Journal of Molecular Modeling

, Volume 19, Issue 6, pp 2285–2298

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

  • Ali Benayahoum
  • Habiba Amira-Guebailia
  • Omar Houache
Original Paper

DOI: 10.1007/s00894-013-1770-7

Cite this article as:
Benayahoum, A., Amira-Guebailia, H. & Houache, O. J Mol Model (2013) 19: 2285. doi:10.1007/s00894-013-1770-7

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.

Keywords

AIPAntioxidant activityDFT methodHOMO and LUMOSpin densityTrans-resveratrol

Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  • Ali Benayahoum
    • 1
  • Habiba Amira-Guebailia
    • 1
  • Omar Houache
    • 2
  1. 1.Laboratory of Applied Chemistry8 Mai 1945 Guelma UniversityGuelmaAlgeria
  2. 2.Petroleum & Chemical Engineering DepartmentSultan Qaboos UniversityMuscatSultanate of Oman