KEGG   ENZYME: 1.14.14.150
Entry
EC 1.14.14.150              Enzyme                                 

Name
costunolide synthase;
CYP71BL2
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
germacra-1(10),4,11(13)-trien-12-oate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (6alpha-hydroxylating)
Reaction(IUBMB)
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH---hemoprotein reductase] + O2 = (+)-costunolide + [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:R09575];
(1a) germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH---hemoprotein reductase] + O2 = 6alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oate + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R12131];
(1b) 6alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oate = (+)-costunolide + H2O (spontaneous) [RN:R12132]
Reaction(KEGG)
Substrate
germacra-1(10),4,11(13)-trien-12-oate [CPD:C19678];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
6alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oate [CPD:C21922]
Product
(+)-costunolide [CPD:C09382];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
6alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oate [CPD:C21922]
Comment
A cytochrome P-450 (heme-thiolate) protein from chicory plants. 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 spontaneously cyclises to form the lactone ring.
History
EC 1.14.14.150 created 2011 as EC 1.14.13.120, transferred 2018 to EC 1.14.14.150
Pathway
ec00909  Sesquiterpenoid and triterpenoid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K20561  costunolide synthase
Genes
HAN: 110928784
LSV: 111885020 111890493 111890503
CCAV: 112526537
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 129:257-68 (2002)
DOI:10.1104/pp.010957
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.150
IUBMB Enzyme Nomenclature: 1.14.14.150
ExPASy - ENZYME nomenclature database: 1.14.14.150
BRENDA, the Enzyme Database: 1.14.14.150

DBGET integrated database retrieval system