Abstract
The biogenic amines, especially tryptamine (Tryp) and histamine (Hist), are toxicologically precarious for human health, causing intoxication. The combination of Tryp and Hist together presents even greater damage to human health, since Tryp increases the toxicity of Hist. Information about the presence of this amine is necessary to assess the quality of the wine and avoid intoxication caused by its ingestion. In this work, the electrocatalytic oxidation of Tryp and Hist on a carbon paste electrode modified with nickel phthalocyanine (CPE-NiPC) was studied, and a square wave voltammetric method was developed for simultaneous determination of these amines in wines. The use of NiPC contributed significantly to the peak current gain in the analytical response of the amines. The optimal response and sensitivity of the two analytes were obtained using phosphate buffer (pH 8.5), yielding a linear response range of 0.49–3.93 ng mL−1 and 0.37–2.9 µg mL−1, a limit of detection of 0.168 ng mL−1 and 0.038 µg mL−1 for Tryp and Hist, respectively. The proposed sensor CPE-NiPC has high selectivity affording greater accuracy in determining those amines and providing recovery values in a range of 82.65–103.02% for the analyzed biogenic amines.
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Data Availability
The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.
References
Anithaa AC, Mayil Vealan SB, Veerapandi G, Sekar C (2021) Highly efficient non-enzymatic electrochemical determination of histamine based on tungsten trioxide nanoparticles for evaluation of food quality. J Appl Electrochem 51:1741–1753. https://doi.org/10.1007/s10800-021-01608-3
Alañón ME, Pérez-Coello MS, Marina ML (2015) Wine science in the metabolomics era. TrAC - Trends Anal Chem 74:1–20. https://doi.org/10.1016/j.trac.2015.05.006
Apetrei IM, Apetrei C (2016) Application of voltammetric e-tongue for the detection of ammonia and putrescine in beef products. Sens. Actuators. B Chem 234:371–379. https://doi.org/10.1016/j.snb.2016.05.005
Altun Y, Koseoglu F (2005) Stability of copper(II), nickel(II) and zinc(II) binary and ternary complexes of histidine, histamine and glycine in aqueous solution. J Solution Chem 34:213–231
Bartowsky EJ, Stockley CS (2011) Histamine in Australian wines—a survey between 1982 and 2009. Ann Microbiol 61:167–172. https://doi.org/10.1007/s13213-010-0070-z
Brett AMO, Brett CMA (1993) Eletroquímica: princípios, métodos e aplicações. Oxford University Press, Oxford
Brown MD, Schoen MH (2018) Catalytic selectivity of metallophthalocyanines for electrochemical nitric oxide sensing. Electrochim Acta 273:98–104. https://doi.org/10.1016/j.electacta.2018.03.139
Cai Y, Sun Z, Chen G, Liu X, Youb J, Zhang C (2016) Rapid analysis of biogenic amines from rice wine with isotope-coded derivatization followed by high performance liquid chromatography–tandem mass spectrometry. Food Chem 192:388–394. https://doi.org/10.1016/j.foodchem.2015.07.024
Costa DJE, Martínez AM, Ribeiro WF, Bichinho KM, Di Nezio MS, Pistonesi MF, Araujo MCU (2016) Determination of tryptamine in foods using square wave adsorptive stripping voltammetry. Talanta 154:134–140. https://doi.org/10.1016/j.talanta.2016.03.063
Degefu H, Amare M, Tessema M, Admassie S (2014) Lignin modified glassy carbon electrode for the electrochemical determination of histamine in human urine and wine samples. Electrochim Acta 121:307–314. https://doi.org/10.1016/j.electacta.2013.12.133
