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Information on EC 1.1.1.247 - codeinone reductase (NADPH) for references in articles please use BRENDA:EC1.1.1.247
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EC Tree
IUBMB Comments Catalyses the reversible reduction of codeinone to codeine, which is a direct precursor of morphine in the opium poppy plant, Papaver somniferum.
The enzyme appears in viruses and cellular organisms
Synonyms
codeine oxidase, codeine: NADP oxidoreductase, codeine:NADP oxidoreductase, codeinone reductase, codeinone reductase (NADPH), CodR, COR, PsCor1.1, reductase, codeinone (reduced nicotinamide adenine dinucleotide phosphate),
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codeine: NADP oxidoreductase
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codeine:NADP oxidoreductase
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codeinone reductase (NADPH)
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reductase, codeinone (reduced nicotinamide adenine dinucleotide phosphate)
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codeinone reductase
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COR
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codeine + NADP+ = codeinone + NADPH + H+
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codeine:NADP+ oxidoreductase
Catalyses the reversible reduction of codeinone to codeine, which is a direct precursor of morphine in the opium poppy plant, Papaver somniferum.
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Codeinone + NADPH
Codeine + NADP+
codeinone + NADPH + H+
codeine + NADP+
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r
Dihydrocodeine + NADP+
?
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Morphinone + NADPH
Morphine + NADP+
additional information
?
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Codeinone + NADPH
Codeine + NADP+
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?
Codeinone + NADPH
Codeine + NADP+
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r
Codeinone + NADPH
Codeine + NADP+
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r
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Codeinone + NADPH
Codeine + NADP+
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r
(-)codeine
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Codeinone + NADPH
Codeine + NADP+
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(-)codeinone
(-)codeine
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Codeinone + NADPH
Codeine + NADP+
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no reaction with NADH and NAD+
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Codeinone + NADPH
Codeine + NADP+
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no reaction with NADH and NAD+
(-)codeine
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Codeinone + NADPH
Codeine + NADP+
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neopinone, which is formed most likely by demethylation of the vinylether of thebaine exists in the plant cell in a thermodynamic equilibrium with codeinone. The presence of the codeinone reductase/NADPH system shifts this equilibrium quantitatively in the direction of codeine, which either accumulates in the latex of the poppy plant or is further demethylated at the 3-OCH3 group yielding morphine
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Codeinone + NADPH
Codeine + NADP+
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biosynthesis of codeine
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Codeinone + NADPH
Codeine + NADP+
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important regulating function in morphine biosynthesis
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Codeinone + NADPH
Codeine + NADP+
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penultimate step in morphine biosynthesis
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r
Hydrocodone + NADPH
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Hydrocodone + NADPH
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110% of the reaction with codeinone
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Hydromorphone + NADPH
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Hydromorphone + NADPH
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90% of the reaction with codeinone
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Morphinone + NADPH
Morphine + NADP+
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Morphinone + NADPH
Morphine + NADP+
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?
Morphinone + NADPH
Morphine + NADP+
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?
Morphinone + NADPH
Morphine + NADP+
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biosynthesis of morphine
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Naloxone + NADPH
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Naloxone + NADPH
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80% of the reaction with codeinone
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Naltrexone + NADPH
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Naltrexone + NADPH
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30% of the reaction with codeinone
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additional information
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the enzyme is involved in biosynthesis of morphinan alkaloids, transcriptional regulation, overview
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additional information
?
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the enzyme is involved in the biosynthesis of morphine and the related antimicrobial alkaloid sanguinarine
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additional information
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the enzyme is involved in biosynthesis of morphinan alkaloids, overview
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additional information
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the enzyme also catalyzes the NADPH-dependent reduction of morphinone to morphine, reaction of EC 1.1.1.218. but codeine can also be directly converted into morphine, overview
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Codeinone + NADPH
Codeine + NADP+
codeinone + NADPH + H+
codeine + NADP+
Q9SQ67
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r
Morphinone + NADPH
Morphine + NADP+
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biosynthesis of morphine
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additional information
?
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Codeinone + NADPH
Codeine + NADP+
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neopinone, which is formed most likely by demethylation of the vinylether of thebaine exists in the plant cell in a thermodynamic equilibrium with codeinone. The presence of the codeinone reductase/NADPH system shifts this equilibrium quantitatively in the direction of codeine, which either accumulates in the latex of the poppy plant or is further demethylated at the 3-OCH3 group yielding morphine
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Codeinone + NADPH
Codeine + NADP+
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biosynthesis of codeine
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Codeinone + NADPH
Codeine + NADP+
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important regulating function in morphine biosynthesis
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Codeinone + NADPH
Codeine + NADP+
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penultimate step in morphine biosynthesis
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r
additional information
?
