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H/D Exchange Processes in Flavonoids: Kinetics and Mechanistic Investigations.

Authors
  • Bonaldo, Federico1
  • Mattivi, Fulvio2
  • Catorci, Daniele1
  • Arapitsas, Panagiotis3
  • Guella, Graziano1
  • 1 Bioorganic Chemistry Laboratory, Department of Physics, University of Trento, 38123 Trento, Italy. , (Italy)
  • 2 Department of Cellular, Computational and Integrative Biology-CIBIO and C3A, University of Trento, 38123 Povo Trento, Italy. , (Italy)
  • 3 Department of Food Quality and Nutrition, Research and Innovation Centre, Fondazione Edmund Mach (FEM), 38098 San Michele all'Adige, Italy. , (Italy)
Type
Published Article
Journal
Molecules
Publisher
MDPI AG
Publication Date
Jun 10, 2021
Volume
26
Issue
12
Identifiers
DOI: 10.3390/molecules26123544
PMID: 34200677
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

Several classes of flavonoids, such as anthocyanins, flavonols, flavanols, and flavones, undergo a slow H/D exchange on aromatic ring A, leading to full deuteration at positions C(6) and C(8). Within the flavanol class, H-C(6) and H-C(8) of catechin and epicatechin are slowly exchanged in D2O to the corresponding deuterated analogues. Even quercetin, a relevant flavonol representative, shows the same behaviour in a D2O/DMSOd6 1:1 solution. Detailed kinetic measurements of these H/D exchange processes are here reported by exploiting the time-dependent changes of their peak areas in the 1H-NMR spectra taken at different temperatures. A unifying reaction mechanism is also proposed based on our detailed kinetic observations, even taking into account pH and solvent effects. Molecular modelling and QM calculations were also carried out to shed more light on several molecular details of the proposed mechanism.

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