Information on EC 1.13.11.12 - linoleate 13S-lipoxygenase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.13.11.12
-
RECOMMENDED NAME
GeneOntology No.
linoleate 13S-lipoxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
alpha-linolenate + O2 = (9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate
show the reaction diagram
(2)
-
-
-
linoleate + O2 = (9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
; (1)
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
redox reaction
-
-
reduction
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
alpha-Linolenic acid metabolism
-
-
Biosynthesis of secondary metabolites
-
-
divinyl ether biosynthesis II
-
-
jasmonic acid biosynthesis
-
-
Linoleic acid metabolism
-
-
Metabolic pathways
-
-
traumatin and (Z)-3-hexen-1-yl acetate biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
linoleate:oxygen 13-oxidoreductase
Contains nonheme iron. A common plant lipoxygenase that oxidizes linoleate and alpha-linolenate, the two most common polyunsaturated fatty acids in plants, by inserting molecular oxygen at the C-13 position with (S)-configuration. This enzyme produces precursors for several important compounds, including the plant hormone jasmonic acid. EC 1.13.11.58, linoleate 9S-lipoxygenase, catalyses a similar reaction at the second available position of these fatty acids.
CAS REGISTRY NUMBER
COMMENTARY hide
9029-60-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strains NRRL 3357, TSHB3.1C and TSHB3.5C
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
f. sp. lycopersici
-
-
Manually annotated by BRENDA team
f. sp. lycopersici
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
cv. Sun Smile
-
-
Manually annotated by BRENDA team
Ipomoea nil Choisy
cv. Sun Smile
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
PCC73102
SwissProt
Manually annotated by BRENDA team
PCC73102
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
gene tomloxD
-
-
Manually annotated by BRENDA team
L. cv Desiree
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(15S)-hydroperoxyeicosatetraenoic acid + O2
(8S,15S)-dihydroperoxyeicosatetraenoic acid + (5S,15S)-dihydroperoxyeicosatetraenoic acid
show the reaction diagram
-
-
-
-
?
(5Z,8Z,11Z,14Z)-eicosatetra-5,8,11,14-enoic acid + O2
?
show the reaction diagram
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid + O2
?
show the reaction diagram
-
-
-
-
?
(7Z,10Z,13Z)-hexadecatrienoic acid + O2
?
show the reaction diagram
-
lipoxygenase 2 produces 7- (21.5%), 8- (12.3%), 10- (12.9%), 11- (14.5%), 13- (14%), and 14- (19.6%) hydroperoxides of 16:3, as well as a significant amount of bis-allylic 9-hydroperoxide (5.2%)
-
-
?
(9Z,12Z)-octadeca-9,12-dienoic acid + O2
?
show the reaction diagram
(9Z,12Z,15Z)-9,12,15-octadecatrienoic acid + O2
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate
show the reaction diagram
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate
show the reaction diagram
all-cis-9,12,15-octadecatrienoic acid + O2
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate
show the reaction diagram
alpha-linolenate + O2
(9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
alpha-linolenate + O2
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
show the reaction diagram
alpha-linolenate + O2
(9Z,11E,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
show the reaction diagram
-
isoenzyme Oep1LOX2 and Oep2LOX2 both produce primarily 13-hydroperoxides from linoleic acid and linolenic acid. Linolenic acid is the preferred substrate for both isoenzymes (Vmax/KM is about 10fold higher for linolenic acid)
-
-
?
alpha-linolenic acid + O2
?
show the reaction diagram
-
-
-
-
?
gamma-linolenate + O2
(6Z,9Z,11E,13S)-13-hydroperoxy-6,9,11-octadecatrienoate
show the reaction diagram
linoleate + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
linoleate + O2
(9Z,11E)-13-hydroperoxy-9,11-octadecadienoate
show the reaction diagram
-
isoenzyme Oep1LOX2 and Oep2LOX2 both produce primarily 13-hydroperoxides from linoleic acid and linolenic acid. Linolenic acid is the preferred substrate for both isoenzymes (Vmax/KM is about 10fold higher for linolenic acid)
-
-
?
linoleate + O2
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
show the reaction diagram
linoleate + O2
(9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoic acid
show the reaction diagram
linoleic acid + O2
13(S)-hydroxyoctadecadienoic acid
show the reaction diagram
-
-
-
-
?
linoleic acid + O2
?
show the reaction diagram
-
-
-
-
?
linolenate + O2
?
show the reaction diagram
the enzyme oxygenates linolenic acid more effectively than linoleic acid
the product is not determined
-
?
linolenic acid + O2
?
show the reaction diagram
linoleyltrimethylammonium ion + O2
13-hydroperoxy-(9Z,11E,13S)-octadecadienyltrimethylammonium ion
show the reaction diagram
-
-
primarily
-
?
