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(14S)-hydroperoxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid + ?
(13S,14S)-epoxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid
-
-
-
?
(Z,Z,Z,E)-5,8,11,13-eicosatetraenoic acid + O2
?
-
-
-
-
?
1-linoleoyl lysophosphatidic acid + O2
(S)-hydroperoxy 1-linoleoyl lysophosphatidic acid
-
i.e. linoleoyl-lysoPA
major product
-
?
1-linoleoyl lysophosphatidylcholine + O2
(S)-hydroperoxy 1-linoleoyl lysophosphatidylcholine
-
i.e. linoleoyl-lysoPC
major product
-
?
11,14,17-eicosatrienoic acid + O2
?
11,14-eicosadienoic acid + O2
?
2 arachidonate + 2 O2 + 2 H+
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate + (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate + H2O
20-hydroxyeicosatetraenoic acid methyl ester + O2
8,20-dihydroxyeicosatetraenoic acid + 12,20-dihydroxyeicosatetraenoic acid + 9,20-dihydroxyeicosatetraenoic acid
-
-
-
-
?
4,7,10,13,16,19-docosahexaenoic acid + O2
(14S)-14-hydroxy-4,7,10,13,16,19-docosahexaenoic acid
-
-
-
-
?
4,7,10,13,16,19-docosahexaenoic acid + O2
14-hydroxy-4,7,10,12,16,19-docosahexaenoic acid
4,7,10,13,16,19-docosahexaenoic acid + O2
?
4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid + O2
(11S)-hydroperoxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid + (14S)-hydroperoxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid + (17S)-hydroperoxy-4Z,7Z,10Z,12E,16Z,19Z-docosahexaenoic acid
-
-
-
?
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
5,15-(5S,15S)-dihydroperoxyarachidonic acid + O2
5S,14R,15S-trihydroperoxy-6,10,12-trans-8-cis-eicosatetraenoic acid
-
-
the product is reduced to 5S,14R,15S,-8-cis-lipoxin B due to 14R-oxygenase activity of the enzyme
?
5,8,11,14,17-eicosapentaenoic acid + O2
(12S)-12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
-
-
-
-
?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
5,8,11-eicosatrienoic acid + O2
12-hydroxy-5,8,10-eicosatrienoic acid
-
activity with platelet-type (12S)-lipoxygenase and epidermal-type (12S)-lipoxygenase, no activity with (12R)-lipoxygenase
-
?
5S,15S-dihydroperoxyeicosatetraenoic acid + O2
lipoxin B4
-
-
-
?
5S-hydroperoxy-6E,8Z,10E,14Z-eicosatetraenoic acid + O2
5S,12S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5S,15S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid
-
-
-
?
5S-hydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + O2
5S,12S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid
-
-
-
?
5S-hydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + O2
5S,12S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5S,15S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid
-
-
-
?
6,9,12-octadecatrienoic acid + O2
13-hydroxy-6,9,12-octadecatrienoic acid
-
-
-
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
adrenic acid + O2
?
-
-
-
-
?
alpha-linolenic acid + O2
13-hydroxy-(9Z,11E,15Z)-octadecatrienoic acid
alpha-linolenic acid + O2
?
arachidonate + O2
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
arachidonate + O2
(5Z,8Z,11Z,13E)-(12S)-12-hydroperoxyicosa-5,8,11,13-tetraenoate + (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
arachidonic acid + O2
(12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid
-
-
the mutant enzyme G441A converts arachidonic acid to 8S-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid and 12R-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid in a 1.4:1 ratio
-
?
arachidonic acid + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
arachidonic acid methyl ester + O2
12-hydroxyeicosatetraenoic acid methyl ester
-
activity with (12R)-lipoxygenase and epidermal-type-(12S)-lipoxygenase, no activity with platelet-type (12S)-lipoxygenase
epidermal-type (12S)-lipoxygenase produces only 12-hydroxyeicosatetraenoic acid methyl ester, (12R)-lipoxygenase produces (12R)-hydroxyeicosatetraenoic acid methyl ester and (4R)-hydroxyeicosatetraenoic acid methyl ester
?
dihomo-gamma linolenic acid + O2
?
