Isolation and Identification of Novel Taste-Modulating N2-Guanosine 5′-Monophosphate Derivatives Generated by Maillard-Type Reactions,Journal of Agricultural and Food Chemistry

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Isolation and Identification of Novel Taste-Modulating N2-Guanosine 5′-Monophosphate Derivatives Generated by Maillard-Type Reactions
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-06-13 , DOI: 10.1021/acs.jafc.4c03485
Daniela M Hartl ₁ , Oliver Frank ₁ , Victoria S Hänel ₁ , Vinzenz Heigl ₁ , Corinna Dawid _{1,

2} , Thomas F Hofmann ₁

Affiliation

Several compounds with taste-modulating properties have been investigated, improving the taste impression without having a pronounced intrinsic taste. The best-known representatives of umami taste-modulating compounds are ribonucleotides and their derivatives. Especially the thio derivatives showed high taste-modulating potential in structure–activity relationship investigations. Therefore, this study focuses on the formation of guanosine 5′-monophosphate derivatives consisting of Maillard-type generated compounds like the aroma-active thiols (2-methyl-3-furanthiol, 3-mercapto-2-pentanone, 2-furfurylthiol) and formaldehyde to gain insights into the potential of combinations of taste and aroma-active compounds. One literature-known (N²-(furfurylthiomethyl)-guanosine 5′-monophosphate) and three new derivatives (N²-(2-methyl-1-furylthiomethyl)-guanosine 5′-monophosphate, N²-((5-hydroxymethyl)-2-methyl-1-furylthiomethyl)-guanosine 5′-monophosphate, N²-((2-pentanon-1-yl)thiomethyl)-guanosine 5′-monophosphate) were successfully produced using green natural deep eutectic solvents and isolated, and their structures were completely elucidated. Besides the intrinsic taste properties, the kokumi and umami taste-modulating effects of the four derivatives were evaluated via psychophysical investigations, ranging from 19 to 22 μmol/L.

中文翻译：

美拉德反应生成的新型口味调节 N2-鸟苷 5'-单磷酸衍生物的分离和鉴定

已经研究了几种具有味道调节特性的化合物，改善了味道印象，但没有明显的内在味道。鲜味调节化合物最著名的代表是核糖核苷酸及其衍生物。尤其是硫代衍生物在构效关系研究中表现出很高的味道调节潜力。因此，本研究重点关注由美拉德型生成的化合物组成的鸟苷 5′-单磷酸衍生物的形成，例如芳香活性硫醇（2-甲基-3-呋喃硫醇、3-巯基-2-戊酮、2-糠基硫醇）和甲醛，以深入了解味道和香气活性化合物组合的潜力。一种文献已知的（ N ² -(糠硫基甲基)-鸟苷 5'-单磷酸）和三种新衍生物（ N ² -(2-甲基-1-呋喃硫甲基)-鸟苷 5'-单磷酸、 N ² -((5-羟甲基利用绿色天然低共熔溶剂成功生产了)-2-甲基-1-呋喃硫甲基)-鸟苷5′-单磷酸、 N ² -((2-戊酮-1-基)硫甲基)-鸟苷5′-单磷酸)并分离得到，并且它们的结构被完全阐明。除了内在的味道特性外，四种衍生物的浓味和鲜味味道调节作用还通过心理物理学研究进行了评估，浓度范围为 19 至 22 μmol/L。

更新日期：2024-06-13

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