Information on EC 2.3.1.95 - trihydroxystilbene synthase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
2.3.1.95
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RECOMMENDED NAME
GeneOntology No.
trihydroxystilbene synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3 malonyl-CoA + 4-coumaroyl-CoA = 4 CoA + trans-resveratrol + 4 CO2
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
resveratrol biosynthesis
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Stilbenoid, diarylheptanoid and gingerol biosynthesis
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:4-coumaroyl-CoA malonyltransferase (cyclizing)
Not identical with EC 2.3.1.74 naringenin-chalcone synthase or EC 2.3.1.146 pinosylvin synthase.
CAS REGISTRY NUMBER
COMMENTARY hide
128449-70-7
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene sts
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Manually annotated by BRENDA team
gene sts
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Manually annotated by BRENDA team
gene sts
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
gene sts
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
tatar rhubarb
SwissProt
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
Sorghum sp.
recombinantly expressed in Arabidopsis plants
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
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stilbene synthase 3 from Arachis hypogaea represents a type III PKS enzyme
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3 malonyl-CoA + 4-coumaroyl-CoA
4 CoA + resveratrol
show the reaction diagram
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out of three enzymes tested, only stilbene synthase from Arachis hypogaea is able to produce resveratrol from 4-coumaric acid
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?
3 malonyl-CoA + 4-coumaroyl-CoA
4 CoA + trans-resveratrol + 4 CO2
show the reaction diagram
3-coumaroyl-CoA + malonyl-CoA
3,3',5-trihydroxystilbene + CoA + CO2
show the reaction diagram
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9% of activity with 4-coumaroyl-CoA
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?
4-coumaroyl-CoA + malonyl-CoA
3,4',5-trihydroxystilbene + CoA + CO2
show the reaction diagram
4-fluorocinnamoyl-CoA + malonyl-CoA
4'-fluoro-trans-3,5-dihydroxystyrylfuran + CoA + CO2
show the reaction diagram
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side products: 49% bis-noryangonin and its derivatives, 8.2% 4-coumaroyltriacetic acid and 0.7% chalcone and its derivatives
?
acetyl-CoA + malonyl-CoA
6-acetonyl-4-hydroxy-2-pyrone + 6-methyl-4-hydroxy-2-pyrone + CoA + CO2
show the reaction diagram
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-
?
benzoyl-CoA + malonyl-CoA
bisnoryangonin-type and p-coumaroyltriacetic acid lactone-type pyrones + CoA + CO2
show the reaction diagram
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-
?
caffeoyl-CoA + malonyl-CoA
3,3',4',5-tetrahydroxystilbene + CoA + CO2
show the reaction diagram
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8% of activity with 4-coumaroyl-CoA
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?
cinnamoyl-CoA + malonyl-CoA
3,5-dihydroxystilbene + CoA + CO2
show the reaction diagram
dihydro-4-coumaroyl-CoA + malonyl-CoA
3,4',5-trihydroxybibenzyl + CoA + CO2
show the reaction diagram
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13% of activity with 4-coumaroyl-CoA
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?
feruloyl-CoA + malonyl-CoA
3,4',5-trihydroxy-3'-methoxystilbene + CoA + CO2
show the reaction diagram
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6% of activity with 4-coumaroyl-CoA
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?
isovaleryl-CoA + malonyl-CoA
bisnoryangonin-type and p-coumaroyltriacetic acid lactone-type pyrones + CoA + CO2
show the reaction diagram
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-
?
n-butyryl-CoA + malonyl-CoA
bisnoryangonin-type and p-coumaroyltriacetic acid lactone-type pyrones + CoA + CO2
show the reaction diagram
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-
?
n-hexanoyl-CoA + malonyl-CoA
bisnoryangonin-type and p-coumaroyltriacetic acid lactone-type pyrones + CoA + CO2
show the reaction diagram
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?
trans-3-(3-thienyl)acryloyl-CoA + malonyl-CoA
trans-3,5-dihydroxystyrylthiophene + CoA + CO2
show the reaction diagram
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side products: 59% bis-noryangonin and its derivatives, 18.4% 4-coumaroyltriacetic acid and 0.5% chalcone and its derivatives
?
trans-3-furanacryloyl-CoA + malonyl-CoA
trans-3,5-dihydroxystyrylfuran + CoA + CO2
show the reaction diagram
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side products: 32% bis-noryangonin and its derivatives, 15% 4-coumaroyltriacetic acid and 0.6% chalcone and its derivatives
?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
3 malonyl-CoA + 4-coumaroyl-CoA
4 CoA + trans-resveratrol + 4 CO2
show the reaction diagram
4-coumaroyl-CoA + malonyl-CoA
3,4',5-trihydroxystilbene + CoA + CO2
show the reaction diagram
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key enzyme of stilbene synthesis
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?
additional information
?
