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Literature summary for 1.1.1.252 extracted from

  • Brunskole, M.; Zorko, K.; Kerbler, V.; Martens, S.; Stojan, J.; Gobec, S.; Lanisnik Rizner, T.
    Trihydroxynaphthalene reductase of Curvularia lunata--a target for flavonoid action? (2009), Chem. Biol. Interact., 178, 259-267.
    View publication on PubMed

Application

Application Comment 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)

Cloned (Comment) Organism
expressed as a glutathione S-transferase (GST)-fusion protein in Escherichia coli BL21-AI cells Curvularia lunata

Inhibitors

Inhibitors Comment 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 Comment 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 UniProt Comment Textmining
Curvularia lunata
-
-
-

Purification (Commentary)

Purification (Comment) 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] Comment Organism
11
-
2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one converted by the recombinant protein Curvularia lunata

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
-
Curvularia lunata 4,5-dihydroxy-2H-benzopyran-2-one + NADPH + H+
-
?

Synonyms

Synonyms Comment Organism
3HNR
-
Curvularia lunata
trihydroxynaphthalene reductase
-
Curvularia lunata

Cofactor

Cofactor Comment Organism Structure
NADP+
-
Curvularia lunata

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment 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
-
quercetin at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C Curvularia lunata
0.012
-
naringenin at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C Curvularia lunata
0.025
-
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 Comment 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 quercetin
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
0.055
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C Curvularia lunata flavone