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Information on EC 2.1.1.117 - (S)-scoulerine 9-O-methyltransferase
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2.1.1.117 (S)-scoulerine 9-O-methyltransferaseIUBMB Comments
The product of this reaction is a precursor for protoberberine alkaloids in plants
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Word Map
- 2.1.1.117
-
alkaloid
-
benzylisoquinoline
- japonica
-
s-scoulerine
-
eschscholzia
- californica
- coptis
- poppy
-
methylenedioxy
-
7-o-methylated
-
opium
- sanguinarine
- noscapine
-
benzophenanthridine
- isoquinoline
- allocryptopine
-
virus-induced
- papaveraceae
- medicine
- analysis
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
(S)-Adenosyl-L-methionine:(S)-scoularine 9-O-methyltransferase, (S)-scoulerine 9-O-methyltransferase, Methyltransferase, (S)-scoularine 9-, Methyltransferase, (S)-scoularine 9- (Coptis japonica clone pCJSMT), scoulerine 9-O-methyltransferase, scoulerine 9-OMT, scoulerine-9-O-methyltransferase, scoulerine/reticuline O-methyltransferase, SMT, SOMT, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
scoulerine 9-O-methyltransferase
scoulerine/reticuline O-methyltransferase
Eschscholzia californica subsp. californica
-
SMT
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + (S)-scoulerine = S-adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:(S)-scoulerine 9-O-methyltransferase
The product of this reaction is a precursor for protoberberine alkaloids in plants
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CAS REGISTRY NUMBER
COMMENTARY
164205-21-4
methyltransferase, (S)-scoularine 9- (Coptis japonica clone pCJSMT)
96380-65-3
-
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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
S-adenosyl-L-homocysteine + (S)-tetrahydropalmatrubine
S-adenosyl-L-homocysteine + (S)-tetrahydropalmatine
Stephania intermedia
-
-
-
?
S-Adenosyl-L-methionine + (R,S)-2,3,9,10-tetrahydroxytetrahydroprotoberberine
?
Berberis wilsoniae
-
methylated at 50% of the rate of (S)-scoulerine
-
-
?
S-Adenosyl-L-methionine + (S)-3,9-dihydroxy-2,10-dimethoxytetrahydroprotoberberine
?
Berberis wilsoniae
-
methylated at 4% of the rate of (S)-scoulerine
-
-
?
S-adenosyl-L-methionine + (S)-norreticuline
S-adenosyl-L-homocysteine + norcodamine + norlaudanine
Eschscholzia californica subsp. californica
-
-
-
?
S-adenosyl-L-methionine + (S)-reticuline
S-adenosyl-L-homocysteine + codamine + laudanine
Eschscholzia californica subsp. californica
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
S-adenosyl-L-methionine + (S)-scoulerine
S-adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine + 2-O-methylscoulerine + tetrahydropalmatine
Eschscholzia californica subsp. californica
-
-
-
?
S-adenosyl-L-methionine + (S)-tetrahydrocolumbamine
S-adenosyl-L-homocysteine + (S)-tetrahydropalmatine
Stephania intermedia
-
-
-
?
S-Adenosyl-L-methionine + 6-O-methylnorlaudanosoline
?
Coptis japonica
-
8% of the activity relative to (S)-scoulerine
-
-
?
S-Adenosyl-L-methionine + norlaudanosoline
?
Coptis japonica
-
2% of the activity relative to (S)-scoulerine
-
-
?
S-Adenosyl-L-methionine + norreticuline
?
Coptis japonica
-
9% of the activity relative to (S)-scoulerine
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
?
Berberis wilsoniae
-
central role in orotoberberine biosynthesis
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
?
Coptis japonica
-
the enzyme is responsible for a late step in the biosynthesis of berberine
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
Berberis stolonifera
-
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
Berberis wilsoniae
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
Coptis chinensis
-
-
-
ir
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
Coptis japonica
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
Coptis japonica
-
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
Coptis teeta
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
Papaver somniferum
-
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
Stephania intermedia
-
-
-
?
additional information
?
