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(2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octa-dienyl-O-(alpha-L-rhamnopyranosyl)-(1''->3')-(4'''-O-cis-p-coumaroyl)-beta-D-glucopyranoside
liguroside B, NMR spectral analysis
(2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octadienyl-O-(alpha-L-rhamnopyranosyl)-(1''->3')-(4'''-O-trans-p-coumaroyl)-beta-D-glucopyranoside
liguroside A, NMR spectral analysis
11-thialinoleic acid
-
is a competitive inhibitor of 12-lipoxygenase with arachidonate as substrate. Presence of inhibitor does not alter the product distribution for 12-lipoxygenase. It does not change the regioselectivity of 12-lipoxygenase
2,2'-dipyridyl
-
1 mM, 87% inactivation, no reactivation by addition of excess Fe2+ or Fe3+
2,3,4,5-tetrabromo-6-(2,4-dibromophenoxy)phenol
-
IC50: 0.0007 mM
2,3,4,5-tetrabromo-6-(4,5-dibromo-2-hydroxyphenoxy)phenol
-
IC50: 0.0041 mM
2,3,5-tribromo-6-(4,5-dibromo-2-hydroxyphenoxy)phenol
-
IC50: 0.00041 mM
2,4-dibromo-6-(2,4-dibromo-6-methoxyphenoxy)phenol
-
IC50: 0.012 mM
2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]phenol
-
IC50: 0.007 mM
2-alkyl benzopyran-4-ones
-
weak inhibition
2-alkyl-6-hydroxy-4-H-benzopyran-4-one
-
weak inhibition
3'-chloro-7,8-dihydroxyisoflavone
-
-
3,15-dihydroxy-8,11,13-eicosatrienoic acid
-
IC50: 0.0075 mM
3,4,6,8-tetrabromooxanthren-1-ol
-
IC50: 0.05 mM
3,4,6-tribromo-2-(2,4-dibromophenoxy)phenol
-
IC50: 0.006 mM
3,4-dibromo-2-(5-bromo-2-hydroxyphenoxy)phenol
-
IC50: 0.047 mM
3,6,8-tribromooxanthren-1-ol
-
IC50: 0.03 mM
3-O-acetyl-11-keto-boswellic acid
-
0.03 mM
3-[3-bromo-5-(2,6-dibromo-4-{2-[2-(3-bromo-4-hydroxy-phenyl)-ethylcarbamoyl]-2-[(E)-hydroxyimino]-ethyl}-phenoxy)-4-methyl-phenyl]-N-[(E)-2-(3,5-dibromo-4-hydroxy-phenyl)-vinyl]-2-[(E)-hydroxyimino]-propionamide
-
IC50: 0.0004 mM
4',6,7-trihydroxyisoflavan
-
-
4',6,7-trihydroxyisoflavanone
-
-
4',6,7-trihydroxyisoflavone
-
-
4'-chloro-7,8-dihydroxyisoflavone
-
-
4,15-dihydroxy-5,8,11,13-eicosatetraenoic acid
-
IC50: 0.0081 mM
4,4'-propane-2,2-diylbis(2,6-dibromophenol)
-
IC50: 0.01 mM
4,5-dichloro-N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
-
4-(2-oxapentadeca-4-yne) phenylpropanoic acid
-
4-(2-oxapentadeca-4-yne)phenylpropanoic acid
4-methyl-2-(4-methylpiperazinyl)pyrimido[4,5-b]benzothiazine
-
-
4-[5-(1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-12 by 5%
4-[5-(7-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide
-
0.01 mM inhibits LOX-12 by 3%
5,15-dihydroxy-5,8,11,13,17-eicosapentaenoic acid
-
IC50: 0.0008 mM
5,8,11,14-Eicosatetraynoic acid
5,8,11-eicosatriynoic acid
-
-
5-(methylamino)-2-(naphthalen-1-yl)-4,5-dihydro-1,3-oxazole-4-carbonitrile
-
-
5-chloro-N-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxamide
-
-
6,17-dihydroxy-4,7,10,13,15,19-eicosahexaenoic acid
-
IC50: 0.0004 mM
6,6a,11,11a-tetrahydro[1]benzothiopyrano[4,3-b]indole
-
-
6,7-dihydroxy-3',4'-methylenedioxyisoflavan
-
-
6,7-dihydroxy-3',4'-methylenedioxyisoflavone
-
-
6,7-dihydroxy-3'-methylisoflavan
-
-
6,7-dihydroxy-3'-methylisoflavanone
-
-
6,7-dihydroxy-4'-methoxyisoflavan
-
-
6,7-dihydroxy-4'-methoxyisoflavanone
-
-
6,7-dihydroxy-4'-methoxyisoflavone
-
-
6,7-dihydroxy-4'-nitroisoflavone
-
-
7,8-dihydroxy-3',4'-dimethoxyisoflavan
-
-
7,8-dihydroxy-3'-methylisoflavone
-
-
7,8-dihydroxy-3'-trifluoromethylisoflavone
-
-
7,8-dihydroxy-4'-methoxyisoflavan
-
-
7,8-dihydroxy-4'-methylisoflavan
-
-
7,8-dihydroxy-4'-methylisoflavone
-
-
7,8-dihydroxyisoflavone
-
-
7-hydroxy-H-benzopyran-4-one derivatives
-
weak inhibition
8-hydroxyquinoline
-
1 mM, 35% inhibition
adamantyl caffeate
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.074 mM
-
alpha-mangostin
