Rapid HPLC analysis of amino acids and biogenic amines in wines during fermentation and evaluation of matrix effect.

A rapid HPLC method has been developed for the simultaneous determination of 23 amino acids, 10 biogenic amines and the ammonium ion in wine. Samples were pre-column derivatised with diethyl ethoxymethylenemalonate and separated using reversed-phase HPLC within 30 min. The matrix effect was evaluated when measuring samples taken from different stages of fermentation. Most compounds showed no obvious matrix effect, whereas proline, ethanolamine and spermine had remarkably different responses to variable concentrations of sugar. High concentrations of sugar affected the pH of the derivatisation reaction system; proline, ethanolamine and spermine derivatives were sensitive to this effect. Matrix-matched calibration was used for the quantification of these compounds. Validation of the method showed that it was accurate, reproducible and efficient for the simultaneous determination of amino acids and biogenic amines in wines during fermentation. As a specific application of the method, red wine samples taken from different stages of fermentation were analysed.

[1]  R. Callejón,et al.  Determination of amino acids in grape-derived products: a review. , 2010, Talanta.

[2]  S. Gómez-Alonso,et al.  Simultaneous HPLC analysis of biogenic amines, amino acids, and ammonium ion as aminoenone derivatives in wine and beer samples. , 2007, Journal of agricultural and food chemistry.

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

[4]  V. Ferreira,et al.  Determination of the biogenic amines in musts and wines before and after malolactic fermentation using 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate as the derivatizing agent. , 2006, Journal of chromatography. A.

[5]  V. Ferreira,et al.  High-Performance Liquid Chromatography Analysis of Amines in Must and Wine: A Review , 2012 .

[6]  F. Pardo,et al.  Study of the evolution of nitrogen compounds during grape ripening. application to differentiate grape varieties and cultivated systems. , 2009, Journal of agricultural and food chemistry.

[7]  M. Kelly,et al.  Rapid automated high performance liquid chromatography method for simultaneous determination of amino acids and biogenic amines in wine, fruit and honey. , 2010, Journal of chromatography. A.

[8]  M. Alaiz,et al.  Amino acid analysis by high-performance liquid chromatography after derivatization with diethyl ethoxymethylenemalonate. , 1992, Journal of chromatography.

[9]  F. Masino,et al.  Occurrence and evolution of amino acids during grape must cooking , 2010 .

[10]  C. Varela,et al.  Comparison of inorganic and organic nitrogen supplementation of grape juice - Effect on volatile composition and aroma profile of a Chardonnay wine fermented with Saccharomyces cerevisiae yeast. , 2011, Food chemistry.

[11]  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 .

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

[13]  J. Marques,et al.  Simultaneous analysis of free amino acids and biogenic amines in honey and wine samples using in loop orthophthalaldeyde derivatization procedure. , 2008, Journal of chromatography. A.

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

[15]  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.

[16]  A. Versari,et al.  High-performance liquid chromatographic analysis of free amino acids in fruit juices using derivatization with 9-fluorenylmethyl-chloroformate. , 2002, Journal of Chromatographic Science.

[17]  J. Mauricio,et al.  Concentration of amino acids in wine after the end of fermentation by Saccharomyces cerevisiae strains , 2003 .

[18]  Carol M. Taylor,et al.  Glycosides of hydroxyproline: some recent, unusual discoveries. , 2012, Glycobiology.

[19]  C. Ancín-Azpilicueta,et al.  Influence of addition of ammonium and different amino acid concentrations on nitrogen metabolism in spontaneous must fermentation , 2007 .

[20]  J. Lombardero,et al.  Ethyl carbamate production by selected yeasts and lactic acid bacteria in red wine , 2006 .

[21]  Ronald S. Jackson,et al.  Wine Science: Principles and Applications , 1994 .

[22]  F. Pardo,et al.  Implications of nitrogen compounds during alcoholic fermentation from some grape varieties at different maturation stages and cultivation systems , 2011 .

[23]  K. Herodes,et al.  Comparison of three buffer solutions for amino acid derivatization and following analysis by liquid chromatography electrospray mass spectrometry. , 2012, Journal of chromatography. A.

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

[25]  D. Torrea,et al.  Content of biogenic amines in a Chardonnay wine obtained through spontaneous and inoculated fermentations. , 2002, Journal of agricultural and food chemistry.

[26]  N. Ratola,et al.  Free amino acids and biogenic amines in wines and musts from the Alentejo region. Evolution of amines during alcoholic fermentation and relationship with variety, sub-region and vintage , 2004 .

[27]  A. Lonvaud-Funel.  Biogenic amines in wines: role of lactic acid bacteria. , 2001, FEMS microbiology letters.

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

[29]  Marina Patricia Arrieta,et al.  Free amino acids and biogenic amines in Alicante Monastrell wines. , 2012, Food chemistry.

[30]  Paul A. Henschke,et al.  Implications of nitrogen nutrition for grapes, fermentation and wine , 2005 .

[31]  M. Raggi,et al.  Recent trends in the analysis of amino acids in fruits and derived foodstuffs , 2013, Analytical and Bioanalytical Chemistry.

[32]  M. Caruso,et al.  Formation of biogenic amines as criteria for the selection of wine yeasts , 2002 .

[33]  Victor Palacios,et al.  Chemical and biochemical transformations during the industrial process of sherry vinegar aging. , 2002, Journal of agricultural and food chemistry.

[34]  María Cruz Martín,et al.  A fast, reliable, ultra high performance liquid chromatography method for the simultaneous determination of amino acids, biogenic amines and ammonium ions in cheese, using diethyl ethoxymethylenemalonate as a derivatising agent. , 2013, Food chemistry.

[35]  Costas G. Biliaderis,et al.  Primary amino acid profiles of Greek white wines and their use in classification according to variety, origin and vintage , 2003 .

[36]  M. Glória,et al.  Influence of alcoholic and malolactic starter cultures on bioactive amines in Merlot wines , 2009 .

[37]  A. Alegría,et al.  Application of the 6-aminoquinolyl-N-hydroxysccinimidyl carbamate (AQC) reagent to the RP-HPLC determination of amino acids in infant foods. , 2006, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.