-
-
-
-
?
docosahexaenoic acid + O2
14-hydroxydocosahexaenoic acid
eicosapentaenoic acid + O2
12-hydroxyeicosapentaenoic acid
gamma linolenic acid + O2
10-hydroxy-octadeca-(6Z,8E,12Z)-trienoic acid
-
poor substrate
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-(6Z,8E,12Z)-trienoic acid
-
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
leukotriene A4 + O2
lipoxin A4
LTA4 can be converted by the action of platelet 12-lipoxygenase (12-LO) to lipoxin A4 (LXA4)
-
-
?
linoleate + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
linoleate + O2
(9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoate
-
-
-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
-
-
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
-
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
linoleic acid methyl ester + O2
(9R)-hydroperoxy-(10E,12Z)-octadecadienoic acid methyl ester
-
-
-
-
?
linoleic acid methyl ester + O2
13(S)-hydroperoxyoctadecadienoic acid methyl ester
-
activity with epidermal-type (12S)-lipoxygenase, no activity with platelet-type (12S)-lipoxygenase and (12R)-lipoxygenase
-
?
linolenic acid + O2
?
-
poor substrate
-
-
?
methyl arachidonate + O2
(15S,5Z,8Z,11Z,13E)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester
-
-
-
-
?
methyl arachidonate + O2
?
-
-
-
-
?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
-
11,14,17-eicosatrienoic acid + O2
?
-
-
-
-
?
11,14,17-eicosatrienoic acid + O2
?
-
no activity with enzyme from platelet
-
-
?
11,14,17-eicosatrienoic acid + O2
?
-
enzyme from leukocyte
-
-
?
11,14,17-eicosatrienoic acid + O2
?
-
leukocyte enzyme: 28% of the activity with arachidonic acid, platelet enzyme: less than 2% of the activity with arachidonic acid
-
-
?
11,14,17-eicosatrienoic acid + O2
?
-
poor substrate
-
-
?
11,14,17-eicosatrienoic acid + O2
?
-
no activity with enzyme from platelet
-
-
?
11,14,17-eicosatrienoic acid + O2
?
-
enzyme from leukocyte
-
-
?
11,14-eicosadienoic acid + O2
?
-
-
-
-
?
11,14-eicosadienoic acid + O2
?
-
no activity with enzyme from platelet
-
-
?
11,14-eicosadienoic acid + O2
?
-
enzyme from leukocyte
-
-
?
11,14-eicosadienoic acid + O2
?
-
leukocyte enzyme: 15% of the activity with arachidonic acid, platelet enzyme: less than 2% of the activity with arachidonic acid
-
-
?
11,14-eicosadienoic acid + O2
?
-
no activity with enzyme from platelet
-
-
?
11,14-eicosadienoic acid + O2
?
-
enzyme from leukocyte
-
-
?
2 arachidonate + 2 O2 + 2 H+
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate + (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate + H2O
-
-
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate increases expression of monocyte chemoattractant protein MCP-1 in macrophages, also but less by 15(S)-hydroxyeicosatetranoic acid, and 12(S)-HETE activates NADPH oxidase, overview, i.e. 12(S)-HPETE and 12(S)-HETE, the first is the predominant product
-
?
2 arachidonate + 2 O2 + 2 H+
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate + (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate + H2O
-
-
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate increases expression of monocyte chemoattractant protein MCP-1 in macrophages, also but less by 15(S)-hydroxyeicosatetranoic acid, and 12(S)-HETE activates NADPH oxidase, overview, i.e. 12(S)-HPETE and 12(S)-HETE, the first is the predominant product
-
?
4,7,10,13,16,19-docosahexaenoic acid + O2
14-hydroxy-4,7,10,12,16,19-docosahexaenoic acid
-
-
-
-
?
4,7,10,13,16,19-docosahexaenoic acid + O2
14-hydroxy-4,7,10,12,16,19-docosahexaenoic acid
-
activity with platelet-type (12S)-lipoxygenase and epidermal-type (12S)-lipoxygenase, no activity with (12R)-lipoxygenase
-
?
4,7,10,13,16,19-docosahexaenoic acid + O2
?
-
-
-
-
?
4,7,10,13,16,19-docosahexaenoic acid + O2
?
-
leukocyte enzyme: 92% of the activity with arachidonic acid, platelet enzyme: 7% of the activity with arachidonic acid
-
-
?
4,7,10,13,16,19-docosahexaenoic acid + O2
?
