines Meat sample 



Analysis of variance


Biogenic amines


Box–Behnken design


Covalent organic framework


Fourier transform-infrared


High-performance liquid chromatography–fluorescence detection


Limits of detection


Limits of quantitation




Scanning electron microscope


Solid phase extraction




Trichloroacetic acid



This study received financial supports from the National Natural Science Foundation of China (No. 31471643, 31571925, 31671930), the Hebei “Double First Class Discipline” Construction Foundation for the Discipline of Food Science and Engineering of Hebei Agricultural University (2016SPGCA18), the Natural Science Foundation of Hebei Province (C2018204076), and the Youth Scientific and Technological Research Foundation of the Department of Education of Hebei for Hebei Provincial Universities (QN2017085) are gratefully acknowledged.

Compliance with Ethical Standards

Conflict of Interest

Qingyun Chang declares that she has no conflict of interest. Xiaohuan Zang declares that he has no conflict of interest. Tong Wu declares that she has no conflict of interest. Mengting Wang declares that she has no conflict of interest. Yachao Pang declares that she has no conflict of interest. Chun Wang declares that she has no conflict of interest. Zhi Wang declares that he has no conflict of interest.

Ethical Approval

This article does not contain any studies with human or animal subjects.

Informed Consent

Not applicable.

Supplementary material

12161_2018_1324_MOESM1_ESM.docx (170 kb)
ESM 1 (DOCX 170 kb)


