KEGG   ORTHOLOGY: K20561Help
Entry
K20561                      KO                                     

Name
CYP71BL2
Definition
costunolide synthase [EC:1.14.13.120]
Pathway
Sesquiterpenoid and triterpenoid biosynthesis
Brite
KEGG Orthology (KO) [BR:ko00001]
 Metabolism
  Metabolism of terpenoids and polyketides
   00909 Sesquiterpenoid and triterpenoid biosynthesis
    K20561  CYP71BL2; costunolide synthase
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
    1.14.13.120  costunolide synthase
     K20561  CYP71BL2; costunolide synthase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP71 family
   K20561  CYP71BL2; costunolide synthase
BRITE hierarchy
Other DBs
RN: 
Genes
AG: 
AEG79727(CYP71BL3) AEI59780(CYP71BL2)
TaxonomyKoalaUniProt
Reference
PMID:21515683 (CYP71BL2)
  Authors
Ikezawa N, Gopfert JC, Nguyen DT, Kim SU, O'Maille PE, Spring O, Ro DK
  Title
Lettuce costunolide synthase (CYP71BL2) and its homolog (CYP71BL1) from sunflower catalyze distinct regio- and stereoselective hydroxylations in sesquiterpene lactone metabolism.
  Journal
J Biol Chem 286:21601-11 (2011)
DOI:10.1074/jbc.M110.216804
  Sequence
Reference
PMID:21858047 (CYP71BL3)
  Authors
Liu Q, Majdi M, Cankar K, Goedbloed M, Charnikhova T, Verstappen FW, de Vos RC, Beekwilder J, van der Krol S, Bouwmeester HJ
  Title
Reconstitution of the costunolide biosynthetic pathway in yeast and Nicotiana benthamiana.
  Journal
PLoS One 6:e23255 (2011)
DOI:10.1371/journal.pone.0023255
  Sequence

KEGG   ENZYME: 1.14.13.120Help
Entry
EC 1.14.13.120              Enzyme                                 

Name
costunolide synthase
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
germacra-1(10),4,11(13)-trien-12-oate,NADPH:oxygen oxidoreductase (6alpha-hydroxylating)
Reaction(IUBMB)
germacra-1(10),4,11(13)-trien-12-oate + NADPH + H+ + O2 = (+)-costunolide + NADP+ + 2 H2O [RN:R09575]
Reaction(KEGG)
Substrate
germacra-1(10),4,11(13)-trien-12-oate [CPD:C19678];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
(+)-costunolide [CPD:C09382];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
A heme-thiolate protein (P-450). The enzyme hydroxylates carbon C-6 of germacra-1(10),4,11(13)-trien-12-oate to give 6alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oate, which probably spontaneously cyclises to form the lactone ring.
History
EC 1.14.13.120 created 2011
Pathway
Sesquiterpenoid and triterpenoid biosynthesis
Biosynthesis of secondary metabolites
Orthology
K20561  
costunolide synthase
Reference
1  [PMID:12011356]
  Authors
de Kraker JW, Franssen MC, Joerink M, de Groot A, Bouwmeester HJ
  Title
Biosynthesis of costunolide, dihydrocostunolide, and leucodin. Demonstration of cytochrome p450-catalyzed formation of the lactone ring present in sesquiterpene  lactones of chicory.
  Journal
Plant. Physiol. 129 (2002) 257-68.
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
KEGG   REACTION: R09575Help
Entry
R09575                      Reaction                               

Name
germacra-1(10),4,11(13)-trien-12-oate,NADPH:oxygen oxidoreductase (6alpha-hydroxylating)
Definition
Germacrene A acid + NADPH + H+ + Oxygen <=> Costunolide + NADP+ + 2 H2O
Equation
Reaction class
C00005_C00006
C09382_C19678
Enzyme
Pathway
Sesquiterpenoid and triterpenoid biosynthesis
Biosynthesis of secondary metabolites
Orthology
K20561  
costunolide synthase [EC:1.14.13.120]
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