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13-Hydroxyoctadecadienoic acid
13-Hydroxyoctadecadienoic acid (13-HODE) is the commonly used term for 13(''S'')-hydroxy-9''Z'',11''E''-octadecadienoic acid (13(''S'')-HODE). The production of 13(''S'')-HODE is often accompanied by the production of its stereoisomer, 13(''R'')-hydroxy-9''Z'',11''E''-octadecadienoic acid (13(''R'')-HODE). The adjacent figure gives the structure for the (''S'') stereoisomer of 13-HODE. Two other naturally occurring 13-HODEs that may accompany the production of 13(''S'')-HODE are its cis-trans (i.e., 9''E'',11''E'') isomers viz., 13(''S'')-hydroxy-9''E'',11''E''-octadecadienoic acid (13(''S'')-''EE''-HODE) and 13(''R'')-hydroxy-9''E'',11''E''-octadecadienoic acid (13(''R'')-''EE''-HODE). Studies credit 13(''S'')-HODE with a range of clinically relevant bioactivities; recent studies have assigned activities to 13(''R'')-HODE that differ from those of 13(''S'')-HODE; and other studies have proposed that that one or more of these HODEs mediate physiological and pathological responses, are markers of various human diseases, and/or contribute to the progression of certain diseases in humans. Since, however, many studies on the identification, quantification, and actions of 13(''S'')-HODE in cells and tissues have employed methods that did not distinguish between these isomers, 13-HODE is used here when the actual isomer studied is unclear.
A similar set of 9-Hydroxyoctadecadienoic acid (9-HODE) metabolites (i.e., 9(S)-HODE), 9(R)-HODE, 9(S)-EE-HODE), and 9(R)-EE-HODE) occurs naturally and particularly under conditions of oxidative stress forms concurrently with the 13-HODEs; the 9-HODEs have overlapping and complementary but not identical activities with the 13-HODEs. Some recent studies measuring HODE levels in tissue have lumped the four 9-HODEs with the four 13-HODEs to report only on total HODEs (tHODEs). tHODEs have been proposed to be markers for certain human disease. Other studies have lumped together the 9-(''S''), 9(''R''), 13 (''S'')-, and 13(''R'')-HODEs along with the two ketone metabolites of these HODEs, 13-oxoODE (13-oxo-9''Z'',12''E''-octadecadienoic acid) and 9-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 13-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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