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EC Tree
IUBMB Comments A cytochrome P-450 (heme-thiolate) protein involved in benzylisoquinoline alkaloid synthesis in higher plants.
The enzyme appears in viruses and cellular organisms
Synonyms
cyp80b1, (s)-n-methylcoclaurine 3'-hydroxylase, (s)-n-methylcoclaurine-3'-hydroxylase, n-methylcoclaurine 3'-hydroxylase, cyp80b3, (s)-methylcoclaurine-3'-hydroxylase,
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(S)-methylcoclaurine-3'-hydroxylase
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(S)-N-methylcoclaurine 3'-hydroxylase
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(S)-N-methylcoclaurine-3'-hydroxylase
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(S)-N-methylcoclaurine-3-hydroxylase
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Cytochrome P450 80B1
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Cytochrome P450 80B2
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EC 1.14.13.71
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formerly
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N-methylcoclaurine 3'-hydroxylase
CYP80B1
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CYP80B3
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N-methylcoclaurine 3'-hydroxylase
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N-methylcoclaurine 3'-hydroxylase
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N-methylcoclaurine 3'-hydroxylase
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NMCH
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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(S)-N-methylcoclaurine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein involved in benzylisoquinoline alkaloid synthesis in higher plants.
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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absolute requirement for an N-methyl group, a 4'-hydroxyl moiety and S-configuration at carbon atom 1
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?
(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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the enzyme is involved in the sanguinarine biosynthetic pathway, overview
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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one of the key enzymes in biosynthesis of benzylisoquinoline alkaloids in the opium poppy, CYP80B1 catalyzes the second to last step in the formation of (S)-reticuline, the last common intermediate in sanguinarine and morphine biosynthesis, overview
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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the catalyzes step 5 in the unique, cell type-specific biosynthesis of benzylisoquinoline alkaloids in the opium poppy, biosynthetic pathway leading from L-DOPA to morphine, overview
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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specific for the substrate
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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the enzyme catalyzes a key regulation step in morphine biosynthesis
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additional information
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the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline
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additional information
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the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline
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additional information
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the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline
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additional information
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the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline. Accumulates in response to elicitor treatment
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
?
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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?
(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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the enzyme is involved in the sanguinarine biosynthetic pathway, overview
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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?
(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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one of the key enzymes in biosynthesis of benzylisoquinoline alkaloids in the opium poppy, CYP80B1 catalyzes the second to last step in the formation of (S)-reticuline, the last common intermediate in sanguinarine and morphine biosynthesis, overview
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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the catalyzes step 5 in the unique, cell type-specific biosynthesis of benzylisoquinoline alkaloids in the opium poppy, biosynthetic pathway leading from L-DOPA to morphine, overview
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(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
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the enzyme catalyzes a key regulation step in morphine biosynthesis
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additional information
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the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline
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additional information
?
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the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline
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additional information
?
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the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline
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additional information
?
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the enzyme is necessary for synthesis of the central tetrahydrobenzylisoquinoline alkaloid intermediate (S)-reticuline. Accumulates in response to elicitor treatment
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NADPH-hemoprotein reductase
A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
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cytochrome P450
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dependent on
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cytochrome P450
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P450-dependent hydroxylase
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Fe2+
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a cytochrome P450 enzyme
Fe2+
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P450-dependent hydroxylase
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additional information
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sequential treatment with methyl jasmonate, salicylic acid, and yeast extract leads to accumulation of benzophenanthridine alkaloids and increased expression of involved synthesizing enzymes, sequential treatment using different signal elicitors is more effective than single elicitor or simultaneous treatment with the elicitors, overview
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additional information
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CYP80B1 is rapidly induced to high levels in response to fungal elicitor treatment
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0.015
(S)-N-methylcoclaurine
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UniProt
brenda
isozyme 2; 2 isozymes, 2 cultivars
UniProt
brenda
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brenda
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brenda
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brenda
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brenda