-
-
-
-
?
4,7,10,13,16,19-docosahexaenoic acid + O2
?
-
-
-
-
?
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
-
enzyme from leukocyte, no activity with enzyme from platelet
-
-
?
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
-
leukocyte enzyme: 15% of the activity with arachidonic acid, platelet enzyme: less than 2% of the activity with arachidonic acid
-
-
?
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
-
weak activity
5S,12S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid and 5S,15S-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid are produced in a ratio of about 8:2
?
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
-
-
-
-
?
5(S)-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid + O2
5,12-(5S,12S)-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + 5,12-(5S,15S)-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid
-
40% of the activity with arachidonic acid
-
-
?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
-
-
-
-
?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
-
leukocyte enzyme: 73% of the activity with arachidonic acid, platelet enzyme: less than 94% of the activity with arachidonic acid
-
-
?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
-
-
-
-
?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
-
-
12-hydroxyeicosapentaenoic acid
?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
-
-
-
?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
-
-
-
-
?
5,8,11,14,17-eicosapentaenoic acid + O2
12-hydroxy-5,8,10,14,17-eicosapentaenoic acid
-
14% of the activity with arachidonic acid
-
-
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
-
-
-
-
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
-
leukocyte enzyme: 78% of the activity with arachidonic acid, platelet enzyme: 7% of the activity with arachidonic acid
-
-
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
-
dihomo-gamma-linolenic acid
-
-
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
-
-
-
-
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
-
-
-
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
-
activity with platelet-type (12S)-lipoxygenase and epidermal-type (12S)-lipoxygenase, no activity with (12R)-lipoxygenase
12-hydroxy-8,10,14-eicosatrienoic acid
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
-
-
-
-
?
8,11,14-eicosatrienoic acid + O2
12-hydroxyeicosatrienoic acid
-
95% of the activity with arachidonic acid
-
-
?
alpha-linolenic acid + O2
13-hydroxy-(9Z,11E,15Z)-octadecatrienoic acid
-
-
-
-
?
alpha-linolenic acid + O2
13-hydroxy-(9Z,11E,15Z)-octadecatrienoic acid
-
-
-
?
alpha-linolenic acid + O2
?
-
-
-
-
?
alpha-linolenic acid + O2
?
-
no activity with enzyme from platelet
-
-
?
alpha-linolenic acid + O2
?
-
leukocyte enzyme: 17% of the activity with arachidonic acid, platelet enzyme: less than 2% of the activity with arachidonic acid
-
-
?
alpha-linolenic acid + O2
?
-
activity with enzyme from leukocyte
-
-
?
alpha-linolenic acid + O2
?
-
-
-
-
?
alpha-linolenic acid + O2
?
-
no activity with enzyme from platelet
-
-
?
alpha-linolenic acid + O2
?
-
activity with enzyme from leukocyte
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
further metabolized to (12S)-hydroxyeicosatetraenoate, which inhibits apoptosis in gastric cancer and activates ERK phosphorylation and the ERK1/2 signalling pathway, 12-LOX activates protein kinase C in AGS cells, overview
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
further metabolized to (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate, 12-HETE, has no effect on the spontaneous and lipopolysaccharide-stimulated growth of leukemic blasts
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
further metabolized to 12(S)-hydroxyeicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
i.e. 12(S)-HETE
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
12/15-LO protein levels and activity are increased in pathologically affected regions of Alzheimers disease brains, enzyme inhibition causes a decrease in amyloid-beta protein, 12/15-LO influences amyloid-beta protein precursor protein metabolism, overview
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
arachidonic acid metabolization by lipoxygenases, overview
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
the platelet-type 12S-lipoxygenase isozyme is involved in angiotensin-II induced signaling in vascular smooth muscle cells
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
regioselective oxidation is achieved through control over the position of hydrogen atom abstraction by the geometry and size of the enzyme active site and through control by the protein over the interaction of molecular oxygen with the generated delocalized substrate radical, analysis of catalytic mechanisms of lipoxygenases using 10,10-dideuterated arachidonic acid, 13,13-dideuterated arachidonic acid, and 0,10,13,13-d4-AA, overview
