Structure of Dihydrochalcones and Related Derivatives and Their Scavenging and Antioxidant Activity against Oxygen and Nitrogen Radical Species 英文参考文献.docVIP

Molecules 2011, 16, 1749-1760; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Structure of Dihydrochalcones and Related Derivatives and Their Scavenging and Antioxidant Activity against Oxygen and Nitrogen Radical Species Alexandre L. A. Bentes, Rosivaldo S. Borges, Waldinei R. Monteiro, Luiz G. M. de Macedo and Cláudio N. Alves * Laboratório de Planejamento e Desenvolvimento de Fármacos, Universidade Federal do Pará, CP 11101, 66075-110, Belém, PA, Brazil * Author to whom correspondence should be addressed; E-Mail: nahum@ufpa.br; Fax: 55-91-3201-7635. Received: 21 November 2010; in revised form: 21 December 2010 / Accepted: 5 January 2011 / Published: 21 February 2011 Abstract: 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 (ΔEiso) 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. Keywords: DFT; antioxidant activity; SAR; dihydrochalcone derivatives; ionization potential