A DFT method for the study of the antioxidant action mechanism of resveratrol derivatives

Ali Benayahoum, Habiba Amira-Guebailia, Omar Houache

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Quantum-chemical calculations using DFT, have been performed to explain the molecular structure antioxidant activity relationship of resveratrol (RSV) (1) analogues: 3,4-dihydroxy-trans-stilbene (3,4-DHS) (2); 4,4′-dihydroxy- trans-stilbene (4,4′-DHS) (3); 4-hydroxy-trans-stilbene (4-HS) (4); 3,5-dihydroxy-trans-stilbene (3,5-DHS) (5); 3,3′-dimethoxy-4,4′- dihydroxy-trans-stilbene (3,3′-DM-4,4′-DHS) (6); 2,4-dihydroxy-trans-stilbene (2,4-DHS) (7) and 2,4,4′-trihydroxy-trans- stilbene (2,4,4′-THS) (8). It was found that all compounds studied were effective antioxidants with the exception of 3, 5-DHS. The high antioxidant activity of both 3, 3′-DM-4, 4′-DHS and 3, 4-DHS may be due to the abstraction of the two hydrogen atoms of the para and ortho-position hydroxyls respectively, to form a quinone structure. Our results revealed that the antioxidant pharmacophore of 2,4-DHS and 2,4,4′-THS, exhibiting higher antioxidant activity than resveratrol, is the 2-hydroxystilbene, rather than 4-hydroxystilbene. Experimental observations were satisfactorily explained and commented.

Original languageEnglish
Pages (from-to)2285-2298
Number of pages14
JournalJournal of Molecular Modeling
Volume19
Issue number6
DOIs
Publication statusPublished - Jun 2013

Fingerprint

Resveratrol
Stilbenes
stilbene
antioxidants
Antioxidants
Discrete Fourier transforms
Derivatives
Molecular structure
resveratrol
Atoms
Hydrogen
quinones
Hydroxyl Radical
hydrogen atoms
molecular structure
analogs

Keywords

  • AIP
  • Antioxidant activity
  • DFT method
  • HOMO and LUMO
  • Spin density
  • Trans-resveratrol

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computer Science Applications
  • Computational Theory and Mathematics
  • Catalysis
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

A DFT method for the study of the antioxidant action mechanism of resveratrol derivatives. / Benayahoum, Ali; Amira-Guebailia, Habiba; Houache, Omar.

In: Journal of Molecular Modeling, Vol. 19, No. 6, 06.2013, p. 2285-2298.

Research output: Contribution to journalArticle

Benayahoum, Ali ; Amira-Guebailia, Habiba ; Houache, Omar. / A DFT method for the study of the antioxidant action mechanism of resveratrol derivatives. In: Journal of Molecular Modeling. 2013 ; Vol. 19, No. 6. pp. 2285-2298.
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