(±)9hode

(±)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, initially extracted from atherosclerotic lesions, is formed through Cu2+-catalyzed oxidation of LDL. Subsequent research demonstrated that 15-LO from rabbit reticulocytes and human monocytes can metabolize cholesteryl linoleate, a major LDL component, into 9-HODE cholesteryl ester.

9(R)-HODE cholesteryl ester, originally extracted from atherosclerotic lesions, has an oxidized fatty acid portion that may result from either enzymatic lipoxygenation or random lipid peroxidation. It serves as a standard for analyzing chiral HODE cholesteryl esters.

9(S)-HODE cholesteryl ester, originally extracted from atherosclerotic lesions, has an uncertain origin of its oxidized fatty acid portion, which may result from either enzymatic lipoxygenation or random lipid peroxidation. This compound can be used as a standard for analyzing chiral HODE cholesteryl esters.

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.