Any feedback?
Information on EC 2.3.1.95 - trihydroxystilbene synthase and Organism(s) Vitis vinifera and UniProt Accession P28343
for references in articles please use BRENDA:EC2.3.1.95Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
2.3.1.95 trihydroxystilbene synthaseIUBMB Comments
Not identical with EC 2.3.1.74 naringenin-chalcone synthase or EC 2.3.1.146 pinosylvin synthase.
Specify your search results
Word Map
- 2.3.1.95
- vitis
-
grapevine
- vinifera
- grape
- chalcone
-
phytoalexins
- berry
- arachis
- hypogaea
- trans-resveratrol
- mildew
- pinosylvin
- piceid
-
tetraketide
-
powdery
- viticola
-
stilbenoids
- p-coumaroyl-coa
- 4-coumarate
- amurensis
-
plasmopara
-
vineyard
-
pinot
-
4-coumarate:coa
-
chs-like
- pseudoreticulata
-
uncinula
-
trans-piceid
-
cabernet
- riparia
-
pgips
- agriculture
- synthesis
- analysis
- pharmacology
The taxonomic range for the selected organisms is: Vitis vinifera
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
stilbene synthase, resveratrol synthase, sbchs8, sbsts1, stilbene synthase 1, stilbene synthase 3, trihydroxystilbene synthase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
resveratrol synthase
stilbene synthase
STS
synthase, resveratrol
-
-
-
-
resveratrol synthase
-
-
-
-
stilbene synthase
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
-
-
-
-
PATHWAY SOURCE
PATHWAYS
-
-
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
128449-70-7
-
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
4-coumaroyl-CoA + malonyl-CoA
3,4',5-trihydroxystilbene + CoA + CO2
-
-
-
?
3 malonyl-CoA + 4-coumaroyl-CoA
4 CoA + trans-resveratrol + 4 CO2
-
-
-
?
3 malonyl-CoA + 4-coumaroyl-CoA
4 CoA + trans-resveratrol + 4 CO2
-
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3 malonyl-CoA + 4-coumaroyl-CoA
4 CoA + trans-resveratrol + 4 CO2
-
-
-
?
3 malonyl-CoA + 4-coumaroyl-CoA
4 CoA + trans-resveratrol + 4 CO2
-
-
-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
-
UV-light greatly stimulates resveratrol synthase mRNA accumulation in berry skin, a weak accumulation is observed during wilting i.e. the post-harvest drying process
a high level in the early stages from 20 to 30 day after full bloom, decreases gradually from 40 to 50 day after full bloom, then reaches the second peak at the ripe stage at 70 day after full bloom, and finally the third peak at the ripe stage at 120 day after full bloom. Stilbene synthase protein already increases at 1 h after incubation at 38°C, reaching a maximum at 8 h before decreasing to the control level. The transcription of stilbene synthase gene is enhanced by heat acclimation
-
stilbene synthase is found in berry exocarp tissues during all stages of fruit development. The stilbene synthase signal decreases gradually from exocarp to mesocarp, where the protein is detected only occasionally. STS localization is the same before and after veraison, the relatively short developmental period during which the firm green berries begin to soften and change color
high protein level in the early stages from 20 to 30 days after full bloom, which decrease gradually from 40 to 50 days after full bloom, then reaches the second peak at the ripe stage at 70 days after full bloom, and finally the third peak at the ripe stage at 120 days after full bloom
low accumulation of product resveratrol, highest level of stilbene synthase mRNA and protein among the tissues analyzed
additional information
immunohistochemical analysis of the tissue-specific distribution of STS in different organs, overview. Distribution of resveratrol and STS in grape is organ-specific and tissue-specific
additional information
-
immunohistochemical analysis of the tissue-specific distribution of STS in different organs, overview. Distribution of resveratrol and STS in grape is organ-specific and tissue-specific. Highest content of resveratrol occurs in the stem phloems, followed by axillary buds, roots, stem xylems, shoot tips and petioles; and lowest in leaves
additional information
immunohistochemical analysis of the tissue-specific distribution of STS in different organs, overview. Distribution of resveratrol and STS in grape is organ-specific and tissue-specific. Highest content of resveratrol occurs in the stem phloems, followed by axillary buds, roots, stem xylems, shoot tips and petioles; and lowest in leaves
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
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
-
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
mainly located on the cell wall, secondary cell wall and chloroplast of the skin tissues during berry development
mainly located on the cell wall, secondary cell wall and chloroplast of the skin tissues during berry development
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
stilbene synthase is a pivotal enzyme that catalyzes the biosynthesis of resveratrol
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). THS1_VITVI
