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EC Tree
The enzyme appears in viruses and cellular organisms
Synonyms
atact, agmatine coumaroyltransferase, agmatine coumaryl transferase,
more
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agmatine coumaroyltransferase
agmatine coumaryl transferase
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coumaroyltransferase, agmatine
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p-coumaroyl-CoA-agmatine N-p-coumaroyltransferase
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ACT
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agmatine coumaroyltransferase
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agmatine coumaroyltransferase
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agmatine coumaroyltransferase
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agmatine coumaroyltransferase
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4-coumaroyl-CoA + agmatine = CoA + N-(4-guanidinobutyl)-4-hydroxycinnamamide
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Acyl group transfer
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4-coumaroyl-CoA:agmatine N4-coumaroyltransferase
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4-coumaroyl-CoA + agmatine
CoA + 4-coumaroylagmatine
caffeoyl-CoA + agmatine
CoA + caffeoylagmatine
cinnamoyl-CoA + agmatine
CoA + cinnamoyl agmatine
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-
?
feruloyl-CoA + agmatine
CoA + feruloyl agmatine
feruloyl-CoA + agmatine
CoA + feruloylagmatine
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?
feruloyl-CoA + putrescine
CoA + feruloylputrescine
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30°C, pH 7.5, pathway analysis with stable isotope-labeled precursors
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?
p-coumaroyl-CoA + agmatine
CoA + p-coumaroylagmatine
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30°C, pH 7.5, pathway analysis with stable isotope-labeled precursors
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?
p-coumaroyl-CoA + putrescine
CoA + p-coumaroylputrescine
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30°C, pH 7.5, pathway analysis with stable isotope-labeled precursors
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?
sinapoyl-CoA + agmatine
CoA + sinapoyl agmatine
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?
4-coumaroyl-CoA + agmatine
CoA + 4-coumaroylagmatine
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?
4-coumaroyl-CoA + agmatine
CoA + 4-coumaroylagmatine
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?
4-coumaroyl-CoA + agmatine
CoA + 4-coumaroylagmatine
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?
4-coumaroyl-CoA + agmatine
CoA + 4-coumaroylagmatine
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no activity with N-carbamoylputrescine, homoagmatine
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?
4-coumaroyl-CoA + agmatine
CoA + 4-coumaroylagmatine
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no activity with putrescine, spermidine, spermine, cadaverine, arginine, homoarginine
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?
4-coumaroyl-CoA + agmatine
CoA + 4-coumaroylagmatine
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no activity with putrescine, spermidine, spermine, cadaverine, arginine, homoarginine
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?
4-coumaroyl-CoA + agmatine
CoA + 4-coumaroylagmatine
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reaction in hordatine anabolism
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?
caffeoyl-CoA + agmatine
CoA + caffeoylagmatine
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?
caffeoyl-CoA + agmatine
CoA + caffeoylagmatine
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?
caffeoyl-CoA + agmatine
CoA + caffeoylagmatine
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?
feruloyl-CoA + agmatine
CoA + feruloyl agmatine
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30°C, pH 7.5, pathway analysis with stable isotope-labeled precursors
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?
feruloyl-CoA + agmatine
CoA + feruloyl agmatine
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feruloyl-CoA + agmatine
CoA + feruloyl agmatine
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?
feruloyl-CoA + agmatine
CoA + feruloyl agmatine
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?
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4-coumaroyl-CoA + agmatine
CoA + 4-coumaroylagmatine
feruloyl-CoA + agmatine
CoA + feruloyl agmatine
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30°C, pH 7.5, pathway analysis with stable isotope-labeled precursors
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?
feruloyl-CoA + agmatine
CoA + feruloylagmatine
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?
feruloyl-CoA + putrescine
CoA + feruloylputrescine
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30°C, pH 7.5, pathway analysis with stable isotope-labeled precursors
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?
p-coumaroyl-CoA + agmatine
CoA + p-coumaroylagmatine
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30°C, pH 7.5, pathway analysis with stable isotope-labeled precursors
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?
p-coumaroyl-CoA + putrescine
CoA + p-coumaroylputrescine
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30°C, pH 7.5, pathway analysis with stable isotope-labeled precursors
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?
