Ligand trans-resveratrol

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Basic Ligand Information

Molecular Structure
Picture of trans-resveratrol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C14H12O3
trans-resveratrol
LUKBXSAWLPMMSZ-OWOJBTEDSA-N
Synonyms:
3,4',5-trihydroxy-stilbene, 3,4',5-trihydroxystilbene, 5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol, E-resveratrol, resveratrol, trans-resveratrol[side 1], trans-resveratrol[side 2]

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
UDP-glucuronate + trans-resveratrol = UDP + trans-resveratrol beta-D-glucuronoside
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
piceid + H2O = resveratrol + beta-D-glucose
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
resveratrol + O2 = ?
show the reaction diagram
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S-adenosyl-L-methionine + resveratrol = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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UDP-glucuronate + trans-resveratrol = UDP + trans-resveratrol beta-D-glucuronoside
show the reaction diagram
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dimethylallyl diphosphate + resveratrol = diphosphate + 3'-dimethylallyl resveratrol
show the reaction diagram
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resveratrol + CO2 = 2,6-dihydroxy-4-[(E)-2-(4-hydroxyphenyl)ethenyl]benzoate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
p-coumaroyl-CoA + malonyl-CoA = resveratrol + CoA + CO2
show the reaction diagram
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polydatin + H2O = D-glucose + 3,4',5-trihydroxystilbene
show the reaction diagram
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2,6-dihydroxy-4-methylbenzoate = resveratrol + CO2
show the reaction diagram
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-

Activator in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
at 25 micromol increases quinone reductase activity by 1.5fold. Resveratrol induces quinone reductase activity of the wild type Hepa-1c1c7 cells to the same extent as the mutant c1 cells that lack a phase I enzyme
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resveratrol restores SIRT1 activity and NAD+ level by an AMPK-dependent mechanism
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0.2 mM resveratrol can stimulate the Sirt5 deacetylase activity against the fluorophore-modified peptide substrate Fluor-de-Lys
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hepsin activity increases in dose-dependent manner in the presence of resveratrol
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causes activation of caspase-8, which in turn results in modulation of mitochondrial apoptotic machinery to promote apoptosis of rheumatoid arthritis fibroblast-like synoviocytes
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activity is increased by resveratrol at concentrations of 0.01 and 0.1 mM, 0.25 mM resveratrol does not affect activity
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Inhibitor in Enzyme-catalyzed Reactions (61 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibits the overall reaction and beta-ketoacyl reductase reaction of FAS with IC50 values of 11.1 microg/ml and 21.9 microg/ml, respectively. In 3 T3-L1 preadipocytes, resveratrol reduces lipid accumulation remarkably
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0.054 mM, 50% inhibition
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inhibits the cell growth as well as the activity of recombinant enzyme. Resveratrol shows antitrypanosomal activity with an IC50 value of 0.00013 mM and moderate antipromastigote activity against Leishmania major with IC50 value: 0.153 mM
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uncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
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resveratrol is 3,5,4'-trihydroxystilbene, potent inhibitor
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decreases adrenal enzyme expression in vivo and in cell culture. Corticosterone production is inhibited 47% by 0.05 mM resveratrol in vitro and 20% ex vivo, while progesterone production is elevated to 400% of control in vitro
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i.e. trans-3,5,4'-trihydroxystilbene
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can also act as enzyme substrate
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i.e. 5[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol, found in grapes as well as in other plants, is a natural phytoalexin, which is biosynthesized in response to pathogenic attack or other stress conditions
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inhibits deacetylase activity
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0.157 microM, results in 50% inhibition in interleukin 1beta effect on catalytic activity
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inhibition of isozymes GST A2-2, M1-1, M2-2, and P1-1
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inhibition of PtdIns 4-kinase activity by resveratrol/phenylarsine oxide reduces Jurkat cell adhesion to matrigel/fibronectin coated surfaces
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inhibition of p56lck
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nonspecific for IKK, anti-inflammatory
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isolated from Psoralea corylifolia
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100 microM, 39% inhibition of enzyme activity in microsomal fraction of mesangial cells
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substrate inhibition
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isolated from seeds of Syagrus romanzoffiana
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inhibits the enzyme activity and the growth of promastigotes
an F1 inhibitor, also inhibits Fe2+ uptake

3D Structure of Enzyme-Ligand-Complex (PDB) (12 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (2 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.062
-
pH 7.5, temperature not specified in the publication
0.722
-
30°C, pH not specified in the publication

KM Value (8 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.012
-
pH 7.5, temperature not specified in the publication
0.019
-
pH 7.5, 30°C
4.46
-
30°C, pH not specified in the publication

Ki Value (9 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0396
-
at pH 7.4 and 37°C
1.7
-
-
0.002
-
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IC50 Value (23 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
-999
-
IC50 value is 21.9 microg/ml, pH 7.0, 37°C
0.0352
-
at pH 7.4 and 37°C
0.00137
-
pH and temperature not specified in the publication
0.0139
-
pH 7.8, 25°C
0.0239
-
pH 6.5, 37°C
0.0657
-
pH 8.0, 37°C

References & Links

Links to other databases for trans-resveratrol

ChEBI
PubChem
ChEBI
PubChem