Neurochemical Aspects of 4-Hydroxynonenal

Abstract

4-Hydroxynonenal (4-HNE) is a major end-product of peroxidation of membrane arachidonic acid (ARA). This nine carbon α, β-unsaturated aldehyde contains three functional groups, which often act in concert and help to explain its high reactivity (Poli and Schaur, 2000). Most importantly, there is a conjugated system of a C=C double bond and a C=O carbonyl group which provide a partial positive charge to carbon 3 due to the presence of mobile pi-electrons. This positive charge is further enhanced by the inductive effect of the hydroxy group at carbon 4. Therefore, 4-HNE is considered to be soft electrophiles and is prone to be attacked by nucleophiles, such as thiol or amino groups. This reaction occurs primarily at carbon 3 and secondarily at the carbonyl carbon 1.