392
0
42840
Swiss-Prot
other Location (Reliability: 3)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
expression of the Vitis vinifera cDNA encoding stilbene synthase in Lycopersicon esculentum leads to accumulation of trans-resveratrol and trans-piceid, in particular in the skin of the mature fruits. Transgenic fruits contain low levels of trans-resveratrol, their the total antioxidant capability and ascorbate content increases significantly
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His6-tagged STS from Escherichia coli strain BL21 Star by nickel affinity chromatography
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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
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
-
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
-
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
-
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
-
resveratrol synthase genes vst1 and vst2 from Vitis vinifera stably expressed in Triticum aestivum. Heterologous vst1 and vst2 genes retain their inducibility in wheat
-
the introduction of the stilbene synthase gene enhances the natural antiradical activity of Lycopersicon esculentum mill
-
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
-
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
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
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
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
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
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
pharmacology
-
expression of the stilbene synthase gene from Vitis vinifera in transgenic Populus alba results in high accumulation of the antioxidant resveratrol glucosides
synthesis
agriculture
-
Carica papaya is transformed 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
agriculture
-
expression of the Vitis vinifera cDNA encoding stilbene synthase in Lycopersicon esculentum leads to accumulation of trans-resveratrol and trans-piceid, in particular in the skin of the mature fruits. Transgenic fruits contain low levels of trans-resveratrol, their the total antioxidant capability and ascorbate content increases significantly
synthesis
expression of stilbene synthase from Vitis vinifera and/or the transcription factor MYB12 from Arabidopsis thaliana in tobacco hairy root cultures. The transgenic cultures are able to biosynthesize stilbenes, achieving a production of 40 microg/L of trans-resveratrol, which is partially metabolized into trans-piceatannol and trans-pterostilbene (up to 2.2 microg/l and 86.4 microg/l, respectively), as well as its glucoside piceid (up to 339.7 microg/l)
synthesis
in Silybum marinum cell cultures stably transformed with Vitis vinifera stilbene synthase 3, the epression of the transgene leads to extracellular trans-resveratrol accumulation at the level of milligrams per litre under elicitation. Resveratrol synthesis occurs at the expense of coniferyl alcohol
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Versari, A.; Parpinello, G.P.; Tornielli, G.B.; Ferrarini, R.; Giulivo, C.
Stilbene compounds and stilbene synthase expression during ripening, wilting, and UV treatment in grape cv. Corvina
J. Agric. Food Chem.
49
5531-5536
2001
Vitis vinifera
Becker, J.V.; Armstrong, G.O.; van der Merwe, M.J.; Lambrechts, M.G.; Vivier, M.A.; Pretorius, I.S.
Metabolic engineering of Saccharomyces cerevisiae for the synthesis of the wine-related antioxidant resveratrol
FEMS Yeast Res.
4
79-85
2003
Vitis vinifera
Zhu, Y.J.; Agbayani, R.; Jackson, M.C.; Tang, C.S.; Moore, P.H.
Expression of the grapevine stilbene synthase gene VST1 in papaya provides increased resistance against diseases caused by Phytophthora palmivora
Planta
220
241-250
2004
Vitis vinifera
Giorcelli, A.; Sparvoli, F.; Mattivi, F.; Tava, A.; Balestrazzi, A.; Vrhovsek, U.; Calligari, P.; Bollini, R.; Confalonieri, M.
Expression of the stilbene synthase (StSy) gene from grapevine in transgenic white poplar results in high accumulation of the antioxidant resveratrol glucosides
Transgenic Res.
13
203-214
2004
Vitis vinifera
Serazetdinova, L.; Oldach, K.H.; Loerz, H.
Expression of transgenic stilbene synthases in wheat causes the accumulation of unknown stilbene derivatives with antifungal activity
J. Plant Physiol.
162
985-1002
2005
Vitis vinifera
Morelli, R.; Das, S.; Bertelli, A.; Bollini, R.; Lo Scalzo, R.; Das, D.K.; Falchi, M.
The introduction of the stilbene synthase gene enhances the natural antiradical activity of Lycopersicon esculentum mill
Mol. Cell. Biochem.
282
65-73
2006
Vitis vinifera
Richter, A.; Jacobsen, H.J.; de Kathen, A.; de Lorenzo, G.; Briviba, K.; Hain, R.; Ramsay, G.; Kiesecker, H.
Transgenic peas (Pisum sativum) expressing polygalacturonase inhibiting protein from raspberry (Rubus idaeus) and stilbene synthase from grape (Vitis vinifera)
Plant Cell Rep.
