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Structure of Dihydrochalcones and Related Derivatives and Their Scavenging and Antioxidant Activity against Oxygen and Nitrogen Radical Species

Laboratório de Planejamento e Desenvolvimento de Fármacos, Universidade Federal do Pará, CP 11101, 66075-110, Belém, PA, Brazil
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Molecules 2011, 16(2), 1749-1760; https://doi.org/10.3390/molecules16021749
Received: 21 November 2010 / Revised: 21 December 2010 / Accepted: 5 January 2011 / Published: 21 February 2011
(This article belongs to the Special Issue Antioxidants)
Quantum mechanical calculations at B3LYP/6-31G** level of theory were employed to obtain energy (E), ionization potential (IP), bond dissociation enthalpy (O-H BDE) and stabilization energies (DEiso) in order to infer the scavenging activity of dihydrochalcones (DHC) and structurally related compounds. Spin density calculations were also performed for the proposed antioxidant activity mechanism of 2,4,6-trihydroxyacetophenone (2,4,6-THA). The unpaired electron formed by the hydrogen abstraction from the phenolic hydroxyl group of 2,4,6-THA is localized on the phenolic oxygen at 2, 6, and 4 positions, the C3 and C6 carbon atoms at ortho positions, and the C5 carbon atom at para position. The lowest phenolic oxygen contribution corresponded to the highest scavenging activity value. It was found that antioxidant activity depends on the presence of a hydroxyl at the C2 and C4 positions and that there is a correlation between IP and O-H BDE and peroxynitrite scavenging activity and lipid peroxidation. These results identified the pharmacophore group for DHC. View Full-Text
Keywords: DFT; antioxidant activity; SAR; dihydrochalcone derivatives; ionization potential; bond dissociation enthalpy; ROS and RNS DFT; antioxidant activity; SAR; dihydrochalcone derivatives; ionization potential; bond dissociation enthalpy; ROS and RNS
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Bentes, A.L.A.; Borges, R.S.; Monteiro, W.R.; De Macedo, L.G.M.; Alves, C.N. Structure of Dihydrochalcones and Related Derivatives and Their Scavenging and Antioxidant Activity against Oxygen and Nitrogen Radical Species. Molecules 2011, 16, 1749-1760.

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