Biogenic Amine Determination by High-Performance Liquid Chromatography Using a Sol Gel Immobilized 2 Hydroxy 5 nitrobenzaldehyde 2,4 dinitro phenyl hydrazone Solid Phase Extractant
DOI:
https://doi.org/10.31643/2028/6445.05Keywords:
HPLC, SPE, extraction, Bas, Sol-Gel.Abstract
This study focuses on the solid phase extraction of biogenic amines (BAs) using a sol-gel adsorbent immobilized with a hydrazone ligand, named 2-hydroxy-5-nitrobenzaldehyde-2,4-dinitrophenylhydrazone. The hydrazone compound was synthesized and characterized through Fourier Transform Infrared Spectroscopy (FT-IR) and Nuclear Magnetic Resonance (NMR) spectroscopy. The efficiency of the sorbent material for extracting BAs was evaluated using the solid phase extraction (SPE) method. Key experimental parameters affecting BA extraction, including pH, equilibrium time, ligand concentration, and biogenic amine (BA) concentration, were systematically investigated. The results indicated a strong recovery of BAs from aqueous samples, demonstrating a significant affinity between the sol-gel matrix containing the hydrazone ligand and the target analytes. The findings demonstrate that incorporating the hydrazone ligand resulted in a marked enhancement of extraction efficiency at a concentation of 17 × 10-3 M. Notably, the method exhibited high selectivity for aliphatic biogenic amines such as putrescine (PUT), cadaverine (CAD), and spermidine (SPD). This extraction method was successfully applied to food samples, yielding good recovery rates.
Downloads
References
Ekegren T, Gomes-Trolin C. Determination of polyamines in human tissues by precolumnderivatization with 9-fluo[renylmethyl chloroformate and high-performance liquid chromatography. Analytical Biochemistry. 2005; 338:179-185. https://doi.org/10.1016/j.ab.2004.11.040
Walters D R. Polyamines and plant disease. Phytochemistry. 2003; 64:97-107. https://doi.org/10.1016/s0031-9422(03)00329-7
Tsai Y-H, Lin C-Y, Chang S-C, Chen H-C, Kung H-F, Wei C-I, Hwang D-F. Occurrence of histamine-forming bacteria in salted mackerel in Taiwan. Food Microbiology. 2005; 22:461-467. https://doi.org/10.1016/j.fm.2004.11.003
Auerswald L, Morren C, Lopata A L. Histamine levels in seventeen species of fresh and processed South African seafood. Food Chemistry. 2006; 98;231-239. https://doi.org/10.1016/j.foodchem.2005.05.071
Özogul F, Özogul Y. Biogenic amine content and biogenic amine quality indices of sardines (Sardinapilchardus) stored in modified atmosphere packaging and vacuum packaging. Food Chemistry. 2006; 99:574-578. https://doi.org/10.1016/j.foodchem.2005.08.029
Gençcelep H, Kaban G, Aksu Mİ, Öz F, Kaya M. Determination of biogenic amines in sucuk. Food Control. 2008; 19:868-872. https://doi.org/10.1016/j.foodcont.2007.08.013
Kalač P, Krausová P. A review of dietary polyamines: Formation, implications for growth and health and occurrence in foods. Food Chemistry. 2005; 90:219-230. https://doi.org/10.1016/j.foodchem.2004.03.044
Chiacchierini E, Restuccia D, Vinci G. Evaluation of two different extraction methods for chromatographic determination of bioactive amines in tomato products. Talanta. 2006; 69:548-555. https://doi.org/10.1016/j.talanta.2005.10.027
Adão RC, Glόria MBA. Bioactive amines and carbohydrate changes during ripening of ‘Prata’ banana (Musa acuminate x M. balbisiana). Food Chemistry. 2005; 90:705-711. https://doi.org/10.1016/j.foodchem.2004.05.020
Valero D, Martínez-Romero D, Serrano M. The role of polyamines in the improvement of the shelf life of fruit. Trends in Food Science & Technology. 2002; 13;228-234. https://doi.org/10.1016/S0924-2244(02)00134-6
