Determination of biogenic amines in wines by pre-column derivatization and high-performance liquid chromatography coupled to mass spectrometry.

A new HPLC method for determining biogenic amines in wines is developed. This method is based on pre-column amine derivatization, further separation of derivatives and on-line hyphenation of HPLC to atmospheric pressure chemical ionization mass spectrometry (APCI-MS). Biogenic amines have been derivatized with 1,2-naphthoquinone-4-sulfonate at 65 degrees C and pH 9.2 for 5 min. The separation of derivatives has been accomplished in a C(18) analytical column using an elution gradient based on increasing the percentage of methanol. Derivatives have been ionized in positive mode and detected by selected ion monitoring. The operating conditions of the APCI-MS system (voltages, temperatures and gases) have been thoroughly optimized to obtain the maximum sensitivity for all analytes. In the selected conditions, APCI-MS spectra display little fragmentation and good signal-to-noise ratio. Depending on the amine characteristics, the main spectral peaks are due to mono- and di-derivative products. Figures of merit of the method have been established under the selected conditions using red wine samples. Recoveries ranging from 94% to 106% have been obtained which prove excellent accuracy of the method in the determination of histamine, putrescine, cadaverine, tryptamine, phenylethylamine, tyramine and serotonin in red wines. The proposed method has been applied to the analysis of commercial wines from different Spanish regions.

[1]  H. Yıldırım,et al.  Evaluation of Biogenic Amines in Organic and Non-Organic Wines by HPLC OPA Derivatization , 2007 .

[2]  M. C. Vidal-Carou,et al.  Histamine and Tyramine in Spanish Wines: Their Formation During the Winemaking Process , 1990 .

[3]  Roberto Romero,et al.  Characterization of selected Spanish table wine samples according to their biogenic amine content from liquid chromatographic determination. , 2002, Journal of agricultural and food chemistry.

[4]  W. Holzapfel,et al.  Biogenic amines and their production by microorganisms in food , 1994 .

[5]  Sara Bover-Cid,et al.  Ion-pair high-performance liquid chromatographic determination of biogenic amines and polyamines in wine and other alcoholic beverages. , 2003, Journal of chromatography. A.

[6]  Huan‐Tsung Chang,et al.  Analysis of biologically active amines by CE , 2006, Electrophoresis.

[7]  Z. Loukou,et al.  Determination of biogenic amines in Greek wines by HPLC and ultraviolet detection after dansylation and examination of factors affecting their presence and concentration , 2007 .

[8]  Ying Zhang,et al.  Development of an automated on-line pre-column derivatization procedure for sensitive determination of histamine in food with high-performance liquid chromatography-fluorescence detection. , 2008, Journal of chromatography. A.

[9]  Javier Saurina,et al.  Characterization of wines through the biogenic amine contents using chromatographic techniques and chemometric data analysis. , 2007, Journal of agricultural and food chemistry.

[10]  J. Saurina,et al.  Strategies for in-capillary derivatization of amino acids in capillary electrophoresis using 1,2-naphthoquinone-4-sulfonate as a labeling reagent. , 2001, Journal of chromatography. A.

[11]  G. Dugo,et al.  Reverse phase HPLC/DAD determination of biogenic amines as dansyl derivatives in experimental red wines , 2006 .

[12]  M. Bayram,et al.  Biogenic Amines in Wines , 2008 .

[13]  Armağan Önal,et al.  A review: Current analytical methods for the determination of biogenic amines in foods , 2007 .

[14]  É. Gelencsér,et al.  Immunoassay method for detection of histamine in foods , 2003 .

[15]  J. Saurina,et al.  Determination of biogenic amines in wines by ion-pair liquid chromatography and post-column derivatization with 1,2-naphthoquinone-4-sulphonate. , 2006, Journal of chromatography. A.

[16]  J. Marques,et al.  Classification of Boal, Malvazia, Sercial and Verdelho wines based on terpenoid patterns , 2007 .

[17]  M. Íñiguez,et al.  Monitoring of the ageing of red wines in oak barrels by means of an hybrid electronic tongue , 2006 .

[18]  J. Saurina,et al.  Chromatographic determination of amino acids by pre-column derivatization using 1,2-naphthoquinone-4-sulfonate as reagent , 1996 .

[19]  Stamatina Kallithraka,et al.  Principal phenolic compounds in Greek red wines , 2006 .

[20]  A. Costantini,et al.  Occurrence of biogenic amines in wine: The role of grapes , 2009 .

[21]  I. M. Gardiner,et al.  Pharmacological analysis of red-wine-induced migrainous headaches , 2003, The Journal of Headache and Pain.

