Structure-antioxidant activity relationships of dendrocandin analogues determined using density functional theory

Ning Zhang; Yilong Wu; Miao Qiao; Wenjuan Yuan; Xingyu Li; Xuanjun Wang; Jun Sheng; Chengting Zi

doi:10.1007/s11224-022-01895-2

Structure-antioxidant activity relationships of dendrocandin analogues determined using density functional theory

Struct Chem. 2022;33(3):795-805. doi: 10.1007/s11224-022-01895-2. Epub 2022 Feb 18.

Authors

Ning Zhang^{1

2}, Yilong Wu^{1

2}, Miao Qiao^{1

2}, Wenjuan Yuan^{1

3}, Xingyu Li³, Xuanjun Wang^{1

3}, Jun Sheng¹, Chengting Zi^{1

3}

Affiliations

¹ Key Laboratory of Pu-Er Tea Science, Ministry of Education, College of Science, Yunnan Agricultural University, Kunming, 650201 China.
² College of Food Science and Technology, Yunnan Agricultural University, Kunming, 650201 China.
³ College of Science, Yunnan Agricultural University, Kunming, 650201 China.

Abstract

Quantum-chemical calculations based on the density functional theory (DFT) at the B3LYP/6-311 + + G(2d,2p)//B3LYP/6-31G(d,p) level were employed to study the relationship between the antioxidant properties and chemical structures of six dendrocandin (DDCD) analogues in the gas phase and two solvents (methanol and water). The hydrogen atom transfer (HAT), electron-transfer-proton-transfer (ET-PT), and sequential proton-loss-electron-transfer (SPLET) mechanisms are explored. The highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), reactivity indices (η, μ, ω, ω ⁺, and ω ^- ), and molecular electrostatic potentials (MEPs) were also evaluated. The results suggest that the D ring plays an important role in mediating the antioxidant activity of DDCDs. For all the studied compounds, indicating that HAT was identified as the most favorable mechanism, whereas the SPLET mechanism was the most thermodynamically favorable pathway in polar solvents. The results of our study should aid in the development of new or modified antioxidant compounds.

Supplementary information: The online version contains supplementary material available at 10.1007/s11224-022-01895-2.

Keywords: Antioxidant mechanism; DFT; Dendrocandin analogues; Radical scavenging activity; Structure activity relationship.