KEGG   ENZYME: 1.14.14.168
Entry
EC 1.14.14.168              Enzyme                                 

Name
germacrene A acid 8beta-hydroxylase;
HaG8H;
CYP71BL1;
CYP71BL6
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 (8beta-hydroxylating)
Reaction(IUBMB)
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH---hemoprotein reductase] + O2 = 8beta-hydroxygermacra-1(10),4,11(13)-trien-12-oate + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R12266]
Reaction(KEGG)
R12266
Substrate
germacra-1(10),4,11(13)-trien-12-oate [CPD:C19678];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
8beta-hydroxygermacra-1(10),4,11(13)-trien-12-oate [CPD:C22049];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein from the plant Helianthus annuus (common sunflower). The cyclisation of 8beta-hydroxygermacra-1(10),4,11(13)-triene-12-oate to inunolide (12,8beta) does not seem to occur spontaneously. The enzyme from Inula hupehensis also forms some 8alpha-hydroxygermacra-1(10),4,11(13)-triene-12-oate, which spontaneously cyclises to 8-epi-inunolide (12,8alpha) (cf. EC 1.14.14.170 8-epi-inunolide synthase).
History
EC 1.14.14.168 created 2018
Orthology
K20767  germacrene A acid 8beta-hydroxylase
K23177  germacrene A acid 8beta-hydroxylase / 8-epi-inunolide synthase
Genes
HAN: 110908155 110937293 110938090 110940256
Reference
1  [PMID:29758164]
  Authors
Frey M, Schmauder K, Pateraki I, Spring O
  Title
Biosynthesis of Eupatolide-A Metabolic Route for Sesquiterpene Lactone Formation Involving the P450 Enzyme CYP71DD6.
  Journal
ACS Chem Biol 13:1536-1543 (2018)
DOI:10.1021/acschembio.8b00126
Reference
2  [PMID:29086444]
  Authors
Gou J, Hao F, Huang C, Kwon M, Chen F, Li C, Liu C, Ro DK, Tang H, Zhang Y
  Title
Discovery of a non-stereoselective cytochrome P450 catalyzing either 8alpha- or 8beta-hydroxylation of germacrene A acid from the Chinese medicinal plant, Inula  hupehensis.
  Journal
Plant J 93:92-106 (2018)
DOI:10.1111/tpj.13760
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.168
IUBMB Enzyme Nomenclature: 1.14.14.168
ExPASy - ENZYME nomenclature database: 1.14.14.168
BRENDA, the Enzyme Database: 1.14.14.168

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