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Yeast Metabolites of Glycated Amino Acids in Beer
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2018-05-10 00:00:00 , DOI: 10.1021/acs.jafc.8b01329 Michael Hellwig 1 , Falco Beer 1 , Sophia Witte 1 , Thomas Henle 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2018-05-10 00:00:00 , DOI: 10.1021/acs.jafc.8b01329 Michael Hellwig 1 , Falco Beer 1 , Sophia Witte 1 , Thomas Henle 1
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Glycation reactions (Maillard reactions) during the malting and brewing processes are important for the development of the characteristic color and flavor of beer. Recently, free and protein-bound Maillard reaction products (MRPs) such as pyrraline, formyline, and maltosine were found in beer. Furthermore, these amino acid derivatives are metabolized by Saccharomyces cerevisiae via the Ehrlich pathway. In this study, a method was developed for quantitation of individual Ehrlich intermediates derived from pyrraline, formyline, and maltosine. Following synthesis of the corresponding reference material, the MRP-derived new Ehrlich alcohols pyrralinol (up to 207 μg/L), formylinol (up to 50 μg/L), and maltosinol (up to 6.9 μg/L) were quantitated for the first time in commercial beer samples by reverse phase high performance liquid chromatography tandem mass spectrometry in the multiple reaction monitoring mode. This is equivalent to ca. 20–40% of the concentrations of the parent glycated amino acids. The metabolites were almost absent from alcohol-free beers and malt-based beverages. Two previously unknown valine-derived pyrrole derivatives were characterized and qualitatively identified in beer. The metabolites investigated represent new process-induced alkaloids that may influence brewing yeast performance due to structural similarities to quorum sensing and metal-binding molecules.
中文翻译：
啤酒中糖化氨基酸的酵母代谢产物
麦芽和酿造过程中的糖基化反应（美拉德反应）对于开发啤酒的独特颜色和风味非常重要。最近，在啤酒中发现了游离的且与蛋白质结合的美拉德反应产物（MRP），例如吡喃啉，甲酰胆碱和麦芽糖苷。此外，这些氨基酸衍生物被酿酒酵母代谢。通过埃里希路径。在这项研究中，开发了一种方法用于定量从吡喃啉，甲酸，和麦芽糖碱衍生的单个Ehrlich中间体。合成相应的参考物质后，首先对MRP衍生的新Ehrlich醇吡咯诺尔（最高207μg/ L），甲醛（最高50μg/ L）和麦芽酚（最高6.9μg/ L）进行定量。反相高效液相色谱串联质谱法在多反应监测模式下测定商业啤酒样品中的时间。这相当于ca。母体糖基化氨基酸浓度的20–40％。无酒精啤酒和麦芽饮料几乎不含代谢产物。在啤酒中对两种先前未知的缬氨酸衍生的吡咯衍生物进行了表征和定性鉴定。
更新日期：2018-05-10
中文翻译：
啤酒中糖化氨基酸的酵母代谢产物
麦芽和酿造过程中的糖基化反应（美拉德反应）对于开发啤酒的独特颜色和风味非常重要。最近，在啤酒中发现了游离的且与蛋白质结合的美拉德反应产物（MRP），例如吡喃啉，甲酰胆碱和麦芽糖苷。此外，这些氨基酸衍生物被酿酒酵母代谢。通过埃里希路径。在这项研究中，开发了一种方法用于定量从吡喃啉，甲酸，和麦芽糖碱衍生的单个Ehrlich中间体。合成相应的参考物质后，首先对MRP衍生的新Ehrlich醇吡咯诺尔（最高207μg/ L），甲醛（最高50μg/ L）和麦芽酚（最高6.9μg/ L）进行定量。反相高效液相色谱串联质谱法在多反应监测模式下测定商业啤酒样品中的时间。这相当于ca。母体糖基化氨基酸浓度的20–40％。无酒精啤酒和麦芽饮料几乎不含代谢产物。在啤酒中对两种先前未知的缬氨酸衍生的吡咯衍生物进行了表征和定性鉴定。
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