Theoretical studies on the antioxidant activity of pinobanksin and its ester derivatives: Effects of the chain length and solvent. (1st February 2018)

• Record Type: Journal Article
• Authors: Zheng, Yan-Zhen; Deng, Geng; Chen, Da-Fu; Liang, Qin; Guo, Rui; Fu, Zhong-Min
• Is Part Of: Food chemistry. Volume 240(2018)
• Page Start: 323
• Page End: 329
• Publication Date: 2018-02-01
• Subjects: Pinobanksin -- Pinobanksin-3-O-ester derivatives -- Structure-antioxidant activity relationship -- Solvent effect -- Density functional theory; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2017.07.133
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: Replacing the 3-hydroxyl by ester group with different alkyl chains does not change much of the antioxidant activity of pinobanksin. Solvent effects can alter the thermodynamically preferred mechanisms. The 7-hydroxyl contributes mainly to the antioxidant activities of the investigated compounds. Abstract: The effects of the ester group and solvent on the structure and antioxidant activity of pinobanksin were carried out using DFT calculation. First, the properties of the intramolecular hydrogen-bonds in the investigated compounds were studied. Second, the antioxidant capacities of the investigated compounds were analyzed by HAT, SET-PT and SPLET mechanisms from thermodynamic point. The conclusions are: (1) HAT mechanism is most favorable in the gas and CCl4 phases, while SPLET mechanism is more favored in the CH3 CN and H2 O phases. In the CHCl3 phase, the thermodynamically preferred mechanism is HAT for the 3−OH and 5−OH groups. While, HAT and SPLET mechanisms may run simultaneously for the 7−OH group. (2) Replacing the 3−OH group by ester group with different alkyl chains does not change much of the antioxidant activity of pinobanksin. (3) Besides, the 7−OH group contributes mainly to the antioxidant activities of the investigated compounds.