25
1166-1173
2006
Vitis vinifera
Huesken, A.; Baumert, A.; Milkowski, C.; Becker, H.C.; Strack, D.; Moellers, C.
Resveratrol glucoside (Piceid) synthesis in seeds of transgenic oilseed rape (Brassica napus L.)
Theor. Appl. Genet.
111
1553-1562
2005
Vitis vinifera
Ma, B.G.; Duan, X.Y.; Niu, J.X.; Ma, C.; Hao, Q.N.; Zhang, L.X.; Zhang, H.P.
Expression of stilbene synthase gene in transgenic tomato using salicylic acid-inducible Cre/loxP recombination system with self-excision of selectable marker
Biotechnol. Lett.
31
163-169
2009
Vitis vinifera (P28343), Vitis vinifera
Schwekendiek, A.; Spring, O.; Heyerick, A.; Pickel, B.; Pitsch, N.T.; Peschke, F.; de Keukeleire, D.; Weber, G.
Constitutive expression of a grapevine stilbene synthase gene in transgenic hop (Humulus lupulus L.) yields resveratrol and its derivatives in substantial quantities
J. Agric. Food Chem.
55
7002-7009
2007
Vitis vinifera
Wang, W.; Wan, S.B.; Zhang, P.; Wang, H.L.; Zhan, J.C.; Huang, W.D.
Prokaryotic expression, polyclonal antibody preparation of the stilbene synthase gene from grape berry and its different expression in fruit development and under heat acclimation
Plant Physiol. Biochem.
46
1085-1092
2008
Vitis vinifera (A8I4W6), Vitis vinifera
Fornara, V.; Onelli, E.; Sparvoli, F.; Rossoni, M.; Aina, R.; Marino, G.; Citterio, S.
Localization of stilbene synthase in Vitis vinifera L. during berry development
Protoplasma
233
83-93
2008
Vitis vinifera
DIntrono, A.; Paradiso, A.; Scoditti, E.; DAmico, L.; De Paolis, A.; Carluccio, M.A.; Nicoletti, I.; DeGara, L.; Santino, A.; Giovinazzo, G.
Antioxidant and anti-inflammatory properties of tomato fruits synthesizing different amounts of stilbenes
Plant Biotechnol. J.
7
422-429
2009
Vitis vinifera
Wang, W.; Tang, K.; Yang, H.R.; Wen, P.F.; Zhang, P.; Wang, H.L.; Huang, W.D.
Distribution of resveratrol and stilbene synthase in young grape plants (Vitis vinifera L. cv. Cabernet Sauvignon) and the effect of UV-C on its accumulation
Plant Physiol. Biochem.
48
142-152
2009
Vitis vinifera, Vitis vinifera (A8I4W6)
Pan, Q.; Wang, L.; Li, J.
Amounts and subcellular localization of stilbene synthase in response of grape berries to UV irradiation
Plant Sci.
176
360-366
2009
Vitis vinifera (A8I4W6)
Lim, C.; Fowler, Z.; Hueller, T.; Schaffer, S.; Koffas, M.
High-yield resveratrol production in engineered Escherichia coli
Appl. Environ. Microbiol.
77
3451-3460
2011
Arachis hypogaea, Pinus densiflora, Pinus strobus, Vitis vinifera, Polygonum cuspidatum, Pinus massoniana, Psilotum nudum
Tang, K.; Fang, F.; Yang, H.; Huang, W.
Effect of UV-C irradiation on stilbene synthase localization in young grape plants
Russ. J. Plant Physiol.
58
603-614
2011
Vitis vinifera (A8I4W6)
-
Hll, J.; Vannozzi, A.; Czemmel, S.; Donofrio, C.; Walker, A.; Rausch, T.; Lucchin, M.; Boss, P.; Dry, I.; Bogsa, J.
The R2R3-MYB transcription factors MYB14 and MYB15 regulate stilbene biosynthesis in Vitis vinifera
Plant Cell
25
4135-4149
2013
Vitis vinifera (A8I4W6)
Hidalgo, D.; Martinez-Marquez, A.; Cusido, R.; Bru-Martixadnez, R.; Palazon, J.; Corchete, P.
Silybum marianum cell cultures stably transformed with Vitis vinifera stilbene synthase accumulate t-resveratrol in the extracellular medium after elicitation with methyl jasmonate or methylated beta-cyclodextrins
Eng. Life Sci.
17
686-694
2017
Vitis vinifera (P51071)
-
EXTERNAL LINKS (specific for EC-Number 2.3.1.95)
Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.
Release 2023.1 (January 2023)
Legal
Curated at
Member of
