KEGG   ORTHOLOGY: K15099Help
Entry
K15099                      KO                                     

Name
CYP76B6, G10H
Definition
geraniol 8-hydroxylase [EC:1.14.13.152]
Pathway
Monoterpenoid biosynthesis
Brite
KEGG Orthology (KO) [BR:ko00001]
 Metabolism
  Metabolism of terpenoids and polyketides
   00902 Monoterpenoid biosynthesis
    K15099  CYP76B6, G10H; geraniol 8-hydroxylase
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
    1.14.13.152  geraniol 8-hydroxylase
     K15099  CYP76B6, G10H; geraniol 8-hydroxylase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP76 family
   K15099  CYP76B6, G10H; geraniol 8-hydroxylase
BRITE hierarchy
Other DBs
RN: 
Genes
AG: 
ACZ48680(CYP76B6) CAC80883(CYP76B6)
TaxonomyKoalaUniProt
Reference
PMID:11718718 (CYP76B6)
  Authors
Collu G, Unver N, Peltenburg-Looman AM, van der Heijden R, Verpoorte R, Memelink J
  Title
Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis.
  Journal
FEBS Lett 508:215-20 (2001)
DOI:10.1016/S0014-5793(01)03045-9
  Sequence
Reference
PMID:21504162 (CYP76B6)
  Authors
Sung PH, Huang FC, Do YY, Huang PL
  Title
Functional expression of geraniol 10-hydroxylase reveals its dual function in the biosynthesis of terpenoid and phenylpropanoid.
  Journal
J Agric Food Chem 59:4637-43 (2011)
DOI:10.1021/jf200259n
  Sequence
Reference
PMID:20699579 (CYP76B10)
  Authors
Wang J, Liu Y, Cai Y, Zhang F, Xia G, Xiang F
  Title
Cloning and functional analysis of geraniol 10-hydroxylase, a cytochrome P450 from Swertia mussotii Franch.
  Journal
Biosci Biotechnol Biochem 74:1583-90 (2010)
DOI:10.1271/bbb.100175
  Sequence

KEGG   ENZYME: 1.14.13.152Help
Entry
EC 1.14.13.152              Enzyme                                 

Name
geraniol 8-hydroxylase;
CYP76B6;
G10H;
CrG10H;
SmG10H
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
geraniol,NADPH:oxygen oxidoreductase (8-hydroxylating)
Reaction(IUBMB)
geraniol + NADPH + H+ + O2 = (6E)-8-hydroxygeraniol + NADP+ + H2O [RN:R08785]
Reaction(KEGG)
Substrate
geraniol [CPD:C01500];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
(6E)-8-hydroxygeraniol [CPD:C17621];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
Requires cytochrome P-450. Also hydroxylates nerol and citronellol, cf. EC 1.14.13.151 linalool 8-monooxygenase. The recommended numbering of geraniol gives 8-hydroxygeraniol as the product rather than 10-hydroxygeraniol as used by references 1-3. See prenol nomenclature {iupac/misc/prenol#p1::Pr-1}. The cloned enzyme also catalysed, but less efficiently, the 3'-hydroxylation of naringenin (cf. EC 1.14.13.21, flavonoid 3'-monooxygenase) [3].
History
EC 1.14.13.152 created 2012
Pathway
Monoterpenoid biosynthesis
Metabolic pathways
Biosynthesis of secondary metabolites
Orthology
K15099  
geraniol 8-hydroxylase
Reference
1  [PMID:11718718]
  Authors
Collu G, Unver N, Peltenburg-Looman AM, van der Heijden R, Verpoorte R, Memelink J.
  Title
Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis.
  Journal
FEBS. Lett. 508 (2001) 215-20.
  Sequence
Reference
2  [PMID:20699579]
  Authors
Wang J, Liu Y, Cai Y, Zhang F, Xia G, Xiang F
  Title
Cloning and functional analysis of geraniol 10-hydroxylase, a cytochrome P450 from Swertia mussotii Franch.
  Journal
Biosci. Biotechnol. Biochem. 74 (2010) 1583-90.
  Sequence
Reference
3  [PMID:21504162]
  Authors
Sung PH, Huang FC, Do YY, Huang PL
  Title
Functional expression of geraniol 10-hydroxylase reveals its dual function in the biosynthesis of terpenoid and phenylpropanoid.
  Journal
J. Agric. Food. Chem. 59 (2011) 4637-43.
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
KEGG   REACTION: R08785Help
Entry
R08785                      Reaction                               

Name
geraniol,NADPH---hemoprotein reductase:oxygen oxidoreductase (8-hydroxylating)
Definition
Geraniol + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (6E)-8-Hydroxygeraniol + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
Comment
geraniol 10-hydroxylase
Reaction class
C01500_C17621
Enzyme
Pathway
Monoterpenoid biosynthesis
Metabolic pathways
Biosynthesis of secondary metabolites
Orthology
K15099  
geraniol 8-hydroxylase [EC:1.14.13.152]
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