NSC30552, a natural product, caspase-3 pathway inhibitor, performs selective inhibition of 12-LO
bestatin 7
-
IC50: 0.0023 mM
bornyl vanillate
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.401 mM
-
caffeic acid
-
0.01 mM, 20-30% inhibition
celecoxib
-
0.01 mM inhibits LOX-12 by 7%
chloroglyoxylic acid ethyl ester
-
-
cinnamyl 3,4-dihydroxy-cyanocinnamate
-
CDC
cinnamyl-3,4-dihydroxy-alpha-cyanocinnamate
cinnamyl-3,4-dihydroxy-cyanocinnamate
-
EDTA
-
1 mM, 40% inhibition
epigallocatechin gallate
-
esculetine
-
inhibits the enzyme and its binding to cytoplasmic muscle fibrills, overview
ethyl 6-chloro-3-[(3S)-3-hydroxy-7-methyloctanoyl]-2,3-dihydro-1H-indole-2-carboxylate
-
-
fenchyl caffeate
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.089 mM
-
gossypol acetic acid
-
non-competitive with respect to arachidonate
GT-E
-
100 mM, dried radix of Glycine tomentella freeze-dried to a powder, IC50: 0.00072 mg/ml
-
H-benzopyran-4-one derivatives
-
weak inhibition
iodoacetate
-
1 mM, 5% inhibition
kudingoside B
NMR spectral analysis
Lubrol
-
0.2%, 60% inhibition
-
methyl-4-pyridyl ketone
-
-
michellamine B
NSC661755, potent but non-selective inhibitor, a natural anti-viral agent
N-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxamide
-
N-(2-chloro-4-fluorophenyl)-1H-pyrazole-3-carboxamide
-
N-(4-chlorophenyl)-N-hydroxy-N'-(3-chlorophenyl)urea
-
-
N-([5-chloro-2-(dimethylamino)-8-hydroxyquinolin-7-yl](furan-2-yl)methyl)acetamide
-
-
N-([5-chloro-8-hydroxy-2-(piperidin-1-yl)quinolin-7-yl](furan-2-yl)methyl)acetamide
-
-
N-benzyl-N-hydroxy-5-phenylpentanamide
N-[(2,5-dichloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
-
-
N-[(4-chloro-1-hydroxynaphthalen-2-yl)(furan-2-yl)methyl]acetamide
-
-
N-[(5-bromo-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
-
-
N-[(5-bromo-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]propanamide
-
-
N-[(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
-
-
N-[(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
-
-
N-[(5-bromofuran-2-yl)(5-chloro-8-hydroxyquinolin-7-yl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxy-1,2,3,4,4a,8a-hexahydroquinolin-7-yl)(furan-2-yl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-fluorophenyl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(5-methylthiophen-2-yl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(cyclopropyl)methyl]acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(cyclopropyl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]-4-methylbenzamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]benzamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)methyl]acetamide
-
-
N-[(5-chloro-8-methoxyquinolin-7-yl)(furan-2-yl)methyl]propanamide
-
-
N-[(5-fluoro-8-hydroxyquinolin-7-yl)(furan-2-yl)methyl]acetamide
-
-
N-[(5-fluoro-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
-
-
N-[(8-hydroxy-5-nitroquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
-
-
N-[(8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
-
-
N-[(R)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
-
-
N-[(R)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
-
-
N-[(S)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
-
-
N-[(S)-(5-bromo-8-hydroxyquinolin-7-yl)(thiophen-2-yl)methyl]propanamide
-
-
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)-2-methylpropyl]acetamide
-
-
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)-2-methylpropyl]propanamide
-
-
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)ethyl]acetamide
-
-
N-[1-(5-chloro-8-hydroxyquinolin-7-yl)ethyl]propanamide
-
-
N-[1-(5-fluoro-8-hydroxyquinolin-7-yl)ethyl]acetamide
-
-
N-[furan-2-yl(8-hydroxy-5-nitroquinolin-7-yl)methyl]propanamide