Soleas G J, Carey M, Goldberg D M. Method development and cultivar-related differences of nine biogenic amines in Ontario wines. Food Chemistry. 1999; 64:49-58. https://doi.org/10.1016/S0308-8146(98)00092-2
Vidal-Carou MC, Lahoz-Portolés F, Bover-Cid S, Mariné-Font A. Ion-pair highperformance liquid chromatographic determination of biogenic amines and polyamines in wine and other alcoholic beverages. Journal of Chromatography A. 2003; 998:235-241. https://doi.org/10.1016/S0021-9673(03)00610-1
Stratton J E, Hutkins R W, Taylor S L. Biogenic amines in Chinese and otherfermented foods: A review. Journal of Food Protection. 1991; 54:460-470. https://doi.org/10.4315/0362-028X-54.6.460
Santos M H S. Biogenic amines: their importance in foods. International Journal of Food Microbiology. 1996; 29: 213-231. https://doi.org/10.1016/0168-1605(95)00032-1
Valero D, Martínez-Romero D, Serrano M. The role of polyamines in the improvement of the shelf life of fruit. Trends in Food Science & Technology. 2002; 13:228-234. https://doi.org/10.1016/S0924-2244(02)00134-6
Anli RE, Vural N, Yilmaz S, Vural ỲH. The determination of biogenic amines in Turkish red wines. Journal of Food Composition and Analysis. 2004; 17:53-62. https://doi.org/10.1016/S0889-1575(03)00104-2
Soleas GJ, Carey M, Goldberg D M. Method development and cultivar-related differences of nine biogenic amines in Ontario wines. Food Chemistry. 1999; 64:49-58. https://doi.org/10.1016/S0308-8146(98)00092-2
Sano M, Nishino I. Assay for spermidine synthase activity by micellar electrokinetic chromatography with laser-induced fluorescence detection. Journal of Chromatography B. 2007; 845:80-83. https://doi.org/10.1016/j.jchromb.2006.07.052
Kvasnička F, Voldřich M. Determination of biogenic amines by capillary zone electrophoresis with conductometric detection. Journal of Chromatography A. 2006; 1103:145-149. https://doi.org/10.1016/j.chroma.2005.11.005
Landete J M, de las Rivas B, Marcobal A, Muñoz R. Molecular methods for the detection of biogenic amine-producing bacteria on foods. International Journal of Food Microbiology. 2007; 117:258-269. https://doi.org/10.1016/j.ijfoodmicro.2007.05.001
Marcobal A, Polo M C, Martín-Álvarez P J, Moreno-Arribas M V. Biogemic amine content of red Spanish wines: comparison of a direct ELISA and an HPLC method for the determination of histamine in wines. Food Research International. 2005; 38:387-394. https://doi.org/10.1016/j.foodres.2004.10.008
Shakila R J, Vasundhara T S, Kumudavally K V. A comparison of the TLC desitometry and HPLC method for the determination of biogenic amines in fish and fishery products. Food Chemistry. 2001; 75:255-259. https://doi.org/10.1016/S0308-8146(01)00173-X
Soufleros E H, Bouloumpasi E, Zotou A, Loukou Z. Determination of biogenic amines in Greek wines by HPLC and ultraviolet detection after dansylation and examination of factors affecting their presence and concentration. Food Chemistry. 2007; 101;704-716. https://doi.org/10.1016/j.foodchem.2006.02.028
Yongmei L, Xin L, Xiaohong C, Mei J, Chao L, Mingsheng D. A survey of biogenic amines in Chinese rice wines. Food Chemistry. 2007; 100:1424-1428. https://doi.org/10.1016/j.foodchem.2005.11.035
Abdassalam A T, Saad B, Makahleh A, Salhin A, Saleh M I. A4-hydroxy-N-[(E)-(2-hydroxyphenyl)methylidene] benzohydrazide-based sorbent material for the extraction-HPLC determination of biogenic amines in food samples. Talanta. 2010; 82:1385-1391. https://doi.org/10.1016/j.talanta.2010.07.004