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the enzyme is involved in biosynthesis of morphinan alkaloids, transcriptional regulation, overview
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additional information
?
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the enzyme is involved in the biosynthesis of morphine and the related antimicrobial alkaloid sanguinarine
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additional information
?
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the enzyme is involved in biosynthesis of morphinan alkaloids, overview
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additional information
?
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Q9SQ67
the enzyme also catalyzes the NADPH-dependent reduction of morphinone to morphine, reaction of EC 1.1.1.218. but codeine can also be directly converted into morphine, overview
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additional information
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10-100fold increase in enzyme activity of enzymes involved in the biosynthesis of morphinan alkaloids by overexpression of regulatory transcription factors, overview
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additional information
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10-100fold increase in enzyme activity of enzymes involved in the biosynthesis of morphinan alkaloids by overexpression of regulatory transcription factors, overview
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0.422 - 0.424
Dihydrocodeine
0.026 - 0.027
Hydrocodone
0.042 - 0.05
Hydromorphone
0.063
morphine
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isoenzymes from capsule tissue
0.076
codeine
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enzyme from cell culture
0.178
codeine
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isoenzymes from capsule tissue
0.009
codeinone
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isoenzymes from capsule tissue
0.023
codeinone
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enzyme from cell culture
0.422
Dihydrocodeine
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isoenzymes from capsule tissue
0.424
Dihydrocodeine
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enzyme from cell culture
0.026
Hydrocodone
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isoenzymes from capsule tissue
0.027
Hydrocodone
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enzyme from cell culture; morphine, enzyme from cell culture
0.042
Hydromorphone
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isoenzymes from capsule tissue
0.05
Hydromorphone
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enzyme from cell culture
0.029
NADP+
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enzyme from cell culture
0.047
NADP+
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isoenzymes from capsule tissue
0.081
NADPH
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isoenzymes from capsule tissue
0.168
NADPH
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enzyme from cell culture
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additional information
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7
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reduction of codeinone
9.1
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oxidation of codeine
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6.2 - 7.6
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50% of maximal activity at pH 6.2 and pH 7.6, reduction of codeinone
8.2 - 9.8
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50% of maximal activity at pH 8.2 and pH 9.8, oxidation of codeine
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40
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reduction of codeinone
46
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oxidation of codeine
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29 - 47
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50% of maximal activity at 29°C and 47°C, reduction of codeinone
34 - 53
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50% of maximal activity at 34°C and 53°C, oxidation of codeine
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brenda
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brenda
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UniProt
brenda
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brenda
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UniProt
brenda
opium poppy
Uniprot
brenda
opium poppy
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brenda
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brenda
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high expression. Peaks of transcription in the capsules wall are at flowering
brenda
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brenda
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brenda
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localization is restricted to the parietal region of sieve elements adjacent or proximal to laticifers. COR transcript is found in the companion cell paired with each sieve element
brenda
additional information
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laticifers are not found in developing root tip, and likewise, codeinone reductase is not detected
brenda
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high expression. The expression increases until pre-flowering and then decreases
brenda
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brenda
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brenda
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localized in laticifers
brenda
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brenda
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high expression. Relative expression has two peaks at bud initiation, the maximum rate, and flowering stages
brenda
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brenda
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high expression in upper stem. Peaks of expression are at flowering and lancing
brenda
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localized in laticifers
brenda
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brenda
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COR11_PAPSO
321
0
35808
Swiss-Prot
COR12_PAPSO
321
0
35705
Swiss-Prot
COR13_PAPSO
321
0
35797
Swiss-Prot
COR14_PAPSO
321
0
35764
Swiss-Prot
COR15_PAPSO
321
0
35794
Swiss-Prot
Q9SQ66_PAPSO
51
0
5637
TrEMBL
Q9SQ65_PAPSO
97
0
10913
TrEMBL
A0A2G9HUU1_9LAMI
273
0
30259
TrEMBL
A0A2I6ZMS8_PAPSO
321
0
35784
TrEMBL
A0A2P6R4C7_ROSCH
48
0
5298
TrEMBL
A0A0H4BJ99_9MAGN
215
0
24243
TrEMBL
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monomer
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34000-35000, SDS-PAGE
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additional information
transgenic codeinone reductase overexpressing Papaver somniferum plants show 75% increase in thebaine besides 58% and 22% increases in codeine and morphine, respectively, compared to the wild-type plants in the field trail
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2 isoenzymes from capsule tissue, enzyme from cell culture
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Ni2+-charged HiTrap column chromatography
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Ni21-charged HiTrap column chromatography
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expressed in Escherichia coli
factors involved in transcriptional regulation, overview
gene codR, expression in Papaver bracteatum in cultured hairy roots, subcloning in Escherichia coli strain DH5alpha. The T-DNA of the vector contains a neomycin phosphoteransferase gene and CodR cDNA with CaMV35S promoter and nos terminator
overexpression of the enzyme in transgenic Papaver somnniferum plants leading to increased enzyme content and capsule alkaloid, morphine and total alkaloid, content without significant alterations of the alkaloid profile, overview
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factors involved in transcriptional regulation, overview
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factors involved in transcriptional regulation, overview
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synthesis
Papaver bracteatum hairy roots expressing CodR gene have a high potential to produce morphinan alkaloids
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Lenz, R.; Zenk, M.H.
