Simulated Sunlight Selectively Modifies Maillard Reaction Products in a Wide Array of Chemical Reactions.
Maillard reaction
advanced glycation
photochemistry
photooxidation
reactive oxygen species
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
11 Oct 2019
11 Oct 2019
Historique:
received:
18
06
2019
pubmed:
18
7
2019
medline:
18
7
2019
entrez:
18
7
2019
Statut:
ppublish
Résumé
The photochemical transformation of Maillard reaction products (MRPs) under simulated sunlight into mostly unexplored photoproducts is reported herein. Non-enzymatic glycation of amino acids leads to a heterogeneous class of intermediates with extreme chemical diversity, which is of particular relevance in processed and stored food products as well as in diabetic and age-related protein damage. Here, three amino acids (lysine, arginine, and histidine) were reacted with ribose at 100 °C in water for ten hours. Exposing these model systems to simulated sunlight led to a fast decay of MRPs. The photodegradation of MRPs and the formation of new compounds have been studied by fluorescence spectroscopy and nontargeted (ultra)high-resolution mass spectrometry. Photoreactions showed strong selectivity towards the degradation of electron-rich aromatic heterocycles, such as pyrroles and pyrimidines. The data show that oxidative cleavage mechanisms dominate the formation of photoproducts. The photochemical transformations differed fundamentally from "traditional" thermal Maillard reactions and indicated a high amino acid specificity.
Identifiants
pubmed: 31314140
doi: 10.1002/chem.201902804
pmc: PMC6856810
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
13208-13217Informations de copyright
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
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