KEGG   ORTHOLOGY: K22089
Entry
K22089                      KO                                     
Symbol
STOX, DBOX
Name
tetrahydroprotoberberine oxidase [EC:1.3.3.8]
Pathway
map00950  Isoquinoline alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00945  Sanguinarine biosynthesis, (S)-reticuline => sanguinarine
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K22089  STOX, DBOX; tetrahydroprotoberberine oxidase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.3  Acting on the CH-CH group of donors
   1.3.3  With oxygen as acceptor
    1.3.3.8  tetrahydroberberine oxidase
     K22089  STOX, DBOX; tetrahydroprotoberberine oxidase
Other DBs
RN: R02880 R03722 R04703 R08795 R11748
GO: 0050328
Genes
ECAD: 122579120
PSOM: 113274966 113303200
AG: ADY15026(STOX) AGL44334(DBOX)
Reference
  Authors
Hagel JM, Beaudoin GA, Fossati E, Ekins A, Martin VJ, Facchini PJ
  Title
Characterization of a flavoprotein oxidase from opium poppy catalyzing the final steps in sanguinarine and papaverine biosynthesis.
  Journal
J Biol Chem 287:42972-83 (2012)
DOI:10.1074/jbc.M112.420414
  Sequence
Reference
  Authors
Gesell A, Chavez ML, Kramell R, Piotrowski M, Macheroux P, Kutchan TM
  Title
Heterologous expression of two FAD-dependent oxidases with (S)-tetrahydroprotoberberine oxidase activity from Arge mone mexicana and Berberis wilsoniae in insect cells.
  Journal
Planta 233:1185-97 (2011)
DOI:10.1007/s00425-011-1357-4
  Sequence
LinkDB

KEGG   ENZYME: 1.5.3.12
Entry
EC 1.5.3.12                 Enzyme                                 
Name
dihydrobenzophenanthridine oxidase
Class
Oxidoreductases;
Acting on the CH-NH group of donors;
With oxygen as acceptor
Sysname
dihydrobenzophenanthridine:oxygen oxidoreductase
Reaction(IUBMB)
(1) dihydrosanguinarine + O2 = sanguinarine + H2O2 [RN:R04703];
(2) dihydrochelirubine + O2 = chelirubine + H2O2 [RN:R04706];
(3) dihydromacarpine + O2 = macarpine + H2O2 [RN:R04768]
Reaction(KEGG)
Substrate
dihydrosanguinarine [CPD:C05191];
O2 [CPD:C00007];
dihydrochelirubine [CPD:C05194];
dihydromacarpine [CPD:C05316]
Product
sanguinarine [CPD:C06162];
H2O2 [CPD:C00027];
chelirubine [CPD:C06327];
macarpine [CPD:C06165]
Comment
A CuII enzyme found in higher plants that produces oxidized forms of the benzophenanthridine alkaloids
History
EC 1.5.3.12 created 1999
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Reference
1  [PMID:24241413]
  Authors
Schumacher HM, Zenk MH
  Title
Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholtzia californica cell suspension cultures.
  Journal
Plant Cell Rep 7:43-6 (1988)
DOI:10.1007/BF00272975
Reference
2  [PMID:1444440]
  Authors
Arakawa H, Clark WG, Psenak M, Coscia CJ.
  Title
Purification and characterization of dihydrobenzophenanthridine oxidase from elicited Sanguinaria canadensis cell cultures.
  Journal
Arch Biochem Biophys 299:1-7 (1992)
DOI:10.1016/0003-9861(92)90236-P
Other DBs
ExplorEnz - The Enzyme Database: 1.5.3.12
IUBMB Enzyme Nomenclature: 1.5.3.12
ExPASy - ENZYME nomenclature database: 1.5.3.12
BRENDA, the Enzyme Database: 1.5.3.12
CAS: 114051-83-1
LinkDB

KEGG   ENZYME: 1.3.3.8
Entry
EC 1.3.3.8                  Enzyme                                 
Name
tetrahydroberberine oxidase;
(S)-THB oxidase
Class
Oxidoreductases;
Acting on the CH-CH group of donors;
With oxygen as acceptor
Sysname
(S)-tetrahydroberberine:oxygen oxidoreductase
Reaction(IUBMB)
(S)-tetrahydroberberine + 2 O2 = berberine + 2 H2O2 [RN:R02880]
Reaction(KEGG)
R02880;
(other) R03722 R04703 R08795 R11748
Substrate
(S)-tetrahydroberberine [CPD:C03329];
O2 [CPD:C00007]
Product
berberine [CPD:C00757];
H2O2 [CPD:C00027]
Comment
The enzyme from Berberis sp. is a flavoprotein; that from Coptis japonica is not. (R)-Tetrahydroberberines are not oxidized.
History
EC 1.3.3.8 created 1990 (EC 1.5.3.8 created 1989, incorporated 1992)
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K22089  tetrahydroprotoberberine oxidase
Genes
ECAD122579120
PSOM113274966 113303200
Reference
1
  Authors
Amann, M., Nagakura, N. and Zenk, M.H.
  Title
(S)-Tetrahydroprotoberberine oxidase the final enzyme in protoberberine biosynthesis.
  Journal
Tetrahedron Lett 25:953-954 (1984)
Reference
2
  Authors
Okada, N., Shinmyo, A., Okada, H. and Yamada, Y.
  Title
Purification and characterization of (S)-tetrahydroberberine oxidase from cultured Coptis japonica cells.
  Journal
Phytochemistry 27:979-982 (1988)
Other DBs
ExplorEnz - The Enzyme Database: 1.3.3.8
IUBMB Enzyme Nomenclature: 1.3.3.8
ExPASy - ENZYME nomenclature database: 1.3.3.8
BRENDA, the Enzyme Database: 1.3.3.8
CAS: 114705-00-9
LinkDB

KEGG   REACTION: R04703
Entry
R04703                      Reaction                               
Name
Dihydrosanguinarine:oxygen oxidoreductase
Definition
Dihydrosanguinarine + Oxygen + H+ <=> Sanguinarine + Hydrogen peroxide
Equation
Reaction class
RC01204  C05191_C06162
RC02755  C00007_C00027
Enzyme
1.3.3.8         1.5.3.12
Pathway
rn00950  Isoquinoline alkaloid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00945  Sanguinarine biosynthesis, (S)-reticuline => sanguinarine
Orthology
K22089  tetrahydroprotoberberine oxidase [EC:1.3.3.8]
Other DBs
RHEA: 16624
LinkDB

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