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1-(4-methoxyphenyl)-2-butanone
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1-(4-methoxyphenyl)acetone
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1-methoxy-4-(2-ethylallyl)benzene
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1-methoxy-4-(2-methylallyl)benzene
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11-thialinoleic acid
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is a competitive inhibitor with respect to linoleic acid and a noncompetitive inhibitor with respect to arachidonic acid
14-thialinoleic acid
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is a competitive inhibitor with respect to linoleic acid
2',4,6-trimethoxy-aurone
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2'-hydroxy-2,4',6'-trimethoxy-chalcone
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exhibits 20% inhibition
2'-hydroxy-2-methoxy-chalcone
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2'-hydroxy-3,4,4',6'-tetra(methoxymethoxy)-chalcone
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exhibits 14.1% inhibition
2'-hydroxy-3,4-dimethoxy-chalcone
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2'-hydroxy-3-methoxy-chalcone
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exhibits 36.4% inhibition
2'-hydroxy-4-chloro-4', 6'-dimethoxy-chalcone
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2'-hydroxy-4-chloro-chalcone
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2'-hydroxy-4-methyl-4',6'-dimethoxy-chalcone
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2'-hydroxy-4-methyl-chalcone
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2'-methoxy-aurone
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exhibits 39.9% inhibition
2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxybenzofuran-3(2H)-one
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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
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2-(3-(hydroxy(phenyl)methyl)phenyl)propanoic acid
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2-(3-benzoylphenyl)-N-(cyclohexylmethyl)propanamide
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2-(3-benzoylphenyl)-N-cyclohexylpropanamide
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2-(3-benzoylphenyl)-N-cyclopentylpropanamide
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2-(3-benzoylphenyl)-N-phenethylpropanamide
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2-(3-benzylphenyl)-N,N-bis(2-hydroxyethyl)propanamide
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2-(3-benzylphenyl)-N-(2-hydroxyethyl)propanamide
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2-(3-benzylphenyl)-N-(3-hydroxypropyl)propanamide
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2-(3-benzylphenyl)-N-(cyclohexylemethyl)propanamide
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2-(3-benzylphenyl)-N-cyclohexylpropanamide
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2-(3-benzylphenyl)-N-cyclopentylpropanamide
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2-(3-benzylphenyl)-N-ethoxypropanamide
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2-(3-benzylphenyl)-N-methoxypropanamide
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12% and 27.5% inhibition at 0.1 and 0.5 mM, respectively
2-(3-benzylphenyl)-N-phenethylpropanamide
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2-(3-benzylphenyl)propanamide
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2-(3-benzylphenyl)propanoic acid
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2-dodecyl-6-hydroxybenzoic acid
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C12:0, competitive inhibitor
2-hydroxy-6-[(8E)-pentadec-8-en-1-yl]benzoic acid
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C15:1, E-isomer, competitive inhibitor
3'-methoxy-aurone
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exhibits 34.9% inhibition
4'-chloro-4, 6-dimethoxy-aurone
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4'-chloro-aurone
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exhibits 26.4% inhibition
4'-methyl-aurone
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exhibits 32.4% inhibition
4,4',6-trimethoxy-aurone
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best LOX inhibitory activity
4-(allyloxy)phenyl benzoate
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4-allylphenyl benzoate
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4-Methoxyphenylacetic acid
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4-methyl-2-(4-methylpiperazinyl)pyrimido[4,5-b]benzothiazine
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6-(2'-ethylheptyl)salicylic acid
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6-(4',8'-dimethylnonyl) salicylic acid
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6-pentadecanylsalicylic acid
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competitive inhibitor, dose-dependent inhibitory effect
6-[2'-(2'',4'',5''-trihydroxyphenyl)etyl]salicylic acid
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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
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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
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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
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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
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from Anacardium occidentale
6-[8(Z),11(Z)-pentadecadienyl]salicylic acid
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from Anacardium occidentale
6-[8(Z)-pentadecenyl]salicylic acid
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from Anacardium occidentale
adamantyl caffeate
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.074 mM
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alpha-tocopherol
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competitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
apigenin
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uncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
bornyl vanillate
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.401 mM
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butyl 2-(4-methoxyphenyl)acetate
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catechin
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competitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
Cd2+
complete inhibition at 1 mM; complete inhibition at 1 mM; complete inhibition at 1 mM
cis-(+)-12-oxophytodienoic acid
