Issue 5, 2010

Antioxidant activity of α-pyridoin and its derivatives: possible mechanism

Abstract

α-Pyridoin (1, 1,2-di(2-pyridyl)-1,2-ethenediol) is a unique enediol antioxidant. To explore the detailed antioxidant mechanism of α-pyridoin, we synthesized α-pyridoin and its 5,5′- or 6,6′-bis-substituted derivatives (2–7) and compared their capacities to scavenge galvinoxyl radical (GO˙) and protect human red blood cells (RBCs) from oxidative haemolysis. It was found that the compounds (5 and 6) with a methyl or methoxy group at the 5-position exhibit significantly higher GO˙-scavenging and anti-haemolysis activities than other derivatives and vitamin C. Kinetic analysis of the GO˙-scavenging reaction and the effect of added base on the reaction rate revealed that in ethyl acetate, the reaction occurs primarily by the direct hydrogen atom transfer (HAT mechanism). However, in ethanol that supports ionization, the kinetics of the process is mostly governed by sequential proton loss electron transfer (SPLET mechanism).

Graphical abstract: Antioxidant activity of α-pyridoin and its derivatives: possible mechanism

Supplementary files

Article information

Article type
Paper
Submitted
03 Nov 2009
Accepted
24 Nov 2009
First published
04 Jan 2010

Org. Biomol. Chem., 2010,8, 1058-1063

Antioxidant activity of α-pyridoin and its derivatives: possible mechanism

L. Cheng, X. Jin, Q. Teng, J. Chang, X. Yao, F. Dai, Y. Qian, J. Tang, X. Li and B. Zhou, Org. Biomol. Chem., 2010, 8, 1058 DOI: 10.1039/B922673G

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