N-linolenoylethanolamide + O2
?
show the reaction diagram
-
-
-
-
?
N-linoleoylethanolamide + O2
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate
show the reaction diagram
-
-
-
-
?
all-cis-9,12,15-octadecatrienoic acid + O2
(9Z,11E,13S,15Z)-13-hydroperoxyoctadeca-9,11,15-trienoate
show the reaction diagram
alpha-linolenate + O2
(9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
linoleate + O2
(9Z,11E)-(13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
linoleate + O2
(9Z,11E,13S)-13-hydroperoxyoctadeca-9,11-dienoate
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
cadmium
-
induces LOX activity. Cd-induced intracellular LOX activity increases equally along the barley root tip, while Cd-induced apoplastic LOX activity is associated mainly with the differentiation zone of the barley root tip. Cd-induced LOX activity in plants growing at 21C increases with increasing temperatures
Fe2+
-
weakly active site-bound, required for catalysis, non-heme iron lipoxygenase
Iron
-
nonheme, iron-containing dioxygenase
additional information
-
specifically binds iron but not manganese
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-(4-methoxyphenyl)-2-butanone
-
-
1-(4-methoxyphenyl)acetone
-
-
1-methoxy-4-(2-ethylallyl)benzene
-
-
1-methoxy-4-(2-methylallyl)benzene
-
-
11-thialinoleic acid
-
is a competitive inhibitor with respect to linoleic acid and a noncompetitive inhibitor with respect to arachidonic acid
14-thialinoleic acid
-
is a competitive inhibitor with respect to linoleic acid
2',4,6-trimethoxy-aurone
-
-
2'-hydroxy-2,4',6'-trimethoxy-chalcone
-
exhibits 20% inhibition
2'-hydroxy-2-methoxy-chalcone
-
-
2'-hydroxy-3,4,4',6'-tetra(methoxymethoxy)-chalcone
-
exhibits 14.1% inhibition
2'-hydroxy-3,4-dimethoxy-chalcone
-
-
2'-hydroxy-3-methoxy-chalcone
-
exhibits 36.4% inhibition
2'-hydroxy-4-chloro-4', 6'-dimethoxy-chalcone
-
-
2'-hydroxy-4-chloro-chalcone
-
-
2'-hydroxy-4-methyl-4',6'-dimethoxy-chalcone
-
-
2'-hydroxy-4-methyl-chalcone
-
-
2'-methoxy-aurone
-
exhibits 39.9% inhibition
2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxybenzofuran-3(2H)-one
-
quercetin is slowly oxidized by hydroperoxides to a rather stable intermediate, 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxybenzofuran-3(2H)-one, which still inhibits the enzymatic oxidation, probably as a chelator
-
2-(3-(hydroxy(phenyl)methyl)phenyl)-N-phenethylpropanamide
-
-
-
2-(3-(hydroxy(phenyl)methyl)phenyl)propanoic acid
-
-
-
2-(3-benzoylphenyl)-N-(cyclohexanemethyl)propanamide
-
-
-
2-(3-benzoylphenyl)-N-cyclohexylpropanamide
-
-
-
2-(3-benzoylphenyl)-N-cyclopentylpropanamide
-
-
-
2-(3-benzoylphenyl)-N-phenethylpropanamide
-
-
-
2-(3-benzylphenyl)-N,N-bis(2-hydroxyethyl)propanamide
-
-
-
2-(3-benzylphenyl)-N-(2-hydroxyethyl)propanamide
-
-
-
2-(3-benzylphenyl)-N-(3-hydroxypropyl)propanamide
-
-
-
2-(3-benzylphenyl)-N-(cyclohexanemethyl)propanamide
-
-
-
2-(3-benzylphenyl)-N-cyclohexylpropanamide
-
-
-
2-(3-benzylphenyl)-N-cyclopentylpropanamide
-
-
-
2-(3-benzylphenyl)-N-ethoxypropanamide
-
-
-
2-(3-benzylphenyl)-N-methoxypropanamide
-
12% and 27.5% inhibition at 0.1 and 0.5 mM, respectively
-
2-(3-benzylphenyl)-N-phenethylpropanamide
-
-
-
2-(3-benzylphenyl)propanamide
-
-
-
2-(3-benzylphenyl)propanoic acid
-
-
-
2-dodecyl-6-hydroxybenzoic acid
-
C12:0, competitive inhibitor
2-hydroxy-6-[(8E)-pentadec-8-en-1-yl]benzoic acid
-
C15:1, E-isomer, competitive inhibitor
3'-methoxy-aurone
-
exhibits 34.9% inhibition
4'-chloro-4, 6-dimethoxy-aurone
-
-
4'-chloro-aurone
-
exhibits 26.4% inhibition
4'-methoxy-aurone
-
-
4'-methyl-aurone
-
exhibits 32.4% inhibition
4,4',6-trimethoxy-aurone
-
best LOX inhibitory activity
4-(allyloxy)phenyl benzoate
-
-
4-allylphenyl benzoate
-
-
4-Methoxyphenylacetic acid
-
-
6-(2'-ethylheptyl)salicylic acid
-
-
6-(4',8'-dimethylnonyl) salicylic acid
-
-
6-pentadecanylsalicylic acid
-