Deon M, Caldas EM, Rosa DS, Menezes EW, Dias SLP, Pereira MB, Costa TMH, Arenas LT, Benvenutti EV (2015) Mesoporous silica xerogel modified with bridged ionic silsesquioxane used to immobilize copper tetrasulfonated phthalocyanine applied to electrochemical determination of dopamine. J Solid State Electrochem 19:2095–2105. https://doi.org/10.1007/s10008-014-2687-5
Devasenathipathy R, Palanisamy S, Chen S-M, Karuppiah C, Mani V, Ramaraj SK, Ali MA, Al-Hemaid FMA (2015) An amperometric biological toxic hydrazine sensor based on multiwalled carbon nanotubes and iron tetrasulfonated phthalocyanine composite modified electrode. Electroanalysis 27:1403–1410. https://doi.org/10.1002/elan.201400659
Enache TA, Oliveira-Brett AM (2011) Pathways of electrochemical oxidation of indolic compounds. Electroanalysis 23:1337–1344. https://doi.org/10.1002/elan.201000671
Fagan-murphy A, Allen MC, Patel BA (2015) Chemically modified multiwall carbon nanotube composite electrodes: an assessment of fabrication strategies. Electrochim Acta 152:249–254. https://doi.org/10.1016/j.electacta.2014.11.129
Geto A, Tessema M, Admassie S (2014) Determination of histamine in fish muscle at multi-walled carbon nanotubes coated conducting polymer modified glassy carbon electrode. Synth Met 191:135–140. https://doi.org/10.1016/j.synthmet.2014.03.005
Haseeb S, Alexander B, Santi RL, Liprandi AS, Baranchuk A (2019) What’s in wine? A clinician’s perspective, Trends Cardiovasc. Med 29:97–106. https://doi.org/10.1016/j.tcm.2018.06.010
Henao-Escobar W, Domínguez-Renedo O, Alonso-Lomillo MA, Arcos-Martínez MJ (2015) Resolution of quaternary mixtures of cadaverine, histamine, putrescine and tyramine by the square wave voltammetry and partial least squares method. Talanta 143:97–100. https://doi.org/10.1016/j.talanta.2015.05.047
Herrera-chacón A, Dinç-zor Ş, Valle M (2020) Integrating molecularly imprinted polymer beads in graphite-epoxy electrodes for the voltammetric biosensing of histamine in wines. Talanta 208:120348. https://doi.org/10.1016/j.talanta.2019.120348
Jastrzebska A, Piasta A, Kowalska S, Krzemiński M, Szłyk E (2016) A new derivatization reagent for determination of biogenic amines in wines. J Food Comp and Analysis 48:111–119. https://doi.org/10.1016/j.jfca.2016.02.012
Jeong J, Kumar RS, Mergu N, Son Y-A (2017) Photophysical, electrochemical, thermal and aggregation properties of new metal phthalocyanines. J Mol Struct 1147:469–479. https://doi.org/10.1016/j.molstruc.2017.06.125
Jerković A, Abou-Ahmed S, Ertl P, Stoeß B, Lengauer V, Samphao A, Kalcher K, Leitinger G, Wernitznig S, Ortner A (2010) Natural deep eutectic solvents-mediated extractions: the way forward for sustainable analytical developments. Anal Chim Acta 1038:1–10. https://doi.org/10.1016/j.aca.2018.07.059
Jia S, Ryu Y, Kwon SW, Lee J (2013) An in situ benzoylation-dispersive liquid–liquid microextraction method based on solidification of floating organic droplets for determination of biogenic amines by liquid chromatography–ultraviolet analysis. J Chromatogr A 1282:1–10. https://doi.org/10.1016/j.chroma.2013.01.041
Karuppiah C, Devasenathipathy R, Chen S-M, Arulraj D, Palanisamy S, Mani V, Vasantha VS (2015) Fabrication of nickel tetrasulfonated phthalocyanine functionalized multiwalled carbon nanotubes on activated glassy carbon electrode for the detection of dopamine. Electroanalysis 27:485–493. https://doi.org/10.1002/elan.201400551
