BRENDA - Enzyme Database show
show all sequences of 1.1.1.252

Trihydroxynaphthalene reductase of Curvularia lunata--a target for flavonoid action?

Brunskole, M.; Zorko, K.; Kerbler, V.; Martens, S.; Stojan, J.; Gobec, S.; Lanisnik Rizner, T.; Chem. Biol. Interact. 178, 259-267 (2009)

Data extracted from this reference:

Application
Application
Commentary
Organism
drug development
flavonoids inhibit 3HNR, which can thus be considered a potential target for flavonoid action. In addition to being a known target for different fungicides, 3HNR can also serve as an interesting and novel target for the development of antimycotics
Curvularia lunata
Cloned(Commentary)
Commentary
Organism
expressed as a glutathione S-transferase (GST)-fusion protein in Escherichia coli BL21-AI cells
Curvularia lunata
Inhibitors
Inhibitors
Commentary
Organism
Structure
3,7-dihydroxyflavone
inhibits by 24%
Curvularia lunata
3-hydroxyflavone
inhibits by 22%
Curvularia lunata
5,7-dihydroxyflavone
inhibits by 88%
Curvularia lunata
5-hydroxyflavone
inhibits by 30%
Curvularia lunata
5-methoxyflavone
inhibits by 12%
Curvularia lunata
6-hydroxyflavone
inhibits by 15%
Curvularia lunata
7,4'-Dihydroxyflavone
inhibits by 51%
Curvularia lunata
7-hydroxyflavone
inhibits by 9%
Curvularia lunata
acacetin
inhibits by 90%
Curvularia lunata
apigenin
acts as competititive inhibitor of 3HNR, inhibits by 90%. The inhibitor is stacked between the phenol ring of Tyr208 and the coenzyme nicotinamide moiety, forming two Hbonds with Ser149 and Ser228, and Ser149 and Tyr163, respectively. It affects fungal pigmentation and growth
Curvularia lunata
baicalein
affects fungal pigmentation and growth, inhibits by 75%
Curvularia lunata
Biochanin A
acts as competititive inhibitor of 3HNR. The inhibitor is stacked between the phenol ring of Tyr208 and the coenzyme nicotinamide moiety, forming two Hbonds with Ser149 and Ser228, and Ser149 and Tyr163, respectively
Curvularia lunata
chrysoeriol
inhibits by 55%
Curvularia lunata
diosmetin
inhibits by 83%
Curvularia lunata
fisetin
inhibits by 12%
Curvularia lunata
flavanone
inhibits by 9%
Curvularia lunata
flavone
inhibits by 38%
Curvularia lunata
genistein
inhibits by 19%
Curvularia lunata
genkwanin
inhibits by 28%
Curvularia lunata
kaempferol
inhibits by 81%
Curvularia lunata
luteolin
inhibits by 83%
Curvularia lunata
additional information
not inhibited by daidzein
Curvularia lunata
myricetin
inhibits by 13%
Curvularia lunata
naringenin
inhibits by 56%
Curvularia lunata
pinostrobin
inhibits by 38%
Curvularia lunata
quercetin
inhibits by 52%
Curvularia lunata
scutellarein
inhibits by 67%
Curvularia lunata
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.033
-
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one
at pH 7.0 and 25°C
Curvularia lunata
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Curvularia lunata
-
-
-
Purification (Commentary)
Commentary
Organism
by affinity binding followed by cleavage with thrombin
Curvularia lunata
Specific Activity [micromol/min/mg]
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
11
-
2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one converted by the recombinant protein
Curvularia lunata
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
-
697274
Curvularia lunata
4,5-dihydroxy-2H-benzopyran-2-one + NADPH + H+
-
-
-
?
Cofactor
Cofactor
Commentary
Organism
Structure
NADP+
-
Curvularia lunata
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.0012
-
apigenin
-
Curvularia lunata
0.0022
-
acacetin
-
Curvularia lunata
0.0026
-
5,7-dihydroxyflavone
-
Curvularia lunata
0.0026
-
diosmetin
-
Curvularia lunata
0.0031
-
luteolin
-
Curvularia lunata
0.0036
-
kaempferol
-
Curvularia lunata
0.0054
-
baicalein
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.0054
-
Biochanin A
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.0068
-
scutellarein
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.0081
-
chrysoeriol
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.01
-
7,4'-Dihydroxyflavone
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.012
-
naringenin
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.012
-
quercetin
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.025
-
flavone
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
IC50 Value
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.0031
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
apigenin
0.0049
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
acacetin
0.0057
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
diosmetin
0.0058
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
5,7-dihydroxyflavone
0.0068
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
luteolin
0.0079
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
kaempferol
0.012
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
baicalein
0.012
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
Biochanin A
0.015
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
scutellarein
0.018
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
chrysoeriol
0.023
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
7,4'-Dihydroxyflavone
0.026
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
naringenin
0.026
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
quercetin
0.055
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
flavone
Application (protein specific)
Application
Commentary
Organism
drug development
flavonoids inhibit 3HNR, which can thus be considered a potential target for flavonoid action. In addition to being a known target for different fungicides, 3HNR can also serve as an interesting and novel target for the development of antimycotics
Curvularia lunata
Cloned(Commentary) (protein specific)
Commentary
Organism
expressed as a glutathione S-transferase (GST)-fusion protein in Escherichia coli BL21-AI cells
Curvularia lunata
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
NADP+
-
Curvularia lunata
IC50 Value (protein specific)
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.0031
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
apigenin
0.0049
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
acacetin
0.0057
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
diosmetin
0.0058
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
5,7-dihydroxyflavone
0.0068
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
luteolin
0.0079
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
kaempferol
0.012
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
baicalein
0.012
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
Biochanin A
0.015
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
scutellarein
0.018
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
chrysoeriol
0.023
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
7,4'-Dihydroxyflavone
0.026
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
naringenin
0.026
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
quercetin
0.055
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
flavone
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
3,7-dihydroxyflavone
inhibits by 24%
Curvularia lunata
3-hydroxyflavone
inhibits by 22%
Curvularia lunata
5,7-dihydroxyflavone
inhibits by 88%
Curvularia lunata
5-hydroxyflavone
inhibits by 30%
Curvularia lunata
