Routes to 4-hydroxynonenal: fundamental issues in the mechanisms of lipid peroxidation.
Although investigation of the toxicological and physiological actions of alpha/beta-unsaturated 4-hydroxyalkenals has made great progress over the last 2 decades, understanding of the chemical mechanism of formation of 4-hydroxynonenal and related aldehydes has advanced much less. The aim of this review is to discuss mechanistic evidence for these non-enzymatic routes, especially of the underappreciated intermolecular pathways that involve dimerized and oligomerized fatty acid derivatives as key intermediates. These cross-molecular reactions of fatty acid peroxyls have also important implications for understanding of the basic initiation and propagation steps during lipid peroxidation and the nature of the products that arise.
Schneider
Claus
C
Department of Pharmacology and the Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37232, USA.
Porter
Ned A
NA
Brash
Alan R
AR
D000447:Aldehydes / Q000378:metabolism*; D000818:Animals; D019281:Dimerization; D005227:Fatty Acids / Q000378:metabolism*; D006801:Humans; D015227:Lipid Peroxidation / Q000502:physiology*
D000447:Aldehydes; D005227:Fatty Acids; C027576:4-hydroxy-2-nonenal