KEGG   ORTHOLOGY: K13608
Entry
K13608            Tight     KO                                     

Name
SNO
Definition
senecionine N-oxygenase [EC:1.14.13.101]
Pathway
ko00960  Tropane, piperidine and pyridine alkaloid biosynthesis
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00960 Tropane, piperidine and pyridine alkaloid biosynthesis
    K13608  SNO; senecionine N-oxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.13  With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.13.101  senecionine N-oxygenase
     K13608  SNO; senecionine N-oxygenase
Other DBs
RN: R07373
GO: 0033784
Genes
AG: CAD12369(SNO)
Reference
  Authors
Naumann C, Hartmann T, Ober D
  Title
Evolutionary recruitment of a flavin-dependent monooxygenase for the detoxification of host plant-acquired pyrrolizidine alkaloids in the alkaloid-defended arctiid moth Tyria jacobaeae.
  Journal
Proc Natl Acad Sci U S A 99:6085-90 (2002)
DOI:10.1073/pnas.082674499
  Sequence

KEGG   ENZYME: 1.14.13.101
Entry
EC 1.14.13.101              Enzyme                                 

Name
senecionine N-oxygenase;
senecionine monooxygenase (N-oxide-forming);
SNO
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
senecionine,NADPH:oxygen oxidoreductase (N-oxide-forming)
Reaction(IUBMB)
senecionine + NADPH + H+ + O2 = senecionine N-oxide + NADP+ + H2O [RN:R07373]
Reaction(KEGG)
R07373
Substrate
senecionine [CPD:C06176];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
senecionine N-oxide [CPD:C15612];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
A flavoprotein. NADH cannot replace NADPH. While pyrrolizidine alkaloids of the senecionine and monocrotaline types are generally good substrates (e.g. senecionine, retrorsine and monocrotaline), the enzyme does not use ester alkaloids lacking an hydroxy group at C-7 (e.g. supinine and phalaenopsine), 1,2-dihydro-alkaloids (e.g. sarracine) or unesterified necine bases (e.g. senkirkine) as substrates [1]. Senecionine N-oxide is used by insects as a chemical defense: senecionine N-oxide is non-toxic, but it is bioactivated to a toxic form by the action of cytochrome P-450 oxidase when absorbed by insectivores.
History
EC 1.14.13.101 created 2006
Pathway
ec00960  Tropane, piperidine and pyridine alkaloid biosynthesis
Orthology
K13608  senecionine N-oxygenase
Reference
1  [PMID:9182998]
  Authors
Lindigkeit R, Biller A, Buch M, Schiebel HM, Boppre M, Hartmann T.
  Title
The two facies of pyrrolizidine alkaloids: the role of the tertiary amine and its N-oxide in chemical defense of insects with acquired plant alkaloids.
  Journal
Eur J Biochem 245:626-36 (1997)
DOI:10.1111/j.1432-1033.1997.00626.x
  Sequence
Reference
2  [PMID:11972041]
  Authors
Naumann C, Hartmann T, Ober D.
  Title
Evolutionary recruitment of a flavin-dependent monooxygenase for the detoxification of host plant-acquired pyrrolizidine alkaloids in the alkaloid-defended arctiid moth Tyria jacobaeae.
  Journal
Proc Natl Acad Sci U S A 99:6085-90 (2002)
DOI:10.1073/pnas.082674499
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.101
IUBMB Enzyme Nomenclature: 1.14.13.101
ExPASy - ENZYME nomenclature database: 1.14.13.101
BRENDA, the Enzyme Database: 1.14.13.101
CAS: 220581-68-0

KEGG   REACTION: R07373
Entry
R07373                      Reaction                               

Name
senecionine,NADPH:oxygen oxidoreductase (N-oxide-forming)
Definition
Senecionine + NADPH + H+ + Oxygen <=> Senecionine N-oxide + NADP+ + H2O
Equation
Reaction class
RC00001  C00005_C00006
RC01995  C06176_C15612
Enzyme
Pathway
rn00960  Tropane, piperidine and pyridine alkaloid biosynthesis
Orthology
K13608  senecionine N-oxygenase [EC:1.14.13.101]
Other DBs
RHEA: 11423

DBGET integrated database retrieval system