Skip to main content

Advertisement

SpringerLink
Log in

Ultra-Performance Liquid Chromatography-Triple Quadruple Mass Spectrometry (UPLC-TQ/MS) for Evaluation of Biogenic Amines in Wine

  • Published:
Food Analytical Methods Aims and scope Submit manuscript

Abstract

In this study, a fast, simple, and sensitive analytical method for direct determination of biogenic amines tryptamine, putrescine, histamine, phenylethylamine, tyramine, cadaverine, spermine, and spermidine in wine has been developed and validated. Detection of analytes was performed with ultra-performance liquid chromatography (UPLC) coupled to triple quadruple mass spectrometer (TQ/MS). The calibration curves of all amines were linear with correlation coefficients (R 2) ranging from 0.9906 for putrescine to 0.9998 for histamine and 2-phenyethylamine. The accuracy of the method was checked with a standard addition method, showing good accuracy, repeatability, and reproducibility (RSD < 10%). The limit of detection (LOD) and limit of quantification (LOQ) ranged from 0.50 to 30 μg/L and 1.50 to 90 μg/L, respectively, for all amines. The validated method was applied to detect and quantify biogenic amines in Macedonian red and white wines. Higher concentration of amines was observed in red wines (5797 μg/L, on average) compared to the white wines (1485 μg/L, on average).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Alcaide-Hidalgo JM, Moreno-Arribas MV, Martín-Álvarez PJ, Polo MC (2007) Influence of malolactic fermentation, postfermentative treatments and ageing with lees on nitrose compounds of red wines. Food Chem 103:572–581

    Article  CAS  Google Scholar 

  • Anli ER, Bayram M (2009) Biogenic amines in wines. Food Rev Int 25:86–102

    Article  CAS  Google Scholar 

  • Arrieta MP, Prats-Moya MS (2012) Free amino acids and biogenic amines in Alicante Monastrell wines. Food Chem 135:1511–1519

    Article  CAS  Google Scholar 

  • Bauza T, Blaise A, Daumas F, Cabanis JC (1995) Determination of biogenic amines and their precursor amino acids in wines of the Vall_ee du Rhone by high-performance liquid chromatography with precolumn derivatization and fluorimetric detection. J Chromatogr A 707:373–379

    Article  CAS  Google Scholar 

  • Daniel D, Dos Santos VB, Vidal DT, Lago CL (2015) Determination of biogenic amines in beer and wine by capillary electrophoresis-tandem mass spectrometry. J Chromatogr A 1416:121–128

    Article  CAS  Google Scholar 

  • EFSA Panel on Biological Hazards (2011) Scientific opinion on risk based control of biogenic amine formation in fermented foods. EFSA J 9(10):1–93

    Google Scholar 

  • Fernandes JO, Ferreira MA (2000) Combined ion-pair extraction and gas chromatography–mass spectrometry for the simultaneous determination of diamines, polyamines and aromatic amines in port wine and grape juice. J Chromatogr A 886:183–195

    Article  CAS  Google Scholar 

  • García-Marino M, Trigueros Á, Escribano-Bailón T (2010) Influence of oenological practices on the formation of biogenic amines in quality red wines. J Food Comp Anal 23:455–462

    Article  Google Scholar 

  • García-Villar N, Hernández-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

    Article  Google Scholar 

  • Goñi DT, Azpilicueta CA (2001) Influence of yeast strain on biogenic amines content in wines: relationship with the utilization of amino acids during fermentation. Am J Enol Viticul 52:185–190

    Google Scholar 

  • Guo YY, Yang YP, Peng Q, Han Y (2015) Biogenic amines in wine: a review. Int J Food Sci Tech 50:1523–1532

    Article  CAS  Google Scholar 

  • Hernández-Orte P, Peña-Gallego A, Ibarz MJ, Cacho J, Ferreira V (2006) Determination of the biogenic amines in musts and wines before and after malolactic fermentation using 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate as the derivatizing agent. J Chromatogr A 1129:160–164

    Article  Google Scholar 

  • Hernández-Orte P, Lapeña AC, Peña-Gallego A, Astrain J, Baron C, Pardo I, Polo L, Ferrer S, Cacho J, Ferreira V (2008) Biogenic amine determination in wine fermented in oak barrels. Factors affecting formation. Food Res Int 41:697–706

