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Information on EC 1.5.3.12 - dihydrobenzophenanthridine oxidase
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1.5.3.12 dihydrobenzophenanthridine oxidaseIUBMB Comments
A CuII enzyme found in higher plants that produces oxidized forms of the benzophenanthridine alkaloids
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Word Map
- 1.5.3.12
- jasmonate
- canadensis
- dihydrosanguinarine
-
sanguinaria
- elicitors
-
papaveraceae
- californica
- poppy
-
deae-sephadex
-
14-fold
-
benzocphenanthridine
-
eschscholtzia
- berberine
- diethyldithiocarbamate
The enzyme appears in viruses and cellular organisms
Reaction Schemes
+
+
=
+
Synonyms
DBO, DBOX, DHBP, Oxidase, dihydrobenzophenanthridine, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
DHBP
-
-
-
-
Oxidase, dihydrobenzophenanthridine
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-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dihydrochelirubine + O2 = chelirubine + H2O2
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-
-
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dihydromacarpine + O2 = macarpine + H2O2
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-
-
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dihydrosanguinarine + O2 = sanguinarine + H2O2
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
dihydrobenzophenanthridine:oxygen oxidoreductase
A CuII enzyme found in higher plants that produces oxidized forms of the benzophenanthridine alkaloids
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CAS REGISTRY NUMBER
COMMENTARY
114051-83-1
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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)-scoulerine + O2
?
-
DBOX does not fully aromatize the C-ring of (S)-scoulerine but instead catalyzes a two-electron oxidation
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-
?
Dihydromacarpine + O2
?
-
terminal step in the formation of benzophenanthridine alkaloids containing methylene dioxy substitutions in ring A and D
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-
?
dihydrosanguinarine + O2
sanguinarine + H2O2
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the enzyme catalyses the last reaction of sanguinarine formation
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-
?
dihydrosanguinarine + O2
sanguinarine + H2O2
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last step in the biogenesis of sanguinarine
-
-
?
dihydrosanguinarine + O2
sanguinarine + H2O2
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induced in a dose-dependent and time-dependent manner up to 4fold to 14fold, respectively when the cells are treated with jasmonate or with acetylsalicylic acid
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-
?
additional information
?
-
-
the recombinant enzyme preferentially catalyzes the oxidation of dihydrosanguinarine to sanguinarine but also converts (RS)-tetrahydropapaverine to papaverine and several protoberberine alkaloids to oxidized forms, including (RS)-canadine to berberine
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-
?
additional information
?
-
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no reaction with: dihydronorsanguinarine, ajmalicine
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-
?
additional information
?
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-
one of the enzymes that catalyzes a later step in the biogenesis of benzo(c)phenanthridine alkaloids
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-
?
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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)-scoulerine + O2
?
-
DBOX does not fully aromatize the C-ring of (S)-scoulerine but instead catalyzes a two-electron oxidation
-
-
?
Dihydromacarpine + O2
?
-
terminal step in the formation of benzophenanthridine alkaloids containing methylene dioxy substitutions in ring A and D
-
-
?
dihydrosanguinarine + O2
sanguinarine + H2O2
-
the enzyme catalyses the last reaction of sanguinarine formation
-
-
?
dihydrosanguinarine + O2
sanguinarine + H2O2
-
last step in the biogenesis of sanguinarine
-
-
?
dihydrosanguinarine + O2
sanguinarine + H2O2
-
induced in a dose-dependent and time-dependent manner up to 4fold to 14fold, respectively when the cells are treated with jasmonate or with acetylsalicylic acid
-
-
?
additional information
?
-
-
the recombinant enzyme preferentially catalyzes the oxidation of dihydrosanguinarine to sanguinarine but also converts (RS)-tetrahydropapaverine to papaverine and several protoberberine alkaloids to oxidized forms, including (RS)-canadine to berberine
-
-
?
additional information
?
