Isolation and Identification of Novel Taste-Modulating N 2‑Guanosine 5′-Monophosphate Derivatives Generated by Maillard-Type Reactions

• Published in: Journal of agricultural and food chemistry Vol. 72; no. 25; pp. 14284 - 14293
• Main Authors: Hartl, Daniela M., Frank, Oliver, Hänel, Victoria S., Heigl, Vinzenz, Dawid, Corinna, Hofmann, Thomas F.
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 26.06.2024; Amer Chemical Soc
• Subjects: Adult; Agriculture; Agriculture, Multidisciplinary; Chemistry; Chemistry and Biology of Aroma and Taste; Chemistry, Applied; Female; Flavoring Agents - chemistry; Food Science & Technology; Guanosine Monophosphate - chemistry; Humans; Life Sciences & Biomedicine; Maillard Reaction; Male; Molecular Structure; Physical Sciences; Science & Technology; Taste; Young Adult; Maillard-type model reactions; umami; taste modulating; 2-methyl-3-furanthiol; guanosine 5′-monophosphate derivatives; Maillard-typemodel reactions; ENHANCING ACTIVITY; SENSORY CHARACTERIZATION; guanosine 5 '-monophosphate derivatives; DISCOVERY; MONOSODIUM GLUTAMATE; N-2-ALKYL; GLUTATHIONE; CONTRIBUTORS; RECEPTORS; UMAMI TASTE; FLAVOR
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.4c03485

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 (N 2-(furfurylthiomethyl)-guanosine 5′-monophosphate) and three new derivatives (N 2-(2-methyl-1-furylthiomethyl)-guanosine 5′-monophosphate, N 2-((5-hydroxymethyl)-2-methyl-1-furylthiomethyl)-guanosine 5′-monophosphate, N 2-((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.