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(9E,11Z,14Z)-icosa-9,11,14-trienoic acid + O2
(9S,11Z,14Z)-9-hydroperoxyicosa-11,14-dienoic acid
-
good substrate
-
-
?
12-hydroperoxy-cis,trans,cis-9,13,15-octadecatrienoic acid + O2
12,13-epoxy-14-hydroxy-cis,cis-9,15-octadecadienoic acid
9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid + O2
9,10-epoxy-11-hydroxy-cis,cis-6,12-octadecadienoic acid
9-hydroperoxy-trans,cis-10,12-octadecadienoic acid + O2
9,10-epoxy-11-hydroxy-cis-12-octadecenoic acid
AA/Lyso-PA + O2
15-HPETE/lyso-PA + 13-HPETE/lyso-PA + 15-HPETE/lyso-PA + 11-HPETE/lyso-PA + 5-HPETE/lyso-PA
-
-
36%, 22%, 21% and 13% yield, respectively
-
?
alpha-linolenate
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
-
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate is the main product
-
?
alpha-linolenate + O2
(10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
alpha-linolenate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
alpha-linolenate + O2
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
alpha-linolenate + O2
?
comparable oxygenase activity with either linoleic acid or linolenic acid
no product determined
-
?
alpha-linolenic acid + O2
(10E,12Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
alpha-linolenic acid + O2
12-hydroperoxy-cis,trans,cis-9,13,15-octadecatrienoic acid
arachidonic acid + O2
5-HPETE + 7-HPETE + 9-HPETE
-
-
22%, 25% and 29% yield, respectively
-
?
gamma-linoleic acid + O2
9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid
gamma-linolenate + O2
(6Z,9S,10E,12Z)-9-hydroperoxy-6,10,12-octadecatrienoate
-
72% (6Z,9S,10E,12Z)-9-hydroperoxy-10,12,15-octadecatrienoate, with racemic 6-, 10-, and 13-gamma-hydroperoxy-(10E,12Z,15Z)-octadecatrienoates as secondary products
-
?
gamma-linolenic acid + O2
9 9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid
-
-
-
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
linoleic acid + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
linoleic acid + O2
9-hydroperoxy-trans,cis-10,12-octadecadienoic acid
-
-
-
-
?
linolenic acid + O2
9-hydroperoxy-6,10,12-octadecatrienoate
-
-
-
-
?
linolenic acid + O2
9-hydroperoxy-trans,cis-10,12-octadecadienoic acid
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-
-
-
?
additional information
?
-
12-hydroperoxy-cis,trans,cis-9,13,15-octadecatrienoic acid + O2

12,13-epoxy-14-hydroxy-cis,cis-9,15-octadecadienoic acid
-
-
-
-
?
12-hydroperoxy-cis,trans,cis-9,13,15-octadecatrienoic acid + O2
12,13-epoxy-14-hydroxy-cis,cis-9,15-octadecadienoic acid
-
-
-
-
?
9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid + O2

9,10-epoxy-11-hydroxy-cis,cis-6,12-octadecadienoic acid
-
-
-
-
?
9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid + O2
9,10-epoxy-11-hydroxy-cis,cis-6,12-octadecadienoic acid
-
-
-
-
?
9-hydroperoxy-trans,cis-10,12-octadecadienoic acid + O2

9,10-epoxy-11-hydroxy-cis-12-octadecenoic acid
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-
-
-
?
9-hydroperoxy-trans,cis-10,12-octadecadienoic acid + O2
9,10-epoxy-11-hydroxy-cis-12-octadecenoic acid
-
-
-
-
?
alpha-linolenate + O2

(10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
-
-
the R/S stereoconfiguration of the product is not determined
-
?
alpha-linolenate + O2
(10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
-
96% (10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate and 2.1% (9Z,11E,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
-
?
alpha-linolenate + O2

(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
alpha-linolenate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
alpha-linolenate + O2

(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
-
12-, 13-, and 16-hydroperoxy-(10E,12Z,15Z)-octadecatrienoates are minor byproducts
-
?
alpha-linolenate + O2
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
comparable oxygenase activity with either linoleic acid or linolenic acid
the enzyme forms exclusively (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
-
?
alpha-linolenate + O2
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
-
-
-
-
?
alpha-linolenate + O2
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
comparable oxygenase activity with either linoleic acid or linolenic acid
more than 96% of the substrate is converted to the the 9-positional hydroperoxide
-
?
alpha-linolenic acid + O2

(10E,12Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
-
-
-
?
alpha-linolenic acid + O2
(10E,12Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
-
-
-
-
?
alpha-linolenic acid + O2

12-hydroperoxy-cis,trans,cis-9,13,15-octadecatrienoic acid
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-
-
-
?
alpha-linolenic acid + O2
12-hydroperoxy-cis,trans,cis-9,13,15-octadecatrienoic acid
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-
-
-
?
arachidonate + O2