isoform LOX2 exhibits 64% residual activity at 2.8 mM; isoform LOX3 exhibits 60% residual activity at 2.8 mM; isoform LOX4 exhibits 21% residual activity at 2.8 mM; isoform LOX6 exhibits 50% residual activity at 2.8 mM
cyanidin
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from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
cyanidin 3-O-arabinoside
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from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
cyanidin 3-O-galactoside
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from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
cyanidin 3-O-glucoside
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from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
cyclohexyl 2-(4-methoxyphenyl)acetate
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cyclopentyl 2-(4-methoxyphenyl)acetate
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delphinidin
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from Vaccinium myrtillus berries, inhibits in a concentration-dependent manner
delphinidin 3-O-arabinoside
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from Vaccinium myrtillus berries, inhibits in a concentration-dependent manner
delphinidin 3-O-galactoside
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from Vaccinium myrtillus berries, most effective inhibitor, uncompetitive type, inhibits in a concentration-dependent manner
delphinidin 3-O-glucoside
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from Vaccinium myrtillus berries, most effective inhibitor, uncompetitive type, inhibits in a concentration-dependent manner
ethyl 2-(4-methoxyphenyl)acetate
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fenchyl caffeate
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.089 mM
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ferulic acid
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noncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
gallic acid
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competitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
hexyl 2-(4-methoxyphenyl)acetate
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isobutyl 2-(4-methoxyphenyl)acetate
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isopropyl 2-(4-methoxyphenyl)acetate
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K+
38% residual activity at 50 mM
L-ascorbic acid
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noncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
methyl jasmonate
isoform LOX2 exhibits 87% residual activity at 2.8 mM; isoform LOX3 exhibits 85% residual activity at 2.8 mM; isoform LOX4 exhibits 95% residual activity at 2.8 mM; isoform LOX6 exhibits 94% residual activity at 2.8 mM
N-(cyclohexylmethyl)-2-{3-[hydroxy(phenyl)methyl]phenyl}propanamide
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N-benzhydryl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
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N-benzhydryl-2-(3-benzoylphenyl)propanamide
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N-benzhydryl-2-(3-benzylphenyl)propanamide
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N-benzyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
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N-benzyl-2-(3-benzoylphenyl)propanamide
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N-benzyl-2-(3-benzylphenyl)propanamide
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N-benzyloxy-2-(3-benzylphenyl)propanamide
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N-cyclohexyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
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N-cyclopentyl-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
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N-ethylmaleimide
isoform LOX2 exhibits 84% residual activity at 2.8 mM; isoform LOX3 exhibits 51% residual activity at 2.8 mM; isoform LOX4 exhibits 11% residual activity at 2.8 mM; isoform LOX6 exhibits 47% residual activity at 2.8 mM
N-hydroxy-2-(3-(hydroxy(phenyl)methyl)phenyl)propanamide
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n-propyl gallate
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causes a strong inhibition of the LOX-catalyzed enzymatic reaction
N1-(4-(allyloxy) phenyl)-1-admantancarboxamide
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best inhibitor
N1-(4-(allyloxy) phenyl)-1-cyclobutanecarboxamide
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N1-(4-(allyloxy) phenyl)-1-cyclohexanecarboxamide
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N1-(4-(allyloxy) phenyl)-1-cyclopantanecarboxamide
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N1-(4-(allyloxy) phenyl)-1-cyclopropanecarboxamide
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N1-(4-(allyloxy) phenyl)-2-methylpropanamide
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N1-(4-(allyloxy) phenyl)-3-chlorobenzamide
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N1-(4-(allyloxy) phenyl)-3-fluorobenzamide
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N1-(4-(allyloxy) phenyl)-3-methoxybenzamide
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N1-(4-(allyloxy) phenyl)-3-methylbenzamide
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N1-(4-(allyloxy) phenyl)-4-chlorobenzamide
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N1-(4-(allyloxy) phenyl)-4-fluorobenzamide
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N1-(4-(allyloxy) phenyl)-4-methoxybenzamide
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N1-(4-(allyloxy) phenyl)-4-methylbenzamide
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N1-(4-(allyloxy) phenyl)benzamide
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nordihydroguaiaretic acid
pentyl 2-(4-methoxyphenyl)acetate
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long chain and lipophile 4-methoxyphenylacetic acid ester, behaves as the best SLO inhibitor
peonidin
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from Vaccinium macrocarpon juice, inhibits in a concentration-dependent manner
peonidin 3-O-arabinoside
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from Vaccinium macrocarpon juice, inhibits in a concentration-dependent manner
peonidin 3-O-galactoside
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from Vaccinium macrocarpon juice, inhibits in a concentration-dependent manner
peonidin 3-O-glucoside
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from Vaccinium macrocarpon juice, inhibits in a concentration-dependent manner
Phenidone
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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
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quercetin
