Polyphenols deriving from chalcones: investigations of redox activities.
The redox properties of a series of hydroxychalcones (a group of polyphenols abundantly present in plants) were investigated by cyclic voltammetry. As for many polyphenols, their beneficial properties have been mainly related to their antioxidant activities, which in turn are directly associated to their redox behavior. Two types of radicals can be produced that are localized on either one of the two aromatic systems. Their thermodynamic and kinetic parameters were extracted and compared to the predictions of density functional theory calculations. When at least one OH is present on each ring, their behaviors are dominated by the conjugated system: phenolic ring A-double bond-ketone, which is the only one to be oxidized. However, the redox properties of this conjugated system are strongly influenced by the presence of ring B. When an OH is present on ring B, an important feature is the existence of strong hydrogen bonding that remains almost unmodified even when ring A is oxidized. It does not considerably change the thermodynamics of ring A but strongly increases the rigidity of the molecule that remains planar under the neutral, anionic, or radical forms. Oxidation potentials of the phenolates range between 0.1 and 0.2 V versus a saturated calomel electrode, which correspond to species that are very easy to oxidize and lead to the rapid formation of nonradical species, underlining the potential antioxidant properties of these molecules.
Cotelle
Nicole
N
Laboratoire de Chimie Organique et Macromoléculaire, UMR CNRS-Université des Sciences et Technologies de Lille, N 8009, F-59655 Villeneuve d'Ascq Cedex, France.
Hapiot
Philippe
P
Pinson
Jean
J
Rolando
Christian
C
Vézin
Hervé
H
D000465:Algorithms; D047188:Chalcones / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D004563:Electrochemistry; D005419:Flavonoids / Q000737:chemistry*; D006860:Hydrogen Bonding; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*; D059808:Polyphenols
D047188:Chalcones; D005419:Flavonoids; D010636:Phenols; D059808:Polyphenols; D004121:Dimethyl Sulfoxide