Human taste and umami receptor responses to chemosensorica generated by Maillard-type N²-alkyl- and N²-arylthiomethylation of guanosine 5'-monophosphates.
Structural modification of the exocyclic amino function of guanosine 5'-monophosphate (5'-GMP) by Maillard-type reactions with reducing carbohydrates was recently found to increase the umami-enhancing activity of the nucleotide upon S-N(2)-1-carboxyalkylation and S-N(2)-(1-alkylamino)carbonylalkylation, respectively. Since the presence of sulfur atoms in synthetic N(2)-alkylated nucleotides was reported to be beneficial for sensory activity, a versatile Maillard-type modification of 5'-GMP upon reaction with glycine's Strecker aldehyde formaldehyde and organic thiols was performed in the present study. A series of N(2)-(alkylthiomethyl)guanosine and N(2)-(arylthiomethyl)guanosine 5'-monophosphates was generated and the compounds were evaluated to what extent they enhance the umami response to monosodium L-glutamate in vivo by a paired-choice comparison test using trained human volunteers and in vitro by means of cell-based umami taste receptor assay. Associated with a high umami-enhancing activity (β-value 5.1), N(2)-(propylthiomethyl)guanosine 5'-monophosphate could be generated when 5'-GMP reacted with glucose, glycine, and the onion-derived odorant 1-propanethiol, thus opening a valuable avenue to produce high-potency umami-enhancing chemosensorica from food-derived natural products by kitchen-type chemistry.
Chair of Food Chemistry and Molecular Sensory Science, Technische Universität München , Lise-Meitner-Straße 34, D-85354 Freising-Weihenstephan, Germany.
Barbara
B
Suess
Anne
A
Brockhoff
Andreas
A
Degenhardt
Sylvia
S
Billmayer
Wolfgang
W
Meyerhof
Thomas
T
Hofmann
D000328:Adult; D002851:Chromatography, High Pressure Liquid; D005260:Female; D006157:Guanosine Monophosphate / Q000031:analogs & derivatives* / Q000737:chemistry*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D008297:Male; D043562:Receptors, G-Protein-Coupled / Q000378:metabolism*; D012970:Sodium Glutamate / Q000008:administration & dosage; D013440:Sulfides / Q000737:chemistry*; D053719:Tandem Mass Spectrometry; D013649:Taste / Q000502:physiology*; D055815:Young Adult
D043562:Receptors, G-Protein-Coupled; D013440:Sulfides; C431926:taste receptors, type 1; D006157:Guanosine Monophosphate; D012970:Sodium Glutamate
Maillard reaction; chemosensorica; guanosine 5′-monophosphate; taste enhancer; umami