9hode

9(S)-HODE is produced by the lipoxygenation of linoleic acid in both plants and animals.[1],[2] It has been detected in atherosclerotic plaques, as an esterified component of membrane phospholipids and in oxidized LDL particles.[3]

9(R)-HODE is one of several monohydroxylated products of linoleic acid. All known mammalian lipoxygenases appear to catalyze the oxygenation of arachidonic and linoleic acid to give products having strictly the (S) configuration at the site of oxygen insertion. However, both human umbilical vein endothelial cells and bovine aorta endothelial cells have been shown to produce 9(R)-HODE when incubated with linoleic acid. The physiological function of 9(R)-HODE and the enzyme that catalyzes its formation have not been determined.

(±)9-HODE is one of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. Approximately equal proportions of both isomers are found in mitochondrial and plasma membranes of rabbit reticulocytes. [1][2] Oxidized LDL contains significant amounts of esterified 9- and 13-HpODEs and HODEs. [3][4]

(±)9-HODE cholesteryl ester was originally extracted from atherosclerotic lesions and shown to be produced by Cu2+-catalyzed oxidation of LDL. Later studies determined that 15-LO from rabbit reticulocytes and human monocytes were able to metabolize cholesteryl linoleate, a major component of LDL, to 9-HODE cholesteryl ester.

9(R)-HODE cholesteryl ester was originally extracted from atherosclerotic lesions. It remains uncertain whether the oxidized fatty acid portion of the molecule results from enzymatic lipoxygenation or from random lipid peroxidation. 9(R)-HODE cholesteryl ester can be used as a standard for analysis of chiral HODE cholesteryl esters.

9(S)-HODE cholesteryl ester was originally extracted from atherosclerotic lesions. It remains uncertain whether the oxidized fatty acid portion of the molecule results from enzymatic lipoxygenation or from random lipid peroxidation. 9(S)-HODE cholesteryl ester can be used as a standard for analysis of chiral HODE cholesteryl esters.