4-coumaroyl-CoA + agmatine
CoA + 4-coumaroylagmatine
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?
4-coumaroyl-CoA + agmatine
CoA + 4-coumaroylagmatine
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reaction in hordatine anabolism
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?
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agmatine
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the presence of this substrate inhibits the enzyme reaction with putrescine
CuSO4
10 mM, 85% inhibition
dithiothreitol
30% inhibition
enterokinase
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the removal of the thioredoxin domain by enterokinase decreases the enzyme activity but does not alter the relative amounts of products
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MnCl2
10 mM, 29% inhibition
p-Coumaroyl-CoA
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the presence of this substrate inhibits the enzyme reaction with feruloyl-CoA
ZnSO4
10 mM, 99% inhibition
additional information
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putrescine or feruloyl-CoA do not inhibit the enzyme reaction with agmantine and p-coumaroyl-CoA
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1-mercapto-2,3-propanediol
1 mM is required for optimal activity
2-mercaptoethanol
1 mM is required for optimal activity
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Infections
Accumulation of hydroxycinnamic acid amides induced by pathogen infection and identification of agmatine coumaroyltransferase in Arabidopsis thaliana.
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0.00074 - 0.0021
4-coumaroyl-CoA
0.0033 - 0.0058
caffeoyl-CoA
0.0013 - 0.0066
feruloyl-CoA
0.00074
4-coumaroyl-CoA
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0.001
4-coumaroyl-CoA
isoenzyme 1
0.0015
4-coumaroyl-CoA
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0.0016
4-coumaroyl-CoA
isoenzyme 3
0.0021
4-coumaroyl-CoA
isoenzyme 2
0.0021
4-coumaroyl-CoA
recombinant enzyme
0.0052
agmatine
isoenzyme 1
0.0052
agmatine
isoenzyme 3
0.0065
agmatine
isoenzyme 2
0.0081
agmatine
recombinant enzyme
0.0033
caffeoyl-CoA
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0.0043
caffeoyl-CoA
isoenzyme 2
0.0043
caffeoyl-CoA
recombinant enzyme
0.0053
caffeoyl-CoA
isoenzyme 3
0.0058
caffeoyl-CoA
isoenzyme 1
0.0013
feruloyl-CoA
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0.0017
feruloyl-CoA
isoenzyme 3
0.0041
feruloyl-CoA
isoenzyme 2
0.0061
feruloyl-CoA
isoenzyme 1
0.0066
feruloyl-CoA
recombinant enzyme
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0.00000003
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with substrates p-coumaroyl-CoA + agmatine + putrescine 0.0018 nmol coumaroylputrescine/mg/protein/h, recombinant enzyme, 30°C, pH 7.5
0.000000085
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with substrates feruloyl-CoA + putrescine 0.0051 nmol feruloylputrescine/mg/protein/h, recombinant enzyme, 30°C, pH 7.5
0.000000933
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with substrates p-coumaroyl-CoA + putrescine 0.056 nmol p-coumaroylputrescine/mg/protein/h, recombinant enzyme, 30°C, pH 7.5
0.00002
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with substrates p-coumaroyl-CoA + feruloyl-CoA + agmatine 1.2 nmol feruloylagmatine/mg/protein/h, recombinant enzyme, 30°C, pH 7.5
0.00004
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with substrates feruloyl-CoA + agmatine 2.4 nmol feruloylagmatine/mg/protein/h, recombinant enzyme, 30°C, pH 7.5
0.000112
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with substrates p-coumaroyl-CoA + agmatine 6.7 nmol p-coumaroylagmatine/mg/protein/h, recombinant enzyme, 30°C, pH 7.5
0.000123
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with substrates p-coumaroyl-CoA + agmatine + putrescine 7.4 nmol p-coumaroylagmatine/mg/protein/h, recombinant enzyme, 30°C, pH 7.5
0.000187
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with substrates p-coumaroyl-CoA + feruloyl-CoA + agmatine 11.2 nmol p-coumaroylagmatine/mg/protein/h, recombinant enzyme, 30°C, pH 7.5
