title: Lipid bilayer membrane affinity rationalizes inhibition of lipid peroxidation by a natural lignan antioxidant.
abstract: 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.
authors.affiliation: Regional Centre of Advanced Technologies and Materials, Department of Physical Chemistry, Faculty of Science, Palacký University, tř. 17 listopadu 12, 771 46 Olomouc, Czech Republic.
authors.forename: Pavlína
authors.initials: P
authors.lastname: Podloucká
authors.forename: Karel
authors.initials: K
authors.lastname: Berka
authors.forename: Gabin
authors.initials: G
authors.lastname: Fabre
authors.forename: Markéta
authors.initials: M
authors.lastname: Paloncýová
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Duroux
authors.forename: Michal
authors.initials: M
authors.lastname: Otyepka
authors.forename: Patrick
authors.initials: P
authors.lastname: Trouillas
mesh_terms: D000975:Antioxidants / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry*; D008051:Lipid Bilayers / Q000737:chemistry*; D015227:Lipid Peroxidation; D013816:Thermodynamics
chemical_list: D000975:Antioxidants; D017705:Lignans; D008051:Lipid Bilayers