california poppy
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brenda
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brenda
cv. C048-6-14-64
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brenda
cv. Louisiana
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brenda
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brenda
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brenda
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brenda
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brenda
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localization in the sieve elements adjacent or proximal to laticifers in the root and hypocotyl of opium poppy seedlings
brenda
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root phloem, the abundance of the enzyme increases rapidly between 1 and 3 days after seed germination
brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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lamina and mid rib
brenda
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brenda
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phloem
brenda
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additional information
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subcellular localization study
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brenda
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membrane-bound, CYP80B1 from opium poppy contains a noncleavable N-terminal ER-signal peptide
brenda
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membrane-bound, in sieve element ER
brenda
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malfunction
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enzyme silencing is associated with a 22% reduction in total alkaloid accumulation, with a notable decrease in the levels of thebaine and codeine compared with controls. In contrast, absolute levels of morphine and papaverine are not affected
physiological function
the expression of isozyme 1 is low in the two cultivars, so it may have little effect on alkaloid contents. The expression of CYP80B, NNU08355, has a positive effect on aporphine alkaloids content in lotus, but exhibits phenotypic lag, which might be because of NMCH which acts early in the benzylisoquinoline alkaloid biosynthetic pathway
metabolism
benzylisoquinoline alkaloid biosynthesis
metabolism
the enzyme is involved in the common pathway of benzylisoquinoline alkaloid biosynthesis and the aporphine alkaloid bisynthesis pathway in lotus, overview. A series of enzymes, norcoclaurine 6-O-methyltransferase (6OMT), coclaurineN-methyltransferase (CNMT), (S)-N-methylcoclaurine-3-hydroxylase (NMCH), and 3-hydroxy-N-methylcoclaurine 4'-O-methyltransferase(4'OMT), exhibit catalytic activity to yield the central branchpoint intermediate (S)-reticuline
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C80B1_ESCCA
487
1
54644
Swiss-Prot
Secretory Pathway (Reliability: 4 )
C80B2_COPJA
488
1
54782
Swiss-Prot
Secretory Pathway (Reliability: 3 )
C80B2_ESCCA
488
1
54896
Swiss-Prot
Secretory Pathway (Reliability: 3 )
C80B3_PAPSO
481
0
54242
Swiss-Prot
other Location (Reliability: 5 )
B9RBW9_RICCO
501
0
55948
TrEMBL
Secretory Pathway (Reliability: 4 )
B9RHX8_RICCO
496
1
56367
TrEMBL
Secretory Pathway (Reliability: 3 )
A0A0B4VFR8_PODPE
510
1
57591
TrEMBL
Secretory Pathway (Reliability: 4 )
B9RC29_RICCO
501
1
56892
TrEMBL
Secretory Pathway (Reliability: 2 )
Q5C9L5_THLFG
491
1
55750
TrEMBL
Secretory Pathway (Reliability: 1 )
B9RHX9_RICCO
426
1
47866
TrEMBL
Secretory Pathway (Reliability: 1 )
B9RBW8_RICCO
377
0
42261
TrEMBL
Secretory Pathway (Reliability: 5 )
B9R9F5_RICCO
496
1
55991
TrEMBL
Secretory Pathway (Reliability: 3 )
B9SRM4_RICCO
525
1
59607
TrEMBL
other Location (Reliability: 5 )
A0A396IK45_MEDTR
210
1
24048
TrEMBL
other Location (Reliability: 2 )
B9RHY2_RICCO
318
1
36214
TrEMBL
Secretory Pathway (Reliability: 2 )
A0A2G9G5H7_9LAMI
293
0
33077
TrEMBL
Secretory Pathway (Reliability: 4 )
A0A1U7Z269_NELNU
496
0
55761
TrEMBL
other Location (Reliability: 1 )
B2BF50_9MAGN
488
0
55036
TrEMBL
Secretory Pathway (Reliability: 1 )
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55040
calculated from amino acids, 488 amino acids, 1680 bp
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expressed in Saccharomyces cerevisiae and Spodoptera frugiperda
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gene cyp80b3, overexpression in Papaver somniferum plants, expression of anti-sense constructs, construction of transgenic plants using the Agrobacterium tumefaciens, strain AGL1, transfection method, expression of antisense cyp80b3 leads to a reduction of total alkaloid in latex up to 84%, phenotype, overview, enzyme overexpression results in an up to 450% increase in the amount of total alkaloid in latex without changing the ratio of the individual alkaloids, or together with an overall increase in the ratio of morphine
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gene LOC104585940 encoding isozyme 2, DNA and amino acid sequence determination and analysis, phylogenetic analysis, quantitative RT-PCR enzyme expression analysis
heterologous expression
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biotechnology
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the enzyme provides practical means to genetically engineer valuable secondary metabolites in this important medicinal plant
medicine
traditional Chinese medicinal plant containing benzylisoquinoline alkaloids as active agents
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Pauli, H.H.; Kutchan, T.M.
Molecular cloning and functional heterologous expression of two alleles encoding (S)-N-methylcoclaurine 3'-hydroxylase (CYP80B1), a new methyl jasmonate-inducible cytochrome P-450-dependent mono-oxygenase of benzylisoquinoline alkaloid biosynthesis
Plant J.
13
793-801
1998
Eschscholzia californica
brenda
Huang, F.C.; Kutchan, T.M.
Distribution of morphinan and benzo[c]phenanthridine alkaloid gene transcript accumulation in Papaver somniferum
Phytochemistry
53
555-564
2000
Papaver bracteatum, Papaver somniferum, Papaver rhoeas, Papaver orientale
brenda
Alcantara, J.; Bird, D.A.; Franceschi, V.R.; Facchini, P.J.
Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment
Plant Physiol.
138
173-183
2005
Papaver somniferum
brenda
Samanani, N.; Alcantara, J.; Bourgault, R.; Zulak, K.G.; Facchini, P.J.
The role of phloem sieve elements and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy
Plant J.
47
547-563
2006
Papaver somniferum
brenda
Cho, H.Y.; Son, S.Y.; Rhee, H.S.; Yoon, S.Y.; Lee-Parsons, C.W.; Park, J.M.
Synergistic effects of sequential treatment with methyl jasmonate, salicylic acid and yeast extract on benzophenanthridine alkaloid accumulation and protein expression in Eschscholtzia californica suspension cultures
J. Biotechnol.
135
117-122
2008
Eschscholzia californica
brenda
Frick, S.; Kramell, R.; Kutchan, T.M.
Metabolic engineering with a morphine biosynthetic P450 in opium poppy surpasses breeding
Metab. Eng.
9
169-176
2007
Papaver somniferum
brenda
Zhou, J.; Peng, S.; Lei, N.; Liao, H.; Chen, F.
Molecular cloning and sequence analysis of (S)-N-methylcoclaurine-3'-hydroxylase gene in Coptis chinensis
Zhong Cao Yao
39
419-423
2008
Coptis chinensis (B2BF50)
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brenda
Desgagne-Penix, I.; Facchini, P.
Systematic silencing of benzylisoquinoline alkaloid biosynthetic genes reveals the major route to papaverine in opium poppy
Plant J.
72
331-344
2012
Papaver somniferum
brenda
Yang, M.; Zhu, L.; Li, L.; Li, J.; Xu, L.; Fen, J.; Liu, Y.
Digital gene expression analysis provides insight into the transcript profile of the genes involved in aporphine alkaloid biosynthesis in lotus (Nelumbo nucifera)
Front. Plant Sci.
8
80
2017
Nelumbo nucifera (A0A1U7Z269)
brenda
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