Liquid chromatographic/electrospray ionization mass spectrometric identification of the oxidation end-products of trans-resveratrol in aqueous solutions.

Laurent Camont, Fabrice Collin, Catherine Marchetti, Daniel Jore, Monique Gardes-Albert, Dominique Bonnefont-Rousselot

Index: Rapid Commun. Mass Spectrom. 24(5) , 634-42, (2010)

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Abstract

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.Copyright 2010 John Wiley & Sons, Ltd.