Purification and properties of codeinone reductase (NADPH) from Papaver somniferum cell cultures and differentiated plants
Eur. J. Biochem.
233
132-139
1995
Papaver somniferum
brenda
Gollwitzer, J.; Lenz, R.; Hampp, N.; Zenk, M.H.
The transformation of neopinone to codeinone in morphine biosynthesis proceeds non-enzymatically
Tetrahedron Lett.
34
5703-5706
1993
Papaver somniferum
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brenda
Lenz, R.; Zenk, M.H.
Stereoselective reduction of codeinone, the penultimate enzymic step during morphine biosynthesis in Papaver somniferum
Tetrahedron Lett.
36
2449-2452
1995
Papaver somniferum
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brenda
Bird, D.A.; Franceschi, V.R.; Facchini, P.J.
A tale of three cell types: alkaloid biosynthesis is localized to sieve elements in opium poppy
Plant Cell
15
2626-2635
2003
Papaver somniferum
brenda
Weid, M.; Ziegler, J.; Kutchan, T.M.
The roles of latex and the vascular bundle in morphine biosynthesis in the opium poppy, Papaver somniferum
Proc. Natl. Acad. Sci. USA
101
13957-13962
2004
Papaver somniferum
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, Papaver somniferum (Q9SQ70)
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
Ziegler, J.; Voigtlaender, S.; Schmidt, J.; Kramell, R.; Miersch, O.; Ammer, C.; Gesell, A.; Kutchan, T.M.
Comparative transcript and alkaloid profiling in Papaver species identifies a short chain dehydrogenase/reductase involved in morphine biosynthesis
Plant J.
48
177-192
2006
Papaver somniferum
brenda
Larkin, P.J.; Miller, J.A.; Allen, R.S.; Chitty, J.A.; Gerlach, W.L.; Frick, S.; Kutchan, T.M.; Fist, A.J.
Increasing morphinan alkaloid production by over-expressing codeinone reductase in transgenic Papaver somniferum
Plant Biotechnol. J.
5
26-37
2007
Papaver somniferum
brenda
Apuya, N.R.; Park, J.H.; Zhang, L.; Ahyow, M.; Davidow, P.; Van Fleet, J.; Rarang, J.C.; Hippley, M.; Johnson, T.W.; Yoo, H.D.; Trieu, A.; Krueger, S.; Wu, C.Y.; Lu, Y.P.; Flavell, R.B.; Bobzin, S.C.
Enhancement of alkaloid production in opium and California poppy by transactivation using heterologous regulatory factors
Plant Biotechnol. J.
6
160-175
2008
Eschscholzia californica, Papaver somniferum
brenda
Sharafi, A.; Sohi, H.H.; Mousavi, A.; Azadi, P.; Khalifani, B.H.; Razavi, K.
Metabolic engineering of morphinan alkaloids by over-expression of codeinone reductase in transgenic hairy roots of Papaver bracteatum, the Iranian poppy
Biotechnol. Lett.
35
445-453
2013
Papaver somniferum, Papaver somniferum (Q9SQ67)
brenda
Rezaei, M.; Naghavi, M.; Hoseinzade, A.; Abbasi, A.
Developmental accumulation of thebaine and some gene transcripts in different organs of Papaver bracteatum
Ind. Crops Prod.
80
262-268
2016
Papaver bracteatum
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brenda
Alagöz, Y.; Gürkök, T.; Parmaksiz, I.; Ünver, T.
Identification and sequence analysis of alkaloid biosynthesis genes in papaver section oxytona
Turk. J. Biol.
40
174-183
2016
Papaver pseudo-orientale (A0A0H4BJ99)
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brenda
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1.1.1.247 codeinone reductase (NADPH)
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