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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
-
-
-
?
(16(R),5Z,8Z,11Z,14Z)-16-fluoroeicosa-5,8,11,14-tetraenoic acid + O2
?
-
wild-type enzyme: 78% of the 15,16(R) product and 22% of the 12,16(R) product
-
?
(16(R),5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
-
wild-type enzyme and mutant enzyme I593A prouce small amounts of unspecific products. Mutant enzyme F353L produces 6% of 15,16(R) product and 94% of the 12,16(R) product
-
?
(16(S),5Z,8Z,11Z,14Z)-16-fluoroeicosa-5,8,11,14-tetraenoic acid + O2
?
-
wild-type enzyme: 69% of the 15,16(S) product and 31% of the 12,16(S) product
-
?
(16(S)5Z,8Z,11Z,14Z)-16-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
-
wild-type enzyme: 93% of the 15,16(S) product and 7% of the 12,16(S) product
-
?
(17(R),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
-
wild-type enzyme: 1% of the 15,17(R) product and 99% of the 12,17(R) product
-
?
(17(S),5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
-
wild-type enzyme: 3% of the 15,17(S) product and 97% of the 12,17(S) product
-
?
(18(R),5Z,8Z,11Z,14Z)-18-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
oxygenation proceeds with little if any enantioselectivity
-
-
?
(18(S),5Z,8Z,11Z,14Z)-18-hydroxyeicosa-5,8,11,14-tetraenoic acid + O2
?
oxygenation proceeds with little if any enantioselectivity
-
-
?
1,2-diarachidonoylglycerophosphocholine + 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
-
?
1-palmitoyl-2-arachidonyl phosphatidyl choline + O2
15S-HpETE + ?
-
-
-
?
1-palmitoyl-2-docosahexaenoyl phosphatidyl choline + O2
17S-HpDHE + ?
-
-
-
?
1-palmitoyl-2-eicosapentaenoyl phosphatidyl choline + O2
15S-HpEPE + ?
-
-
-
?
1-palmitoyl-2-linoleoyl phosphatidyl choline + O2
13S-HpODE + ?
-
-
-
?
1-stearoyl-2-arachidonoyl glycerol + O2
15-HETE + ?
-
-
-
?
1-stearoyl-2-linoleoyl glycerol + O2
13S-HPODE + ?
-
-
-
?
11,14,17-eicosatrienoic acid + O2
15-hydroperoxy-11,13,17-eicosatrienoic acid
-
-
-
?
2 arachidonate + 2 O2 + H+
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate + (5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate + H2O
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
-
-
-
?
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-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
-
-
-
?
5S-hydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid + O2
5S,15S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid
-
-
-
?
8,11,14-eicosatrienoic acid + O2
15-hydroperoxy-8,11,13-eicosatrienoic acid
-
-
-
?
alpha-linoleic acid + O2
?
72% activity compared to arachidonate
-
-
?
alpha-linolenate + O2
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid + (9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid
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 + O2
(5Z,8Z,11Z,13E)-(15S)-12-hydroperoxyicosa-5,8,11,13-tetraenoate + (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
arachidonate + O2
(5Z,8Z,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
-
ratio of (5Z,8Z,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate to (5Z,8Z,11Z,13E,15R)-15-hydroperoxyicosa-5,8,11,13-tetraenoate is 92:8
-
?
arachidonate + O2
(6E,8Z,11Z,14Z)-(5S)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
-
-
-
-
?
arachidonic acid + O2
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid
arachidonic acid + O2
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid + (12S,5Z,8Z,10E,14Z)-12-hydroperoxyeicosa-5,8,10,14-tetraenoic acid
arachidonic acid + O2
13-hydroperoxyeicosatetraenoic acid + (5Z,8Z,11R,12E,14Z)-11-hydroperoxyicosa-5,8,12,14-tetraenoic acid + (5Z,8E,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
arachidonic acid + O2
15S-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid
-
-
-
-
?
arachidonic acid + O2
?
-
-
-
-
?
cholesteryl arachidonate + O2
15S-HpETE + ?
-
-
-
?
cholesteryl linoleate + O2
13S-HpODE + ?
-
-
-
?
cholesteryl linolenate + O2
13S-HpOTE + ?