-
Eschscholzia californica subsp. californica
enzyme is a scoulerine-9-O-methyltransferase for the biosynthesis of chelerythrine in California poppy, it produces 7-O-methylated, 3'-O-methylated and dual O-methylated products from reticuline and norreticuline, and 9-O-methylated tetrahydrocolumbamine, 2-O-methylscoulerine and tetrahydropalmatine from scoulerine
-
-
-
additional information
?
-
Stephania intermedia
enzyme catalyzes O-methylation at C-9 and C-2, and O-methylation events occur first at C-9 and then at C-2
-
-
-
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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
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
S-Adenosyl-L-methionine + (S)-scoulerine
?
Berberis wilsoniae
-
central role in orotoberberine biosynthesis
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
?
Coptis japonica
-
the enzyme is responsible for a late step in the biosynthesis of berberine
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
Coptis chinensis
-
-
-
ir
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
Papaver somniferum
-
-
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
Eschscholzia californica subsp. californica
divalent cations are not required
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
Eschscholzia californica subsp. californica
not inhibitory: Mg2+, Mn2+, Fe2+
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0382
(S)-norreticuline
Eschscholzia californica subsp. californica
product norlaudanine, pH 8.4, 35°C
0.187
(S)-reticuline
Eschscholzia californica subsp. californica
product codamine, pH 8.4, 35°C
0.393
(S)-reticuline
Eschscholzia californica subsp. californica
product laudanine, pH 8.4, 35°C
0.0219
(S)-scoulerine
Eschscholzia californica subsp. californica
product 2-O-methylscoulerine, pH 8.4, 35°C
0.0245
(S)-scoulerine
Eschscholzia californica subsp. californica
product (S)-tetrahydrocolumbamine, pH 8.4, 35°C
0.0093
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-scoulerine, product (S)-tetrahydrocolumbamine, pH 8.4, 35°C
0.0145
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-reticuline, product codamine, pH 8.4, 35°C
0.0157
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-reticuline, product norlaudanine, pH 8.4, 35°C
0.0288
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-scoulerine, product 2-O-methylscoulerine, pH 8.4, 35°C
0.119
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-reticuline, product laudanine, pH 8.4, 35°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.01
(S)-norreticuline
Eschscholzia californica subsp. californica
product norlaudanine, pH 8.4, 35°C
0.05
(S)-reticuline
Eschscholzia californica subsp. californica
product codamine, pH 8.4, 35°C
0.24
(S)-reticuline
Eschscholzia californica subsp. californica
product laudanine, pH 8.4, 35°C
0.01
(S)-scoulerine
Eschscholzia californica subsp. californica
product 2-O-methylscoulerine, pH 8.4, 35°C
0.02
(S)-scoulerine
Eschscholzia californica subsp. californica
product (S)-tetrahydrocolumbamine, pH 8.4, 35°C
0.01
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-reticuline, product norlaudanine, pH 8.4, 35°C
0.01
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-scoulerine, product (S)-tetrahydrocolumbamine, pH 8.4, 35°C
0.01
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-scoulerine, product 2-O-methylscoulerine, pH 8.4, 35°C
0.08
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-reticuline, product codamine, pH 8.4, 35°C
0.12
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-reticuline, product laudanine, pH 8.4, 35°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.26
(S)-norreticuline
Eschscholzia californica subsp. californica
product norlaudanine, pH 8.4, 35°C
0.27
(S)-reticuline
Eschscholzia californica subsp. californica
product codamine, pH 8.4, 35°C
0.61
(S)-reticuline
Eschscholzia californica subsp. californica
product laudanine, pH 8.4, 35°C
0.46