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7.5
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6.9 - 8.1
half-maximal activity at pH 6.9 and pH 8.1
7 - 8
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approx. half-maximal activity at pH 7.0 and 8.0
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SwissProt
brenda
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UniProt
brenda
wild-type and mutants, infection of rosette leaves with the fungus Alternaria brassicicola strain MAFF237450
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brenda
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brenda
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SwissProt
brenda
barley, cv. claret
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brenda
cv. Proctor
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brenda
isoenzymes 1-3
SwissProt
brenda
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cut off rosette leaves infected with the fungus Alternaria brassicicola
brenda
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brenda
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brenda
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shoots, not seeds
brenda
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maximal activity 3-4 days after germination at 22°C in the dark
brenda
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brenda
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metabolism
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last step in the synthesis of hydroxycinnamic acid amides in plants (anti-pathogenic metabolites), in Arabidopsis thaliana infected with Alternaria brassicicola p-coumaroylagmatine, feruloylagmatine, p-coumaroylputrescine, and feruloylputrescine are identified as anti-fungal agents in vitro and in vivo
metabolism
the enzyme catalyzes the last reaction of the hydroxycinnamic acid amides biosynthesis
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AGCT1_HORVU
439
0
47467
Swiss-Prot
other Location (Reliability: 3 )
AGCT2_HORVU
439
0
47641
Swiss-Prot
other Location (Reliability: 3 )
AGCT_ARATH
452
0
51075
Swiss-Prot
other Location (Reliability: 5 )
A0A2I0BF85_9ASPA
458
0
50301
TrEMBL
Chloroplast (Reliability: 4 )
A0A2I0ALV7_9ASPA
449
0
49251
TrEMBL
other Location (Reliability: 2 )
A0A2I0ALR8_9ASPA
448
0
48158
TrEMBL
other Location (Reliability: 2 )
A0A2I0BF55_9ASPA
462
0
49736
TrEMBL
Chloroplast (Reliability: 5 )
A0A2I0BF53_9ASPA
405
0
43484
TrEMBL
Mitochondrion (Reliability: 4 )
A0A2I0BF80_9ASPA
463
0
50616
TrEMBL
Chloroplast (Reliability: 5 )
A0A2I0BF73_9ASPA
439
0
47926
TrEMBL
other Location (Reliability: 5 )
A0A2I0BF68_9ASPA
470
0
51266
TrEMBL
Secretory Pathway (Reliability: 4 )
Q84QG5_WHEAT
353
0
38586
TrEMBL
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48000
1 * 48000, SDS-PAGE
40000
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monomer
1 * 48000, SDS-PAGE
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additional information
enzyme expression in Torenia hybrida leads to accumulation of hydroxycinnamic acids, predominantly p-coumaroylagmatine, in transgenic plants, and the hydroxycinnamic acids are isomerized from the trans-form to the cis-form in planta. The transgenic line which accumulates the highest amount of endogenous hydroxycinnamic acids, i.e. total hydroxycinnamic acids at 47.5 mM, is resistant to the necrotrophic fungus, Botrytis cinerea. The transformants are not significantly resistant to three representative herbivores, Frankliniella occidentalis, Aphis gossypii, and Tetranychus ludeni
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2-mercaptoethanol stabilizes
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-40°C, concentrated preparation at least 1 month, negligible loss of activity
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0°C, 100 mM Tris, pH 7.5, 1 mM EDTA, 10 mM 2-mercaptoethanol, 50 mM KCl
