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

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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.

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Authors and Affiliations

  1. Laboratory of Applied Chemistry, 8 Mai 1945 Guelma University, Guelma, 24000, Algeria

    Ali Benayahoum & Habiba Amira-Guebailia

  2. Petroleum & Chemical Engineering Department, Sultan Qaboos University, P.O. Box 33, AlKhoud 123, Muscat, Sultanate of Oman

    Omar Houache

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  1. Ali Benayahoum
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  2. Habiba Amira-Guebailia
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  3. Omar Houache
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Correspondence to Habiba Amira-Guebailia.

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Benayahoum, A., Amira-Guebailia, H. & Houache, O. A DFT method for the study of the antioxidant action mechanism of resveratrol derivatives. J Mol Model 19, 2285–2298 (2013). https://doi.org/10.1007/s00894-013-1770-7

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  • DOI: https://doi.org/10.1007/s00894-013-1770-7

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