An Electrospray Ionization Mass Spectrometric Study on Reactivity of Resveratrol Induced by Metal Ions

Tamboli, Vajir Fakirsab (2011) An Electrospray Ionization Mass Spectrometric Study on Reactivity of Resveratrol Induced by Metal Ions. PhD thesis, University of Trento.

PDF - Doctoral Thesis


Resveratrol is a polyphenolic compound produced by various plants and present in dietary sources such as red wine. In recent years, its beneficial effects for human health, including protection from heart diseases and cancer prevention, have attracted increasing interest. Resveratrol acts both as an antioxidant and a prooxidant agent when works in vivo with Cu(II) ions occurring naturally in living organisms. The aim of this work is to study the gas phase reactivity of resveratrol in presence of copper and iron ions, in order to more insights on the role of copper in the proposed biological mechanism. By electrospray ionization (ESI) mass spectrometry we have produced and detected some resveratrol-copper complexes by using a resveratrol/CuSO4 solution in acetonitrile/water, and their most stable structures have been calculated at the B3LYP/6-311G(d) level of theory. The formation of dehydrodimer product was also detected in ESI-MS/MS experiments and its structure assigned with evidences for isomeric compounds from copper and iron reactions with resveratrol. Density Functional Theory (DFT) calculations have been carried out to elucidate reaction mechanisms. Finally, the crucial role of the para-OH group in resveratrol structure has been demonstrated by investigating reactions with copper sulfate of synthetic analogues, bearing different number and position of OH groups.

Item Type:Doctoral Thesis (PhD)
Doctoral School:Physics
PhD Cycle:XXIV
Subjects:Area 03 - Scienze chimiche > CHIM/06 CHIMICA ORGANICA
Area 03 - Scienze chimiche > CHIM/01 CHIMICA ANALITICA
Uncontrolled Keywords:Resveratrol, ESI-Mass spectrometry, DFT calculations, Metal complexes, Synthetic analogues
Repository Staff approval on:02 Jan 2012 12:48

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