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. 2011 Feb 21;16(2):1749-60.
doi: 10.3390/molecules16021749.

Structure of dihydrochalcones and related derivatives and their scavenging and antioxidant activity against oxygen and nitrogen radical species

Alexandre L A Bentes  1 , Rosivaldo S Borges, Waldinei R Monteiro, Luiz G M de Macedo, Cláudio N Alves
Affiliations

Structure of dihydrochalcones and related derivatives and their scavenging and antioxidant activity against oxygen and nitrogen radical species

Alexandre L A Bentes et al. Molecules. .

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 (DE(iso)) 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.

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Figures

Figure 1
Figure 1
Structure and numeration of flavonoids derivatives.
Figure 2
Figure 2
Structure of dihydrochalcones and related derivatives.
Figure 3
Figure 3
HOMO of dihydrochalcone-semiquinone and related derivatives.
Figure 4
Figure 4
MEPs of dihydrochalcone derivative IX.
Figure 5
Figure 5
Spin densities for the more stable semiquinone derivatives.
See this image and copyright information in PMC

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