    Article  Google Scholar 

  • Herrero M, García-Cañas V, Simo C, Cifuentes A (2014) Recent advances in the application of capillary electromigration methods for food analysis and foodomics. Electrophoresis 35:147–169

    Article  Google Scholar 

  • Hlabangana L, Hernandez-Cassou S, Saurina J (2006) Determination of biogenic amines in wines by ion-pair liquid chromatography and post-column derivatization with 1,2-naphthoquinone-4-sulphonate. J Chromatogr A 1130:130–136

    Article  CAS  Google Scholar 

  • Jastrzębska A, Piasta A, Kowalska S, Krzemiński M, Szłyk E (2016) A new derivatization reagent for determination of biogenic amines in wines. J Food Comp Anal 48:111–119

    Article  Google Scholar 

  • Kelly MT, Blaise A, Larroque M (2010) Rapid automated high performance liquid chromatography method for simultaneous determination of amino acids and biogenic amines in wine, fruit and honey. J Chromatogr A 1217:7385–7392

    Article  CAS  Google Scholar 

  • Landete JM, Ferrer S, Pardo I (2007) Biogenic amine production by lactic acid bacteria, acetic bacteria and yeast isolated from wine. Food Control 103:1475–1486

    Google Scholar 

  • Lange J, Wittmann C (2002) Enzyme sensor array for the determination of biogenic amines in food samples. Anal Bioanal Chem 372:276–283

    Article  CAS  Google Scholar 

  • Littlewood JT, Gibbs C, Glover V, Sandler M, Davies PTG, Rose F (1988) Red wine as a cause of migraine. Lancet 1(8585):558–559

    Article  CAS  Google Scholar 

  • Lonvaud-Funel A (2001) Biogenic amines in wines: role of lactic acid bacteria. FEMS Microbiol Lett 199:9–13

    Article  CAS  Google Scholar 

  • 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 996:103–113

    Article  CAS  Google Scholar 

  • Maintz L, Novak N (2007) Histamine and histamine intolerance. Am J Clin Nutr 85:1185–1196

    CAS  Google Scholar 

  • Manetta AC, Di Giuseppe L, Tofalo R, Martuscelli M, Schirone M, Giammarco M, Suzzi G (2016) Evaluation of biogenic amines in wine: determination by an improved HPLC-PDA method. Food Control 62:351–356

    Article  CAS  Google Scholar 

  • Marcobal A, de la Rivas B, Muñoz R (2006) Methods for the detection of bacteria producing biogenic amines on foods: a survey. J Verbrauch Lebensm 1:187–196

    Article  CAS  Google Scholar 

  • Marques AP, Leitão MC, San Romão MV (2008) Biogenic amines in wines: influence of oenological factors. Food Chem 107:853–860

    Article  CAS  Google Scholar 

  • Martín-Álvarez PJ, Marcobal A, Polo C, Moreno-Arribas MV (2006) Influence of technological practices on biogenic amine contents in red wine. Eur Food Res Technol 222:420–424

    Article  Google Scholar 

  • Martuscelli M, Arfelli G, Manetta AC, Suzzi G (2013) Biogenic amines content as a measure of the quality of wines of Abruzzo (Italy). Food Chem 140:590–597

    Article  CAS  Google Scholar 

  • Millies KD, Zimlich D (1988) Histamingehalte von Weinen und Schaumweinen. Weinwirtsch Tech 1:21–24

    Google Scholar 

  • Moreno-Arribas VM, Polo MC (2005) Winemaking biochemistry and microbiology: current knowledge and future trends. Crit Rev Food Sci Nutr 45:265–286

    Article  CAS  Google Scholar 

  • Onal A (2007) A review: current analytical methods for the determination of biogenic amines in foods. Food Chem 103:1475–1486

    Article  Google Scholar 

  • Ozdestan O, Üren A (2009) A method for benzoyl chloride derivatization of biogenic amines for high performance liquid chromatography. Talanta 78:1321–1326

    Article  Google Scholar 

  • Pérez-Serradilla JA, Luque de Castro MD (2008) Role of lees in wine production: a review. Food Chem 111:447–456

    Article  Google Scholar 

  • Preti R, Vinci G (2016) Biogenic amine content in red wines from different protected designations of origin of southern Italy: chemometric characterization and classification. Food Anal Method 9:2280–2287

    Article  Google Scholar 

  • Preti R, Vieri S, Vinci G (2016) Biogenic amine profiles and antioxidant properties of Italian red wines from different price categories. J Food Comp Anal 46:7–14

