Effect of resveratrol-related stilbenoids on biomembrane models

The interactions of the two resveratrol analogues 2-hydroxy-3,5,3′,5′-tetramethoxystilbene (4) and 2-hydroxy-3,5,3′,4′-tetramethoxystilbene (5) with modelbiomembranes were studied. The aim of this investigation was to highlight possibledifferences in the interactions with such biomembranes related to the minimal structuraldifferences between these isomeric stilbenoids. In particular, different experiments onstilbenoid/biomembrane model systems using both differential scanning calorimetry(DSC) and Langmuir−Blodgett techniques were carried out to evaluate stilbenoid/multilamellar vesicle and stilbenoid/phospholipid monolayer interactions, respectively.Dimyristoylphosphatidylcholine was used as constituent of the biomembrane models andpermitted the experiments to be carried out at 37 °C, close to body temperature. Kineticstudies were also run by DSC to evaluate the uptake of the resveratrol derivatives by thebiomembrane model in an aqueous medium and when transported by a lipophilic carrier.The results indicated that both of the resveratrol analogues influenced the behavior of multilamellar vesicles and monolayers,biomembrane models, with 4 producing a larger effect than 5. These results are useful for better understanding the mechanism ofaction of these compounds. Moreover, the kinetic results could be of importance for future design of lipophilic delivery systemsfor these stilbenoids.