Occurrence of (Z)-3,4-Dideoxyglucoson-3-ene in Different Types of Beer and Malt Beer as a Result of 3-Deoxyhexosone Interconversion

Abstract

In beer, 3-deoxyglucosone (3-DG) and 3-deoxygalactosone (3-DGal) are important sugar degradation products, but little is known about the relevance of the interconversion reaction between these compounds in different types of beer. In the present study, 3-DG was quantitated at concentrations of 12.9-52.7 mg/L and 3-DGal at concentrations of 6.0-26.4 mg/L in different types of beer (pilsner, wheat, bock, dark, and alcohol-free beers). The concentrations in malt beer tended to be higher. Largely overlapping concentration ranges precluded a classification of beers by their 3-deoxyglycosone contents. 3,4-Dideoxyglucoson-3-ene (3,4-DGE) was identified as an important intermediate and quantitated in beer and malt beer for the first time. The E and Z isomers of the corresponding quinoxaline were synthesized by a new synthetic approach and isolated by semipreparative HPLC. An assay was developed for quantitation of (E)- and (Z)-3,4-DGE by HPLC-MS/MS, and the Z isomer was determined at concentrations of 0.3-1.7 mg/L in beer and 0.5-4.8 mg/L in malt beer samples. The E isomer was shown to be of little importance. Concentrations of 5-hydroxymethylfurfural (HMF) were twice as high as those of (Z)-3,4-DGE in beer samples (0.4-3.7 mg/L) but much higher in malt beer samples (1.6-336 mg/L).

Transformation of Free and Dipeptide‐Bound Glycated Amino Acids by Two Strains of Saccharomyces cerevisiae

“…In comparison with the high concentrations of 1,2-dicarbonyl compounds and peptide-bound glycated amino acids in beer, only very small amountso ft he lysine derivatives pyrraline (10), formyline (11), and maltosine (12,S cheme 2) are presenti nt he free amino acid fraction of beer. [25,28] Therefore, we hypothesized that S. cerevisiae is able to metabolize certain glycated amino acids, either when presenti nt he free form or bound to peptides. One top-fermentinga nd one bottom-fermenting yeast strain were included in the study.I np arallel with the incubations of MRPs in the presence of yeast,t he stability of the products in medium without addition of yeast wasa ssessed.…”

“…In the second stage of the reaction, Amadori products are degraded to 1,2-dicarbonyl compounds. [25] Moreover,metabolization not only of ARPs, but also of AGEs by microorganisms such as Escherichia coli has been described. All of these products have already been quantitated in food samples (milk products,b akery products,c offee, beer).…”

“…[21][22][23][24] The pattern of free and protein-bound MRPsi na variety of beer samples allowed us to postulate that the MRPs pyrraline( 10), formyline (11), and maltosine (12)a re removed from wort by yeastduring fermentation. [25] Moreover,metabolization not only of ARPs, but also of AGEs by microorganisms such as Escherichia coli has been described. [26,27] It was there-fore the aim of this study to examine the "handling" of free and dipeptide-boundg lycated amino acids by S. cerevisiae.W e show for the first time their metabolization by two yeast strains and the identification of metabolites of different AGEs, which occurs most probablyb yt ransamination followed by different forms of a-keto acid degradation.…”

Quantification of 3-deoxyglucosone (3DG) as an aging marker in natural and forced aged wines

“…Moreover, the production of Amadori compounds in wines has already been described by Hashiba 1978, and more recently several Maillard-like compounds have been identified in typical and ageing aromas of champagne wines (thiazoles and oxazoles like: 2,4-dimethylthiazole, 4-methylthiazole, 2-acetylthiazole, 2-acetyl-2-thiazoline, or 2,4,5-trimethyloxazole; and furanthiols like furan-2-yl-methanethiol) (Keim, de Revel, Marchand, & Bertrand, 2002;Tominaga, Guimbertau, & Dubourdieu, 2003) Formation of 3DG has been evaluated in model systems (Usui et al, 2007;Fiedler & Kroh, 2007;Golon & Kuhnert, 2013), biological samples (Hoffman, Kappler, Passmore, & Mehta, 2003;Hurtado-Sanchez, Espinosa-Mansilla, Rodrıguez-Caceres, Martın-Tornero & Durán-Merás, 2012), and food products such as: sake (Oka, 1969), soy sauce (Hashiba, 1976;Kim & Lee, 2008), balsamic vinegars (Daglia, Amoroso, Rossi, Mascherpa, & Maga, 2013), carbonated soft drinks (Gensberger, Glomb, & Pischetsrieder, 2013), milk products (Hellwig, Degen, & Henle, 2010), high-fructose corn syrups (Lo et al, 2008;Gensberger, Mittelmaier, Glomb, & Pischetsrieder, 2012;RuizMatute, Vazquez, Hernández-Hernández, Sanza, & Martínez-Castro, 2015), beers (Bravo et al, 2008;Hellwig, Nobis, Witte, & Henle, 2016), commercial honey samples (Weigel, Opitz, & Henle, 2004;Mavric, Wittmann, Barth, & Henle, 2008;Marceau & Yaylayan, 2009;Ruiz-Matute et al, 2015), bee feeds (Ruiz-Matute et al, 2015), coffee substitutes (Ruiz-Matute et al, 2015), baby foods (Kocadağlı & Gökmen, 2014) and wines (in nonsweet wines: 2.2 to 13.5 mg·L -1 ; and in sweet wines: 39 to 133 mg·L -1 ) ( Therefore, dry white and sweet red Port wines were derivatized with orthophenylenediamine and the corresponding 3DG quinoxalines determined by HPLC with photodiode array detector (HPLC-DAD) coupled to tandem mass spectrometry (MS n ). In orde...…”

Insights into chemical and sensorial aspects to understand and manage beer aging using chemometrics

“…Although mostly known for its role in food appearance and flavor, the Maillard reaction gained attention as several Maillard and Maillard-derivate products are known as beer aging compounds (Table 1). Great importance has been given to α-dicarbonyl compounds in recent studies on beer aging as they contribute to beer flavor instability, and are related to aged flavor (Hellwig, Nobis, Witte, & Henle, 2016;Kanzler, Schestkowa, Haase, & Kroh Fermentation by-product Banana, estery Secondary (Lee, Villa, Patino, & Company, 1995;Saison et al, 2009Saison et al, , 2010Stenroos, 1973) (e,e)-2,4-decadienal Oxidation of lineic acid Deep-fried, papery…”