Khan MZH, Liu X, Zhu J, Ma F, Hu W, Liu X (2018) Electrochemical detection of tyramine with ITO/APTES/ErGO electrode and its application in real sample analysis. Biosens Bioelectron 108:76–81. https://doi.org/10.1016/j.bios.2018.02.042
Koita D, Tzedakis T, Kane C, Diaw M, Sock O, Lavedan P (2014) Study of the histamine electrochemical oxidation catalyzed by nickel sulfate. Electroanalysis 26:2224–2236. https://doi.org/10.1002/elan.201400155
Kumar N, Goyal RN (2018) Silver nanoparticles decorated graphene nanoribbon modified pyrolytic graphite sensor for determination of histamine. Sens. Actuators. B Chem 268:383–391. https://doi.org/10.1016/j.snb.2018.04.136
Li X, Zheng B-D, Peng X-H, Li S-Z, Ying J-W, Zhao Y, Huang J-D, Yoon J (2019) Phthalocyanines as medicinal photosensitizers: developments in the last five yearsCoord. Chem Rev 379:147–160. https://doi.org/10.1016/j.ccr.2017.08.003
Lin Y, Chen C, Lin MS (2018) Enzyme-free amperometric method for rapid determination of histamine by using surface oxide regeneration behavior of copper electrode. Sensors and Actuators B 255:2838–2843. https://doi.org/10.1016/j.snb.2017.09.101
Liu S-J, Xu J-J, Ma C-L, Guo C-F (2018) A comparative analysis of derivatization strategies for the determination of biogenic amines in sausage and cheese by HPLC. Food Chem 266:275–283. https://doi.org/10.1016/j.foodchem.2018.06.001
Liu Y, Han F, Liu Y, Wang W (2020) Determination of biogenic amines in wine using modified liquid-liquid extraction with high performance liquid chromatography-fluorescence detector. Food Anal Methods 13:911–922. https://doi.org/10.1007/s12161-020-01710-w
Lourenço AS, Nascimento RF, Silva AC, Ribeiro WF, de Araujo MCU, Oliveira SCB, Nascimento VB (2018) Voltammetric determination of tartaric acid in wines by electrocatalytic oxidation on a cobalt(II)-phthalocyanine-modified electrode associated with multiway calibration. Anal Chim Acta 1008:29–37. https://doi.org/10.1016/j.aca.2018.01.005
Lucena NC, Miyazaki CM, Shimizu FM, Constantino CJL, Ferreira M (2018) Layer-by-layer composite film of nickel phthalocyanine and montmorillonite clay for synergistic effect on electrochemical detection of dopamine. Appl Surf Sci 436:957–966. https://doi.org/10.1016/j.apsusc.2017.12.117
Madhuri KP, John NS (2018) Supercapacitor application of nickel phthalocyanine nanofibres and its composite with reduced graphene oxide Appl. Surf Sci 449:528–536. https://doi.org/10.1016/j.apsusc.2017.12.021
Magnusson B, Örnemark U (eds.) Eurachem guide: the fitness for purpose of analytical methods – a laboratory guide to method validation and related topics, (2nd ed. 2014). ISBN: 978–91–87461–59–0
Mahmoud AM, Alkahtani SA, Alyami BA, El-Wekil MM (2020) Dual-recognition molecularly imprinted aptasensor based on gold nanoparticles decorated carboxylated carbon nanotubes for highly selective and sensitive determination of histamine in different matrices. Anal Chim Acta 1133:58–65. https://doi.org/10.1016/j.aca.2020.08.001
Manetta AC, Di Giuseppe L, Tofalo R, Martuscelli M, Schironea M, Giammarco M, Suzzi G (2016) Evaluation of biogenic amines in wine: determination by an improved HPLC-PDA method. Food Control 62:351–356. https://doi.org/10.1016/j.foodcont.2015.11.009
Meng X, Guo W, Qin X, Liu Y, Zhu X, Pei M, Wang L (2014) A molecularly imprinted electrochemical sensor based on gold nanoparticles and multiwalled carbon nanotube–chitosan for the detection of tryptamine. RSC Adv 4:38649–38654. https://doi.org/10.1039/C4RA04503C
