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QSAR study of anthocyanins, anthocyanidins and catechin as inhibitors of lipid peroxidation

Catechins, anthocyanidins and their glycoside – anthocyanins, compounds that belong to the natural antioxidant - polyphenols, present in foods of plant origin, are potentially beneficial to human health. Antioxidative effects of those phytochemicals are based on the ability to scavenge different free radicals or the protection of biological molecules against oxidation. In the present study lipid peroxidation inhibitory effect [1] of mentioned polyphenols is correlated with molecular descriptors and physicochemical parameters calculated from three-dimensional structure, since studied compounds contain stereoisomers with different activities. Six groups of 3D descriptors have been used to generate a quantitative structure-activity relationship (QSAR) models: geometrical ; GETAWAY (Geometry, Topology, and Atom Weights AssemblY) ; 3D-MoRSE, RDF (Radial Distribution Function) descriptors ; Randic molecular profiles and WHIM (WeigHted Covariance Matrices) descriptors. Geometries of molecules were optimized using the molecular mechanic MM+ force field method applying the HyperChem 8.0 Evaluation software package. The 3D molecular descriptors used in this study have been calculated applying the on-line software Parameter Client (PCLIENT), an extension of E-Dragon. Physicochemical parameters (connolly accessible area, connolly molecular area, connolly solvent excluded volume, ovality, volume and surface area of molecule and hydration energy) were calculated using HyperChem 8.0 and Chem3D Ultra 10 Trial Version. Only 3D molecular descriptors and physicochemical parameters with ability to discriminate stereoisomers were chosen for multiple regression analysis. The selection of predictor variables for multiple regression was performed by best-subset method. Present work should provide the better understanding of structural factors that relate the antioxidant activity of polyphenols.

QSAR; anthocyanins; anthocyanidins; catechin; lipid peroxidation

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