Sakuranetin interacting with cell membranes models: Surface chemistry combined with molecular simulation

Sakuranetin, a natural compound with activity in lipidic biointerfaces, was isolated from Baccharis retusa and studied with two models of lipid membranes: Langmuir monolayers and Molecular Simulation. For that, the mammalian lipid DPPC was chosen. Sakuranetin condensed the monolayers at high surface pressures, decreased the surface compressional modulus, reduced the molecular order of the acyl chains (diminution of all-trans/gauche conformers ratio), and increased the heterogeneity of the interface, forming aggregates. Molecular simulation data gave information on the bioactive compound's most favorable thermodynamic positions along the lipid monolayer, which was the lipid-air interface. These combined results lead to the conclusion that this lipophilic compound may interact with the lipidic layers, preferentially at the lipid-air interface, to minimize the free energy, and reaches this conformation disturbing the thermodynamic, structural, mechanical, rheological, and morphological properties of the well-packed DPPC monolayer.