Synthesis, antioxidant activity, and density functional theory study of catechin derivatives. Issue 85 (24th November 2017)

• Record Type: Journal Article
• Authors: Wang, Jing; Tang, Han; Hou, Bo; Zhang, Pan; Wang, Qi; Zhang, Bang-Lei; Huang, Ye-Wei; Wang, Ya; Xiang, Ze-Min; Zi, Cheng-Ting; Wang, Xuan-Jun; Sheng, Jun
• Is Part Of: RSC advances. Volume 7:Issue 85(2017)
• Page Start: 54136
• Page End: 54141
• Publication Date: 2017-11-24
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7ra11496f
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Catechin derivatives were synthesized, and their structures were characterized by 1 H-NMR, 13 C-NMR, and mass spectrometry. Abstract : Catechin derivatives were synthesized, and their structures were characterized by 1 H-NMR, 13 C-NMR, and mass spectrometry. The target compounds were evaluated for their antioxidant activities. Compound 2 showed the highest antioxidant activity, with an IC50 value of 136.637 μM, whereas methylated derivatives showed weak activity. Density functional theory (DFT) studies were carried out at the B3LYP/6-311++G (d, p) level of theory. According to the geometries, molecular electrostatic potential (MEP), bond dissociation enthalpy (EDE), the HOMO and LUMO, and reactivity indices ( η, μ, ω, ω +, and ω − ), we predicted the free radical scavenging capacity of catechins and their derivatives from their structures. We also found that the B-ring of catechins is a stronger electron donor than the A- or D-ring, and that there is a good relationship between the bond dissociation enthalpies (BDEs). These theoretical results will be helpful in the development of new or modified antioxidant compounds.