competitive inhibitor, dose-dependent inhibitory effect
6-[2'-(2'',4'',5''-trihydroxyphenyl)etyl]salicylic acid
-
inhibits lipoxygenase-catalyzed oxidation of linoleic acid, but to a lesser extent compared to 6-pentadecanylsalicylic acid
6-[2'-(2'',4''-dihydroxyphenyl)ethyl]salicylic acid
-
inhibits lipoxygenase-catalyzed oxidation of linoleic acid, but to a lesser extent compared to 6-pentadecanylsalicylic acid
6-[2'-(2'',5''-dihydroxyphenyl)ethyl]salicylic acid
-
inhibits lipoxygenase-catalyzed oxidation of linoleic acid, but to a lesser extent compared to 6-pentadecanylsalicylic acid
6-[2'-(3'',4''-dihydroxyphenyl)ethyl]salicylic acid
-
inhibits lipoxygenase-catalyzed oxidation of linoleic acid, but to a lesser extent compared to 6-pentadecanylsalicylic acid
6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid
-
from Anacardium occidentale
6-[8(Z),11(Z)-pentadecadienyl]salicylic acid
-
from Anacardium occidentale
6-[8(Z)-pentadecenyl]salicylic acid
-
from Anacardium occidentale
alpha-tocopherol
-
competitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
apigenin
-
uncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
beta-carotene
-
-
butyl 2-(4-methoxyphenyl)acetate
-
-
caffeic acid
-
-
catechin
-
competitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
Cu2+
-
inhibits Oep2LOX2 by 49%
cyanidin
-
from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
cyanidin 3-O-arabinoside
-
from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
cyanidin 3-O-galactoside
-
from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
cyanidin 3-O-glucoside
-
from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
cyclohexyl 2-(4-methoxyphenyl)acetate
-
-
cyclopentyl 2-(4-methoxyphenyl)acetate
-
-
delphinidin
-
from Vaccinium myrtillus berries, inhibits in a concentration-dependent manner
delphinidin 3-O-arabinoside
-
from Vaccinium myrtillus berries, inhibits in a concentration-dependent manner
delphinidin 3-O-galactoside
-
from Vaccinium myrtillus berries, most effective inhibitor, uncompetitive type, inhibits in a concentration-dependent manner
delphinidin 3-O-glucoside
-
from Vaccinium myrtillus berries, most effective inhibitor, uncompetitive type, inhibits in a concentration-dependent manner
esteragol
-
-
estragol
-
-
ethyl 2-(4-methoxyphenyl)acetate
-
-
Eugenol
-
-
eugenyl benzoate
-
-
Fe3+
-
slight inactivation
ferulic acid
-
noncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
gallic acid
-
competitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
glutathione
-
-
hexyl 2-(4-methoxyphenyl)acetate
-
-
Hg2+
-
inhibits Oep1LOX2 by 60% and totally inactivates Oep2LOX2
isobutyl 2-(4-methoxyphenyl)acetate
-
-
isopropyl 2-(4-methoxyphenyl)acetate
-
-
kaempferol
-
-
Ketoprofen
-
-
L-ascorbic acid
-
noncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
lauric acid
-
-
lauroylethanolamide
-
-
methyleugenol
-
-
N-benzhydryl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
-
-
-
N-benzhydryl-2-(3-benzoylphenyl)propanamide
-
-
-
N-benzhydryl-2-(3-benzylphenyl)propanamide
-
-
-
N-benzyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
-
-
-
N-benzyl-2-(3-benzoylphenyl)propanamide
-
-
-
N-benzyl-2-(3-benzylphenyl)propanamide
-
-
-
N-benzyloxy-2-(3-benzylphenyl)propanamide
-
-
-
N-cyclohexanemethyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
-
-
-
N-cyclohexyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
-
-
-
N-cyclopentyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
-
-
-
N-hydroxy-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
-
-
-
n-propyl gallate
-
causes a strong inhibition of the LOX-catalyzed enzymatic reaction
N1-(4-(allyloxy) phenyl)-1-admantancarboxamide
-
best inhibitor
N1-(4-(allyloxy) phenyl)-1-cyclobutanecarboxamide
-
-
N1-(4-(allyloxy) phenyl)-1-cyclohexanecarboxamide
-
-
N1-(4-(allyloxy) phenyl)-1-cyclopantanecarboxamide
-
-
N1-(4-(allyloxy) phenyl)-1-cyclopropanecarboxamide
-
-
