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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-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
-
-
?
additional information
?
-
S-Adenosyl-L-methionine + (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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0.0382
(S)-norreticuline
product norlaudanine, pH 8.4, 35°C
0.187 - 0.393
(S)-reticuline
0.0219 - 1.6
(S)-scoulerine
0.0093 - 0.17
S-adenosyl-L-methionine
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
0.0536
(S)-scoulerine
pH 9, 37°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
0.042
S-adenosyl-L-methionine
-
-
0.119
S-adenosyl-L-methionine
cosubstrate (S)-reticuline, product laudanine, pH 8.4, 35°C
0.17
S-adenosyl-L-methionine
-
-
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0.01
(S)-norreticuline
product norlaudanine, pH 8.4, 35°C
0.05 - 0.24
(S)-reticuline
0.01 - 0.02
(S)-scoulerine
0.01 - 0.12
S-adenosyl-L-methionine
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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0.26
(S)-norreticuline
product norlaudanine, pH 8.4, 35°C
0.27 - 0.61
(S)-reticuline
0.46 - 0.82
(S)-scoulerine
0.35 - 5.5
S-adenosyl-L-methionine
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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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