i.e. 12-HPETE, 12-hLO also forms small amounts of 11-HPETE, 8-HPETE, and 15-HPETE, overview
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
two molecules of arachidonic acid bind to one molecule of the enzyme, role of the PLAT domain in activity and membrane binding, overview
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
high oxygen affinity is important for effective catalysis, L367 is involved in oxygen access, channel structure, overview, arachidonic acid closes the substrate-binding pocket for oxygen diffusion but opens a fourth oxygen access channel
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
further metabolized to (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
arachidonate induces cellular membrane disturbance and alters the mitochondrial membrane potential. 12-LOX is involved in covalent binding of alpha-naphthol to arachidonic acid in intact platelets, peroxidase-mediated co-oxidation with arachidonic acid, and peroxidase-mediated xenobiotic activation of alpha-naphthol cytotoxicity, overview
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
arachidonic acid promotes the glutamate-induced cell death, reduces caspase-3 activity, and diminishes internucleosomal DNA fragmentation, it also reduces intracellular NAD, ATP and membrane potentials due to mitochondrila membrane dysfunction, and reduces the inhibitory effect of N-alpha-tosyl-L-phenylalanine chloromethyl ketone and 3,4-dichloroisocumarin on the glutamate-induced cell death, overview
is further metabolized to 12(S)-hydroxyeicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
poly(ADP-ribose) polymerase activation of 12-LOX, but not NADPH oxidase, following zinc release, might play an important role in reactive oxygen species generation and decrease of viability in glucose-reload-treated neurons, overview
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
the enzyme is involved in production of biologically active lipid mediators, (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate, 13-HODE, and 13-HOTE, in the intestine of iron-deficient rats, the lipids are almoste absent in wild-type rats, overview
further metabolized to (5Z,8Z,10E,14Z)-(12S)-12-hydroxyeicosa-5,8,10,14-tetraenoate
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
15-H(p)ETE is the major reaction product independent of the pH
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
12-hydroxyeicosatetraenoic acid and 15-hydroxyeicosatetraenoic acid
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
12-H(p)ETE is the major reaction product of 12/15-LOX independent of the pH
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
activity with platelet-type (12S)-lipoxygenase and epidermal-type (12S)-lipoxygenase, no activity with (12R)-lipoxygenase
platelet-type (12S)-lipoxygenase produces (12S)-hydroxyeicosatetraenoic acid and (8R)-hydroxyeicosatetraenoic acid, epidermal-type (12S)-lipoxygenase produces only 12-hydroxyeicosatetraenoic acid
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
leukocyte-type enzyme produces 12-hydroxyeicosatetraenoic acid and 15-hydroxyeicosatetraenoic acid, platelet-type enzyme produces only 12-hydroxyeicosatetraenoic acid
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
platelet-type (12S)-lipoxygenase produces (12S)-hydroxyeicosatetraenoic acid and (8R)-hydroxyeicosatetraenoic acid, epidermal-type (12S)-lipoxygenase produces only 12-hydroxyeicosatetraenoic acid
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
12-hydroxyeicosatetraenoic acid and 15-hydroxyeicosatetraenoic acid in the ratio of 6:1
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
H2QBX9
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
12-monohydroxy derivatives + 14-monohydroxy derivatives + a mixture of the 8,11,12- and 10,11,12-trihydroxy products of arachidonic acid and 10,13,14- and 12,13,14-trihydroxy derivatives of docosahexaenoic acid
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
12/15LO eicosanoid products reduce cholesterol efflux to high density lipoproteins, regulate ATP-binding cassette transporter G1 expression and enhance ATP-binding cassette transporter G1 degradation and ATP-binding cassette transporter G1 serine phosphorylation
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
-
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
selective oxygenation at carbon 14 yields only the S-isomer
?
arachidonate + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid
the 12-(S)-enantiomer is the predominant product
?
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
mouse Alox12b protein, 12R-LOX, oxygenates arachidonate methyl ester rather than arachidonic acid to 12(R)-hydroperoxyeicosatetraenoic acid, HETE, and to 12(R)-HETE methyl ester
-
-
?
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
mouse Alox12b protein, 12R-LOX, oxygenates arachidonate methyl ester rather than arachidonic acid to 12(R)-hydroperoxyeicosatetraenoic acid, HETE
-
-
?