N1-(4-(allyloxy) phenyl)-2-methylpropanamide
-
-
N1-(4-(allyloxy) phenyl)-3-chlorobenzamide
-
-
N1-(4-(allyloxy) phenyl)-3-fluorobenzamide
-
-
N1-(4-(allyloxy) phenyl)-3-methoxybenzamide
-
-
N1-(4-(allyloxy) phenyl)-3-methylbenzamide
-
-
N1-(4-(allyloxy) phenyl)-4-chlorobenzamide
-
-
N1-(4-(allyloxy) phenyl)-4-fluorobenzamide
-
-
N1-(4-(allyloxy) phenyl)-4-methoxybenzamide
-
-
N1-(4-(allyloxy) phenyl)-4-methylbenzamide
-
-
N1-(4-(allyloxy) phenyl)benzamide
-
-
NDGA
-
-
nordihydroguaiaretic acid
PD146176
-
-
pentyl 2-(4-methoxyphenyl)acetate
-
long chain and lipophile 4-methoxyphenylacetic acid ester, behaves as the best SLO inhibitor
peonidin
-
from Vaccinium macrocarpon juice, inhibits in a concentration-dependent manner
peonidin 3-O-arabinoside
-
from Vaccinium macrocarpon juice, inhibits in a concentration-dependent manner
peonidin 3-O-galactoside
-
from Vaccinium macrocarpon juice, inhibits in a concentration-dependent manner
peonidin 3-O-glucoside
-
from Vaccinium macrocarpon juice, inhibits in a concentration-dependent manner
Phenidone
-
inhibits the LOX-dependent defence response of the plant, whereby this inhibition can influence the behaviour of members of the associated insect community. Plants treated with phenidone are less attractive to Cotesia glomerata parasitoids than controls. Herbivores Pieris rapae and Pieris brassicae are less sensitive to changes in plant metabolic profiles induced by caterpillar feeding and LOX inhibition respectively than their natural enemy Cotesia glomerata. Preference of Plutella xylostella for Pieris rapae-infested plants over uninfested plants is LOX dependent, since phenidone treatment of uninfested and infested plants eliminates the preference. The inhibitor reduces the accumulation of internal signalling compounds in the octadecanoid pathway of the plant downstream of the step catalysed by LOX, i.e. 12-oxo-phytodienoic acid and jasmonic acid
propyl 2-(4-methoxyphenyl)acetate
-
-
propyl gallate
is a competitive inhibitor
quercetin
-
noncompetitive inhibition by initially reducing the ferric form of the enzyme to an inactive ferrous form
resveratrol
-
uncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
rutin
-
-
sec-butyl 2-(4-methoxyphenyl)acetate
-
-
tert-butyl 2-(4-methoxyphenyl)acetate
-
-
Trolox
-
noncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction. At physiological pH 7.0 the LOX/4-nitroso-N,N-dimethylaniline assay is more sensitive to trolox inhibition
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
13-hydroperoxy-linoleic acid
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00337
(5Z,8Z,11Z,14Z)-eicosatetra-5,8,11,14-enoic acid
-
pH 8.0, 22C
0.0348
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
-
pH 8.0, 22C
0.00689
(9Z,12Z)-octadeca-9,12-dienoic acid
-
pH 8.0, 22C
0.0316
(9Z,12Z,15Z)-9,12,15-octadecatrienoic acid
-
pH 8.0, 22C
0.028 - 0.14
alpha-linolenate
0.0146 - 0.13
linoleate
0.0117 - 0.1749
linoleic acid
0.028 - 0.3437
linolenic acid
0.015
N-linolenoylethanolamide
-
in 0.1 M borate (pH 9.0), temperature not specified in the publication
0.027
N-linoleoylethanolamide
-
in 0.1 M borate (pH 9.0), temperature not specified in the publication
additional information
additional information
-
Michaelis-Menten kinetics
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.71
(5Z,8Z,11Z,14Z)-eicosatetra-5,8,11,14-enoic acid
Fusarium oxysporum
-
pH 8.0, 22C
18.58
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Fusarium oxysporum
-
pH 8.0, 22C
2.611
(9Z,12Z)-octadeca-9,12-dienoic acid
Fusarium oxysporum
-
pH 8.0, 22C
1.566
(9Z,12Z,15Z)-9,12,15-octadecatrienoic acid
Fusarium oxysporum
-
pH 8.0, 22C
48.16 - 64
linoleic acid
47.78
linolenic acid
Olea europaea
B6D1W5
pH 6.0, 25C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
25 - 280
linoleic acid
140
linolenic acid
Olea europaea
B6D1W5
-
1413
additional information
additional information
Olea europaea
-