Milheiro J, Ferreira LC, Filipe-Ribeiro L, Cosme F, Nunes FM (2019) Food Chem. A Simple Dispersive Solid Phase Extraction Clean-up/concentration Method for Selective and Sensitive Quantification of Biogenic Amines in Wines Using Benzoyl Chloride Derivatisation 274:110–117. https://doi.org/10.1016/j.foodchem.2018.08.116
Yang M, Zhang J, Chen X (2015) Competitive electrochemical immunosensor for the detection of histamine based on horseradish peroxidase initiated deposition of insulating film. J Electroanal Chem 736:88–92. https://doi.org/10.1016/j.jelechem.2014.11.002
Nascimento RF, Selva TMG, Ribeiro WF, Belian MF, Angnes L, Nascimento VB (2013) Flow-injection electrochemical determination of citric acid using a cobalt(II)–phthalocyanine modified carbon paste electrode. Talanta 105:354–359. https://doi.org/10.1016/j.talanta.2012.10.055
Nosuhi M, Nezamzadeh-Ejhieh A (2018) An indirect application aspect of zeolite modified electrodes for voltammetric determination of iodate. J Electroanal Chem 810:119–128. https://doi.org/10.1016/j.jelechem.2017.12.075
Núñez C, Arancibia V, José J (2018) A new strategy for the modification of a carbon paste electrode with carrageenan hydrogel for a sensitive and selective determination of arsenic in natural waters. Talanta 187:259–264. https://doi.org/10.1016/j.talanta.2018.05.028
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
Perestrelo R, Bordiga M, Locatelli M, Silva C, Câmara JS (2020) Polyphenols, biogenic amines and amino acids patterns in Verdelho wines according to vintage. Microchem. J. 153:104383. https://doi.org/10.1016/j.microc.2019.104383
Płotka-Wasylka J, Simeonovb V, Morrisonc C, Namieśnik J (2018) Impact of selected parameters of the fermentation process of wine and wine itself on the biogenic amines content: evaluation by application of chemometric tools. Microchem J 142:187–194. https://doi.org/10.1016/j.microc.2018.06.038
Puthongkham P, Lee ST, Venton BJ (2019) Mechanism of histamine oxidation and electropolymerization at carbon electrodes. Anal Chem 91:8366–8373. https://doi.org/10.1021/acs.analchem.9b01178
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
Rio B, Redruello B, Fernandeza M, Martina MC, Ladero V, Alvarez MA (2020) The biogenic amine tryptamine, unlike β-phenylethylamine, shows in vitro cytotoxicity at concentrations that have been found in foods. Food Chem 331:127303. https://doi.org/10.1016/j.foodchem.2020.127303
Romano A, Klebanowski H, La Guerche S, Beneduce L, Spano G, Murat M-L, Lucas P (2012) Determination of biogenic amines in wine by thin-layer chromatography/densitometry. Food Chem 135:1392–1396. https://doi.org/10.1016/j.foodchem.2012.06.022
Saghatforoush L, Hasanzadeh M, Shadjou N (2014) ß-Cyclodextrin/graphene oxide grafted sulfonic acid: application for electro-oxidation and determination of cadaverine in fish samples. J Electroanal Chem 714:79–84. https://doi.org/10.1016/j.jelechem.2013.12.021
Samphao A, Kalcher K (2016) Electrochemical determination of histamine in fish sauce using heterogeneous carbon electrodes modified with rhenium(IV) oxide. Sens. Actuators. B Chem 228:774–781. https://doi.org/10.1016/j.snb.2016.01.085
Knežević S, Ognjanović M, Nedić N, Jose FMLM, Milanović Z, Petković B, Antić B, Djurić SV, Stanković D (2020) A single drop histamine sensor based on AuNPs/MnO2 modified screen printed electrode. Microchem J 155:104778. https://doi.org/10.1016/j.microc.2020.104778
