Ligand luteolin

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Basic Ligand Information

Molecular Structure
Picture of luteolin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H10O6
luteolin
IQPNAANSBPBGFQ-UHFFFAOYSA-N
Synonyms:
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one, 3',4',5,7-tetrahydroxy-flavone, 3',4',5,7-tetrahydroxyflavone, 5,7,3',4'-tetrahydroxyflavone, cis- and trans-dihydroquercetins, digitoflavone

Show all pahtways known for Show all pathways known for luteolin

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavone = S-adenosyl-L-homocysteine + 5,7,4'-trihydroxy-3'-methoxyflavone
show the reaction diagram
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UDPglucuronic acid + luteolin = UDP + luteolin 7-O-glucuronide
show the reaction diagram
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UDP-glucose + 3',4',5,7-tetrahydroxyflavone = UDP + 7-O-beta-D-glucosyl-3',4',5,7-tetrahydroxyflavone
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
apigenin + [reduced NADPH-hemoprotein reductase] + O2 = luteolin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
2R,3S,4S-cis-leucoanthocyanidin + 2-oxoglutarate + O2 = cis- and trans-dihydroquercetins + succinate + CO2 + 2 H2O
show the reaction diagram
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-

Substrate in Enzyme-catalyzed Reactions (29 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
luteolin + [reduced NADPH-hemoprotein reductase] + O2 = 3',8-dihydroxyapigenin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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luteolin + O2 = ?
show the reaction diagram
-
S-adenosyl-L-methionine + luteolin = S-adenosyl-L-homocysteine + scoparol
show the reaction diagram
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luteolin = ?
show the reaction diagram
-
S-adenosyl-L-methionine + 5,7,3',4'-tetrahydroxyflavone = S-adenosyl-L-homocysteine + 7-methoxy-5,3',4'-tetrahydroxyflavone
show the reaction diagram
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S-adenosyl-L-methionine + luteolin = S-adenosyl-L-homocysteine + 3,4',5-trihydroxy-7-methoxyflavanone
show the reaction diagram
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sucrose + luteolin = luteolin-3'-O-alpha-D-glucopyranoside + luteolin-4'-O-alpha-D-glucopyranoside
show the reaction diagram
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UDP-D-glucuronate + luteolin = UDP + luteolin 7-O-beta-D-glucuronoside
show the reaction diagram
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UDPglucose + luteolin = UDP + luteolin 7-O-glucoside
show the reaction diagram
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UDP-glucose + luteolin = UDP + luteolin 7-O-beta-D-glucoside
show the reaction diagram
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UDP-glucose + luteolin = UDP + luteolin 3'-O-beta-D-glucoside + luteolin 7-O-beta-D-glucoside + luteolin 7,3'-di-O-beta-D-glucoside
show the reaction diagram
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luteolin + sucrose = luteolin-3'-O-alpha-D-glucopyranoside + luteolin-4'-O-alpha-D-glucopyranoside
show the reaction diagram
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UDP-glucose + luteolin = UDP + ?
show the reaction diagram
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dimethylallyl diphosphate + luteolin = diphosphate + ?
show the reaction diagram
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luteolin + H2O = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2 = luteolin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
apigenin + [reduced NADPH-hemoprotein reductase] + O2 = luteolin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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luteolin 7-O-beta-D-glucopyranoside + H2O = luteolin + D-glucose
show the reaction diagram
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luteolin 3'-O-beta-glucuronide + H2O = luteolin + D-glucuronate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
EC50 value of 0.27 mM
-
0.05 mM, 7fold increase in DNA-cleavage activity for isoform II beta, 3fold increase for isoform II alpha
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Inhibitor in Enzyme-catalyzed Reactions (77 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.02 mM inhibits by ca. 50%
-
noncompetitive, IC50: 0.190 mM
-
IC50: 780 nM
-
remarkable noncompetitive inhibition
-
complete inhibition at 0.01 mM
-
IC50: 0.045 mM
-
0.14 mM, 60% inhibition
-
0.1 mM, 50% inhibition
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0.02 mM, 50% inhibition
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30% inhibition at 0.1 mM
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1 microM, 75.8% inhibition of isoform PI3Kalpha
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inhibition of p56lck
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IC50: 0.026 mM
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a flavonoid inhibitor of CDK5 and CDK1
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minimal inhibitory concentration for growth of Xanthomonas oryzae pv. oryzae, 186 microg/ml
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IC50: 0.0101 mM, PDB3; IC50: 0.0133 mM, PDB2; IC50: 0.0215 mM, PDB1
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IC50: 0.0193 mM, PDB5
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60.2% inhibition at 0.03 mM
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isolated from methanolic extracts of Perilla frutescens
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3D Structure of Enzyme-Ligand-Complex (PDB) (4 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (1 result)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.03
-
pH 7.5, 30C

KM Value (12 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.008
-
-
0.084
-
pH 8.1, 25C
0.12
-
pH 7.0, 30C
0.0015
-
-

Ki Value (14 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0031
-
-
0.0133
-
-
0.0071
-
pH 7.5, 22C
0.166
-
-
0.118
-
pH not specified in the publication, 30C
0.062
-
-
0.035
-
in the presence of increasing amounts of inhibitor at different concentrations of the substrates methylglyoxal and glutathione, Dixon plot analysis, significantly lower inhibition than that with curcumin, competitive inhibition, pH 7.0, 30C

IC50 Value (43 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0374
-
-
0.0006
-
IC50: 0.0006 mM
0.19
-
noncompetitive, IC50: 0.190 mM
0.00078
-
IC50: 780 nM
0.0116
-
pH 7.0, 23C
0.00422
-
-
0.00059
-
pH 7.5, 25C
0.002
-
IC50: 2 microM
0.00011
-
pH 7.5, 22C
0.00085
-
pH and temperature not specified in the publication
0.045
-
IC50: 0.045 mM
0.062
-
pH 7.0, 37C
0.0297
-
pH 6.8, 25C
0.7
-
pH 5.5, 20C
0.0041
-
at pH 8.0 and 37C
0.00083
-
pH not specified in the publication, temperature not specified in the publication
0.026
-
IC50: 0.026 mM
0.00081
-
pH 7.5, 37C
0.0474
-
in 0.1 M sodium phosphate buffer, pH 7.0, at 30C
0.0281
-
at pH 7.0 and 25C
0.0193
-
IC50: 0.0193 mM, PDB5
0.021
-
pH 6.8, 30C
0.0084
-
at 37C in 10 mM potassium phosphate buffer, pH 7.4, containing 0.05% (w/v) emulphogen
0.0082
-
at 37C in 10 mM potassium phosphate buffer, pH 7.4, containing 0.05% (w/v) emulphogene
0.29
-
37C
0.052
-
pH and temperature not specified in the publication
0.0005
-
non-competitive inhibition
0.03
-
-
0.007
-
indicate that the hydroxy groups at the B ring of flavonoids contribute to the human GLO I inhibitory activity of the flavonoid compounds at 25C, pH 7.0

References & Links

Links to other databases for luteolin

ChEBI
PubChem
ChEBI
PubChem