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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
-
benzylisoquinoline
- coptis
-
s-scoulerine
- japonica
- poppy
- californica
-
eschscholzia
-
s-tetrahydrocolumbamine
-
n-methylated
-
regio-specific
- papaveraceae
- n-methyltransferase
- norreticuline
-
methylenedioxy
- isoquinoline
-
benzophenanthridine
-
opium
-
virus-induced
- sanguinarine
-
7-o-methylated
- allocryptopine
- noscapine
- 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
(S)-Adenosyl-L-methionine:(S)-scoularine 9-O-methyltransferase
-
-
-
-
Methyltransferase, (S)-scoularine 9-
-
-
-
-
Methyltransferase, (S)-scoularine 9- (Coptis japonica clone pCJSMT)
-
-
-
-
scoulerine 9-O-methyltransferase
scoulerine/reticuline O-methyltransferase
-
SMT
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
methyl group transfer
-
-
-
-
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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
-
-
-
?
S-Adenosyl-L-methionine + (R,S)-2,3,9,10-tetrahydroxytetrahydroprotoberberine
?
-
methylated at 50% of the rate of (S)-scoulerine
-
-
?
S-Adenosyl-L-methionine + (S)-3,9-dihydroxy-2,10-dimethoxytetrahydroprotoberberine
?
-
methylated at 4% of the rate of (S)-scoulerine
-
-
?
S-adenosyl-L-methionine + (S)-norreticuline
S-adenosyl-L-homocysteine + norcodamine + norlaudanine
-
-
-
?
S-adenosyl-L-methionine + (S)-reticuline
S-adenosyl-L-homocysteine + codamine + laudanine
-
-
-
?
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
-
-
-
?
S-adenosyl-L-methionine + (S)-tetrahydrocolumbamine
S-adenosyl-L-homocysteine + (S)-tetrahydropalmatine
-
-
-
?
S-Adenosyl-L-methionine + 6-O-methylnorlaudanosoline
?
-
8% of the activity relative to (S)-scoulerine
-
-
?
S-Adenosyl-L-methionine + norlaudanosoline
?
-
2% of the activity relative to (S)-scoulerine
-
-
?
S-Adenosyl-L-methionine + norreticuline
?
-
9% of the activity relative to (S)-scoulerine
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
?
-
central role in orotoberberine biosynthesis
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
?
-
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
-
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
-
-
-
ir
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
-
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
-
-
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
-
-
-
?
additional information
?
-
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
?
-
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
?
-
central role in orotoberberine biosynthesis
-
-
?
S-Adenosyl-L-methionine + (S)-scoulerine
?
-
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
-
-
-
ir
S-Adenosyl-L-methionine + (S)-scoulerine
S-Adenosyl-L-homocysteine + (S)-tetrahydrocolumbamine
-
-
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
divalent cations are not required
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
not inhibitory: Mg2+, Mn2+, Fe2+
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0382
(S)-norreticuline
product norlaudanine, pH 8.4, 35°C
0.187
(S)-reticuline
product codamine, pH 8.4, 35°C
0.393
(S)-reticuline
product laudanine, pH 8.4, 35°C
0.0219
(S)-scoulerine
product 2-O-methylscoulerine, pH 8.4, 35°C
0.0245
(S)-scoulerine
product (S)-tetrahydrocolumbamine, pH 8.4, 35°C
0.0093
S-adenosyl-L-methionine
cosubstrate (S)-scoulerine, product (S)-tetrahydrocolumbamine, pH 8.4, 35°C
0.0145
S-adenosyl-L-methionine
cosubstrate (S)-reticuline, product codamine, pH 8.4, 35°C
0.0157
S-adenosyl-L-methionine