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ammonium sulfate, Biogel A, Sepharose 4B-agmatine
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Blue Sepharose, t-butyl-Sepharose, Resource Q, Superose 12 HR
frozen leaves are homogenized in 100 mM Tris buffer, pH 7.5, containing 10 mM 2-mercaptoethanol and 5 mM DTT, centrifugation, supernatant applied to Sephadex G-50 column, fluent used for enzyme assays, or recombinant Escherichia coli cells are harvested and resuspended in 100 mM Tris buffer, pH 7.5, containing 1 mM EDTA, 50 mM NaCl, 10% glycerol, lysed with lysozyme, sonicated, centrifuged, supernatant used for enzyme assays and SDS-PAGE
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expression in Escherichia coli
expression in Torenia hybrida
PCR-amplification, expression in Escherichia coli BL21(DE3)
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enzyme expression is induced by a combination of jasmonic acid and ethylene. ORA59 binds to the enzyme gene promoter
upon infection with Alternaria brassicicola enzyme activity in leaves increases markedly from near zero to almost 20 nmol/mg protein/h within 24 h coinciding with an increase in gene transcripts and in the synthesis products, that accumulate in the area of the lesion, slow decrease beyond 24 h
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agriculture
enzyme expression in Torenia hybrida leads to accumulation of hydroxycinnamic acids, predominantly p-coumaroylagmatine, in transgenic plants, and the hydroxycinnamic acids are isomerized from the trans-form to the cis-form in planta. The transgenic line which accumulates the highest amount of endogenous hydroxycinnamic acids, i.e. total hydroxycinnamic acids at 47.5 mM, is resistant to the necrotrophic fungus, Botrytis cinerea. The transformants are not significantly resistant to three representative herbivores, Frankliniella occidentalis, Aphis gossypii, and Tetranychus ludeni
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Bird, C.R.; Smith, T.A.
The biosynthesis of coumaroylagmatine in barley seedlings
Phytochemistry
20
2345-2346
1981
Hordeum vulgare
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brenda
Bird, C.R.; Smith, T.A.
Agmatine coumaroyltransferase (barley seedlings)
Methods Enzymol.
94
344-347
1983
Hordeum vulgare
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brenda
Bird, C.R.; Smith, T.A.
Agmatine coumaroyltransferase from barley seedlings
Phytochemistry
22
2401-2403
1983
Hordeum vulgare
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brenda
Burhenne, K.; Kristensen, B.K.; Rasmussen, S.K.
A new class of N-hydroxycinnamoyltransferases. Purification, cloning, and expression of barley agmatine coumaroyltransferase (EC 2.3.1.64)
J. Biol. Chem.
278
13919-13927
2003
Hordeum vulgare (A9ZPJ6), Hordeum vulgare
brenda
Nomura, T.; Ishizuka, A.; Kishida, K.; Islam, A.K.; Endo, T.R.; Iwamura, H.; Ishihara, A.
Chromosome arm location of the genes for the biosynthesis of hordatines in barley
Genes Genet. Syst.
82
455-464
2007
Hordeum vulgare (A9ZPJ6), Hordeum vulgare, Triticum aestivum (Q84QG5), Triticum aestivum
brenda
Muroi, A.; Ishihara, A.; Tanaka, C.; Ishizuka, A.; Takabayashi, J.; Miyoshi, H.; Nishioka, T.
Accumulation of hydroxycinnamic acid amides induced by pathogen infection and identification of agmatine coumaroyltransferase in Arabidopsis thaliana
Planta
230
517-527
2009
Arabidopsis thaliana
brenda
Muroi, A.; Matsui, K.; Shimoda, T.; Kihara, H.; Ozawa, R.; Ishihara, A.; Nishihara, M.; Arimura, G.
Acquired immunity of transgenic torenia plants overexpressing agmatine coumaroyltransferase to pathogens and herbivore pests
Sci. Rep.
2
689
2012
Arabidopsis thaliana (Q9FNP9)
brenda
Li, J.; Zhang, K.; Meng, Y.; Hu, J.; Ding, M.; Bian, J.; Yan, M.; Han, J.; Zhou, M.
Jasmonic acid/ethylene signaling coordinates hydroxycinnamic acid amides biosynthesis through ORA59 transcription factor
Plant J.
95
444-457
2018
Arabidopsis thaliana (Q9FNP9), Arabidopsis thaliana
brenda
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