BRENDA - Enzyme Database

Inhibitory effects of dietary flavonoids on purified hepatic NADH-cytochrome b5 reductase: structure-activity relationships

Celik, H.; Ko?ar, M.; Chem. Biol. Interact. 197, 103-109 (2012)

Data extracted from this reference:

Application
EC Number
Application
Commentary
Organism
1.6.2.2
drug development
flavonoids, regarding b5 reductase inhibition, indicate a potential for significant flavonoid–drug and/or flavonoid–xenobiotic interactions which may have important therapeutic and toxicological outcomes for certain drugs and/or xenobiotics.
Bos taurus
Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
1.6.2.2
(+)-catechin
-
Bos taurus
1.6.2.2
(-)-epicatechin
-
Bos taurus
1.6.2.2
apigenin
-
Bos taurus
1.6.2.2
luteolin
-
Bos taurus
1.6.2.2
luteolin-7-O-glucoside
-
Bos taurus
1.6.2.2
additional information
inhibitory potencies of flavonoids on the enzyme, structure-activity relationship, overview. No inhibition by naringenin, naringin, and chrysin. Flavonoids containing two hydroxyl groups in ring B and a carbonyl group at C-4 in combination with a double bond between C-2 and C-3 produced a much stronger inhibition, whereas substitution of a hydroxyl group at C-3 is associated with a less inhibitory effect
Bos taurus
1.6.2.2
morin
-
Bos taurus
1.6.2.2
myricetin
-
Bos taurus
1.6.2.2
quercetin
-
Bos taurus
1.6.2.2
quercitrin
-
Bos taurus
1.6.2.2
rutin
-
Bos taurus
Localization
EC Number
Localization
Commentary
Organism
GeneOntology No.
Textmining
1.6.2.2
microsome
-
Bos taurus
-
-
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
1.6.2.2
Bos taurus
-
-
-
Purification (Commentary)
EC Number
Commentary
Organism
1.6.2.2
native enzyme from liver microsomes by anion exchange chromatography and affinity chromatography
Bos taurus
Source Tissue
EC Number
Source Tissue
Commentary
Organism
Textmining
1.6.2.2
liver
-
Bos taurus
-
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1.6.2.2
2 ferricyanide + NADH
-
724717
Bos taurus
2 ferrocyanide + NAD+ + H+
-
-
-
?
Temperature Optimum [°C]
EC Number
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
1.6.2.2
22
-
assay at room temperature
Bos taurus
pH Optimum
EC Number
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
1.6.2.2
7.5
-
assay at
Bos taurus
Cofactor
EC Number
Cofactor
Commentary
Organism
Structure
1.6.2.2
NADH
-
Bos taurus
Ki Value [mM]
EC Number
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
1.6.2.2
additional information
-
additional information
inhibition kinetics
Bos taurus
IC50 Value
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
1.6.2.2
0.00011
-
pH 7.5, 22°C
Bos taurus
luteolin
1.6.2.2
0.00081
-
pH 7.5, 22°C
Bos taurus
morin
1.6.2.2
0.0011
-
pH 7.5, 22°C
Bos taurus
quercetin
1.6.2.2
0.0012
-
pH 7.5, 22°C
Bos taurus
quercitrin
1.6.2.2
0.0015
-
pH 7.5, 22°C
Bos taurus
myricetin
1.6.2.2
0.0024
-
pH 7.5, 22°C
Bos taurus
luteolin-7-O-glucoside
1.6.2.2
0.0032
-
pH 7.5, 22°C
Bos taurus
(-)-epicatechin
1.6.2.2
0.0045
-
pH 7.5, 22°C
Bos taurus
(+)-catechin
1.6.2.2
0.036
-
pH 7.5, 22°C
Bos taurus
apigenin
1.6.2.2
0.057
-
pH 7.5, 22°C
Bos taurus
rutin
Application (protein specific)
EC Number
Application
Commentary
Organism
1.6.2.2