-
-
NCTT-956
-
12-LOX inhibition attenuates platelet aggregation
NEM
-
1 mM, 15% inhibition
neodysidenin
natural product from marine sponge Dysidea herbacea from Papua New Guinea, extraction and purification, overview, steady-state inhibition kinetics, competitive mode of inhibition, selective for 12-LO
nordihydroguaiaretic acid
NSC172033
a synthetic compound from the NCI library
NSC292213
a synthetic compound from the NCI library
NSC617570
a synthetic compound from the NCI library
p-hydroxymercuribenzoate
-
1 mM, 75% inhibition
siRNA
-
inhibition of p12-LOX in JB6 P+ cells by siRNA transfection, causes a significant suppression of 12-O-tetradecanoylphorbol-13-acetate-induced neoplastic transformation by 61% compared with that in control cells
-
stylosin
IC50 value of cytotoxicity against PC-3 cells, 24 h, is 0.101 mM
-
Zn2+
-
3.7 mM, complete inhibition
4-(2-oxapentadeca-4-yne)phenylpropanoic acid
-
mixed type inhibition towards the ferric form of 12-lipoxygenase
4-(2-oxapentadeca-4-yne)phenylpropanoic acid
-
shows the oxidation of the inactive ferrous enzyme to the active ferric enzyme and competes with arachidonic acid for the ferric enzyme
5,8,11,14-Eicosatetraynoic acid
-
0.001 mM, 77% inhibition
5,8,11,14-Eicosatetraynoic acid
-
0.01 mM, 86% inhibition
5,8,11,14-Eicosatetraynoic acid
-
-
5,8,11,14-Eicosatetraynoic acid
-
IC50: 0.00006 mM
5,8,11,14-Eicosatetraynoic acid
-
-
AA861
-
prevents cell death, the 12/15-LOX inhibitor and the proteasome protect against exogenous glutamate, but not by preventing glutathione depletion. LOX inhibition, but not proteasome inhibition, reduces oxidative stress in glutamate-treated HT22 cells. The mitochondrial membrane potential is protected by coinhibition with baicalien
AA861
-
a 12-LOX inhibitor
arachidonic acid
-
substrate inhibition
arachidonic acid
-
inhibits reaction with 5-hydroxy-6,8,11,14-eicodatetraenoic acid
baicalein
-
inhibits the enzyme and its binding to cytoplasmic muscle fibrills, overview
baicalein
-
potent in vitro inhibitor of platelet 12-LOX
baicalein
-
inhibition of 12-LOX enzymatic activity using baicalein inhibits MMP9 expression in PC3 cells
baicalein
-
12-LOX inhibition attenuates platelet aggregation
baicalein
the 12LO inhibitor induces a 2-2.5fold increase in cell death, which appears to result from apoptosis, as indicated by DNA fragmentation, activation of procaspase 3 to caspase 3 and cytochrome c release from the mitochondria to the cytosol. This apoptosis can be prevented by treatment with the 12LO product, 12 hydroxyeicosatetraenoic acid (12HETE)
baicalein
-
p12-LOX specific inhibitor, suppresses proliferation of JB6 P+ cells when cells are seeded at a low density in a culture plate by 81%
baicalein
-
prevents cell death, the 12/15-LOX inhibitor and the proteasome protect against exogenous glutamate, but not by preventing glutathione depletion. LOX inhibition, but not proteasome inhibition, reduces oxidative stress in glutamate-treated HT22 cells. The mitochondrial membrane potential is protected by coinhibition with AA861
BW755C
-
0.01 mM, 13% inhibition
BW755C
-
0.01 mM, 72% inhibition
cinnamyl-3,4-dihydroxy-alpha-cyanocinnamate
-
-
cinnamyl-3,4-dihydroxy-alpha-cyanocinnamate
-
eicosatetraynoic acid
-
-
eicosatetraynoic acid
-
0.01 mM, 90-95% inhibition
eicosatetraynoic acid
-
-
eicosatetraynoic acid
-
0.1 mM, complete inhibition
esculetin
-
0.01 mM, 90-95% inhibition
esculetin
-
0.01 mM, complete inhibition
ML355
a selective 12-LOX inhibitor, blocks both FcgammaRIIa-induced platelet aggregation and (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate production
ML355
-