[22]  J. Kiss,et al.  Protection of originality of Tokaji Aszú: amines and organic acids in botrytized wines by high-performance liquid chromatography. , 2005, Journal of agricultural and food chemistry.

[23]  P. Lehtonen.  Determination of Amines and Amino Acids in Wine — A Review , 1996, American Journal of Enology and Viticulture.

[24]  Agnes Sass-Kiss,et al.  Multivariate statistical analysis of botrytised wines of different origin , 2008 .

[25]  K. Héberger,et al.  Principal component analysis of biogenic amines and polyphenols in Hungarian wines. , 2002, Journal of agricultural and food chemistry.

[26]  L. Márk,et al.  Polyphenols, anthocyanins, and trans-resveratrol in red wines from the Hungarian Villány region , 2006 .

[27]  António S. Barros,et al.  Rapid tool for distinction of wines based on the global volatile signature. , 2006, Journal of chromatography. A.

[28]  C. Ancín-Azpilicueta,et al.  Current Knowledge about the Presence of Amines in Wine , 2008, Critical reviews in food science and nutrition.

[29]  E. G. Romero,et al.  Amino acids and biogenic amines during spontaneous malolactic fermentation in Tempranillo red wines , 2008 .

[30]  A. Dubois,et al.  Intolerance to dietary biogenic amines: a review. , 2003, Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology.

[31]  Richard A Mathies,et al.  Analysis of neuroactive amines in fermented beverages using a portable microchip capillary electrophoresis system. , 2007, Analytical chemistry.

[32]  M. Komaitis,et al.  Determination of biogenic amines in wines by HPLC with precolumn dansylation and fluorimetric detection , 2008 .

[33]  Z. Loukou,et al.  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. , 2003, Journal of chromatography. A.

[34]  M.H.Silla Santos,et al.  Biogenic amines: their importance in foods. , 1996, International journal of food microbiology.

[35]  J. Saurina,et al.  Determination of histamine in wines with an on-line pre-column flow derivatization system coupled to high performance liquid chromatography. , 2005, The Analyst.

[36]  J. Saurina,et al.  Capillary electrophoresis determination of biogenic amines by field‐amplified sample stacking and in‐capillary derivatization , 2006, Electrophoresis.

[37]  Alejandro Cifuentes,et al.  Ion-trap versus time-of-flight mass spectrometry coupled to capillary electrophoresis to analyze biogenic amines in wine. , 2008, Journal of chromatography. A.

[38]  N. Unceta,et al.  Simple and rapid determination of biogenic amines in wine by liquid chromatography-electrospray ionization ion trap mass spectrometry. , 2007, Analytica chimica acta.

[39]  M. Moreno-Arribas,et al.  Biogenic amine content of red Spanish wines: comparison of a direct ELISA and an HPLC method for the determination of histamine in wines , 2005 .

[40]  V. Ferreira,et al.  Biogenic amine determination in wine fermented in oak barrels: Factors affecting formation , 2008 .

[41]  J. Saurina,et al.  High-performance liquid chromatographic determination of biogenic amines in wines with an experimental design optimization procedure. , 2006, Analytica chimica acta.

[42]  J. A. Pérez-Serradilla,et al.  Role of lees in wine production: A review. , 2008, Food chemistry.

[43]  I. Fleet,et al.  Determination of biogenic diamines with a vaporisation derivatisation approach using solid-phase microextraction gas chromatography-mass spectrometry. , 2008, Food chemistry.

[44]  Károly Héberger,et al.  Principal component and linear discriminant analyses of free amino acids and biogenic amines in hungarian wines. , 2003, Journal of agricultural and food chemistry.

[45]  Ricard Boqué,et al.  Determination of ageing time of spirits in oak barrels using a headspace–mass spectrometry (HS-MS) electronic nose system and multivariate calibration , 2005, Analytical and bioanalytical chemistry.

[46]  S. Bardócz.  Polyamines in food and their consequences for food quality and human health , 1995 .

[47]  S. Fanali,et al.  Nano-liquid chromatography analysis of dansylated biogenic amines in wines. , 2007, Journal of chromatography. A.

[48]  Joseph L Evans,et al.  Enhancing capillary liquid chromatography/tandem mass spectrometry of biogenic amines by pre-column derivatization with 7-fluoro-4-nitrobenzoxadiazole. , 2004, Rapid communications in mass spectrometry : RCM.

[49]  S. Oguri,et al.  Selective analysis of histamine in food by means of solid-phase extraction cleanup and chromatographic separation. , 2007, Journal of chromatography. A.

[50]  A. P. Marques,et al.  Biogenic amines in wines: Influence of oenological factors , 2008 .