drug development
flavonoids, regarding b5 reductase inhibition, indicate a potential for significant flavonoid–drug and/or flavonoid–xenobiotic interactions which may have important therapeutic and toxicological outcomes for certain drugs and/or xenobiotics.
Bos taurus
Cofactor (protein specific)
EC Number
Cofactor
Commentary
Organism
Structure
1.6.2.2
NADH
-
Bos taurus
IC50 Value (protein specific)
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
1.6.2.2
0.00011
-
pH 7.5, 22°C
Bos taurus
luteolin
1.6.2.2
0.00081
-
pH 7.5, 22°C
Bos taurus
morin
1.6.2.2
0.0011
-
pH 7.5, 22°C
Bos taurus
quercetin
1.6.2.2
0.0012
-
pH 7.5, 22°C
Bos taurus
quercitrin
1.6.2.2
0.0015
-
pH 7.5, 22°C
Bos taurus
myricetin
1.6.2.2
0.0024
-
pH 7.5, 22°C
Bos taurus
luteolin-7-O-glucoside
1.6.2.2
0.0032
-
pH 7.5, 22°C
Bos taurus
(-)-epicatechin
1.6.2.2
0.0045
-
pH 7.5, 22°C
Bos taurus
(+)-catechin
1.6.2.2
0.036
-
pH 7.5, 22°C
Bos taurus
apigenin
1.6.2.2
0.057
-
pH 7.5, 22°C
Bos taurus
rutin
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
1.6.2.2
(+)-catechin
-
Bos taurus
1.6.2.2
(-)-epicatechin
-
Bos taurus
1.6.2.2
apigenin
-
Bos taurus
1.6.2.2
luteolin
-
Bos taurus
1.6.2.2
luteolin-7-O-glucoside
-
Bos taurus
1.6.2.2
additional information
inhibitory potencies of flavonoids on the enzyme, structure-activity relationship, overview. No inhibition by naringenin, naringin, and chrysin. Flavonoids containing two hydroxyl groups in ring B and a carbonyl group at C-4 in combination with a double bond between C-2 and C-3 produced a much stronger inhibition, whereas substitution of a hydroxyl group at C-3 is associated with a less inhibitory effect
Bos taurus
1.6.2.2
morin
-
Bos taurus
1.6.2.2
myricetin
-
Bos taurus
1.6.2.2
quercetin
-
Bos taurus
1.6.2.2
quercitrin
-
Bos taurus
1.6.2.2
rutin
-
Bos taurus
Ki Value [mM] (protein specific)
EC Number
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
1.6.2.2
additional information
-
additional information
inhibition kinetics
Bos taurus
Localization (protein specific)
EC Number
Localization
Commentary
Organism
GeneOntology No.
Textmining
1.6.2.2
microsome
-
Bos taurus
-
-
Purification (Commentary) (protein specific)
EC Number
Commentary
Organism
1.6.2.2
native enzyme from liver microsomes by anion exchange chromatography and affinity chromatography
Bos taurus
Source Tissue (protein specific)
EC Number
Source Tissue
Commentary
Organism
Textmining
1.6.2.2
liver
-
Bos taurus
-
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1.6.2.2
2 ferricyanide + NADH
-
724717
Bos taurus
2 ferrocyanide + NAD+ + H+
-
-
-
?
Temperature Optimum [°C] (protein specific)
EC Number
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
1.6.2.2
22
-
assay at room temperature
Bos taurus
pH Optimum (protein specific)
EC Number
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
1.6.2.2
7.5
-
assay at
Bos taurus
General Information
EC Number
General Information
Commentary
Organism
1.6.2.2
additional information
structure-activity relationship, overview
Bos taurus
General Information (protein specific)
EC Number
General Information
Commentary
Organism
1.6.2.2
additional information
structure-activity relationship, overview
Bos taurus