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
mouse Alox12b protein, 12R-LOX, oxygenates arachidonate methyl ester rather than arachidonic acid to 12(R)-hydroperoxyeicosatetraenoic acid, HETE, and to 12(R)-HETE methyl ester
-
-
?
arachidonate methyl ester + O2
(5Z,8Z,10E,14Z)-(12R)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate methyl ester
mouse Alox12b protein, 12R-LOX, oxygenates arachidonate methyl ester rather than arachidonic acid to 12(R)-hydroperoxyeicosatetraenoic acid, HETE
-
-
?
arachidonic acid + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate
-
-
-
?
arachidonic acid + O2
?
-
-
-
-
?
arachidonic acid + O2
?
-
-
-
-
?
arachidonic acid + O2
?
-
-
-
-
?
docosahexaenoic acid + O2
14-hydroxydocosahexaenoic acid
-
-
-
-
?
docosahexaenoic acid + O2
14-hydroxydocosahexaenoic acid
-
-
-
?
eicosapentaenoic acid + O2
12-hydroxyeicosapentaenoic acid
-
-
-
-
?
eicosapentaenoic acid + O2
12-hydroxyeicosapentaenoic acid
-
-
-
?
eicosapentaenoic acid + O2
12-hydroxyeicosapentaenoic acid
-
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
leukocyte enzyme: 32% of the activity with arachidonic acid, platelet enzyme: less than 2% of the activity with arachidonic acid
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
enzyme from leukocyte, no activity with enzyme from platelet
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
i.e. 6,9,12-octadecatrienoic acid
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
-
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
weak activity
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
-
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
101% of the activity with arachidonic acid
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
-
-
-
?
gamma-linolenic acid + O2
10-hydroxy-octadeca-6Z,8E,12Z-trienoic acid
-
-
-
?
linoleate + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
-
-
-
?
linoleate + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
-
-
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
-
no activity with enzyme from platelet
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
-
enzyme from leukocyte
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
-
leukocyte enzyme: 11% of the activity with arachidonic acid, platelet enzyme: less than 2% of the activity with arachidonic acid
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
-
i.e. 9,12-octadecadienoic acid
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
-
-
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
-
no activity with enzyme from platelet
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
-
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
-
activity with platelet-type (12S)-lipoxygenase and epidermal-type (12S)-lipoxygenase, no activity with (12R)-lipoxygenase
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
-
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
-
-
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
-
35% of the activity with arachidonic acid
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
-
-
-
?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
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enzyme from leukocyte
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?
linoleic acid + O2
13(S)-hydroperoxy-9Z,11E-octadecadienoic acid
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19% of the activity with arachidonic acid
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?
linoleic acid + O2
?
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4% of the activity with arachidonate
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?
linoleic acid + O2
?
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-
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?
linoleic acid + O2
?
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reaction of EC 1.13.11.12
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?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
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?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
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leukocyte enzyme: 18% of the activity with arachidonic acid, platelet enzyme: 6% of the activity with arachidonic acid
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?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
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enzyme possesses 14,15-leukotriene A4 synthase activity, 8-oxygenase activity and 14-oxygenase activity
14R,15S-dihydroxy-5Z,8Z,10E,12E-eicosatetraenoic acid + 14S,15S-dihydroxy-5Z,8Z,10E,12E-eicosatetraenoic acid + 8S,15S-dihydroxy-5Z,9E,11Z,13E-eicosatetraenoic acid + 8R,15S-dihydroxy-5Z,9E,11Z,13E-eicosatetraenoic acid + 8R,15S-dihydroxy-5Z,9E,11E,13E-eicosatetraenoic acid + 8S,15S-dihydroxy-5Z,9E,11E,13E-eicosatetraenoic acid
?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
-
-
-
-
-
?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
-
-
-
14R,15S-dihydroxy-5Z,8Z,10E,12E-eicosatetraenoic acid + 14R,15S-epoxy-5Z,8Z,10E,12E-eicosatetraenoic acid
?
15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid + O2
additional information
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-
-
(8S,15S)-dihydroperoxy-5Z,9E,11Z,13E-eicosatetraenoic acid + (14R,15S)-erythro-dihydroperoxy-5Z,8Z,10E,12E-eicosatetraenoic acid
?
additional information
?
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structure-function analysis
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-
?
additional information
?
-
-
structure-function analysis
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-
?
additional information
?
-
-
no reaction with mead acid and methyl esters of linolenic acid and arachidonate
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-
?
additional information
?
