Density functional study of the antioxidant activity of some recently synthesized resveratrol analogues

•Antioxidant properties of five recently synthesized cis-resveratrol analogues.•DFT calculations on HAT and SET mechanisms.•The C2′–C6 bond in cResv enhances both delocalization and conjugation effects.•Prediction of UV–Vis absorption spectra show the p-band sensibly red-shifted. In this paper we ha...

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Bibliographic Details
Published in:Food chemistry 2013-12, Vol.141 (3), p.2017-2024
Main Authors: Mazzone, Gloria, Malaj, Naim, Russo, Nino, Toscano, Marirosa
Format: Article
Language:English
Subjects:
Antioxidant mechanism
Antioxidants - chemical synthesis
Antioxidants - chemistry
Biological and medical sciences
Bond dissociation energy (BDE) and ionization potential (IP)
cis-Resveratrol analogues
Electron Transport
Food toxicology
Medical sciences
Molecular Structure
Stilbenes - chemical synthesis
Stilbenes - chemistry
Toxicology
UV–Vis characterization
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Summary:•Antioxidant properties of five recently synthesized cis-resveratrol analogues.•DFT calculations on HAT and SET mechanisms.•The C2′–C6 bond in cResv enhances both delocalization and conjugation effects.•Prediction of UV–Vis absorption spectra show the p-band sensibly red-shifted. In this paper we have investigated the two main working mechanisms (H atom and single-electron transfer) of five new potential antioxidant analogues of cis-resveratrol. The O–H bond dissociation energy (BDE) and ionization potential (IP) key parameters were computed in methanol. Results obtained indicate that all the examined compounds are more efficient antioxidants than the molecule from which they derive, mainly due to their higher degree of conjugation and the capability to delocalize the π-electrons which contribute to the stabilization of the radical species. The enhancement of these stabilizing effects is in part a result of the introduction of a single bond between the C2′ and C6 carbon atoms of cis-resveratrol that generates a new central aromatic ring. However, the number of hydroxyl groups and in particular the presence of the catechol moiety remains the most significant features in determining the order of radical scavenging potentiality. Spectroscopic UV–Vis characterization is also reported and discussed.
ISSN:0308-8146
1873-7072
DOI:10.1016/j.foodchem.2013.05.071