(S)-scoulerine
Eschscholzia californica subsp. californica
product 2-O-methylscoulerine, pH 8.4, 35°C
0.82
(S)-scoulerine
Eschscholzia californica subsp. californica
product (S)-tetrahydrocolumbamine, pH 8.4, 35°C
0.35
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-scoulerine, product 2-O-methylscoulerine, pH 8.4, 35°C
0.64
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-reticuline, product norlaudanine, pH 8.4, 35°C
1
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-reticuline, product laudanine, pH 8.4, 35°C
1.07
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-scoulerine, product (S)-tetrahydrocolumbamine, pH 8.4, 35°C
5.5
S-adenosyl-L-methionine
Eschscholzia californica subsp. californica
cosubstrate (S)-reticuline, product codamine, pH 8.4, 35°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Coptis japonica
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Coptis japonica
-
activity of high berberine-producing cells is higher than that of non-selected cells
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
Sequence
A0A224ALZ8_ESCCA
Eschscholzia californica subsp. californica
362
0
39765
TrEMBL
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PDB
SCOP
CATH
UNIPROT
ORGANISM
Thalictrum flavum subsp. glaucum
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
canadine-producing Saccharomyces cerevisiae strain harbors expression cassettes for seven heterologous enzymes: Papaper somniferum norcoclaurine 6-O-methyltransferase (Ps6OMT), Papaver somniferum 3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase 2 (Ps4'OMT), Papapver somniferum coclaurine N-methyltransferase (PsCNMT), Papaver somniferum berberine bridge enzyme (PsBBE), Thalictrum flavum scoulerine 9-O-methyltransferase (TfS9OMT), Thalictrum flavum canadine synthase (TfCAS), and Arabidopsis thaliana cytochrome P450 reductase 1 (CPR). The expression cassettes for the methyltransferases Ps6OMT, PsCNMT, and Ps4'OMT and the cytochrome P450 reductase CPR were chromosomally integrated, TfS9OMT and TfCAS are expressed from a high-copy plasmid, and PsBBE is expressed from a second high-copy plasmid
Thalictrum flavum subsp. glaucum
expression in Escherichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
Coptis japonica
transient RNA silencing of scoulerine 9-O-methyltransferase expression by double stranded RNA in Coptis japonica protoplasts. Utility of gene silencing based on in vitro synthesized dsRNA to study function and behavior of endogenous enzymes
medicine
Thalictrum flavum subsp. glaucum
a Saccharomyces cerevisiae strain is engineered to express seven heterologous enzymes (Papaper somniferum norcoclaurine 6-O-methyltransferase (Ps6OMT), Papaver somniferum 3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase 2 (Ps4'OMT), Papapver somniferum coclaurine N-methyltransferase (PsCNMT), Papaver somniferum berberine bridge enzyme (PsBBE), Thalictrum flavum scoulerine 9-O-methyltransferase (TfS9OMT), Thalictrum flavum canadine synthase (TfCAS), and Arabidopsis thaliana cytochrome P450 reductase 1 (CPR)), resulting in protoberberine alkaloid production from a simple benzylisoquinoline alkaloid precursor. A number of strategies are implemented to improve flux through the pathway, including enzyme variant screening, genetic copy number variation, and culture optimization. This leads to an over 70-fold increase in canadine titer up to 1.8 mg/l. Increased canadine titers enable extension of the pathway to produce berberine, a major constituent of several traditional medicines in a microbial host. This strain is viable at pilot scale
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Fujiwara, H.; Takeshita, N.; Terano, Y.; Fitchen, J.H.; Tsujita, T.; Katagiri, Y.; Sato, F.; Yamada, Y.
Expression of (S)-scoulerine 9-O-methyltransferase in Coptis japonica plants
Phytochemistry
34
949-954
1993
Coptis japonica
-
brenda
Sato, F.; Takeshita, N.; Fitchen, J.H.; Fujiwara, H.; Yamada, Y.