-
-
the 12-lipoxygenase pathway plays a critical role in angiogenesis
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-
?
additional information
?
-
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endogenous phospholipid hydroperoxide glutathione peroxidase plays a pivotal role in the regulation of 12(S)-lipoxygenase and cyclooxygenase 1 activities by reducing the level of intracellular lipid hydroperoxides in arachidonate metabolism in A431 cells
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-
?
additional information
?
-
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interaction between c-Jun and Sp1 may account for the functional regulation of 12(S)-lipoxygenase gene regulation. The direct and cooperative interaction between c-Jun and Sp1 induced by EGF or PMA activates the expression of the human 12(S)-lipoxygenase gene. Sp1 may serve at least in part as a carrier to bring c-Jun to the promoter, thus transactivating the transcriptional activity of the human 12(S)-lipoxygenase gene
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?
additional information
?
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the 12/15-LOX metabolic pathway is increased and correlates with an oxidative imbalance in the Alzheimers disease brain, implying that this enzyme might contribute to the pathogenesis of this neurodegenerative disorder
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?
additional information
?
-
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12-lipoxygenase induces apoptosis of human gastric cancer AGS cells via the ERK1/2 signal pathway, overview
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-
?
additional information
?
-
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exogenously added arachidonic acid and 12(S)-hydroxyeicosatetraenoate, but not 12(R)-hydroxyeicosatetraenoate, as well as 2-arachidonoylglycerol increase invasion by PC-3 cancer cells, overview
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-
?
additional information
?
-
-
a bifunctional enzyme exhibiting 12-lipoxygenase and 15-lipoxygenase, EC 1.13.11.33, activities
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-
?
additional information
?
-
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a bifunctional enzyme exhibiting 12-LO and 15-LO activity
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-
?
additional information
?
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product distributions of lipoxygenases under various conditions, overview
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-
?
additional information
?
-
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product distributions of lipoxygenases under various conditions, overview
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-
?
additional information
?
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15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type subject produces 21% 12-hydroperoxyicosatetraenoate and 79% 15-hydroperoxyicosatetraenoate
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-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
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-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
the 12-lipoxygenase pathway plays a critical role in angiogenesis
-
-
?
additional information
?
-
-
12-lipoxygenase metabolites of arachidonic acid mediate metabotropic glutamate receptor-dependent long-term depression at hippocampal CA3-CA1 synapses
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-
?
additional information
?
-
-
increased expression of 12-LO has deleterius effects in beta cells
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-
?
additional information
?
-
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lipoxin A4 and docosahexaenoic acid-derived neuroprotectin D1 are lipid autacoids formed by 12/15-lipoxygenase pathway that exhibit anti-inflammatory and neuroprotective properties. The enzyme also shows action in wound healing that is distinct from the anti-inflammatory properties
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-
?
additional information
?
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Alox12b deficiency in mice leads to a lack of epidermal permeability barrier function and perinatal lethality
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-
?
additional information
?
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-
Alox12b deficiency in mice leads to a lack of epidermal permeability barrier function and perinatal lethality
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-
?
additional information
?
-
-
a bifunctional enzyme exhibiting 12-LO and 15-LO activity, the enzyme is also able to catalyze stereoselective oxidation of linoleic acid at position 13 over 9 to preferentially form 13(S)-hydroperoxyoctadienoic acid, which enhances MCP-1 expression, overview
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-
?
additional information
?
-
-
reactive oxygen species formation catalyzed by 12-LOX
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-
?
additional information
?
-
12/15-LOX generates (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate and (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate, when arachidonic acid is the substrate, the enzyme produces small amounts of 15S-HETE and primarily 12S-HETE (ratio of 1:3). In case of linolenic acid as a substrate, 13S-hydroxyoctadecadienoic acid (13S-HODE) is generated via the interstage product 13S-hydroperoxyoctadecadienoic acid (13SHPODE). Inflammatory eicosanoids are produced by eosinophils in a 12/15-LOX dependent manner. Another family of 12/15-LOX products are hepoxilins. They are enzymatic products of the conversion of 12S-HPETE, but can also be produced by non-enzymatic modification of 12S-HPETE or 12RHPETE. In the latter case, hemine or haemoglobin may act as a non-specific catalyst
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?
additional information
?