linolenic acid is the preferred substrate for both isoenzymes (Vmax/KM is about 10fold higher for linolenic acid)
2
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.022
11-thialinoleic acid
-
-
0.035
14-thialinoleic acid
-
-
0.0096
2-dodecyl-6-hydroxybenzoic acid
-
pH 9.0
0.0028
2-hydroxy-6-[(8E)-pentadec-8-en-1-yl]benzoic acid
-
pH 9.0
0.0064
6-pentadecanylsalicylic acid
-
pH 9.0
1.1
alpha-tocopherol
-
-
3.4
apigenin
-
-
13.6
catechin
-
-
10.7
ferulic acid
-
-
6.7
gallic acid
-
-
14
L-ascorbic acid
-
-
0.0084 - 0.015
lauric acid
0.0005 - 0.0009
lauroylethanolamide
0.00409
nordihydroguaiaretic acid
pH 6.0, 25C
0.00188
propyl gallate
pH 6.0, 25C
1.7
resveratrol
-
-
7
Trolox
-
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.033
1-(4-methoxyphenyl)-2-butanone
Glycine max
-
pH 9.0, 20C
0.043
1-(4-methoxyphenyl)acetone
Glycine max
-
pH 9.0, 20C
0.145
1-methoxy-4-(2-ethylallyl)benzene
Glycine max
-
pH 9.0, 20C
0.137
1-methoxy-4-(2-methylallyl)benzene
Glycine max
-
pH 9.0, 20C
0.1
2',4,6-trimethoxy-aurone
0.0675
2'-hydroxy-3,4-dimethoxy-chalcone
Glycine max
-
at pH 9.0
0.082
2'-hydroxy-4-chloro-4', 6'-dimethoxy-chalcone
Glycine max
-
at pH 9.0
0.056
2'-hydroxy-4-chloro-chalcone
Glycine max
-
at pH 9.0
0.053
2'-hydroxy-4-methyl-4',6'-dimethoxy-chalcone
Glycine max
-
at pH 9.0
0.0525
2'-hydroxy-4-methyl-chalcone
Glycine max
-
at pH 9.0
0.12
2-(3-(hydroxy(phenyl)methyl)phenyl)-N-phenethylpropanamide
Glycine max
-
25C, pH not specified in the publication
-
0.13
2-(3-(hydroxy(phenyl)methyl)phenyl)propanoic acid
Glycine max
-
25C, pH not specified in the publication
-
0.053
2-(3-benzoylphenyl)-N-(cyclohexanemethyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.12
2-(3-benzoylphenyl)-N-cyclohexylpropanamide
Glycine max
-
25C, pH not specified in the publication
-
0.0615
2-(3-benzoylphenyl)-N-cyclopentylpropanamide
Glycine max
-
25C, pH not specified in the publication
-
0.065
2-(3-benzoylphenyl)-N-phenethylpropanamide
Glycine max
-
25C, pH not specified in the publication
-
0.4
2-(3-benzylphenyl)-N,N-bis(2-hydroxyethyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.27
2-(3-benzylphenyl)-N-(2-hydroxyethyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.28
2-(3-benzylphenyl)-N-(3-hydroxypropyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.08
2-(3-benzylphenyl)-N-(cyclohexanemethyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.0375
2-(3-benzylphenyl)-N-cyclohexylpropanamide
Glycine max
-
25C, pH not specified in the publication
-
0.082
2-(3-benzylphenyl)-N-cyclopentylpropanamide
Glycine max
-
25C, pH not specified in the publication
-
0.385
2-(3-benzylphenyl)-N-ethoxypropanamide
Glycine max
-
25C, pH not specified in the publication
-
0.043
2-(3-benzylphenyl)-N-phenethylpropanamide
Glycine max
-
25C, pH not specified in the publication
-
0.325
2-(3-benzylphenyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.415
2-(3-benzylphenyl)propanoic acid
Glycine max
-
25C, pH not specified in the publication
-
0.00207
2-dodecyl-6-hydroxybenzoic acid
Glycine max
-
pH 9.0
0.0068
2-hydroxy-6-[(8E)-pentadec-8-en-1-yl]benzoic acid
Glycine max
-
pH 9.0
0.07
4'-methoxy-aurone
Glycine max
-
at pH 9.0
0.05
4,4',6-trimethoxy-aurone
Glycine max
-
at pH 9.0
0.0062
4-(allyloxy)phenyl benzoate
Glycine max
-
pH 9.0, 20C
0.0067
4-allylphenyl benzoate
Glycine max
-
pH 9.0, 20C
0.0562
4-Methoxyphenylacetic acid
Glycine max
-
pH 9.0, 20C
0.0188
6-(2'-ethylheptyl)salicylic acid
Glycine max
-
pH 9.0
0.0105
6-(4',8'-dimethylnonyl) salicylic acid
Glycine max
-
pH 9.0
0.0143
6-pentadecanylsalicylic acid
Glycine max
-
pH 9.0
0.4
6-[2'-(2'',5''-dihydroxyphenyl)ethyl]salicylic acid
Glycine max
-
pH 9.0
0.0078
beta-carotene
Glycine max
-
-
0.0038
butyl 2-(4-methoxyphenyl)acetate
Glycine max
-
pH 9.0, 20C
0.6
caffeic acid
0.58
cyanidin
Glycine max
-
-
1.24
cyanidin 3-O-arabinoside
Glycine max
-
-
0.18
cyanidin 3-O-galactoside
Glycine max
-
-
0.25
