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9-Hydroxyoctadecadienoic acid
9-Hydroxyoctadecadienoic acid (9-hydroxy-10(''E''),12(''Z'')-octadecadienoic acid or 9-HODE) has been used in the literature to designate either or both of two stereoisomer metabolites of the essential fatty acid, linoleic acid: 9(''S'')-hydroxy-10(''E''),12(''Z'')-octadecadienoic acid (9(''S'')-HODE) and 9(''R'')-hydroxy-10(''E''),12(''Z'')-octadecadienoic acid (9(''R'')-HODE); these two metabolites differ in having their hydroxy residues in the ''S'' or ''R'' configurations, respectively. The accompanying figure gives the structure for 9(''S'')-HETE. Two other 9-hydroxy linoleic acid derivatives occur in nature, the 10''E'',12''E'' isomers of 9(''S'')-HODE and 9''(R'')-HODE viz., 9(''S'')-hydroxy-10''E'',12''E''-octadecadienoic acid (9(''S'')-''EE''-HODE) and 9(''R'')-hydroxy-10''E'',12''E''-octadecadienoic acid (13(''R'')-''EE''-HODE); these two derivatives have their double bond at carbon 12 in the ''E'' or trans configuration as opposed to the ''Z'' or cis configuration. The four 9-HODE isomers, particularly under conditions of oxidative stress, may form together in cells and tissues; they have overlapping but not identical biological activities and significances. Because many studies have not distinguished between the ''S'' and ''R'' stereoisomers and, particularly in identifying tissue levels, the two ''EE'' isomers, 9-HODE is used here when the isomer studied is unclear.
A similar set of 13-Hydroxyoctadecadienoic acid (13-HODE) metabolites (13(S)-HODE), 13(R)-HODE, 13(S)-EE-HODE), and 13(R)-EE-HODE) also occurs naturally and, again particularly under conditions of oxidative stress, may form concurrently with 9-HODEs; these 13-HODEs also have overlapping and complementary but not identical activities with the 9-HODEs. Some recent studies measuring HODE levels in tissue have lumped the four 9-HODEs and four 13-HODEs together to report only on total HODEs (tHODEs): tHODEs have been proposed to be markers for certain human disease. Other recent studies have lumped together the 9-(''S''), 9(''R''), 13 (''S'')-, and 13(''R'')-HODE along with the two ketone metabolites of these HODEs, 9-oxoODE (9-oxo-10(''E''),12(''Z'')-octadecadienoic acid) and 13-oxoODE, reporting only on total OXLAMs (oxidized linoleic acid metabolites); the OXLAMs have been implicated in working together to signal for pain perception.
== Pathways making 9-HODEs ==
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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