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Information on EC 2.3.1.146 - pinosylvin synthase
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EC Tree
2.3.1.146 pinosylvin synthaseIUBMB Comments
Not identical with EC 2.3.1.74 (naringenin-chalcone synthase) or EC 2.3.1.95 (trihydroxystilbene synthase).
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Word Map
- 2.3.1.146
- pinus
- sylvestris
- synthases
- resveratrol
-
botrytis
-
scots
-
phytoalexins
-
protoplasts
-
plantlets
-
elicitor-responsive
- wood
- beta-glucuronidase
- agriculture
-
grapevine
- chalcone
- cinerea
The expected taxonomic range for this enzyme is: Pinus
Synonyms
pine stilbene synthase, pinosylvin synthase, stilbene synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
pine stilbene synthase
-
-
-
-
pinosylvin synthase
-
-
-
-
stilbene synthase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
3 malonyl-CoA + cinnamoyl-CoA = 4 CoA + pinosylvin + 4 CO2
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
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SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:cinnamoyl-CoA malonyltransferase (cyclizing)
Not identical with EC 2.3.1.74 (naringenin-chalcone synthase) or EC 2.3.1.95 (trihydroxystilbene synthase).
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CAS REGISTRY NUMBER
COMMENTARY
72994-49-1
-
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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-hydroxycinnamoyl-CoA + malonyl-CoA
cis-2-acetylresveratrol + CoA + CO2
-
-
-
?
dihydrocinnamoyl-CoA + 3 malonyl-CoA
dihydropinosylvin + 4 CoA + 4 CO2
-
-
-
-
?
p-coumaroyl-CoA + malonyl-CoA
2-malonylresveratrol + CoA + CO2
-
-
-
?
additional information
?
-
enzyme does not precisely control the number of condensations leading to diverse products
-
-
?
cinnamoyl-CoA + malonyl-CoA
3,5-dihydroxystilbene + CoA + CO2
-
-
-
?
cinnamoyl-CoA + malonyl-CoA
3,5-dihydroxystilbene + CoA + CO2
-
plays a key role in the stilbenoid synthesis
-
-
?
cinnamoyl-CoA + malonyl-CoA
3,5-dihydroxystilbene + CoA + CO2
-
-
-
-
?
cinnamoyl-CoA + malonyl-CoA
3,5-dihydroxystilbene + CoA + CO2
-
-
i.e. pinosylvin
?
cinnamoyl-CoA + malonyl-CoA
3,5-dihydroxystilbene + CoA + CO2
-
-
i.e. pinosylvin
?
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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
cinnamoyl-CoA + malonyl-CoA
3,5-dihydroxystilbene + CoA + CO2
-
plays a key role in the stilbenoid synthesis
-
-
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
maximal response to treatment with UV-light of PST-1 after 20 h
-
additional information
-
maximal response to treatment with conidia Botrytis cinerea after 35 h
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Eastern white pine, two encoding genes STS1 and STS2, STS1 has only 3-5% of activity of STS2
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
young seedlings are more susceptible to treatment with a suspension of conidia of Botrytis cinerea
brenda
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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). DPS1_PINST
396
0
43080
Swiss-Prot
other Location (Reliability: 2)
DPS2_PINST
396
0
43112
Swiss-Prot
other Location (Reliability: 3)
DPSS_PINSY
393
0
42735
Swiss-Prot
other Location (Reliability: 3)
Q9LDG3_PINDE
41
0
4169
TrEMBL
other Location (Reliability: 3)
Q9LDG5_PINDE
41
0
4267
TrEMBL
other Location (Reliability: 3)
Q9MBB0_PINDE
393
0
42741
TrEMBL
other Location (Reliability: 3)
Q9MBA4_PINDE
41
0
4205
TrEMBL
other Location (Reliability: 3)
Q9MBA8_PINDE
42
0
4392
TrEMBL
other Location (Reliability: 3)
Q9LDQ0_PINDE
42
0
4337
TrEMBL
other Location (Reliability: 3)
Q9LDQ2_PINDE
42
0
4277
TrEMBL
other Location (Reliability: 3)
Q9MBA5_PINDE
42
0
4291
TrEMBL
other Location (Reliability: 3)
Q9MBA9_PINDE
312
0
34061
TrEMBL
other Location (Reliability: 3)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
a male cone-specific promoter from Pinus radiata D. Don is used to express a stilbene synthase gene in anthers of transgenic Nicotiana tabacum plants, resulting in complete male sterility in 70% of the transformed plants
-
expressed in Escherichia coli
