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Information on EC 2.3.1.146 - pinosylvin synthase and Organism(s) Pinus sylvestris and UniProt Accession Q02323

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EC Tree
     2 Transferases
         2.3 Acyltransferases
             2.3.1 Transferring groups other than aminoacyl groups
                2.3.1.146 pinosylvin synthase
IUBMB Comments
Not identical with EC 2.3.1.74 (naringenin-chalcone synthase) or EC 2.3.1.95 (trihydroxystilbene synthase).
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This record set is specific for:
Pinus sylvestris
UNIPROT: Q02323
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Word Map
The taxonomic range for the selected organisms is: Pinus sylvestris
The expected taxonomic range for this enzyme is: Pinus
Reaction Schemes
Synonyms
pinosylvin synthase, pine stilbene synthase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pine stilbene synthase
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-
-
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pinosylvin synthase
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-
-
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stilbene synthase
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
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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).
CAS REGISTRY NUMBER
COMMENTARY hide
72994-49-1
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-hydroxycinnamoyl-CoA + malonyl-CoA
cis-2-acetylresveratrol + CoA + CO2
show the reaction diagram
-
-
-
?
p-coumaroyl-CoA + 4 malonyl-CoA
2-malonylresveratrol + 5 CoA + 5 CO2
show the reaction diagram
-
-
-
?
phenylpropionyl-CoA + malonyl-CoA
? + CoA + CO2
show the reaction diagram
-
-
-
?
cinnamoyl-CoA + malonyl-CoA
3,5-dihydroxystilbene + CoA + CO2
show the reaction diagram
phenylpropionyl-CoA + malonyl-CoA
?
show the reaction diagram
-
-
-
-
?
additional information
?
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enzyme does not precisely control the number of condensations leading to diverse products
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-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
cinnamoyl-CoA + malonyl-CoA
3,5-dihydroxystilbene + CoA + CO2
show the reaction diagram
-
-
-
-
?
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0005 - 0.002
cinnamoyl-CoA
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-
0.003 - 0.008
phenylpropionyl-CoA
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-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
Uniprot
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
DPSS_PINSY
393
0
42735
Swiss-Prot
other Location (Reliability: 3)
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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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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transfected into Nicotiana tabacum cv. Petit Havana SR1
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
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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
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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
-
Manually annotated by BRENDA team
Schanz, S.; Schroeder, G.; Schroeder, J.
Stilbene synthase from Scots pine (Pinus sylvestris)
FEBS Lett.
313
71-74
1992
Pinus sylvestris
Manually annotated by BRENDA team
Schwekendiek, A.; Pfeffer, G.; Kindl, H.
Pine stilbene synthase cDNA, a tool for probing environmental stress
FEBS Lett.
301
41-44
1992
Pinus sylvestris
Manually annotated by BRENDA team
Schppner, A.; Kindl, H.
Stilbene synthase (pinosylvine synthase) and its induction by ultraviolet light
FEBS Lett.
108
349-352
1979
Pinus sylvestris
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team