Differences between coumaric and cinnamic acids in membrane permeation as evidenced by time-dependent calorimetry.
We carried out an investigation by differential scanning calorimetry (DSC) on the effect of two structurally similar bioactive plant phenols, cinnamic and p-coumaric acids, on the phase transition of model membranes constituted by dimyristoylphosphatidylcholine (DMPC) vesicles. The aim was to evaluate how pH and molecular substituents influence liposolubility and thereby modify vesicle permeability. A change in permeability would result in modifications to the phase transition for DMPC liposomes such that the transition temperature would be lowered and the enthalpy changes should be little affected. Evidence of differences in permeability was obtained by comparing the effects exerted by the two compounds left in touch with unilamellar and multilamellar vesicles, at two different pHs (4 and 7.4). While the p-coumaric acid was unable to appreciably modify the thermotropic behavior of the model membrane, the cinnamic acid interacted with lipid vesicles at both pH's, even if at acidic pH the effect was greater than neutral. It can be hypothesized that the interaction between the cinnamic acid and the lipidic layers is due to the lack of a hydroxyl group. This interaction is enhanced by an acidic pH, where the carboxylic acid is in a protonated form.
Castelli
F
F
Dipartimento Scienze Chimiche, Università di Catania, Catania, Italy, CIRASAIA, Università della Calabria, Arcavacata di Rende, Cosenza, Italy. fcastelli@dipchi.unict.it
Uccella
N
N
Trombetta
D
D
Saija
A
A
D002152:Calorimetry, Differential Scanning / Q000379:methods; D002934:Cinnamates / Q000737:chemistry*; D003373:Coumaric Acids / Q000737:chemistry*; D004134:Dimyristoylphosphatidylcholine; D008081:Liposomes; D010539:Permeability; D010636:Phenols / Q000737:chemistry*; D013329:Structure-Activity Relationship
D002934:Cinnamates; D003373:Coumaric Acids; D008081:Liposomes; D010636:Phenols; D004134:Dimyristoylphosphatidylcholine