Silva AC, Lourenço AS, De Araujo MCU (2018) Simultaneous voltammetric determination of four organic acids in fruit juices using multiway calibration. Food Chem 266:232–239. https://doi.org/10.1016/j.foodchem.2018.06.005
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 101:704–716. https://doi.org/10.1016/j.foodchem.2006.02.028
Souza SC, Theodoro KH, Souza ÉR, da Motta S, Glória MBA (2005) Bioactive amines in Brazilian wines: types, levels and correlation with physico-chemical parameters Brazilian Arch. Biol Technol 48:53–62. https://doi.org/10.1590/S1516-89132005000100009
Stojanović ZS, Mehmeti E, Kalcher K, Guzsvány V, Stanković DM (2016) SWCNT-modified carbon paste electrode as an electrochemical sensor for histamine determination in alcoholic beverages. Food Anal Methods 9:2701–2710. https://doi.org/10.1007/s12161-016-0452-3
Tuberoso CIG, Serreli G, Montoro P, D’Urso G, Congiu F, Kowalczyk A (2018) Biogenic amines and other polar compounds in long aged oxidized Vernaccia di Oristano white wines. Food Res Int 111:97–103. https://doi.org/10.1016/j.foodres.2018.05.020
Xing X, Liu S, Yu J, Lian W, Huang J (2012) Electrochemical sensor based on molecularly imprinted film at polypyrrole-sulfonated graphene/hyaluronic acid-multiwalled carbon nanotubes modified electrode for determination of tryptamine. Biosens Bioelectron 31:277–283. https://doi.org/10.1016/j.bios.2011.10.032
Yuwen Xu, Cheng Y, Jia Y, Ye B-C (2020) Synthesis of MOF-derived Ni@C materials for the electrochemical detection of histamine. Talanta 219:121360. https://doi.org/10.1016/j.talanta.2020.121360
Zagal JH, Griveau S, Silva JF, Nyokong T, Bedioui F (2010) Metallophthalocyanine-based molecular materials as catalysts for electrochemical reactions. Coord Chem Rev 254:2755–2791. https://doi.org/10.1016/j.ccr.2010.05.001
Zaib M, Athar MM, Saeed A, Farooq U (2015) Electrochemical determination of inorganic mercury and arsenic - A review. Biosens Bioelectron 74:895–908. https://doi.org/10.1016/j.bios.2015.07.058
Zhong J-P, Fan Y-J, Wang H, Wang R-X, Fan L-L, Shen X-C, Shi Z-J (2013) Highly active Pt nanoparticles on nickel phthalocyanine functionalized graphene nanosheets for methanol electrooxidation. Electrochim Acta 113:653–660. https://doi.org/10.1016/j.electacta.2013.09.092
Acknowledgements
This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) under the Finance Code No. 001. The authors would like to thank the Brazilian agencies Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and CAPES for the research fellowships and scholarships and research grant no. 465768/2014-8 (INCTAA-CNPq). The English text of this paper has been revised by Sidney Pratt, Canadian, MAT (The Johns Hopkins University), RSAdip-TESL (Cambridge University).
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Conceptualization: ASL and MCUA; formal analysis: ASL and ACS; investigation and methodology: ASL, ACS, and TAN; software: ACS; funding acquisition and resources: MCUA; supervision: WFR and MCUA; visualization: ASL; writing—original draft: ASL and ACS; writing—review and editing: ASL, ACS, WFR, and MCUA.
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Lourenço, A.S., Nunes, T.A., Silva, A.C. et al. Simultaneous Voltammetric Determination of Tryptamine and Histamine in Wines Using a Carbon Paste Electrode Modified with Nickel Phthalocyanine. Food Anal. Methods 15, 3257–3269 (2022). https://doi.org/10.1007/s12161-022-02390-4
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DOI: https://doi.org/10.1007/s12161-022-02390-4