Antioxidant properties of resveratrol and piceid on lipid peroxidation in micelles and monolamellar liposomes.
The antioxidant activities of trans-resveratrol (trans-3,5,4'-trihydroxystilbene) and trans-piceid (trans-5,4'-dihydroxystilbene-3-O-beta-D-glucopyranoside), its more widespread glycosilate derivative, have been compared measuring their inhibitory action on peroxidation of linoleic acid (LA) and the radical scavenging ability towards different free radicals (such as DPPH) and radical initiators. It has been found that the two stilbenes have similar antioxidant capacity, while the comparison with BHT (2,6-di-tert-butyl-4-methylphenol) and alpha-tocopherol (vitamin E, vit. E), taken as reference, points out a slower but prolonged protective action against lipid peroxidation. Furthermore, piceid appears more efficacious than resveratrol as a consequence of the reaction of the latter with its radical form. The DSC profiles of phosphatidylcholine liposomes of various chain lengths, and EPR measurements of spin labelled liposomes demonstrated that the susceptible hydroxyl group of these compounds are located in the lipid region of the bilayer close to the double bonds of polyunsaturated fatty acids, making these stilbenes particularly suitable for the prevention and control of the lipid peroxidation of the membranes.
Fabris
Sabrina
S
Department of Physical Chemistry, University of Venice, Dorsoduro 2137, Venice, Italy.
Momo
Federico
F
Ravagnan
Giampietro
G
Stevanato
Roberto
R
D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D002084:Butylated Hydroxytoluene / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry / Q000494:pharmacology*; D015227:Lipid Peroxidation / Q000187:drug effects*; D008823:Micelles; D008954:Models, Biological; D015394:Molecular Structure; D000077185:Resveratrol; D013267:Stilbenes / Q000737:chemistry / Q000494:pharmacology*; D053835:Unilamellar Liposomes / Q000737:chemistry*; D014810:Vitamin E / Q000737:chemistry
D000975:Antioxidants; D005960:Glucosides; D008823:Micelles; D013267:Stilbenes; D053835:Unilamellar Liposomes; D014810:Vitamin E; D002084:Butylated Hydroxytoluene; D000077185:Resveratrol; C058229:polydatin