cyanidin 3-O-glucoside
Glycine max
-
-
0.064
cyclohexyl 2-(4-methoxyphenyl)acetate
Glycine max
-
pH 9.0, 20C
0.0565
cyclopentyl 2-(4-methoxyphenyl)acetate
Glycine max
-
pH 9.0, 20C
0.27
delphinidin
Glycine max
-
-
0.49
delphinidin 3-O-arabinoside
Glycine max
-
-
0.00046
delphinidin 3-O-galactoside
Glycine max
-
-
0.00043
delphinidin 3-O-glucoside
Glycine max
-
-
0.0641
esteragol
0.032
ethyl 2-(4-methoxyphenyl)acetate
Glycine max
-
-
0.0382
Eugenol
Glycine max
-
pH 9.0, 20C
0.007
eugenyl benzoate
Glycine max
-
pH 9.0, 20C
0.0197
glutathione
Glycine max
-
-
0.035
hexyl 2-(4-methoxyphenyl)acetate
Glycine max
-
pH 9.0, 20C
0.0881
isobutyl 2-(4-methoxyphenyl)acetate
Glycine max
-
pH 9.0, 20C
0.0344
isopropyl 2-(4-methoxyphenyl)acetate
Glycine max
-
pH 9.0, 20C
0.13
Ketoprofen
Glycine max
-
25C, pH not specified in the publication
0.0961
methyleugenol
Glycine max
-
pH 9.0, 20C
0.0205
N-benzhydryl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.0645
N-benzhydryl-2-(3-benzoylphenyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.05
N-benzhydryl-2-(3-benzylphenyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.2
N-benzyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.0875
N-benzyl-2-(3-benzoylphenyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.0745
N-benzyl-2-(3-benzylphenyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.1
N-benzyloxy-2-(3-benzylphenyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.295
N-cyclohexanemethyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.425
N-cyclohexyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.23
N-cyclopentyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.2
N-hydroxy-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
Glycine max
-
25C, pH not specified in the publication
-
0.00067
N1-(4-(allyloxy) phenyl)-1-admantancarboxamide
Glycine max
-
pH 9.0, 20C
0.0022
N1-(4-(allyloxy) phenyl)-1-cyclobutanecarboxamide
Glycine max
-
pH 9.0, 20C
0.0064
N1-(4-(allyloxy) phenyl)-1-cyclohexanecarboxamide
Glycine max
-
pH 9.0, 20C
0.0041
N1-(4-(allyloxy) phenyl)-1-cyclopantanecarboxamide
Glycine max
-
pH 9.0, 20C
0.0061
N1-(4-(allyloxy) phenyl)-1-cyclopropanecarboxamide
Glycine max
-
pH 9.0, 20C
0.0129
N1-(4-(allyloxy) phenyl)-2-methylpropanamide
Glycine max
-
pH 9.0, 20C
0.0081
N1-(4-(allyloxy) phenyl)-3-chlorobenzamide
Glycine max
-
pH 9.0, 20C
0.0056
N1-(4-(allyloxy) phenyl)-3-fluorobenzamide
Glycine max
-
pH 9.0, 20C
0.017
N1-(4-(allyloxy) phenyl)-3-methoxybenzamide
Glycine max
-
pH 9.0, 20C
0.0067
N1-(4-(allyloxy) phenyl)-3-methylbenzamide
Glycine max
-
pH 9.0, 20C
0.0088
N1-(4-(allyloxy) phenyl)-4-chlorobenzamide
Glycine max
-
pH 9.0, 20C
0.0038
N1-(4-(allyloxy) phenyl)-4-fluorobenzamide
Glycine max
-
pH 9.0, 20C
0.0138
N1-(4-(allyloxy) phenyl)-4-methoxybenzamide
Glycine max
-
pH 9.0, 20C
0.0101
N1-(4-(allyloxy) phenyl)-4-methylbenzamide
Glycine max
-
pH 9.0, 20C
0.0033
N1-(4-(allyloxy) phenyl)benzamide
Glycine max
-
pH 9.0, 20C
0.04
nordihydroguaiaretic acid
Glycine max
-
at pH 9.0
0.0019
pentyl 2-(4-methoxyphenyl)acetate
Glycine max
-
pH 9.0, 20C
0.59
peonidin
Glycine max
-
-
31
peonidin 3-O-arabinoside
Glycine max
-
-
37.7
peonidin 3-O-galactoside
Glycine max
-
-
37.5
peonidin 3-O-glucoside
Glycine max
-
-
0.0116
propyl 2-(4-methoxyphenyl)acetate
Glycine max
-
pH 9.0, 20C
0.0048
quercetin
Glycine max
-
in 0.1M Tris-HCl (pH 8.0), at 25C
0.0357
sec-butyl 2-(4-methoxyphenyl)acetate
Glycine max
-
pH 9.0, 20C
0.0387
tert-butyl 2-(4-methoxyphenyl)acetate
Glycine max
-
pH 9.0, 20C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10.2
-
crude extract, with linoleic acid as substrate
12
-
crude extract, with alpha-linolenic acid as substrate
23.4
26fold purified enzyme, with linoleic acid as substrate
28.3
-
purified recombinant enzyme, pH 7.5, 25C
474
-
55fold purified enzyme, with alpha-linolenic acid as substrate
564
-
55fold purified enzyme, with linoleic acid as substrate