-
-
-
?
dihomo-gamma-linolenic acid + O2
?
44% activity compared to arachidonate
-
-
?
dilinoleoyl phosphatidic acid + O2
(S)-hydroperoxy dilinoleoyl phosphatidic acid
-
i.e. dilinoleoylPA
-
-
?
dilinoleoyl phosphatidylcholine + O2
(S)-hydroperoxy dilinoleoyl phosphatidylcholine
-
i.e. dilinoleoylPC
-
-
?
docosahexaenoic acid + O2
?
72% activity compared to arachidonate
-
-
?
eicosadienoic acid + O2
?
33% activity compared to arachidonate
-
-
?
eicosapentaenoic acid + O2
15-hydroxyeicosapentaenoic acid
-
-
-
-
?
eicosapentanoic acid + O2
?
61% activity compared to arachidonate
-
-
?
eicosatrienoic acid + O2
?
-
-
-
-
?
gamma-linolenic acid + O2
?
44% activity compared to arachidonate
-
-
?
linoleate + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
-
-
-
-
?
linoleate + O2
(9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoate
-
-
-
?
linoleate + O2
(9Z,11R,12Z)-11-hydroperoxyoctadeca-9,12-dienoate + (9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoate + (9R,10E,12Z)-9-hydroperoxyoctadeca-10,12-dienoate
linoleate + O2
?
-
-
-
-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxy-octadeca-9,11-dienoate
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
linoleic acid + O2
13(S)-hydroxyoctadecadienoic acid
-
-
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
-
?
linoleic acid + O2
13-hydroperoxy-(9Z,11E)-linoleic acid
linoleic acid + O2
13-hydroxylinoleic acid
linoleic acid + O2
13-hydroxyoctadecadienoic acid
-
-
-
-
?
linoleic acid + O2
13-S-hydroxyoctadecadienoic acid
-
both 15-LOX-1, 15-LOX-2 reacts with linoleic acid poorly
-
-
?
linolenate + O2
11-hydroperoxyoctadecatrienoic acid + 9-hydroperoxyoctadecatrienoic acid + 13-hydroperoxyoctadecatrienoic acid
lipoic acid + O2
?
-
-
-
-
r
additional information
?
-
1,2-diarachidonoylglycerophosphocholine + O2
?
-
-
-
?
1,2-diarachidonoylglycerophosphocholine + O2
?
-
-
-
?
2 arachidonate + 2 O2 + H+
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate + (5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate + H2O
-
-
(5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate slightly increases expression of monocyte chemoattractant protein MCP-1 in macrophages, also but more potent by 12(S)-hydroxyeicosatetranoic acid, overview, i.e. 15(S)-HPETE and 15(S)-HETE, the first is the predominant product
-
?
2 arachidonate + 2 O2 + H+
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate + (5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate + H2O
-
-
(5Z,8Z,11Z,13E)-(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoate slightly increases expression of monocyte chemoattractant protein MCP-1 in macrophages, also but more potent by 12(S)-hydroxyeicosatetranoic acid, overview, i.e. 15(S)-HPETE and 15(S)-HETE, the first is the predominant product
-
?
alpha-linolenate + O2
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid + (9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid
-
-
-
?
alpha-linolenate + O2
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoic acid + (9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic 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,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
671247, 672376, 672543, 672899, 672902, 673030, 675201, 675909, 676263, 676923, 676925, 676927, 677239, 685266, 685525, 685526, 685584, 686173, 687052, 687235, 688159, 688509, 688751, 712712 -
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
and small amounts of (5Z,8Z,10E,14Z)-12-hydro(pero)xy-5,8,10,14-icosatetraenoic acid
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
15-hydroperoxy-5,8,11,13-eicosatetraenoic acid + 15-hydroxy-5,8,11,13-eicosatetraenoic acid
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
-
formation of 15S-hydroxyeicosatetraenoic acid and 12S-hydroxyeicosatetraenoic acid in a ratio of 12:1, double oxygenation products 14R,15S-dihydroxyeicosatetraenoic acid and various 8,15-dihydroxyeicosatetraenoic acids are also produced
?
1.13.11.33 arachidonate 15-lipoxygenase
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