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

Ali Benayahoum, Habiba Amira-Guebailia*, Omar Houache

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)


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
Issue number6
Publication statusPublished - Jun 2013


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

ASJC Scopus subject areas

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


Dive into the research topics of 'A DFT method for the study of the antioxidant action mechanism of resveratrol derivatives'. Together they form a unique fingerprint.

Cite this