-
the enzymatic peroxidation reaction consists of four consecutive steps: At first a hydrogen atom is stereoselectively abstracted from one of the bisallylic methylene-groups forming an enzyme-bound radical. Secondly one of the two associated cis-double bonds is rearranged and forms a conjugated cis-trans-diene. Consecutively a peroxy radical is produced by inserting molecular oxygen. Finally the radical is reduced by antarafacial re-inserting of a hydrogen atom. The resulting product of this peroxidation reaction depends on the respective fatty acid, which is used as a substrate
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-
?
additional information
?
-
Alox12b deficiency in mice leads to a lack of epidermal permeability barrier function and perinatal lethality
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-
?
additional information
?
-
-
a bifunctional enzyme exhibiting 12-LO and 15-LO activity, the enzyme is also able to catalyze stereoselective oxidation of linoleic acid at position 13 over 9 to preferentially form 13(S)-hydroperoxyoctadienoic acid, which enhances MCP-1 expression, overview
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-
?
additional information
?
-
-
no substrates: gamma-linolenic acid and linoleic acid
-
-
-
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 54% 12-hydroperoxyicosatetraenoate and 46% 15-hydroperoxyicosatetraenoate with 76% overall activity compared to the human enzyme activity
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-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
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-
?
additional information
?
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the bifunctional enzyme also forms (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate, the product of 15-LO activity, EC 1.13.11.33, in a ratio of 9:1 15(S)-HPETE to 12(S)-HPETE
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-
?
additional information
?
-
-
binding of allosteric effector [13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid] shifts the monomer-dimer equilibrium toward dimer formation
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-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 3% 12-hydroperoxyicosatetraenoate and 97% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 3% 12-hydroperoxyicosatetraenoate and 97% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
H2QBX9
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 20% 12-hydroperoxyicosatetraenoate and 80% 15-hydroperoxyicosatetraenoate with 135% overall activity compared to the human enzyme activity
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-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 20% 12-hydroperoxyicosatetraenoate and 80% 15-hydroperoxyicosatetraenoate with 135% overall activity compared to the human enzyme activity
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-
?
additional information
?
-
H2QBX9
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
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-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 78% 12-hydroperoxyicosatetraenoate and 22% 15-hydroperoxyicosatetraenoate with 37% overall activity compared to the human enzyme activity
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-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
the enzyme might, in a fast and effective way, be involved in the formation of signal and/or defense molecules thus contributing to the breoad resistance of mosses against pathogens
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?
additional information
?
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the enzyme might, in a fast and effective way, be involved in the formation of signal and/or defense molecules thus contributing to the breoad resistance of mosses against pathogens
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-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview
-
-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 14% 12-hydroperoxyicosatetraenoate and 86% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
-
15-lipoxygenating ALOX15 orthologs exhibit significantly higher lipoxin-synthesizing capacities than 12-lipoxygenating. Product pattern of primate ALOX15 orthologues, overview. The wild-type animal produces 14% 12-hydroperoxyicosatetraenoate and 86% 15-hydroperoxyicosatetraenoate
-
-
?
additional information
?
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
prediction of reaction specificity of mammalian ALOX15 orthologues, and reaction specificity of ALOX15 orthologues during late primate evolution
-
-
?
additional information
?
-
-
the 12-lipoxygenase pathway plays a critical role in angiogenesis
-
-
?
additional information
?
-
intestinal leukocyte-type isozyme Alox15 shows poor or no 15-lipoxygenase activity, EC 1.13.11.33
-
-
?
additional information
?
-
in the brain, the principal 12/15-LOX metabolites of arachidonate are (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate and (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate, cf. EC 1.13.11.33
-
-
?
additional information
?
-
in the brain, the principal 12/15-LOX metabolites of arachidonate are (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate and (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate, cf. EC 1.13.11.33
-
-
?
additional information
?
-
-
enzyme shows 14R-oxygenase activity and 14,15-leukotriene A synthase activity
-
-
?
additional information
?
-
-
pathway of lipoxin biosynthesis
-
-
?
additional information
?
-
-
stereo-selectivity in LOX-catalyzed oxygenation of lysophospholipids, overview
-
-
?
additional information
?
-
enzyme additionally shows membrane oxygenase activity
-
-
-
additional information
?
-
enzyme additionally shows membrane oxygenase activity
-
-
-