Chanbasha B, Weishan W, Ahmad M, Abdassalam AT, Abdussalam S, Bahruddin S, Hian K L. Hydrazone-based ligands for micro-solid phase extraction-high performance liquid chromatographic determination of biogenic amines in orange juice. Journal of Chromatograph A. 2011; 1218:4332– 4339. https://doi.org/10.1016/j.chroma.2011.04.073
Oana Stamatoiu, Alexej Bubnov, Isabela Ţârcomnicu, Mircea Iovu. Synthesis and spectral characterisation of new amido-ether Schiff bases. Journal of Molecular Structure. 2008; 886:187–196. https://doi.org/10.1016/j.molstruc.2007.11.025
Monfared, Hassan Hosseini, Pouralimardan, Omid and Janiak, Christoph. Synthesis and Spectral Characterization of Hydrazone Schiff Bases Derived from 2,4-Dinitrophenylhydrazine. Crystal Structure of Salicylaldehyde-2,4-Dinitrophenylhydrazone. Zeitschrift für Naturforschung B. 2007; 62(5):717-720. https://doi.org/10.1515/znb-2007-0515
Runmo W, Yu Z, Yaqun W, Ze Y. Aromatic conjugated organic small molecules achieve ultra-stable NH4+ deprotonation storage. Chemical Engineering Journal. 2025; 522:168029. https://doi.org/10.1016/j.cej.2025.168029
Tu W, Zeng S, Bai Y, Zhang X, Dong H, Zhang X P. Theoretical Insights into NH3 Absorption Mechanisms with Imidazolium-based Protic Ionic Liquids. Industrial Chemistry & Materials. 2023; 1:262-270. https://doi.org/10.1039/d2im00041e
Soad S, Abd E-H, Magda E, Khaled M, Adel E I. Cost-effective, green HPLC determination of losartan, valsartan and their nitrosodiethylamine impurity: application to pharmaceutical dosage forms. R Soc Open Sci. 2022; 9(6):20250. https://doi.org/10.1098/rsos.220250
Bhushan R, Kumar V. Synthesis of chiral hydrazine reagents and their application for liquid chromatographic separation of carbonyl compounds via diastereomer formation. Journal of Chromatography A. 2008; 1190:86-94. https://doi.org/10.1016/j.chroma.2008.02.084
Mehta M, Mehta D, Mashru R. Recent application of green analytical chemistry: eco-friendly approaches for pharmaceutical analysis. Futur J Pharm Sci. 2024; 10:83. https://doi.org/10.1186/s43094-024-00658-6
Mahmoud A A, Ashraf AM. A systematic review of layered double hydroxide-based materials for environmental remediation of heavy metals and dye pollutants. Inorganic Chemistry Communications. 2023; 148:110325. https://doi.org/10.1016/j.inoche.2022.110325
Scott ED, Wen-Tau TC, Houk KN, Peng L. Development of Chiral Bis-hydrazone Ligands for the Enantioselective Cross-Coupling Reactions of Aryldimethylsilanolates. The Journal of Organic Chemistry. 2014; 80(1):313-366. https://doi.org/10.1021/jo502388r
Rampazzo G, Depau G, Pagliuca G, Zironi E, Serraino A, Savini F, Gazzotti T. A Rapid LC-MS/MS Method for Quantification of Biogenic Amines in Meat: Validation and Application for Food Safety Monitoring. Methods Protoc. 2025; 8(5):106. https://doi.org/10.3390/mps8050106
Jindal D P, Bedi V, Jit B, Karkra N, Guleria S, Bansal R, Palusczak A, Hartmann R W. Synthesis and study of some new N-substituted imide derivatives as potential anticancer agents. II Farmaco. 2005; 60:283-290. https://doi.org/10.1016/j.farmac.2005.01.011
Ramanathan K, Kamalasanan MN, Malhotra B D, Pradhan D R, Chandra S. Immobilization and characterization of lactate dehydrogenase on TEOS derived sol-gel films. Journal of Sol-Gel Science and Technology. 1997; 10:309-316. https://doi.org/10.1023/A:1018329518938
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2026 Abdassalam Abdelhafiz Tameem, Salam Salhin Mohamed, Afiyah Alnaas, Eny Kusrini

This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.









