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DFT Studies on the Antioxidant Activity of Naringenin and Its Derivatives: Effects of the Substituents at C3

1
College of Bee Science, Fujian Agriculture and Forestry University, Fuzhou 350002, China
2
Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2019, 20(6), 1450; https://doi.org/10.3390/ijms20061450
Received: 18 February 2019 / Revised: 11 March 2019 / Accepted: 12 March 2019 / Published: 22 March 2019
(This article belongs to the Special Issue DFT Applications to Biomolecules and Complex Reactions)
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Abstract

The radical scavenging activity of a flavonoid is largely influenced by its structure. The effects of the substituents at C3 position on the antioxidant activity of naringenin were carried out using the density functional theory (DFT) method. The reaction enthalpies related with the three well-established mechanisms were analyzed. Excellent correlations were found between the reaction enthalpies and Hammett sigma constants. Equations obtained from the linear regression can be helpful in the selection of suitable candidates for the synthesis of novel naringenin derivatives with enhanced antioxidant properties. In the gas and benzene phases, the antioxidant activity of naringenin was enhanced by the electron-donating substituents via weakening the bond dissociation enthalpy (BDE). In the water phase, it was strengthened by electron-withdrawing groups—via lowering the proton affinity (PA). The electronic effect of the substituent on the BDE of naringenin is mainly governed by the resonance effect, while that on the ionization potential (IP) and PA of naringenin is mainly controlled by the field/inductive effect. View Full-Text
Keywords: naringenin; substituent effect; structure-antioxidant activity relationship; Hammett sigma constants; density functional theory naringenin; substituent effect; structure-antioxidant activity relationship; Hammett sigma constants; density functional theory
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Zheng, Y.-Z.; Deng, G.; Guo, R.; Chen, D.-F.; Fu, Z.-M. DFT Studies on the Antioxidant Activity of Naringenin and Its Derivatives: Effects of the Substituents at C3. Int. J. Mol. Sci. 2019, 20, 1450.

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