?
-
-
-
?
arachidonate + O2
?
-
-
-
?
gamma-linoleic acid + O2

9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid
-
-
-
-
?
gamma-linoleic acid + O2
9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid
-
-
-
-
?
linoleate + O2

(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
oxylipins produced by the 9-lipoxygenase pathway in Arabidopsis regulate lateral root development and defense responses through a specific signaling cascade
-
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
no formation of 13-hydroperoxy-(10E,12Z)-octadecadienoate. The R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
no formation of 13-hydroperoxy-(10E,12Z)-octadecadienoate. The R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
the R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate is main product. The R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate is main product. The R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
linoleate (abundant in membrane lipids of tubers) is preferred to linolenate as substrate
the R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
recombinant ZmLOX5 protein displays clear 9-LOX regiospecificity at both neutral and slightly alkaline pH
the R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2

(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
the main product (94%) is (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate, primarily S configuration
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
the product of the wild-type enzyme is 98.8% (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and 1.2% (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate. The product of mutant enzyme A562G is 68.9% (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and 31.1% (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
oxylipins produced by the 9-lipoxygenase pathway in Arabidopsis regulate lateral root development and defense responses through a specific signaling cascade
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
comparable oxygenase activity with either linoleic acid or linolenic acid
the enzyme forms exclusively (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
regiospecificity of Nb-9-LOX, overview
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
low catalytic activity with complex substrates as compared to free linoleic acid. Residual relative activities lower than 1% with the substrates dilinolein, trilinolein, and 1-palmitoyl-2-linoleoyl-glycero-3-phosphocholine and with extracted lipids from malt confirm this supposition. However, LOX1 catalyzes HPODE formation from PamLinGroPCho with high regioselectivity (9-hydroperoxy-(10E,12Z)-octadecadienoate:13-hydroperoxy-(10E,12Z)-octadecadienoate) and high (9S)-hydroperoxy-(10E,12Z)-octadecadienoate stereoselectivity (S:R) (92:8)
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
the enzyme specifically forms the 9-H(p)ODE isomer by 99.5%, 97.7% of which is in S-form
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-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
regiospecificity of Nb-9-LOX, overview
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
comparable oxygenase activity with either linoleic acid or linolenic acid
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
the product of the wild-type enzyme is 99.1% (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and 0.9% (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate. The product of mutant enzyme A564G is 59.9% (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and 40.1% (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
98% (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate, almost exclusively S stereoconfiguration. (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate is a minor byproduct
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
9-lipoxygenase does not utilize docosadienoic acid and catalyzes eicosadienoic acid dioxygenation 20fold slower than linoleic acid dioxygenation
the enzyme specifically forms the S-stereoisomer
-
?
additional information