a selective 12-LOX inhibitor, blocks both FcgammaRIIa-induced platelet aggregation and (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate production
N-benzyl-N-hydroxy-5-phenylpentanamide
-
-
N-benzyl-N-hydroxy-5-phenylpentanamide
-
-
N-benzyl-N-hydroxy-5-phenylpentanamide
-
-
nordihydroguaiaretic acid
-
0.01 mM, 90-95% inhibition
nordihydroguaiaretic acid
-
0.04 mM, 65-75% inhibition
nordihydroguaiaretic acid
-
IC50: 0.0051 mM
nordihydroguaiaretic acid
-
100 mM, IC50: 0.0016 mg/ml
nordihydroguaiaretic acid
-
0.01 mM, 48% inhibition
nordihydroguaiaretic acid
-
0.01 mM, 97% inhibition
nordihydroguaiaretic acid
-
IC50: 0.0022 mM
nordihydroguaiaretic acid
-
-
PD146176
-
-
PD146176
-
selective inhibitor of 12/15-LOX, macrophages treated with PD146176 elaborate reduced levels of interleukin-12 in response to Toxoplasma gondii antigen
Sn2+
-
3.7 mM, complete inhibition
Sn2+
-
5 mM SnCl2, complete inhibition
additional information
development of an assay method for high throughput screening of libraries for platelet-type 12-hLO selective inhibitors, four organo-mercurial compounds with NCI library IDs NSC20410, NSC268879, NSC321237, and NSC321239, are also found to be selectively inhibitory, but not pursued further due to their potentially toxic side effects, overview
-
additional information
-
development of an assay method for high throughput screening of libraries for platelet-type 12-hLO selective inhibitors, four organo-mercurial compounds with NCI library IDs NSC20410, NSC268879, NSC321237, and NSC321239, are also found to be selectively inhibitory, but not pursued further due to their potentially toxic side effects, overview
-
additional information
-
comparison of structural requirements for flavonoid inhibitory potency and selectivity against platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2, the two latter belong to EC 1.13.11.33, overview, catechols are essential for high potency, isoflavones and isoflavanones tend to select against 12-hLO, isoflavans tend to select against isozyme 15-hLO-1, but few flavonoids target isozyme 15-hLO-2, molecular modeling analysis, overview
-
additional information
-
the histone deacetylase inhibitor trichostatin A inhibits EGF-induced 12(S)-lipoxygenase expression via downregulation of c-Jun and Sp1 expression, enhancement of Sp1 acetylation, and inhibition of Sp1, c-Jun, and p300 recruitment to the gene promoter of 12-LO, overview
-
additional information
-
enzyme inhibition causes a decrease in amyloid-beta protein
-
additional information
-
0.01 mM 4-[5-(6-chloro-1H-indol-3-yl)-3-trifluoromethyl-4,5-dihydropyrazol-1-yl]-benzenesulfonamide or rofecoxib do not inhibit LOX-12
-
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
-
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
-
additional information
-
physico-chemical state of the substrate and the complex equilibrium between fatty acid monomers, acid soaps and micelles may impact the reaction specificity of LOX-isoforms
-
additional information
Chinese tea Qing Shan Lu Shui, which contains lower catechin levels than the other tested teas, inhibits the enzyme activity, 12-LOX inhibitory activityguided fractionation of the aqueous ethanol extract are used to isolate twp components: monoterpene glycosides liguroside A and liguroside B, i.e. (2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octadienyl-O-(alpha-L-rhamnopyranosyl)-(1''->3')-(4'''-O-trans-p-coumaroyl)-beta-D-glucopyranoside and (2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octa-dienyl-O-(alpha-L-rhamnopyranosyl)-(1''->3')-(4'''-O-cis-p-coumaroyl)-beta-D-glucopyranoside, respectively. Inhibitory effect on leukocyte-type 12-LOX activity and catechin contents of 12 Chinese teas, overview
-