pinosylvin-synthase-encoding gene from Pinus sylvestris is transferred into aspen (Populus tremula) and two hybrid aspen clones (Populus tremula tremuloides) by Agrobacterium tumefaciens mediated transformation. Transgenic plants accumulated pinosylvin synthase-specific mRNA and showed stilbene synthase enzyme activity in vitro. Transgenic aspen line H4 showed increased resistance to Phellinus tremulae, while two hybrid aspen transformants decayed faster than the control trees. No accumulation of stilbenes in the transgenic plantlets
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pss from Pinus sylvestris are stably transformed into bread wheat. The expression of the target genes is regulated by stress-inducible grapevine promoters. pss Transgenic lines accumulate stilbene derivatives upon induction by UV light. None of the four tested pss expressing lines showes an increased fungal resistance
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
agriculture
-
even though pinosylvin, due to its high antifungal activity, could offer new possibilities in engineering disease resistance, its synthesis in heterologous plants may be restricted by factors related to 4-coumarate:CoA ligase-substrate specificity, or metabolic channelling. Cotransformation of pinosylvin-forming stilbene synthase and cinnamate-specific 4-coumarate:CoA ligase could offer a feasible tool to avoid these restrictions
agriculture
-
the promoter-stilbene synthase construct may be useful for the ablation of pollen formation in coniferous gymnosperms and male sterility may potentially be viewed as a prerequisite for the commercial use of transgenic conifers
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Kodan, A.; Kuroda, H.; Sakai, F.
A stilbene synthase from Japanese red pine (Pinus densiflora): implications for phytoalexin accumulation and down-regulation of flavonoid biosynthesis
Proc. Natl. Acad. Sci. USA
99
3335-3339
2002
Pinus densiflora
brenda
Chiron, H.; Drouet, A.; Lieutier, F.; Payer, H.D.; Ernst, D.; Sandermann, H.Jr.
Gene induction of stilbene biosynthesis in Scots pine in response to ozone treatment, wounding, and fungal infection
Plant Physiol.
124
865-872
2000
Pinus sylvestris
brenda
Preisig-Muller, R.; Schwekendiek, A.; Brehm, I.; Reif, H.J.; Kindl, H.
Characterization of a pine multigene family containing elicitor-responsive stilbene synthase genes
Plant Mol. Biol.
39
221-229
1999
Pinus sylvestris
brenda
Raiber, S.; Schroeder, G.; Schroeder, J.
Molecular and enzymic characterization of two stilbene synthases from Eastern white pine (Pinus strobus). A single Arg/His difference determines the activity and the pH dependence of the enzymes
FEBS Lett.
361
299-302
1995
Pinus strobus
brenda
Lange, B.M.; Trost, M.; Heller, W.; Langebartels, C.; Sandermann, H.Jr.
Elicitor-induced formation of free and cell-wall-bound stilbenes in cell-suspension cultures of Scots pine (Pinus sylvestris)
Planta
194
143-148
1994
Pinus sylvestris
-
brenda
Schanz, S.; Schroeder, G.; Schroeder, J.
Stilbene synthase from Scots pine (Pinus sylvestris)
FEBS Lett.
313
71-74
1992
Pinus sylvestris
brenda
Schwekendiek, A.; Pfeffer, G.; Kindl, H.
Pine stilbene synthase cDNA, a tool for probing environmental stress
FEBS Lett.
301
41-44
1992
Pinus sylvestris
brenda
Schöppner, A.; Kindl, H.
Stilbene synthase (pinosylvine synthase) and its induction by ultraviolet light
FEBS Lett.
108
349-352
1979
Pinus sylvestris
brenda
Seppanen, S.K.; Syrjala, L.; von Weissenberg, K.; Teeri, T.H.; Paajanen, L.; Pappinen, A.
Antifungal activity of stilbenes in in vitro bioassays and in transgenic Populus expressing a gene encoding pinosylvin synthase
Plant Cell Rep.
22
584-593
2004
Pinus sylvestris
brenda
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
Pinus sylvestris
brenda
Hoefig, K.P.; Moeller, R.; Donaldson, L.; Putterill, J.; Walter, C.
Towards male sterility in Pinus radiata - a stilbene synthase approach to genetically engineer nuclear male sterility
Plant Biotechnol. J.
4
333-343
2006
Pinus radiata
brenda
Li, T.L.; Spiteller, D.; Spencer, J.B.
Identification of a pentaketide stilbene produced by a type III polyketide synthase from Pinus sylvestris and characterisation of free coenzyme A intermediates
ChemBioChem
10
896-901
2009
Pinus sylvestris (Q02323)
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