S-Adenosyl-L-methionine:scoulerine-9-O-methyltransferase from cultured Coptis japonica cells
Phytochemistry
32
659-664
1993
Coptis japonica
-
brenda
Takeshita, N.; Fujiwara, H.; Mimura, H.; Fitchen, J.H.; Yamada, Y.; Sato, F.
Molecular cloning and characterization of S-adenosyl-L-methionine:scoulerine 9-O-methyltransferase from cultured cells of Coptis japonica
Plant Cell Physiol.
36
29-36
1995
Coptis japonica
brenda
Galneder, E.; Rueffer, M.; Wanner, G.; Tabata, M.; Zenk, M.H.
Alternative final steps in berberine biosynthesis in Coptis japonica cell cultures
Plant Cell Rep.
7
1-4
1988
Berberis stolonifera, Coptis japonica
brenda
Muemmler, S.; Rueffer, M.; Nagakura, N.; Zenk, M.H.
S-Adenosyl-L-methionine:(S)-scoulerine 9-O-methyltransferase, a highly stereo- and regio-specific enzyme in tetrahydroprotoberberine biosynthesis
Plant Cell Rep.
4
36-39
1985
Berberis wilsoniae
brenda
Dubouzet, J.G.; Morishige, T.; Fujii, N.; An, C.I.; Fukusaki, E.; Ifuku, K.; Sato, F.
Transient RNA silencing of scoulerine 9-O-methyltransferase expression by double stranded RNA in Coptis japonica protoplasts
Biosci. Biotechnol. Biochem.
69
63-70
2005
Coptis japonica (Q39522), Coptis japonica
brenda
Takemura, T.; Ikezawa, N.; Iwasa, K.; Sato, F.
Metabolic diversification of benzylisoquinoline alkaloid biosynthesis through the introduction of a branch pathway in Eschscholzia californica
Plant Cell Physiol.
51
949-959
2010
Coptis japonica
brenda
Dang, T.T.; Facchini, P.J.
Cloning and characterization of canadine synthase involved in noscapine biosynthesis in opium poppy
FEBS Lett.
588
198-204
2014
Papaver somniferum
brenda
Zhu, Q.; Zhou, J.; Zhang, G.; Liao, H.
Homology modeling and molecular docking studies of (S)-scoulerine 9-O-methyltransferase from Coptis chinensis
Chin. J. Chem.
30
2533-2538
2012
Coptis chinensis (E0W6R9)
-
brenda
Galanie, S.; Smolke, C.
Optimization of yeast-based production of medicinal protoberberine alkaloids
Microb. Cell Fact.
14
144
2015
Thalictrum flavum subsp. glaucum (Q5C9L2)
brenda
Zhao, W.; Shen, C.; Zhu, J.; Ou, C.; Liu, M.; Dai, W.; Liu, X.; Liu, J.
Identification and characterization of methyltransferases involved in benzylisoquinoline alkaloids biosynthesis from Stephania intermedia
Biotechnol. Lett.
42
461-469
2019
Stephania intermedia (A0A5P9PAM0)
brenda
He, S.; Liang, Y.; Cong, K.; Chen, G.; Zhao, X.; Zhao, Q.; Zhang, J.; Wang, X.; Dong, Y.; Yang, J.; Zhang, G.; Qian, Z.; Fan, W.; Yang, S.
Identification and characterization of genes involved in benzylisoquinoline alkaloid biosynthesis in coptis species
Front. Plant Sci.
9
731
2018
Coptis teeta (A0A2Z5FRS0), Coptis teeta
brenda
Purwanto, R.; Hori, K.; Yamada, Y.; Sato, F.
Unraveling additional O-methylation steps in benzylisoquinoline alkaloid biosynthesis in California poppy (Eschscholzia californica)
Plant Cell Physiol.
58
1528-1540
2017
Eschscholzia californica subsp. californica (A0A224ALZ8)
brenda
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