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Literature summary 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

EC Number Application Comment Organism
1.1.1.252 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)

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

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.252 3,7-dihydroxyflavone inhibits by 24% Curvularia lunata
1.1.1.252 3-hydroxyflavone inhibits by 22% Curvularia lunata
1.1.1.252 5,7-dihydroxyflavone inhibits by 88% Curvularia lunata
1.1.1.252 5-hydroxyflavone inhibits by 30% Curvularia lunata
1.1.1.252 5-methoxyflavone inhibits by 12% Curvularia lunata
1.1.1.252 6-hydroxyflavone inhibits by 15% Curvularia lunata
1.1.1.252 7,4'-Dihydroxyflavone inhibits by 51% Curvularia lunata
1.1.1.252 7-hydroxyflavone inhibits by 9% Curvularia lunata
1.1.1.252 acacetin inhibits by 90% Curvularia lunata
1.1.1.252 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
1.1.1.252 baicalein affects fungal pigmentation and growth, inhibits by 75% Curvularia lunata
1.1.1.252 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
1.1.1.252 chrysoeriol inhibits by 55% Curvularia lunata
1.1.1.252 diosmetin inhibits by 83% Curvularia lunata
1.1.1.252 fisetin inhibits by 12% Curvularia lunata
1.1.1.252 flavanone inhibits by 9% Curvularia lunata
1.1.1.252 flavone inhibits by 38% Curvularia lunata
1.1.1.252 genistein inhibits by 19% Curvularia lunata
1.1.1.252 genkwanin inhibits by 28% Curvularia lunata
1.1.1.252 kaempferol inhibits by 81% Curvularia lunata
1.1.1.252 luteolin inhibits by 83% Curvularia lunata
1.1.1.252 additional information not inhibited by daidzein Curvularia lunata
1.1.1.252 myricetin inhibits by 13% Curvularia lunata
1.1.1.252 naringenin inhibits by 56% Curvularia lunata
1.1.1.252 pinostrobin inhibits by 38% Curvularia lunata
1.1.1.252 quercetin inhibits by 52% Curvularia lunata
1.1.1.252 scutellarein inhibits by 67% Curvularia lunata

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.1.1.252 0.033
-
 2,3-Dihydro-2,5-dihydroxy-4H-benzopyran-4-one at pH 7.0 and 25°C Curvularia lunata

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.252 Curvularia lunata
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.1.1.252 by affinity binding followed by cleavage with thrombin Curvularia lunata

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
1.1.1.252 11
-
 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one converted by the recombinant protein Curvularia lunata

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.252 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one + NADP+
-
 Curvularia lunata 4,5-dihydroxy-2H-benzopyran-2-one + NADPH + H+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.1.1.252 3HNR
-
 Curvularia lunata
1.1.1.252 trihydroxynaphthalene reductase
-
 Curvularia lunata

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.252 NADP+
-
 Curvularia lunata

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.1.1.252 0.0012
-
 apigenin
-
 Curvularia lunata
1.1.1.252 0.0022
-
 acacetin
-
 Curvularia lunata
1.1.1.252 0.0026
-
 5,7-dihydroxyflavone
-
 Curvularia lunata
1.1.1.252 0.0026
-
 diosmetin
-
 Curvularia lunata
1.1.1.252 0.0031
-
 luteolin
-
 Curvularia lunata
1.1.1.252 0.0036
-
 kaempferol
-
 Curvularia lunata
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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
1.1.1.252 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