The influence of C2C3 double bond on the antiradical activity of flavonoid: Different mechanisms analysis. (January 2019)

• Record Type: Journal Article
• Authors: Zheng, Yan-Zhen; Deng, Geng; Chen, Da-Fu; Guo, Rui; Lai, Rong-Cai
• Is Part Of: Phytochemistry. Volume 157(2019)
• Page Start: 1
• Page End: 7
• Publication Date: 2019-01
• Subjects: Antiradical activity -- Flavonoid -- C2C3 double bond -- Structural features -- Density functional theory; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2018.10.015
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Flavonoids widely found in bee products are excellent antioxidants. The structural features are important in evaluating the antiradical activity of flavonoid. In this work, the density functional theory (DFT) methods were applied to investigate the influence of C2C3 double bond on the antiradical activity of flavonoid based on three prevalently accepted radical scavenging mechanisms from the thermodynamic aspect. It is found that the hydroxyl groups in different rings are affected variously by the C2C3 double bond and the 3OH group is most influenced. For the compounds that only differ with the C2C3 double bond, the antiradical activity of flavone or flavonol (possessing C2C3 double bond) is not always stronger than that of flavanone: in the weak polarity phases, only the antiradical activities of chrysin, galangin and morin are stronger than those of pinocembrin, pinobanksin and dihydro-morin, respectively. In polar phases, the C2C3 double bond would weaken the antiradical activity of flavonoid via enlarging the proton affinity and the antiradical activity of flavone or flavonol is weaker than that of flavanone. Graphical abstract: The influence of the C2C3 double bond on the antiradical activity of flavonoid.Image Highlights: Antiradical mechanisms were analyzed for flavonoids differing with C2C3 bond. C2C3 bond has different influences on the various hydroxyl group. The 3OH group is most influenced. In polar phases, C2C3 double bond weakens the antiradical activity of flavonoid. In polar phases, the flavanone is better than flavone/flavonol as antioxidant.