%0 Journal Article %T Lipid bilayer membrane affinity rationalizes inhibition of lipid peroxidation by a natural lignan antioxidant. %+ Department of Physical Chemistry %+ Pharmacologie des Immunosuppresseurs et de la Transplantation (PIST) %+ Laboratoire de Chimie des Substances Naturelles (LCSN) %+ Service de Chimie des Matériaux Nouveaux %A Podloucká, Pavlína %A Berka, Karel %A Fabre, Gabin %A Paloncýová, Markéta %A Duroux, Jean-Luc %A Otyepka, Michal %A Trouillas, Patrick %Z The authors gratefully acknowledge support from the Operational Program Research and Development for Innovations European Regional Development Fund (project CZ.1.05/ 2.1.00/03.0058 of the Ministry of Education, Youth and Sports of the Czech Republic), the Operational Program Education for CompetitivenessEuropean Social Fund (projects CZ.1.07/ 2.3.00/20.0017 and CZ.1.07/2.3.00/20.0058 of the Ministry of Education, Youth and Sports of the Czech Republic), and the Grant Agency of the Czech Republic (P208/12/G016). The authors also thank the "Conseil Régional du Limousin" for financial support and CALI (CAlcul en LImousin). The research based in Limoges was also supported by the COST action CM0804 "Chemical Biology with Natural Compounds". %< avec comité de lecture %@ 1520-6106 %J Journal of Physical Chemistry B %I American Chemical Society %V 117 %N 17 %P 5043-9 %8 2013-05-02 %D 2013 %R 10.1021/jp3127829 %M 23560800 %Z Life Sciences [q-bio]/Pharmaceutical sciencesJournal articles %X Lipid peroxidation is a degenerative oxidative process that modifies the structure of membranes, influencing their biological functions. Lignans, natural polyphenolic antioxidants widely distributed in plants, can prevent this membrane damage by free-radical scavenging. Here, we rationalize the difference in lipid peroxidation inhibition activity of argenteane, a natural dilignan isolated from wild nutmeg, and 3,3'-dimethoxy-1,1'-biphenyl-2,2'-diol, which represents the central part of argenteane responsible for its antioxidant activity. Although both compounds have the same capacity to scavenge free radicals, argenteane is a more active inhibitor of lipid peroxidation. We show that both compounds penetrate into DOPC and PLPC lipid bilayers and adopt similar positions and orientations, which therefore does not explain the difference in their lipid peroxidation inhibition activity. However, free energy profiles indicate that argenteane has a significantly higher affinity to the lipid bilayer, and thus a higher effective concentration to scavenge radicals formed during lipid peroxidation. This finding explains the higher activity of argenteane to inhibit lipid peroxidation. %G English %2 https://inserm.hal.science/inserm-00835586/document %2 https://inserm.hal.science/inserm-00835586/file/JPCB_2013.pdf %L inserm-00835586 %U https://inserm.hal.science/inserm-00835586 %~ INSERM %~ UNILIM %~ CNRS %~ UMR-S850 %~ LCSN %~ GEIST %~ IPPRITT %~ PEIRENE %~ OMEGAHEALTH