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SbSTS1, encodes an enzyme with stilbene synthase activity, suggesting that Sorghum accumulates stilbene-derived defense metabolites
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetyl-CoA
mercuribenzoate
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inactivation, reactivation by excess of dithiothreitol
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.002 - 0.0119
4-Coumaroyl-CoA
0.0084
4-Fluorocinnamoyl-CoA
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0.00086 - 0.031
malonyl-CoA
0.016 - 0.022
p-Coumaroyl-CoA
0.0075
trans-3-(3-thienyl)acryloyl-CoA
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0.0066
trans-3-furanacryloyl-CoA
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0005 - 0.02
4-Coumaroyl-CoA
0.0113
4-Fluorocinnamoyl-CoA
Arachis hypogaea
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0.0108
trans-3-(3-thienyl)acryloyl-CoA
Arachis hypogaea
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0.00533
trans-3-furanacryloyl-CoA
Arachis hypogaea
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.107 - 0.314
4-Coumaroyl-CoA
448
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.02 - 0.97
acetyl-CoA
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 8.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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; accumulation of product resveratrol
Manually annotated by BRENDA team
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callus culture
Manually annotated by BRENDA team
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induced in Sorghum mesocotyls following inoculation with Cochliobolus heterotrophus and Colletotrichum sublineolum
Manually annotated by BRENDA team
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; accumulation of product resveratrol
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
of the phloem in stems and roots
Manually annotated by BRENDA team
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stilbene synthase is found predominantly within vesicles (of varying size), along the plasma membrane and in the cell wall, suggesting protein secretion in the apoplast compartment
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
90000
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gel filtration, sucrose density gradient centrifugation
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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2 * 45000, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
the apo form and enzyme in complex with resveratrol, sitting drop vapor diffusion method
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2.1 A crystal structure, vapor diffusion hanging drop method
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 1 mM dithiothreitol, 10% sucrose, 3 weeks, 30% loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate, DE52 cellulose, hydroxylapatite
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recombinant fusion enzyme
recombinant His6-tagged STS from Escherichia coli strain BL21 Star by nickel affinity chromatography
recombinant resveratrol synthase, Co-affinity chromatography
recombinant resveratrol synthase, Ni-affinity chromatography
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recombinant resveratrol synthase, Ni2+-iminodiacetic acid-Sepharose
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
co-expression of AhSTS3 with Sorghum bicolor O-methyltransferase OMT3, EC 2.1.1.240, in Arabidopsis thaliana and Nicotiana tabacum using the CaMV 35S promoter and the Agrobacterium tumefaciens transfection method, quantitative realtime RT-PCR expression analysis in transgenic leaf samples, phenotypic analysis of pCRO1 transformants, overview. Subcloning in Escherichia coli. Binary vector construction
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expression in Escherichia coli
expression in Escherichia coli and Oryza sativa
expression in Escherichia coli; expression of fusion enzymes in Escherichia coli
expression of wild-type, P375G and G374L mutant enzyme in Escherichia coli
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gene sts, phylogenetic analysis, sequence comparisons and homology modeling, overview. Expression of His6-tagged STS in Escherichia coli strain BL21 Star, functional co-expression with 4-coumaroyl:CoA ligase, 4CL, from Petroselinum crispum or Arabidopsis thaliana in Escherichia coli strain BW27784 leading to resveratrol biosynthesis
Humulus lupulus plants of the Tettnang variety are transformed with a gene encoding for STS from grapevine. Under the control of the constitutive 35S cauliflower mosaic virus promoter, expression of the transgene results in accumulation of resveratrol and high levels of its glycosylated derivatives in leaves and inflorescences. Piceid, the predominant derivative, reaches a concentration of up to 560 microg/g of fresh weight in hop cones, whereas no stilbenes are detected in nontransformed controls (wild type). In Humulus lupulus constitutive expression of sts interferes neither with plant development nor with the biosynthesis of secondary metabolites relevant for the brewing industry. Since resveratrol is a well-known phytoalexin and antioxidant, transgenic Humulus lupulus plants could display enhanced pathogen resistance against microbial pathogens, exhibit new beneficial properties for health, and open new venues for metabolic engineering
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PcRS gene , recombinant expression in Arabidopsis thaliana under the control of CaMV 35S promoter using the Agrobacterium tumefaciens LBA 4404 transfection method
Pisum sativum is transformed via Agrobacterium tumefaciens-mediated gene transfer with pGPTV binary vectors containing the stilbene synthase (Vst1) from Vitis vinifera L. driven by its own elicitor-inducible promoter
