Occurrence of (Z)-3,4-Dideoxyglucoson-3-ene in Different Types of Beer and Malt Beer as a Result of 3-Deoxyhexosone Interconversion
Publikation: Beitrag in Fachzeitschrift › Forschungsartikel › Beigetragen › Begutachtung
Beitragende
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).
Details
Originalsprache | Englisch |
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Seiten (von - bis) | 2746-2753 |
Seitenumfang | 8 |
Fachzeitschrift | Journal of Agricultural and Food Chemistry |
Jahrgang | 64 |
Ausgabenummer | 13 |
Publikationsstatus | Veröffentlicht - 6 Apr. 2016 |
Peer-Review-Status | Ja |
Externe IDs
Scopus | 84964319645 |
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WOS | 000373747800012 |
ORCID | /0000-0001-8528-6893/work/166765106 |
Schlagworte
Schlagwörter
- Maillard reaction, glycation, beer, malt beer, 3,4-dideoxyglucoson-3-ene, 3,4-DGE, 3-deoxygalactosone, 3-deoxyglucosone, ALPHA-DICARBONYL COMPOUNDS, PERITONEAL-DIALYSIS FLUIDS, MAILLARD REACTION, 3-DEOXYGLUCOSONE, QUANTIFICATION, METHYLGLYOXAL, CYTOTOXICITY, DEGRADATION, 3,4-DIDEOXYGLUCOSONE-3-ENE, HPLC