Antioxidant properties of trans-epsilon-viniferin as compared to stilbene derivatives in aqueous and nonaqueous media.
trans-Epsilon-viniferin, the dimer of resveratrol, extracted from Vitis vinifera, has been evaluated for its antioxidant capacity. Its properties have been compared to those of resveratrol and synthetic stilbenic derivatives (4-hydroxystilbene, 4,4'-dihydroxystilbene, 3,5-dihydroxystilbene, and trimethylresveratrol), in regard to their liposolubility using two media with different polarity. The bleaching of beta-carotene by lipoperoxyl (LOO.) radicals in an oil/water (O/W) emulsion and the scavenging of superoxide anions (O(-)(2) in dimethyl sulfoxide (DMSO) using 5,5-dimethyl-1-pyrroline-N-oxide as a spin trap were followed using UV-visible and electron paramagnetic resonance, respectively. Epsilon-viniferin exhibits the best antioxidant capacity in the DMSO/O(-)(2) polar system (IC(50) = 0.14 mM) while 4,4'-dihydroxystilbene presents the highest antioxidant capacity in the O/W/LOO. system (inhibition of beta-carotene bleaching, 82%). Partition coefficients and kinetics of partition between 1-octanol and water were measured to discuss the antioxidant efficiency of the compounds in relation with their chemical structure.
Privat
Christelle
C
Laboratoire Pharmacophores Redox, Phytochimie et Radiobiologie, EA-3030, Université Paul Sabatier, 35 Chemin des Maraîchers, 31062 Toulouse Cedex 4, France.
Telo
João Paulo
JP
Bernardes-Genisson
Vania
V
Vieira
Abel
A
Souchard
Jean-Pierre
JP
Nepveu
Françoise
F
D000975:Antioxidants; D001572:Benzofurans / Q000737:chemistry*; D005638:Fruit / Q000737:chemistry; D008054:Lipid Peroxides; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D012996:Solutions; D013267:Stilbenes / Q000737:chemistry*; D014867:Water
D000975:Antioxidants; D001572:Benzofurans; D008054:Lipid Peroxides; D010936:Plant Extracts; D012996:Solutions; D013267:Stilbenes; D014867:Water; C091891:epsilon-viniferin