Reduction of 5-Hydroxymethylfurfural and 1,2-Dicarbonyl Compounds by Saccharomyces cerevisiae in Model Systems and Beer,Journal of Agricultural and Food Chemistry

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Reduction of 5-Hydroxymethylfurfural and 1,2-Dicarbonyl Compounds by Saccharomyces cerevisiae in Model Systems and Beer
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2021-10-21 , DOI: 10.1021/acs.jafc.1c04760
Michael Hellwig _{1,

2} , Marie Börner ₂ , Thomas Henle ₂

Affiliation

Glycation and caramelization reactions in malt lead to the formation of 1,2-dicarbonyl compounds, which come in contact with yeast during fermentation. In the present study, the metabolic fate of 5-hydroxymethylfurfural (HMF) and 1,2-dicarbonyl compounds (3-deoxyglucosone, 3-deoxygalactosone, 3-deoxypentosone, 3,4-dideoxyglucosone-3-ene) was assessed in the presence of Saccharomyces cerevisiae. HMF is degraded very fast by yeast with the formation of 2,5-bis(hydroxymethyl)furan (BHMF). By contrast, only 7–30% of 250 μM dicarbonyl compounds is degraded within 48 h. The respective deoxyketoses, 3-deoxyfructose (3-DF), 3-deoxytagatose, 3-deoxypentulose, and 3,4-dideoxyfructose, were identified as metabolites. While 17.8% of 3-deoxyglucosone was converted to 3-deoxyfructose, only about 0.1% of 3-deoxypentosone was converted to 3-deoxypentulose during 48 h. Starting with the parent dicarbonyl compounds, the synthesis of all deoxyketose metabolites was achieved by applying a metal-catalyzed reduction in the presence of molecular hydrogen. In a small set of commercial beer samples, BHMF and all deoxyketoses were qualitatively detected. 3-DF was quantitated in the four commercial beer samples at concentrations between 0.4 and 10.1 mg/L.

中文翻译：

酿酒酵母在模型系统和啤酒中还原 5-羟甲基糠醛和 1,2-二羰基化合物

麦芽中的糖化和焦糖化反应导致 1,2-二羰基化合物的形成，这些化合物在发酵过程中与酵母接触。在本研究中，评估了 5-羟甲基糠醛 (HMF) 和 1,2-二羰基化合物（3-脱氧葡萄糖酮、3-脱氧半乳糖、3-脱氧戊酮、3,4-双脱氧葡萄糖酮-3-烯）的代谢归宿。的酿酒酵母. HMF 被酵母快速降解，形成 2,5-双（羟甲基）呋喃 (BHMF)。相比之下，250 μM 二羰基化合物中只有 7-30% 在 48 小时内降解。相应的脱氧酮糖、3-脱氧果糖 (3-DF)、3-脱氧塔格糖、3-脱氧戊酮糖和 3,4-双脱氧果糖被鉴定为代谢物。虽然 17.8% 的 3-脱氧葡萄糖酮转化为 3-脱氧果糖，但在 48 小时内只有约 0.1% 的 3-脱氧戊酮糖转化为 3-脱氧戊酮糖。从母体二羰基化合物开始，所有脱氧酮糖代谢物的合成都是通过在分子氢存在下应用金属催化还原来实现的。在一小部分商业啤酒样品中，定性检测到 BHMF 和所有脱氧酮症。对四种商业啤酒样品中的 3-DF 进行了定量分析，浓度介于 0.4 和 10.1 mg/L 之间。

更新日期：2021-11-03

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