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 8.5
broad optimum with a maximum at pH 8.0, substrate: linoleate
6.25
-
isoform Oep1LOX2
6.3
-
isoenzyme Oep2LOX2
6.75
-
isoform Oep2LOX2
6.8
-
isoenzyme Oep1LOX2
7 - 9
-
linoleic acid is a considerably better substrate for SBLO-1 at pH 9.0 than at pH 7.0, while the activity with linoleyltrimethylammonium ion is the same at pH 7.0 and pH 9.0
7.2
-
triolein as substrate
7.5
-
recombinant enzyme
8.8
-
for linoleic acid
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 8
-
activity range, overview
5.6 - 8.5
-
pH 5.6. about 50% of maximal activity, pH 8.5: about 70% of maximal activity
7 - 10.5
-
activity range, overview. Low activity below pH 7.0, maximum activity at pH 8.0, 75% of maximal activity at up to pH 10.5
7.8 - 8.4
-
at pH 7.8, ca. 50% of maximal activity, at pH 8.4, ca. 30% of maximal activity, substrate alpha-linoleic acid
8.5 - 8.9
-
at pH 8.5, ca. 30% of maximal activity, at pH 8.9, ca. 80% of maximal activity, substrate linolenic acid
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
-
assay at room temperaature
35
-
isoenzyme Oep2LOX2; isoform Oep2LOX2
45
-
isoenzyme Oep1LOX2; isoform Oep1LOX2
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
15 - 55
-
more than 85% of maximal activity in the temperature-range: 15-55C, isoenzyme Oep1LOX2; recombinant Oep1LOX2 exhibits more than 85% of its maximal activity, whereas Oep2LOX2 displays about 50-100% of its maximal activity
20 - 60
-
activity range, overview
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.9
-
sequence analysis, isoform Oep2LOX2
5.95
calculated from sequence
7.2
-
sequence analysis, isoform Oep1LOX2
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
Oep2LOX2 shows the highest expression levels in mature mesocarp tissue
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
95000
-
Western blotting and gel filtration
101700
-
sequence analysis, isoform Oep2LOX2
103400
-
sequence analysis, isoform Oep1LOX2
160000
-
about, recombinant His-tagged enzyme, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
monomer
1 * 105000, SDS-PAGE, His-tagged enzyme
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20 - 65
-
purified extracellular enzyme, 25C, 7 min, stable at up to 35C, loss of 10% activity at 40C, and of 20% at 50C, 10% activity remaining at 60C, inactivation at 65C
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80C, 100 mM borate buffer, pH 10, 30% glycerol
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate precipitation, anion-exchange column chromatography and hydrophobic column chromatography
-
by affinity chromatography; isoenzyme Oep1LOX2 and Oep2LOX2
-
by ammonium sulphate precipitation and ion-exchange chromatography, 55fold with a yield of 5.6%
-
by Ni-affinity chromatography and gel filtration, 26fold
by sonication, centrifugation and gel filtration
-
recombinant extracellular enzyme 13.5fold from Escherichia coli strain Rosetta (DE3) cell supernatant b two different steps of anion exchange chromatography
-
soluble LOX purified with His bind kits
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Escherichia coli BL21 cells carrying the plasmid PT7-7/L1 VTSLO-11
-
expressed in Escherichia coli BL21(DE3)pLysS and Rosetta(DE3)pLysS cells
-
expression in Escherichia coli
expression in insect cells; expression in insect cells; expression in insect cells; expression in insect cells; recombinant baculovirus expressing LOX2 (pFastBac) plasmid transferred into Escherichia coli DH10Bac containing the baculovirus shuttle vector bMON14272 and the helper plasmid pMON7124. Recombinant bacmid DNA transfected into High Five insect cells; recombinant baculovirus expressing LOX3 (pFastBac) plasmid transferred into Escherichia coli DH10Bac containing the baculovirus shuttle vector bMON14272 and the helper plasmid pMON7124. Recombinant bacmid DNA transfected into High Five insect cells; recombinant baculovirus expressing LOX4 (pFastBac) plasmid transferred into Escherichia coli DH10Bac containing the baculovirus shuttle vector bMON14272 and the helper plasmid pMON7124. Recombinant bacmid DNA transfected into High Five insect cells; recombinant baculovirus expressing LOX6 (pFastBac) plasmid transferred into Escherichia coli DH10Bac containing the baculovirus shuttle vector bMON14272 and the helper plasmid pMON7124. Recombinant bacmid DNA transfected into High Five insect cells