    Article  CAS  Google Scholar 

  • Rios AL, Valcarel M (1998) Direct determination of biogenic amines in wine by integrating continuous flow clean-up and capillary electrophoresis with indirect UV detection. J Chromatogr A 803:249–260

    Article  Google Scholar 

  • Romero R, Gázquez D, Bagur MG, Sánchez-Vinas M (2000) Optimization of chromatographic parameters for the determination of biogenic amines in wines by reversed-phase high-performance liquid chromatography. J Chromatogr A 871:75–83

    Article  CAS  Google Scholar 

  • Sagratini G, Fernandez-Franzon M, De Berardinis F, Font G, Vittori S, Manes J (2012) Simultaneous determination of eight underivatised biogenic amines in fish by solid phase extraction and liquid chromatography tandem mass spectrometry. Food Chem 132:537–543

    Article  CAS  Google Scholar 

  • Sentellas S, Nuñez Ó, Saurina J (2016) Recent advances in the determination of biogenic amines in food samples by (U)HPLC. J Agric Food Chem 64:7667–7678

    Article  CAS  Google Scholar 

  • Smit AY, du Toit WJ, du Toit M (2008) Biogenic amines in wine: understanding the headache. S Afr J Enol Vitic 29:109–127

    CAS  Google Scholar 

  • Soufleros E, Barrios M, Bertrand A (1998) Correlation between the content of biogenic amines and other wine compounds. Am J Enol Vitic 49:266–278

    CAS  Google Scholar 

  • Spano G, Russo P, Lonvaud-Funel A, Lucas P, Alexandre H, Grandvalet C, Coton E, Coton M, Barnavon L, Bach B, Rattray F, Bunte A, Magni C, Ladero V, Alvarez M, Fernández M, Lopez P, de Palencia PF, Corbi A, Trip H, Lolkema JS (2010) Biogenic amines in fermented foods. Eur J Clin Nutr 64:S95–S100

    Article  CAS  Google Scholar 

  • Tašev K, Ivanova-Petropulos V, Stefova M (2016) Optimization and validation of a derivatization method for analysis of biogenic amines in wines using RP-HPLC-DAD. Maced J Chem Chem En 35:19–28

    Article  Google Scholar 

  • Vidal-Carou MC, Lahoz-Portoles F, Bover-Cid S, Marine-Font A (2003) Ion-pair high-performance liquid chromatographic determination of biogenic amines and polyamines in wine and other alcoholic beverages. J Chromatogr A 98:235–241

    Article  Google Scholar 

Download references

Acknowledgements

Financial support provided by the Macedonian Ministry of Education and Science for the bilateral project between Republic of Macedonia and Montenegro titled “Biogenic amines and aroma in Vranec wines from Macedonia and Montenegro and effect of malolactic fermentation on their formation” is gratefully acknowledged.

Author information

Authors and Affiliations

  1. State Phytosanitary Laboratory, bul. Alexander the Great bb, 1000, Skopje, Republic of Macedonia

    Krste Tašev

  2. Institute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss Cyril and Methodius University, Arhimedova 5, Skopje, Republic of Macedonia

    Krste Tašev & Marina Stefova

  3. Faculty of Agriculture, “Goce Delčev” University, Krste Misirkov bb, Štip, Republic of Macedonia

    Violeta Ivanova-Petropulos

Authors
  1. Krste Tašev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Violeta Ivanova-Petropulos
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Marina Stefova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Violeta Ivanova-Petropulos.

Ethics declarations

Funding

Funding was provided by the Macedonian Ministry of Education and Science of the Republic of Macedonia.

Conflict of Interest

Krste Tašev declares that he has no conflict of interest. Violeta Ivanova-Petropulos declares that she has no conflict of interest. Marina Stefova declares that she has no conflict of interest.

Ethical Approval

This article does not contain any studies with animals.

Informed Consent

It was obtained from all individual participants included in the study.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tašev, K., Ivanova-Petropulos, V. & Stefova, M. Ultra-Performance Liquid Chromatography-Triple Quadruple Mass Spectrometry (UPLC-TQ/MS) for Evaluation of Biogenic Amines in Wine. Food Anal. Methods 10, 4038–4048 (2017). https://doi.org/10.1007/s12161-017-0936-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12161-017-0936-9

Keywords

Search

Navigation