?
-
arachidonic acid is a poor substrate
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-
?
additional information
?
-
arachidonic acid is a poor substrate
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-
?
additional information
?
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arachidonic acid is a poor substrate
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?
additional information
?
-
from arachidonate the wild-type enzyme forms 47% 11-hydroxyeicosatetraenoic acid, 23% 5-hydroxyeicosatetraenoic acid, 11% 9-hydroxyeicosatetraenoic acid, 9% 12-hydroxyeicosatetraenoic acid, 4.5% 8-hydroxyeicosatetraenoic acid and 4.5% 15-hydroxyeicosatetraenoic acid. Wild-type enzyme converts anandamide mainly to 11S-hydroperoxyanandamide (99.4%). The mutant A562G forms (11S)-hydroperoxyanandamide and (15R)-hydroperoxyanandamide in the ratio 3:2. No activity detected with 1-palmitoyl-2-linoleoylphosphatidylcholine. A model is tested that predicts a relationship between substrate binding orientation and product stereochemistry
-
-
?
additional information
?
-
-
from arachidonate the wild-type enzyme forms 47% 11-hydroxyeicosatetraenoic acid, 23% 5-hydroxyeicosatetraenoic acid, 11% 9-hydroxyeicosatetraenoic acid, 9% 12-hydroxyeicosatetraenoic acid, 4.5% 8-hydroxyeicosatetraenoic acid and 4.5% 15-hydroxyeicosatetraenoic acid. Wild-type enzyme converts anandamide mainly to 11S-hydroperoxyanandamide (99.4%). The mutant A562G forms (11S)-hydroperoxyanandamide and (15R)-hydroperoxyanandamide in the ratio 3:2. No activity detected with 1-palmitoyl-2-linoleoylphosphatidylcholine. A model is tested that predicts a relationship between substrate binding orientation and product stereochemistry
-
-
?
additional information
?
-
low activity with arachidonate, the C20 fatty acid is converted into a mixture of racemic products
-
-
?
additional information
?
-
-
low activity with arachidonate, the C20 fatty acid is converted into a mixture of racemic products
-
-
?
additional information
?
-
in chitosan-treated Adelostemma gracillimum seedlings 9-LOX-derived oxylipins, namely 9,10,11-trihydroxy-12-octadecenoic acid, accumulate
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-
?
additional information
?
-
-
in chitosan-treated Adelostemma gracillimum seedlings 9-LOX-derived oxylipins, namely 9,10,11-trihydroxy-12-octadecenoic acid, accumulate
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-
?
additional information
?
-
the enzyme converted linoleic and linolenic acids almost exclusively to their 9-hydroperoxides
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-
?
additional information
?
-
-
the enzyme converted linoleic and linolenic acids almost exclusively to their 9-hydroperoxides
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-
?
additional information
?
-
regio- and stereospecificity analysis of isozyme substrate specificity, recombinant LOX1:Md:1a, LOX1:Md:1c, LOX2:Md:2a, and LOX2:Md:2b isozymes show 13/9-LOX, 9-LOX, 13/9-LOX and 13-LOX activity with linoleic acid, respectively. While products of LOX1:Md:1c and LOX2:Md:2b are S-configured, LOX1:Md:1a and LOX2:Md:2a form 13(R)-hydroperoxides as major products. Oxygenation in the carbon backbone of linoleic acid occurs either at carbon atom 9 (9-LOX) or 13 (13-LOX), forming the corresponding hydroperoxy derivatives, respectively. LOX enzymes are not perfectly specific and biocatalysts that produce more than 10% of the alternative regio-isomer are called dual positional specific LOX
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?
additional information
?
-
-
regio- and stereospecificity analysis of isozyme substrate specificity, recombinant LOX1:Md:1a, LOX1:Md:1c, LOX2:Md:2a, and LOX2:Md:2b isozymes show 13/9-LOX, 9-LOX, 13/9-LOX and 13-LOX activity with linoleic acid, respectively. While products of LOX1:Md:1c and LOX2:Md:2b are S-configured, LOX1:Md:1a and LOX2:Md:2a form 13(R)-hydroperoxides as major products. Oxygenation in the carbon backbone of linoleic acid occurs either at carbon atom 9 (9-LOX) or 13 (13-LOX), forming the corresponding hydroperoxy derivatives, respectively. LOX enzymes are not perfectly specific and biocatalysts that produce more than 10% of the alternative regio-isomer are called dual positional specific LOX
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?
additional information
?
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Nb-9-LOX possesses both 9-lipoxygenase and 13-lipoxygenase, EC 1.13.11.12, specificity, with high predominance for the 9-LOX function
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-
?
additional information
?
-
from arachidonate the wild-type enzyme forms 11-hydroxyeicosatetraenoic acid and 5-hydroxyeicosatetraenoic acid in essentially equal amounts (38-39%), 11% 8-hydroxyeicosatetraenoic acid, 4% 12-hydroxyeicosatetraenoic acid, 3% 15-hydroxyeicosatetraenoic acid and 2% 9-hydroxyeicosatetraenoic acid. Wild-type enzyme converts anandamide mainly to (11S)-hydroperoxyanandamide (71%), plus 16% (5S)-hydroperoxyanandamide. The mutant enzyme A564G forms two additional prominent products, 15-hydroperoxyanandamide (34%) and 9-hydroperoxyanandamide (19%). No activity detected with 1-palmitoyl-2-linoleoylphosphatidylcholine. A model is tested that predicts a relationship between substrate binding orientation and product stereochemistry
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-
?
additional information
?
-
-
from arachidonate the wild-type enzyme forms 11-hydroxyeicosatetraenoic acid and 5-hydroxyeicosatetraenoic acid in essentially equal amounts (38-39%), 11% 8-hydroxyeicosatetraenoic acid, 4% 12-hydroxyeicosatetraenoic acid, 3% 15-hydroxyeicosatetraenoic acid and 2% 9-hydroxyeicosatetraenoic acid. Wild-type enzyme converts anandamide mainly to (11S)-hydroperoxyanandamide (71%), plus 16% (5S)-hydroperoxyanandamide. The mutant enzyme A564G forms two additional prominent products, 15-hydroperoxyanandamide (34%) and 9-hydroperoxyanandamide (19%). No activity detected with 1-palmitoyl-2-linoleoylphosphatidylcholine. A model is tested that predicts a relationship between substrate binding orientation and product stereochemistry
-
-
?
additional information
?
-
low activity with arachidonate, the C20 fatty acid is converted into a mixture of racemic products
-
-
?
additional information
?
-
-
low activity with arachidonate, the C20 fatty acid is converted into a mixture of racemic products
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-
?
additional information
?
-
-
the enzyme catalyzes oxygenation at the n-12 position of C20 and C22 polyunsaturated fatty acids to form 9S- and 11S-hydroperoxy fatty acids, which are reduced to 9S- and 11S-hydroxy fatty acids by cysteine, respectively, and it catalyzes again oxygenation at the n-6 position of 11S-hydroxy fatty acids to form 9S,15S- and 11S,17S-dihydroxy fatty acids, respectively
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