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Structural Basis for Antioxidant Activity of trans-Resveratrol: Ab Initio Calculations and Crystal and Molecular Structure
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Abstract
From the experimental crystal structure and ab initio calculations on resveratrol and its derivatives, structural features of mechanistic importance are described. The molecular structure reveals the relative coplanarity of the trans-stilbene skeleton, and the molecular packing in the solid state shows an extensive hydrogen bond network that elucidates the flip-flop motion of the three hydroxyl groups that alternately form and break H bonds with each of the neighboring phenolic oxygens. The dynamic behavior provoked by the alternation of hydrogen bond formation and breaking can result in the ready mobility of up to three hydrogen atoms per resveratrol molecule that can be transferred to reactive oxidants that are rich in electron density. In addition, theoretical studies confirm the planarity of resveratrol as well as for half of the molecule of a condensation dimeric derivative of resveratrol, trans-σ-viniferin. Furthermore, these studies show the p-4‘-OH group to be more acidic compared to the other two m-OH groups. These features correlate with the biological activity of resveratrol as an antioxidant and support earlier studies showing H-atom transfer to be the dominant mechanism by which phenolic antioxidants intercept free radicals.
Keywords: Resveratrol; crystal structure; ab initio calculations; flip-flop hydrogen bonding; structural features; antioxidant activity
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This article has been cited by 8 ACS Journal articles (5 most recent appear below).
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Radical-Scavenging Activity and Mechanism of Resveratrol-Oriented Analogues: Influence of the Solvent, Radical, and Substitution
Ya-Jing Shang, Yi-Ping Qian, Xiao-Da Liu, Fang Dai, Xian-Ling Shang, Wen-Qiang Jia, Qiang Liu, Jian-Guo Fang and Bo ZhouThe Journal of Organic Chemistry2009 74 (14), 5025-5031Radical-Scavenging Activity and Mechanism of Resveratrol-Oriented Analogues: Influence of the Solvent, Radical, and Substitution
Ya-Jing Shang, Yi-Ping Qian, Xiao-Da Liu, Fang Dai, Xian-Ling Shang, Wen-Qiang Jia, Qiang Liu, Jian-Guo Fang and Bo ZhouThe Journal of Organic Chemistry2009 74 (14), 5025-5031Resveratrol (3,5,4′-trihydroxy-trans-stilbene, 3,5,4′-THS) is a well-known natural antioxidant and cancer chemopreventive agent that has attracted much interest in the past decade. To find a more active antioxidant and investigate the antioxidative ...
Effect of Protonation and Aggregation State of (E)-Resveratrol on Its Hydroperoxidation by Lipoxygenase
José Manuel López-Nicolás, Manuela Pérez-Gilabert and Francisco García-CarmonaJournal of Agricultural and Food Chemistry2009 57 (11), 4630-4635Effect of Protonation and Aggregation State of (E)-Resveratrol on Its Hydroperoxidation by Lipoxygenase
José Manuel López-Nicolás, Manuela Pérez-Gilabert and Francisco García-CarmonaJournal of Agricultural and Food Chemistry2009 57 (11), 4630-4635The protonation and aggregation states of (E)-resveratrol were used as tools to investigate the kinetic properties of lipoxygenase (LOX). It was found that the deprotonation of the 4′-hydroxyl group at pH values higher than the pKa1 of (E)-resveratrol ...
Crystal and Molecular Structure of Piceatannol; Scavenging Features of Resveratrol and Piceatannol on Hydroxyl and Peroxyl Radicals and Docking with Transthyretin
Miriam Rossi, Francesco Caruso, Cristian Opazo and Justin SalciccioliJournal of Agricultural and Food Chemistry2008 56 (22), 10557-10566Crystal and Molecular Structure of Piceatannol; Scavenging Features of Resveratrol and Piceatannol on Hydroxyl and Peroxyl Radicals and Docking with Transthyretin
Miriam Rossi, Francesco Caruso, Cristian Opazo and Justin SalciccioliJournal of Agricultural and Food Chemistry2008 56 (22), 10557-10566The mechanism by which the naturally occurring polyphenolic compounds resveratrol (RES), C14H12O3, and its metabolite piceatannol (PIC), C14H12O4, scavenge free radicals is studied using experimental and density functional theory (DFT) methods. PIC’s ...
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History
- Published In Issue December 01, 2004
- Received for review July 20, 2004. Revised manuscript received September 9, 2004. Accepted September 13, 2004.
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