-
-
one of the enzymes that catalyzes a later step in the biogenesis of benzo(c)phenanthridine alkaloids
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
sensitive, rapid and convenient fluorimetric assay
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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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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
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virus-induced gene silencing to reduce DBOX transcript levels results in a corresponding reduction in sanguinarine, dihydrosanguinarine, and papaverine accumulation in opium poppy roots
metabolism
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DBOX as a multifunctional oxidative enzyme in benzylisoquinoline alkaloid metabolism, overview. The two-electron oxidation of dihydrosanguinarine catalyzed by dihydrobenzophenanthridine oxidase is the final step in sanguinarine biosynthesis. The formation of the fully conjugated ring system in sanguinarine is similar to the four-electron oxidations of (S)-canadine to berberine and (S)-tetrahydropapaverine to papaverine
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
77000
-
x * 77000, SDS-PAGE, the lower MW bands include enzymes of the polyphenol oxidase family that copurify with dihydrobenzophenanthridine oxidase
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 77000, SDS-PAGE, the lower MW bands include enzymes of the polyphenol oxidase family that copurify with dihydrobenzophenanthridine oxidase
?
-
a major component of MW 77000 and two minor components with MW between 59000 and 67000 are detected by SDS-PAGE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
baculo virus-induced gene silencing in planta using Agrobacterium tumefaciens strain GV3101 transfection to reduce DBOX transcript levels, real-time quantitative PCR expression analysis
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, phylogenetic tree, quantitative real-time quantitative PCR expression analysis, expression in Pichia pastoris
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme activity increases in the yeast extract-exposed cultures, but not in the methyl jasmonate-exposed cultures. There is a slight increase in activity during the first 24 h, whereas maximal response occurred at 48 h and it was maintained for up 72 h
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Ignatov, A.; Clark, W.G.; Cline, S.D.; Psenak, M.; Krueger, R.J.; Coscia, C.J.
Elicitation of dihydrobenzophenanthridine oxidase in Sanguinaria canadensis cell culture
Phytochemistry
43
1141-1144
1996
Sanguinaria canadensis
brenda
Schumacher, H.M.; Zenk, M.H.
Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholtzia californica cell suspension cultures
Plant Cell Rep.
7
43-46
1988
Eschscholzia californica
brenda
Arakawa, H.; Clark, W.G.; Psenak, M.; Coscia, C.J.
Purification and characterization of dihydrobenzophenanthridine oxidase from elicited Sanguinaria canadensis cell cultures
Arch. Biochem. Biophys.
299
1-7
1992
Sanguinaria canadensis
brenda
Psenak, M.
A fluorimetric assay of dihydrobenzophenanthridine oxidase
Biologia (Bratisl. )
46
1109-1112
1991
Papaver somniferum, Sanguinaria canadensis
-
brenda
Ignatov, A.; Neuman, M.C.; Barg, R.; Krueger, R.J.; Coscia, C.J.
Immunoblot analyses of the elicited Sanguinaria canadensis enzyme, dihydrobenzophenanthridine oxidase: evidence for resolution from a polyphenol oxidase isozyme
Arch. Biochem. Biophys.
347
208-212
1997
Sanguinaria canadensis
brenda
Hagel, J.M.; Beaudoin, G.A.; Fossati, E.; Ekins, A.; Martin, V.J.; Facchini, P.J.
Characterization of a flavoprotein oxidase from opium poppy catalyzing the final steps in sanguinarine and papaverine biosynthesis
J. Biol. Chem.
287
42972-42983
2012
Papaver somniferum
brenda
Guizar-Gonzalez, C.; Monforte-Gonzalez, M.; Vazquez-Flota, F.
Yeast extract induction of sanguinarine biosynthesis is partially dependent on the octadecanoic acid pathway in cell cultures of Argemone mexicana L., the Mexican poppy
Biotechnol. Lett.
38
1237-1242
2016
Argemone mexicana
brenda
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