gene FoxLOX, DNA and amino acid sequence determination and analysis, phylogenetic analysis and sequence comparison, recombinnat expression of His-tagged enzyme
-
gene tomloxD, overexpression in transgenic tomato plants, introduction of the binary vector pLoxD into Agrobacterium tumefaciens LBA4404 by the freeze-thaw method, phenotype, overview
-
into a pcDNA3.1 vector and introduced into HCT-116 and HT-29 cells
-
isoenzyme Oep1LOX2 and Oep2LOX2; Oep1LOX2 and Oep2LOX2 ligated into vector pQE-80 L and overexpressed in Escherichia coli strain XL1-Blue
-
LOX1 ORF cloned into vector pET30a(+) for overexpression in Escherichia coli. LOX1-green GFP fusion construct, under the control of the cauliflower mosaic virus 35S promoter, expressed in Arabidopsis plants. Transgenic rice lines carrying either sense or antisense constructs under the control of a cauliflower mosaic virus 35S promoter
overexpression and secretion of extracellular enzyme in Escherichia coli strain Rosetta(DE3) using the enzyme's endogenous signal peptide
-
vector pQE30-LOX expressed in Escherichia coli M15 cells
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
0.04 mM honokiol markedly activates cellular 15-LOX-1 expression
-
cadmium induces lipoxygenase activity
-
expression of the tomato gene encoding 13-lipoxygenase, TomloxD, is stimulated by wounding, pathogen infection, jasmonate, and systemin
-
in all antisense transgenic rice lines and more than half of the sense lines the expression levels of LOX1, the levels of enzyme activity, and the levels of the endogenous LOX1 products (jasmonic acid, (Z)-3-hexenal and colneleic acid) at 6, 48, and 48 h after brown planthopper feeding respectively, are below the levels found in non-transgenic control plants
Lox is a low-expression gene, no expression in wild-type strain NRRL 3357
Lox is expressed in the complemented strains TSHB3.1C and TSHB3.5C. While complemented strain TSHB3.1C (harboring a single-copy insertion) expresses a clear transcript, complemented strain TSHB3.5C (harboring at least two copies of lox and likely more) produces a greatly increased transcript and also produces an additional smaller band, which is absent in the single-copy strain TSHB3.1C
LOX1 transcripts accumulate rapidly and transiently in response to wounding or brown planthopper attack, reaching a peak 3 h after wounding and 6 h after insect feeding. Transgenic rice lines show altered LOX1 activity
Oep2LOX2 transcript levels increase in Picual and Arbequina mesocarps during development and ripening, showing a maximum at turning stage, whereas Oep1LOX2 exhibits constant expression levels in both olive varieties and tissues
-
the LOX2 gene is upregulated after wounding plus water and wounding plus Manduca sexta oral secretions treatment; the LOX3 gene is upregulated after wounding plus water and wounding plus Manduca sexta oral secretions treatment
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Q599H
converts the enzyme to a pure 13-LOX
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
-
the tomloxD gene encoding the enzyme has potential applications in engineering cropping plants that are resistant to biotic and/or abiotic stress factors
food industry
medicine
additional information
the manipulating of the expression of the LOX gene may provide a basis for advancing both the fundamental and applied biology of rice