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Positioning of Antioxidant Quercetin and Its Metabolites in Lipid Bilayer Membranes: Implication for Their Lipid-Peroxidation Inhibition

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LCSN−EA1069, School of Pharmacy, Université de Limoges, 2 rue du Dr. Marcland, 87025 Limoges, France
Regional Center of Advanced Technologies and Materials, Department of Physical Chemistry, Faculty of Science, Palacký University, 17. listopadu 1192/12, 77146 Olomouc, Czech Republic
§ Laboratoire de Chimie des Matériaux Nouveaux, Université de Mons, Place du Parc 20, 7000 Mons, Belgium
Cite this: J. Phys. Chem. B 2012, 116, 4, 1309–1318
Publication Date (Web):December 27, 2011
Copyright © 2011 American Chemical Society

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    Among numerous biological activities, natural polyphenols are antioxidants widely distributed in plants capable of inhibiting lipid peroxidation, which belongs to the most serious degenerative cell processes. Positioning of antioxidants in lipid bilayers can provide an insight to the lipid-peroxidation inhibition at the molecular level. This work aims at determining the location and orientation of quercetin and its most representative (glucuronidated, methylated, and sulfated) metabolites in lipid bilayer via molecular dynamic simulations. We show that quercetin derivatives penetrate the lipid bilayer and that the depths of penetration depend on molecular charge and substitutional variations. In the presence of charged substituents (sulfates and glucuronidates), the molecule is pulled toward the lipid bilayer surface. The orientation also depends on substitution as H-bonds are formed between the polar head groups of the bilayer and the (i) OH groups, (ii) sugar, and (iii) sulfate moieties of the antioxidants. As flavonoids and their derivatives are preferentially localized in the lipid bilayer membrane or on the bilayer/water interface, they readily concentrate in a relatively narrow membrane region. Despite the low concentrations of flavonoids in food, their spatial confinement in the membrane greatly enhances their local concentration in this vital region, thus increasing their importance for in vivo biological activities including oxidative stress defense.

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    Position of the center of mass along the MD simulations for all compounds (molecules described by RESP charges and PRODRG charges), distribution curve of angle defined by bilayer normal and plane defined by atoms C2, C3, and C6 of quercetin (molecules described by RESP charges and PRODRG charges), number densities describing position of compounds in lipid bilayer (compounds described by PRODRG charges), free energy profile for quercetin described by PRODRG charges, average distances of different molecule groups from membrane center, average number of H-bonds (compounds described by PRODRG charges), atomic partial charges and dipole moments of quercetin obtained by different RESP methods, and atomic partial charges of atoms obtained by PRODRG and RESP method. This material is available free of charge via the Internet at

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