Computational Studies of Free Radical-Scavenging Properties of Phenolic Compounds

Abstract

For more than half a century free radical-induced alterations at cellular and organ levels have been investigated as a probable underlying mechanism of a number of adverse health conditions. Consequently, significant research efforts have been spent for discovering more effective and potent antioxidants / free radical scavengers for treatment of these adverse conditions. Being by far the most used antioxidants among natural and synthetic compounds, mono- and polyphenols have been the focus of both experimental and computational research on mechanisms of free radical scavenging. Quantum chemical studies have provided a significant amount of data on mechanisms of reactions between phenolic compounds and free radicals outlining a number of properties with a key role for the radical scavenging activity and capacity of phenolics. The obtained quantum chemical parameters together with other molecular descriptors have been used in quantitative structure-activity relationship (QSAR) analyses for the design of new more effective phenolic antioxidants and for identification of the most useful natural antioxidant phenolics. This review aims at presenting the state of the art in quantum chemical and QSAR studies of phenolic antioxidants and at analysing the trends observed in the field in the last decade.

Antioxidant Properties of Kynurenines: Density Functional Theory Calculations

“…The hydroxyl group BDE and adiabatic IP are the most important determinants for the radical scavenging activity of substituted phenols [55]. According to our data, the antioxidant properties of 3HOK and 3HAA are determined by their 2-aminophenolic moiety.…”

“…High radical stability and even spin distribution are among the factors predisposing low BDE and IP values [55]. Conjugated bonds system facilitates electron delocalization after HAT or single electron transfer (SET).…”

Bond dissociation energies and enthalpies of formation of flavonoids: A G4 and M06-2X investigation

“…In order to facilitate the discussion of the B-OH bond dissociation energies at 0K (BDE, hereafter) we have numbered the atoms of the flavonoids following the notation used in previous works [10][11][12][13][14][15][16]. This can be seen in Figure 1.…”

“…For this reason, several investigations have been conducted to identify the sites where the lowest CO-H bond dissociation energies (BDE) can be found [10][11][12][13][14][15][16][17]. Almost all of the determinations hitherto available for C-OH BDE were obtained at the DFT level [10][11][12][13][14][15][16].…”

Capture and Purification of Polyphenols Using Functionalized Hydrophobic Resins

“…1 These molecules are secondary metabolites naturally produced by plants, which can act as radical scavengers due to the high stabilization provided by ring aromaticity. 2 Over the last years, research on their health properties has grown considerably, 3 with authors studying the properties of these molecules in the prevention of diseases such as Alzheimer’s and several types of cancer. 4 Furthermore, the increasing interest in these compounds has led to the creation of projects such as the BacHBerry project (), funded by the seventh Framework Programme of the European commission.…”