cosubstrate (S)-reticuline, product norlaudanine, pH 8.4, 35°C
0.0288
S-adenosyl-L-methionine
cosubstrate (S)-scoulerine, product 2-O-methylscoulerine, pH 8.4, 35°C
0.119
S-adenosyl-L-methionine
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
product norlaudanine, pH 8.4, 35°C
0.05
(S)-reticuline
product codamine, pH 8.4, 35°C
0.24
(S)-reticuline
product laudanine, pH 8.4, 35°C
0.01
(S)-scoulerine
product 2-O-methylscoulerine, pH 8.4, 35°C
0.02
(S)-scoulerine
product (S)-tetrahydrocolumbamine, pH 8.4, 35°C
0.01
S-adenosyl-L-methionine
cosubstrate (S)-reticuline, product norlaudanine, pH 8.4, 35°C
0.01
S-adenosyl-L-methionine
cosubstrate (S)-scoulerine, product (S)-tetrahydrocolumbamine, pH 8.4, 35°C
0.01
S-adenosyl-L-methionine
cosubstrate (S)-scoulerine, product 2-O-methylscoulerine, pH 8.4, 35°C
0.08
S-adenosyl-L-methionine
cosubstrate (S)-reticuline, product codamine, pH 8.4, 35°C
0.12
S-adenosyl-L-methionine
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
product norlaudanine, pH 8.4, 35°C
0.27
(S)-reticuline
product codamine, pH 8.4, 35°C
0.61
(S)-reticuline
product laudanine, pH 8.4, 35°C
0.46
(S)-scoulerine
product 2-O-methylscoulerine, pH 8.4, 35°C
0.82
(S)-scoulerine
product (S)-tetrahydrocolumbamine, pH 8.4, 35°C
0.35
S-adenosyl-L-methionine
cosubstrate (S)-scoulerine, product 2-O-methylscoulerine, pH 8.4, 35°C
0.64
S-adenosyl-L-methionine
cosubstrate (S)-reticuline, product norlaudanine, pH 8.4, 35°C
1
S-adenosyl-L-methionine
cosubstrate (S)-reticuline, product laudanine, pH 8.4, 35°C
1.07
S-adenosyl-L-methionine
cosubstrate (S)-scoulerine, product (S)-tetrahydrocolumbamine, pH 8.4, 35°C
5.5
S-adenosyl-L-methionine
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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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
transient RNA silencing of scoulerine 9-O-methyltransferase expression by double stranded RNA in Coptis japonica protoplasts
Uniprot
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
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
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). SMT_COPJA
381
0
41665
Swiss-Prot
other Location (Reliability: 3)
OMT2B_PAPSO
356
0
39163
Swiss-Prot
other Location (Reliability: 3)
SOMT1_PAPSO
390
0
42699
Swiss-Prot
other Location (Reliability: 2)
SOMT2_PAPSO
356
0
39087
Swiss-Prot
other Location (Reliability: 3)
SOMT3_PAPSO
339
0
37687
Swiss-Prot
other Location (Reliability: 3)
OMT3B_PAPSO
339
0
37691
Swiss-Prot
other Location (Reliability: 3)
A0A2P6QGQ1_ROSCH
116
0
13527
TrEMBL
other Location (Reliability: 3)
A0A2P6PAG7_ROSCH
364
0
40324
TrEMBL
other Location (Reliability: 5)
A0A2P6Q5T8_ROSCH
361
0
40736
TrEMBL
other Location (Reliability: 3)
A0A1P7ZIM6_ARGME
277
0
30390
TrEMBL
other Location (Reliability: 3)
A0A2P6QE06_ROSCH
169
0
18683
TrEMBL
other Location (Reliability: 4)
A0A5P9PAM0_9MAGN
350
0
37671
TrEMBL
other Location (Reliability: 5)
A0A2P6PEX7_ROSCH
365
0
40072
TrEMBL
Mitochondrion (Reliability: 5)
A0A2P6PA32_ROSCH
362
0
40180
TrEMBL
other Location (Reliability: 4)
Q5C9L2_THLFG
355
0
38591
TrEMBL
Secretory Pathway (Reliability: 5)
A0A224ALZ8_ESCCA
362
0
39765
TrEMBL
-
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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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
expression in Escherichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
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
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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