  1. Anderson AA, Goetzen T, Shackelford SA, Tsank S (2000) A convenient one-step synthesis of 2-Hydroxy-1,3,5-Benzenetricarbaldehyde. Synth Commun 30:3227–3232. CrossRefGoogle Scholar
  2. Baranowska I, Płonka J (2014) Simultaneous determination of biogenic amines and methylxanthines in foodstuff—sample preparation with HPLC-DAD-FL analysis. Food Anal Methods 8:963–972. CrossRefGoogle Scholar
  3. Bedia Erim F (2013) Recent analytical approaches to the analysis of biogenic amines in food samples. Trends Anal Chem 52:239–247. CrossRefGoogle Scholar
  4. Biswal BP, Chandra S, Kandambeth S, Lukose B, Heine T, Banerjee R (2013) Mechanochemical synthesis of chemically stable isoreticular covalent organic frameworks. J Am Chem Soc 135:5328–5331. CrossRefGoogle Scholar
  5. Chandra S, Kandambeth S, Biswal BP, Lukose B, Kunjir SM, Chaudhary M, Babarao R, Heine T, Banerjee R (2013) Chemically stable multilayered covalent organic nanosheets from covalent organic frameworks via mechanical delamination. J Am Chem Soc 135:17853–17861.
  6. Chong JH, Sauer M, Patrick BO, MacLachlan MJ (2003) Highly stable keto-enamine salicylideneanilines. Org Lett 5:3823–3826. CrossRefGoogle Scholar
  7. De Mey E, Drabik-Markiewicz G, De Maere H, Peeters MC, Derdelinckx G, Paelinck H, Kowalska T (2012) Dabsyl derivatisation as an alternative for dansylation in the detection of biogenic amines in fermented meat products by reversed phase high performance liquid chromatography. Food Chem 130:1017–1023. CrossRefGoogle Scholar
  8. Er D, Dong L, Shenoy VB (2016) Mechanisms for engineering highly anisotropic conductivity in a layered covalent-organic framework. J Phys Chem 120:174–178. Google Scholar
  9. Fu Y, Zhou Z, Li Y, Lu X, Zhao C, Xu G (2016) High-sensitivity detection of biogenic amines with multiple reaction monitoring in fish based on benzoyl chloride derivatization. J Chromatogr A 1465:30–37. CrossRefGoogle Scholar
  10. Garcia-Villar N, Hernandez-Cassou S, Saurina J (2009) Determination of biogenic amines in wines by pre-column derivatization and high-performance liquid chromatography coupled to mass spectrometry. J Chromatogr A 1216:6387–6393. CrossRefGoogle Scholar
  11. Guo B, Yang Y, Hu Z, An Y, Zhang Q, Yang X, Wang X, Wu H (2017) Redox-active organic molecules functionalized nitrogen-doped porous carbon derived from metal-organic framework as electrode materials for supercapacitor. Electrochim Acta 223:74–84. CrossRefGoogle Scholar
  12. Huang J, Ou C, Lv F, Cao Y, Tang H, Zhou Y, Gan N (2017) Determination of aliphatic amines in food by on-fiber derivatization solid-phase microextraction with a novel zeolitic imidazolate framework 8-coated stainless steel fiber. Talanta 165:326–331. CrossRefGoogle Scholar
  13. Huang KJ, Jin CX, Song SL, Wei CY, Liu YM, Li J (2011) Development of an ionic liquid-based ultrasonic-assisted liquid-liquid microextraction method for sensitive determination of biogenic amines: application to the analysis of octopamine, tyramine and phenethylamine in beer samples. J Chromatogr B 879:579–584. CrossRefGoogle Scholar
  14. Kaleeswaran D, Antony R, Sharma A, Malani A, Murugavel R (2017) Catalysis and CO2 capture by palladium incorporated covalent organic frameworks. Chempluschem 82:1253–1265. CrossRefGoogle Scholar
  15. Karak S, Kandambeth S, Biswal BP, Sasmal HS, Kumar S, Pachfule P, Banerjee R (2017) Constructing ultraporous covalent organic frameworks in seconds via an organic terracotta process. J Am Chem Soc 139:1856–1862. CrossRefGoogle Scholar
  16. Kung TA, Tsai CW, Ku BC, Wang WH (2015) A generic and rapid strategy for determining trace multiresidues of sulfonamides in aquatic products by using an improved QuEChERS method and liquid chromatography-electrospray quadrupole tandem mass spectrometry. Food Chem 175:189–196. CrossRefGoogle Scholar
  17. Lázaro CA, Conte-Júnior CA, Cunha FL, Mársico ET, Mano SB, Franco RM (2013) Validation of an HPLC methodology for the identification and quantification of biogenic amines in chicken meat. Food Anal Methods 6:1024–1032. CrossRefGoogle Scholar
  18. Lee YJ, Talapaneni SN, Coskun A (2017) Chemically activated covalent triazine frameworks with enhanced textural properties for high capacity gas storage. ACS Appl Mater Interfaces 9:30679–30685. CrossRefGoogle Scholar
  19. Mayr CM, Schieberle P (2012) Development of stable isotope dilution assays for the simultaneous quantitation of biogenic amines and polyamines in foods by LC-MS/MS. J Agric Food Chem 60:3026–3032. CrossRefGoogle Scholar
  20. Melo A, Cunha SC, Mansilha C, Aguiar A, Pinho O, Ferreira IM (2012) Monitoring pesticide residues in greenhouse tomato by combining acetonitrile-based extraction with dispersive liquid-liquid microextraction followed by gas-chromatography-mass spectrometry. Food Chem 135:1071–1077. CrossRefGoogle Scholar
  21. Parchami R, Kamalabadi M, Alizadeh N (2017) Determination of biogenic amines in canned fish samples using head-space solid phase microextraction based on nanostructured polypyrrole fiber coupled to modified ionization region ion mobility spectrometry. J Chromatogr A 1481:37–43. CrossRefGoogle Scholar
  22. Saaid M, Saad B, Hashim NH, Mohamed Ali AS, Saleh MI (2009) Determination of biogenic amines in selected Malaysian food. Food Chem 113:1356–1362. CrossRefGoogle Scholar
  23. Self RL, Wu WH, Marks HS (2011) Simultaneous quantification of eight biogenic amine compounds in tuna by matrix solid-phase dispersion followed by HPLC-orbitrap mass spectrometry. J Agric Food Chem 59:5906–5913. CrossRefGoogle Scholar
  24. Shinde DB, Aiyappa HB, Bhadra M, Biswal BP, Wadge P, Kandambeth S, Garai B, Kundu T, Kurungot S, Banerjee R (2016) A mechanochemically synthesized covalent organic framework as a proton-conducting solid electrolyte. J Mater Chem A 4:2682–2690.
  25. Sirocchi V, Caprioli G, Ricciutelli M, Vittori S, Sagratini G (2014) Simultaneous determination of ten underivatized biogenic amines in meat by liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). J Mass Spectrom 49:819–825. CrossRefGoogle Scholar
  26. Wang J, Hao L, Wang C, Wu Q, Wang Z (2017) Nanoporous carbon as the solid-phase extraction adsorbent for the extraction of endocrine disrupting chemicals from juice samples. Food Anal Methods 10:2710–2717. CrossRefGoogle Scholar
  27. Wongsa N, Burakham R (2012) A simple solid-phase extraction coupled to high-performance liquid chromatography–UV detection for quantification of Pyrethroid residues in fruits and vegetables. Food Anal Methods 5:849–855. CrossRefGoogle Scholar
  28. Yang S-S, Yang Y-N, Li X-L, Zhang Y (2016) Determination of biogenic amines in cheese by on-line solid phase extraction coupled with capillary high performance liquid chromatography. Chin J Anal Chem 44:396–402. CrossRefGoogle Scholar
  29. Yáñez KP, Martín MT, Bernal JL, Nozal MJ, Bernal J (2014) Trace analysis of seven neonicotinoid insecticides in bee pollen by solid–liquid extraction and liquid chromatography coupled to electrospray ionization mass spectrometry. Food Anal Methods 7:490–499. CrossRefGoogle Scholar
  30. Zhu H, Yang S, Zhang Y, Fang G, Wang S (2016) Simultaneous detection of fifteen biogenic amines in animal derived products by HPLC-FLD with solid-phase extraction after derivatization with dansyl chloride. Anal Methods 8:3747–3755. CrossRefGoogle Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Chemistry, College of ScienceHebei Agricultural UniversityBaodingChina

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