5-methoxyflavone
inhibits by 12%
Curvularia lunata
6-hydroxyflavone
inhibits by 15%
Curvularia lunata
7,4'-Dihydroxyflavone
inhibits by 51%
Curvularia lunata
7-hydroxyflavone
inhibits by 9%
Curvularia lunata
acacetin
inhibits by 90%
Curvularia lunata
apigenin
acts as competititive inhibitor of 3HNR, inhibits by 90%. The inhibitor is stacked between the phenol ring of Tyr208 and the coenzyme nicotinamide moiety, forming two Hbonds with Ser149 and Ser228, and Ser149 and Tyr163, respectively. It affects fungal pigmentation and growth
Curvularia lunata
baicalein
affects fungal pigmentation and growth, inhibits by 75%
Curvularia lunata
Biochanin A
acts as competititive inhibitor of 3HNR. The inhibitor is stacked between the phenol ring of Tyr208 and the coenzyme nicotinamide moiety, forming two Hbonds with Ser149 and Ser228, and Ser149 and Tyr163, respectively
Curvularia lunata
chrysoeriol
inhibits by 55%
Curvularia lunata
diosmetin
inhibits by 83%
Curvularia lunata
fisetin
inhibits by 12%
Curvularia lunata
flavanone
inhibits by 9%
Curvularia lunata
flavone
inhibits by 38%
Curvularia lunata
genistein
inhibits by 19%
Curvularia lunata
genkwanin
inhibits by 28%
Curvularia lunata
kaempferol
inhibits by 81%
Curvularia lunata
luteolin
inhibits by 83%
Curvularia lunata
additional information
not inhibited by daidzein
Curvularia lunata
myricetin
inhibits by 13%
Curvularia lunata
naringenin
inhibits by 56%
Curvularia lunata
pinostrobin
inhibits by 38%
Curvularia lunata
quercetin
inhibits by 52%
Curvularia lunata
scutellarein
inhibits by 67%
Curvularia lunata
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.0012
-
apigenin
-
Curvularia lunata
0.0022
-
acacetin
-
Curvularia lunata
0.0026
-
5,7-dihydroxyflavone
-
Curvularia lunata
0.0026
-
diosmetin
-
Curvularia lunata
0.0031
-
luteolin
-
Curvularia lunata
0.0036
-
kaempferol
-
Curvularia lunata
0.0054
-
baicalein
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.0054
-
Biochanin A
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.0068
-
scutellarein
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.0081
-
chrysoeriol
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.01
-
7,4'-Dihydroxyflavone
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.012
-
naringenin
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.012
-
quercetin
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
0.025
-
flavone
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
Curvularia lunata
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.033
-
2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one
at pH 7.0 and 25°C
Curvularia lunata
Purification (Commentary) (protein specific)
Commentary
Organism
by affinity binding followed by cleavage with thrombin
Curvularia lunata
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
11
-
2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one converted by the recombinant protein
Curvularia lunata
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
-
697274
Curvularia lunata
4,5-dihydroxy-2H-benzopyran-2-one + NADPH + H+
-
-
-
?
Other publictions for EC 1.1.1.252
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
723949
Schaetzle
Tetrahydroxynaphthalene reduct ...
Magnaporthe grisea
Angew. Chem. Int. Ed. Engl.
51
2643-2646
2012
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1
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2
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14
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1
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1
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1
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1
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14
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3
3
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697274
Brunskole
Trihydroxynaphthalene reductas ...
Curvularia lunata
Chem. Biol. Interact.
178
259-267
2009
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1
1
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27
1
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7
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1
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1
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1
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1
14
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14
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1
1
1
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14
27
14
1
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1
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1
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1
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697275
Stojan
Simultaneous binding of coenzy ...
Curvularia lunata
Chem. Biol. Interact.
178
268-273
2009
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1
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2
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2
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1
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1
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1
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1
1
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1
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697279
Kristan
Two homologous fungal carbonyl ...
Curvularia lunata
Chem. Biol. Interact.
178
295-302
2009
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1
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11
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1
-
4
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1
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12
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1
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1
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10
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1
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10
11
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1
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1
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12
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1
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1
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713194
Zhang
-
Resistance development in rice ...
Magnaporthe grisea
Pestic. Biochem. Physiol.
94
43-47
2009
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1
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1
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1
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685550
Brunskole
Towards the first inhibitors o ...
Curvularia lunata
Bioorg. Med. Chem.
16
5881-5889
2008
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1
1
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7
-
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1
-
4
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1
1
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2
1
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1
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1
6
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1
1
1
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7
6
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