Interaction of the antioxidant flavonoid quercetin with planar lipid bilayers.
Our capacitance and conductance measurements on reconstituted planar lipid bilayers (BLM) suggest an insertion of the flavonoid quercetin (QCT) in the membranes, which is concentration- and pH-dependent. Interaction of the flavonoid with the membrane has no impact on either structure or integrity of the lipid bilayer. The QCT molecules penetrate the lipid bilayer by intercalating between the flexible acyl chains of the phospholipids, the deepest insertion occuring in acidic medium, when QCT is neutral and completely liposoluble. Results indicated that aggregation of QCT within the hydrophobic core is accompanied by an increase of the transmembrane conductance following an alteration of the hydrophobic barrier for small electrolytes. By contrast, within alkaline media where QCT is deprotonated, the reaction site of the flavonoid is restricted to the hydrophilic domain of the membrane. This significantly changes the double layer capacitance as the negatively charged QCT molecules become sandwiched between polar headgroups at the bilayer surface. At highest alkaline pH, the transmembrane conductance was not affected, since QCT did not perturb the molecular packing of the hydrocarbonic acyl chains of the phospholipids. Results also demonstrated that changes in physical properties of the lipid bilayers following interstitial QCT embedding within either the hydrophobic domain or the polar headgroup domain may be related to both its lipophilic nature and interactions with the electric dipole moments of the polar headgroups of phospholipids. Data also demonstrated that translocation of QCT in the polar part of the lipid bilayer, at physiological pH and salt conditions, may be correlated with its optimized radical scavenging activity. This paper discusses the significance of the free radical scavenging capacity and antioxidant efficiency of QCT.
Movileanu
L
L
Department of Medical Biochemistry and Genetics, Texas A&M Health Science Center, 440 Reynolds Medical Building, College Station, Texas 77843-1114, USA. movileanu@medicine.tamu.edu
Neagoe
I
I
Flonta
M L
ML
D000975:Antioxidants / Q000737:chemistry / Q000493:pharmacokinetics*; D004305:Dose-Response Relationship, Drug; D005419:Flavonoids / Q000737:chemistry / Q000493:pharmacokinetics*; D006863:Hydrogen-Ion Concentration; D008051:Lipid Bilayers / Q000378:metabolism*; D008560:Membrane Fluidity / Q000187:drug effects*; D010743:Phospholipids / Q000378:metabolism*; D011794:Quercetin / Q000737:chemistry / Q000493:pharmacokinetics*
D000975:Antioxidants; D005419:Flavonoids; D008051:Lipid Bilayers; D010743:Phospholipids; D011794:Quercetin