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| - Radical Scavenging Potential of Phenolic CompoundsEncountered in O. europaea Products as Indicated byCalculation of Bond Dissociation Enthalpy and IonizationPotential Values
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| - The radical scavenging potential of phenolic compounds occurring in Oleaeuropaea and of recentlyidentified hydroxytyrosol metabolites was evaluated by means of quantum chemical calculations.The bond dissociation enthalpy (BDE) of phenolic hydroxyl groups and the ionization potential (IP)were calculated as descriptors to predict the H-atom-donating and electron-donating abilities ofantioxidants, respectively. Catechol derivatives had the lowest BDE values (77.7−80.1 kcal/mol)whereas the lignans, pinoresinol and 1-acetoxypinoresinol, and other monophenols had much higherBDE values (85.1−88.0 kcal/mol), which suggested a lower potential for radical scavenging. Sidechain characteristics were not found to affect the size of BDE values although differences in lipophilicity(on the basis of calculated Log P values) indicate variability in the activity in real systems. Conclusionsfor the antioxidant potential could not be drawn based on the IP values. Lack of experimental datafor most of the studied compounds due to oxidative instability and difficulties in synthesis or isolationsupports the usefulness of a computational approach for those interested in the antioxidant potentialof phenolics encountered in O. europaea products. Keywords: Bond dissociation enthalpy; density functional theory; ionization potential; lignans; O.europaea products; oleuropein; hydroxytyrosol metabolites
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