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Populus alba is transformed with a construct containing cDNA insert encoding stilbene synthase under the control of the cauliflower mosaic virus 35S promoter and a kanamycin resistance gene
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production of the resveratrol beta-glucoside piceid by Saccharomyces cerevisiae by introduction of two key enzymes that are not present in Saccharomyces cerevisiae, coenzyme-A ligase and resveratrol synthase
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resveratrol synthase genes vst1 and vst2 from Vitis vinifera stably expressed in Triticum aestivum. Heterologous vst1 and vst2 genes retain their inducibility in wheat
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RS gene DNA and amino acid sequence determination and analysis, phylogenetic analysis, subcloning of the RS gene from peanut roots in Escherichia coli strain DH5alpha, expression in Escherichia coli strain BL21 (DE3). Transgenic expression of resveratrol synthase from Arachis hypogaea in Ipomoea batatas using Agrobacterium tumefaciens strain LBA4404 transfection method, transfection of leaves and stem sections, method, overview
SbCHS8 is overexpressed in transgenic Arabidopsis thaliana tt4 (transparent testa) mutants defective in chalcone synthase activities. SbCHS8 fails to complement the mutation
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sequence alignment with naringenin-chalcone synthase, EC 2.3.1.74
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the introduction of the stilbene synthase gene enhances the natural antiradical activity of Lycopersicon esculentum mill
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the stilbene synthase gene (vst1) from Vitis vinifera L. is cloned into pCLKSCLA25. The expression of vst1 gene contributes to the accumulation of trans-reveratrol from 3.4 to 8.7 microg/g fresh weight in different marker-free transgenic tomato lines
the stilbene synthase gene is isolated from Vitis vinifera L. is cloned under control of the seed-specific napin promotor and introduced into Brassica napus by Agrobacterium-mediated co-transformation together with a ds-RNA-interference construct deduced from the sequence of the key enzyme for sinapate ester biosynthesis biosynthesis, UDP-glucose:sinapate glucosyltransferase
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to construct a vector for STS expression in lettuce plant, a cDNA-encoding STS of Parthenocissus henryana is fused to the Cauliflower mosaic virus (CaMV) 35S promoter, and the bar gene is used as a selective marker gene. To increase the expression of STS, the expression cassette is flanked by matrix attachment regions. A high level of free trans-resveratrol is obtained in transgenic lettuce
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transformation of Carica papaya with Vitis vinifera stilbene synthase construct pVst1, containing the Vst1 gene and its pathogen-inducible promoter. RNA transcripts of stilbene synthase and resveratrol glycoside are induced in plant lines transformed with the grapevine pVst1 construct shortly after pathogen inoculation, and the transformed papaya lines exhibit increased resistance to Phytophthora palmivora
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
accumulation of endogenous resveratrol and stilbene synthase mRNA occurrs rapidly and significantly in response to UV-C irradiation. Applying resveratrol before UV-C irradiation mitigates rusty spots and wilting of peanut leaves, and inhibition of resveratrol by applying 3,4-methylenedioxycinnamic acid worsens UV-C damage
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cultures expressing plant oncogene rolB of Agrobacterium rhizogenes show an 1.3- to 3.8fold increase in expression of phenylalanine ammonia-lyase and stilbene synthase, resulting in increased resveratrol production
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R2R3-MYB-type transcription factors MYB14 and MYB15 strongly coexpress with STS genes, both in leaf tissues under biotic and abiotic stress and in the skin and seed of healthy developing berries during maturation. MYB14 and MYB15 specifically activate the promoters of STS genes, and the ectopic expression of MYB15 in grapevine hairy roots results in increased STS expression and in the accumulation of glycosylated stilbenes in planta
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significant accumulation of STS mRNA and new STS protein during early heat acclimation
STS is induced by UV-C irradiation. UV-induced STS occurs in palisade tissues of grape leaves and phloem tissues of grape leaf veins, stems, and roots
UV-C irradiation intensely stimulates STS in grape leaves, increasing the resveratrol level; UV-C irradiation leads to intense accumulation of enzyme and its product resveratrol
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UV-induced increase in stilbene synthase amount is developmental stage-dependent and time course-dependent, with response of stiblene synthase being postponed concomitantly with the progressive development of berry
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
G374L
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no condensing activity
P375G
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product profile of p-coumaroyl condensing reaction changed to: 42% p-coumaroyltriacetic acid, 27% resveratrol, 24% bisnoryangonin and 7.3% naringenin
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
analysis
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use of expression of stilbene synthases in Nicotiana benthamiana via Agrobacterium tumefaciens-mediated transient expression as a rapid and direct approach to perform functional analysis of stilbene synthases
pharmacology
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expression of the stilbene synthase gene from Vitis vinifera in transgenic Populus alba results in high accumulation of the antioxidant resveratrol glucosides
synthesis