Liquid chromatographic/electrospray ionization mass spectrometric identification of the oxidation end-products of trans-resveratrol in aqueous solutions.
trans-Resveratrol (3,5,4'-trihydroxystilbene) is a natural polyphenolic compound that exhibits antioxidant properties. Our study aimed at studying the HO*-induced oxidation of resveratrol (100 micromol.L(-1)) in aerated aqueous solutions. Gamma radiolysis of water was used to generate HO*/O(2)(*-) free radicals (I = 10 Gy.min(-1), dose = 400 Gy). Oxidation products were identified by direct infusion mass spectrometry and high-performance liquid chromatography/mass spectrometry. For each product, structural elucidation was based on simple mass spectra, fragmentation spectra and deuterium/hydrogen exchange spectra; the comparison with mass spectra of synthetic products provided valuable information allowing the complete identification of the oxidation products. Four products resulting from the direct attack of HO* radicals towards resveratrol were identified respectively as piceatannol (trans-3,5,3',4'-tetrahydroxystilbene), 3,5-dihydroxybenzoic acid, 3,5-dihydroxybenzaldehyde and 4-hydroxybenzaldehyde.
Département de Biochimie (EA 3617), Université Paris Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4 avenue de l'Observatoire, 75006 Paris, France.
Laurent
L
Camont
Fabrice
F
Collin
Catherine
C
Marchetti
Daniel
D
Jore
Monique
M
Gardes-Albert
Dominique
D
Bonnefont-Rousselot
D001547:Benzaldehydes / Q000737:chemistry; D002853:Chromatography, Liquid / Q000379:methods*; D005720:Gamma Rays; D062385:Hydroxybenzoates / Q000737:chemistry; D010084:Oxidation-Reduction; D012118:Resorcinols; D000077185:Resveratrol; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D013267:Stilbenes / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D001547:Benzaldehydes; D062385:Hydroxybenzoates; D012118:Resorcinols; D013267:Stilbenes; D014867:Water; C112784:2,5-dihydroxybenzaldehyde; C076950:alpha-resorcylic acid; C041525:3,3',4,5'-tetrahydroxystilbene; C011483:4-hydroxybenzaldehyde; D000077185:Resveratrol