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noncompetitive inhibition by initially reducing the ferric form of the enzyme to an inactive ferrous form
resveratrol
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uncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
Salicylhydroxamic acid
70% inhibition in the presence of 1 mM salicylhydroxamic acid
salicylic acid
isoform LOX2 exhibits 96% residual activity at 2.8 mM
sec-butyl 2-(4-methoxyphenyl)acetate
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stylosin
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.101 mM
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tert-butyl 2-(4-methoxyphenyl)acetate
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traumatic acid
isoform LOX2 exhibits 95% residual activity at 2.8 mM
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Trolox
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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
Cu2+
complete inhibition at 1 mM; complete inhibition at 1 mM; complete inhibition at 1 mM; isoform LOX2 exhibits 50% residual activity at 1 mM
Cu2+
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required for optimal activity, activates at 0.1 mM, inhibits at 1 mM
Cu2+
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about 70% inhibition at 20 mM
Cu2+
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inhibits Oep2LOX2 by 49%
Fe3+
complete inhibition at 10 mM
Fe3+
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slight inactivation
Hg2+
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about 80% inhibition at 20 mM
Hg2+
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inhibits Oep1LOX2 by 60% and totally inactivates Oep2LOX2
nordihydroguaiaretic acid
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nordihydroguaiaretic acid
is a noncompetitive inhibitor
propyl gallate
is a competitive inhibitor
propyl gallate
almost complete inhibition (99%) in the presence of 1 mM propyl gallate
Zn2+
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activates at 1 mM, inhibits at 0.1 mM
Zn2+
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complete inhibition at 20 mM
Zn2+
53% residual activity at 50 mM
additional information
isoform LOX3 is not inhibited by traumatic acid and salicylic acid; isoform LOX4 is not inhibited by traumatic acid and salicylic acid; isoform LOX4 is not inhibited by traumatic acid and salicylic acid
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additional information
isoform LOX3 is not inhibited by traumatic acid and salicylic acid; isoform LOX4 is not inhibited by traumatic acid and salicylic acid; isoform LOX4 is not inhibited by traumatic acid and salicylic acid
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additional information
isoform LOX3 is not inhibited by traumatic acid and salicylic acid; isoform LOX4 is not inhibited by traumatic acid and salicylic acid; isoform LOX4 is not inhibited by traumatic acid and salicylic acid
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additional information
isoform LOX3 is not inhibited by traumatic acid and salicylic acid; isoform LOX4 is not inhibited by traumatic acid and salicylic acid; isoform LOX4 is not inhibited by traumatic acid and salicylic acid
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additional information
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4-allyloxyaniline amides designed as inhibitors on the basis of eugenol and esteragol structures. Compounds are docked in SLO active site and fixed by hydrogen bonding with two conserved His513 and Gln716. Molecular volume of the amide moiety is a major factor in inhibitory potency variation of the synthetic amides, where the hydrogen bonding of the amide group can involve in the activity of the inhibitors
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additional information
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4-methoxyphenylacetic acid esters designed as inhibitors on the basis of eugenol and esteragol structures are docked in SLO active site and show that carbonyl group of compounds is oriented toward the FeIII-OH moiety in the active site of enzyme and fixed by hydrogen bonding with hydroxyl group. Lipophilic interaction of ligand-enzyme is in charge of inhibiting the enzyme activity. Is not inhibited by 6-methoxy-2-methylene-1,2,3,4-tetrahydronaphthalene
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additional information
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chalcones exhibit superior LOX inhibitory activity than aurones. 2'-hydroxy-4-methoxy-chalcone, 2'-hydroxy-3,4,4',6'-tetramethoxy-chalcone, 2'-hydroxy-4,4',6'-trimethoxy-chalcone, 2',3,4,4',6'-pentahydroxy-chalcone, aureusidin, 4,6-dimethoxy-4'-methyl-aurone and 3',4,4',6-tetra(methoxymethyl)-aurone have no or very low LOX inhibitory activity
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additional information
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LOX/4-nitroso-N,N-dimethylaniline reaction is not inhibited by inulin
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additional information
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is not inhibited by malvidin 3-O-glucoside from Vaccinium myrtillus berries
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additional information
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presence of inhibitor does not change the regioselectivity of lipoxygenase-1
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additional information
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3,4-dihydro-7-hydroxycadalin, 7-hydroxycadalin, 3-hydroxyphenylacetic acid, 4-hydroxy-3-methoxyphenylacetic acid, and 3,4-dihydroxyphenylacetic acid do not inhibit the soybean lipoxygenase-1 catalyzed lipid peroxidation
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additional information
stylosin and some similar synthetic monoterpenoids show inhibitory effects on 15-LOX. A strong positive correlation is observed between 15-LOX inhibition potential and cytotoxicity of the compounds with apoptosis being the predominant mechanism of induced cell death
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additional information
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stylosin and some similar synthetic monoterpenoids show inhibitory effects on 15-LOX. A strong positive correlation is observed between 15-LOX inhibition potential and cytotoxicity of the compounds with apoptosis being the predominant mechanism of induced cell death
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additional information
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enzyme LOX1 is not inhibited by jasmonic acid; enzyme LOX2 is not inhibited by jasmonic acid
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