KEGG   ENZYME: 1.14.13.88Help
Entry
EC 1.14.13.88               Enzyme                                 

Name
flavanoid 3',5'-hydroxylase;
flavonoid 3',5'-hydroxylase
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
flavanone,NADPH:oxygen oxidoreductase
Reaction(IUBMB)
a flavanone + 2 NADPH + 2 H+ + 2 O2 = a 3',5'-dihydroxyflavanone + 2 NADP+ + 2 H2O (overall reaction) [RN:R10069];
(1a) a flavanone + NADPH + H+ + O2 = a 3'-hydroxyflavanone + NADP+ + H2O [RN:R07369];
(1b) a 3'-hydroxyflavanone + NADPH + H+ + O2 = a 3',5'-dihydroxyflavanone + NADP+ + H2O [RN:R07370]
Reaction(KEGG)
Substrate
flavanone [CPD:C00766];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007];
3'-hydroxyflavanone [CPD:C15204]
Product
3',5'-dihydroxyflavanone [CPD:C15609];
NADP+ [CPD:C00006];
H2O [CPD:C00001];
3'-hydroxyflavanone [CPD:C15204]
Comment
A heme-thiolate protein (P-450). The 3',5'-dihydroxyflavanone is formed via the 3'-hydroxyflavanone. In Petunia hybrida the enzyme acts on naringenin, eriodictyol, dihydroquercetin (taxifolin) and dihydrokaempferol (aromadendrin). The enzyme catalyses the hydroxylation of 5,7,4'-trihydroxyflavanone (naringenin) at either the 3' position to form eriodictyol or at both the 3' and 5' positions to form 5,7,3',4',5'-pentahydroxyflavanone (dihydrotricetin). The enzyme also catalyses the hydroxylation of 3,5,7,3',4'-pentahydroxyflavanone (taxifolin) at the 5' position, forming ampelopsin. NADH is not a good substitute for NADPH.
History
EC 1.14.13.88 created 2004
Pathway
ec00941  Flavonoid biosynthesis
ec00944  Flavone and flavonol biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K13083  flavonoid 3',5'-hydroxylase
Genes
GMX: 547705(W1)
CAM: 101503703
VVI: 100243414 100246462 100248071 100251607 100261319(F3'5'H) 100266025 100852531
SLY: 100736504
SOT: 102577676(P)
DOSA: Os03t0367101-00(Os03g0367101)
BDI: 100832240 100842616
SBI: 8080780 8082602
SITA: 101754995
Taxonomy
Reference
1  [PMID:12232356]
  Authors
Menting J, Scopes RK, Stevenson TW.
  Title
Characterization of Flavonoid 3[prime],5[prime]-Hydroxylase in Microsomal Membrane Fraction of Petunia hybrida Flowers.
  Journal
Plant Physiol 106:633-642 (1994)
Reference
2  [PMID:10567704]
  Authors
Shimada Y, Nakano-Shimada R, Ohbayashi M, Okinaka Y, Kiyokawa S, Kikuchi Y.
  Title
Expression of chimeric P450 genes encoding flavonoid-3', 5'-hydroxylase in transgenic tobacco and petunia plants(1).
  Journal
FEBS Lett 461:241-5 (1999)
DOI:10.1016/S0014-5793(99)01425-8
  Sequence
Reference
3  [PMID:9892710]
  Authors
de Vetten N, ter Horst J, van Schaik HP, de Boer A, Mol J, Koes R.
  Title
A cytochrome b5 is required for full activity of flavonoid 3', 5'-hydroxylase, a cytochrome P450 involved in the formation of blue flower colors.
  Journal
Proc Natl Acad Sci U S A 96:778-83 (1999)
DOI:10.1073/pnas.96.2.778
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.88
IUBMB Enzyme Nomenclature: 1.14.13.88
ExPASy - ENZYME nomenclature database: 1.14.13.88
BRENDA, the Enzyme Database: 1.14.13.88
CAS: 94047-23-1

DBGET integrated database retrieval system