KEGG   ENZYME: 1.14.13.101Help
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
BRITE hierarchy
Sysname
senecionine,NADPH:oxygen oxidoreductase (N-oxide-forming)
Reaction(IUBMB)
senecionine + NADPH + H+ + O2 = senecionine N-oxide + NADP+ + H2O [RN:R07373]
Reaction(KEGG)
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
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 (1997) 626-36.
  Sequence
[up:Q8MP06]
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 (2002) 6085-90.
  Sequence
[up:Q8MP06]
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
220581-68-0

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