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Information on EC 1.5.3.12 - dihydrobenzophenanthridine oxidase for references in articles please use BRENDA:EC1.5.3.12
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EC Tree
IUBMB Comments A CuII enzyme found in higher plants that produces oxidized forms of the benzophenanthridine alkaloids
The enzyme appears in viruses and cellular organisms
Synonyms
DBO, DBOX, DHBP, Oxidase, dihydrobenzophenanthridine,
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Oxidase, dihydrobenzophenanthridine
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dihydrochelirubine + O2 = chelirubine + H2O2
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dihydromacarpine + O2 = macarpine + H2O2
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dihydrosanguinarine + O2 = sanguinarine + H2O2
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dihydrobenzophenanthridine:oxygen oxidoreductase
A CuII enzyme found in higher plants that produces oxidized forms of the benzophenanthridine alkaloids
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(RS)-canadine + O2
berberine + H2O2
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(RS)-tetrahydrocolumbamine + O2
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(RS)-tetrahydropalmitine + O2
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(RS)-tetrahydropapaverine + O2
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(RS)-tetrahydropapaverine + O2
papaverine + H2O2
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(S)-scoulerine + O2
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DBOX does not fully aromatize the C-ring of (S)-scoulerine but instead catalyzes a two-electron oxidation
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(S)-stylopine + O2
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dihydrochelerythrine + O2
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dihydrochelerythrine + O2
chelerythine + H2O2
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dihydrochelerythrine + O2
chelerythrine + H2O2
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dihydrochelirubine + O2
chelirubine + H2O2
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Dihydromacarpine + O2
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terminal step in the formation of benzophenanthridine alkaloids containing methylene dioxy substitutions in ring A and D
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Dihydromacarpine + O2
Macarpine + H2O2
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dihydrosanguinarine + O2
sanguinarine + H2O2
additional information
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dihydrosanguinarine + O2
sanguinarine + H2O2
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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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dihydrosanguinarine + O2
sanguinarine + H2O2
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dihydrosanguinarine + O2
sanguinarine + H2O2
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best substrate
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dihydrosanguinarine + O2
sanguinarine + H2O2
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dihydrosanguinarine + O2
sanguinarine + H2O2
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dihydrosanguinarine + O2
sanguinarine + H2O2
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dihydrosanguinarine + O2
sanguinarine + H2O2
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last step in the biogenesis of sanguinarine
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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
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substrate specificity, overview
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additional information
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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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(RS)-canadine + O2
berberine + H2O2
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(RS)-tetrahydrocolumbamine + O2
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(RS)-tetrahydropalmitine + O2
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(RS)-tetrahydropapaverine + O2
papaverine + H2O2
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(S)-scoulerine + O2
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DBOX does not fully aromatize the C-ring of (S)-scoulerine but instead catalyzes a two-electron oxidation
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(S)-stylopine + O2
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dihydrochelerythrine + O2
chelerythine + H2O2
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Dihydromacarpine + O2
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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
additional information
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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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best substrate
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dihydrosanguinarine + O2
sanguinarine + H2O2
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last step in the biogenesis of sanguinarine
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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
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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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one of the enzymes that catalyzes a later step in the biogenesis of benzo(c)phenanthridine alkaloids
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flavin
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inhibition pattern indicates the presence of bound flavine
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copper
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might be a copper metalloenzyme
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1,4-DL-dithiothreitol
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diethyldithiocarbamate
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dicoumarin
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0.146
(S)-scoulerine
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pH 8.8, 37°C
0.012
Dihydrochelerythrine
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0.008
dihydrochelirubine
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0.016 - 0.201
Dihydrosanguinarine
0.006
Dihydromacarpine
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0.006
Dihydromacarpine
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dihydrosanguinarine
0.016
Dihydrosanguinarine
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0.201
Dihydrosanguinarine
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pH 8.8, 37°C
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additional information
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additional information
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additional information
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sensitive, rapid and convenient fluorimetric assay
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5.5 - 8
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about 50% of maximal activity at pH 5.5 and 8.0
6 - 8.5
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about 50% of maximal activity at pH 6.0 and 8.5
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very low level compared to roots
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very low level compared to roots
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predominantly
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very low level compared to roots
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additional information
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enzyme expression patterns, overview
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elicited cell suspension
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elicited cell suspension; elicited tissues
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elicited cells
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elicited cell suspension; elicited tissues
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elicited cell suspension
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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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77000
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x * 77000, SDS-PAGE, the lower MW bands include enzymes of the polyphenol oxidase family that copurify with dihydrobenzophenanthridine oxidase
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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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x * 77000, SDS-PAGE, the lower MW bands include enzymes of the polyphenol oxidase family that copurify with dihydrobenzophenanthridine oxidase
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additional information
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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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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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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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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
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1141-1144
1996
Sanguinaria canadensis
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Schumacher, H.M.; Zenk, M.H.
Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholtzia californica cell suspension cultures
Plant Cell Rep.
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43-46
1988
Eschscholzia californica
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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
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Psenak, M.
A fluorimetric assay of dihydrobenzophenanthridine oxidase
Biologia (Bratisl. )
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1109-1112
1991
Papaver somniferum, Sanguinaria canadensis
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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
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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
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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
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