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Molecules 2018, 23(8), 1989; https://doi.org/10.3390/molecules23081989

The Substituent Effect on the Radical Scavenging Activity of Apigenin

1,†
,
1,†,* , 2
and
1
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
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 9 July 2018 / Revised: 23 July 2018 / Accepted: 30 July 2018 / Published: 10 August 2018
(This article belongs to the Collection Bioactive Compounds)
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Abstract

Flavonoids widely found in natural foods are excellent free radical scavengers. The relationship between the substituent and antioxidative activity of flavonoids has not yet been completely elucidated. In this work, the antioxidative activity of apigenin derivatives with different substituents at the C3 position was determined by density functional theory (DFT) calculations. The bond dissociation enthalpy (BDE), ionization potential (IP), and proton affinity (PA) were calculated. Donator acceptor map (DAM) analysis illustrated that the studied compounds are worse electron acceptors than F and also are not better electron donors than Na. The strongest antioxidative group of apigenin derivatives was the same as apigenin. Excellent correlations were found between the BDE/IP/PA and Hammett sigma constants. Therefore, Hammett sigma constants can be used to predict the antioxidative activity of substituted apigenin and to design new antioxidants based on flavonoids. In non-polar phases, the antioxidative activity of apigenin was increased by the electron-withdrawing groups, while it was reduced by the electron-donating groups. Contrary results occurred in the polar phase. The electronic effect of the substituents on BDE(4′-OH), BDE(5-OH), PA(4′-OH), and IP is mainly controlled by the resonance effect, while that on BDE(7-OH), PA(5-OH), and PA(7-OH) is governed by the field/inductive effect. View Full-Text
Keywords: apigenin; substituent effect; structure–antioxidant activity relationship; Hammett sigma constants; density functional theory apigenin; substituent effect; structure–antioxidant activity relationship; Hammett sigma constants; density functional theory
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Zheng, Y.-Z.; Chen, D.-F.; Deng, G.; Guo, R. The Substituent Effect on the Radical Scavenging Activity of Apigenin. Molecules 2018, 23, 1989.

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