KEGG   ENZYME: 1.14.14.81Help
Entry
EC 1.14.14.81               Enzyme                                 

Name
flavanoid 3',5'-hydroxylase;
flavonoid 3',5'-hydroxylase
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
BRITE hierarchy
Sysname
flavanone,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3',5'-dihydroxylating)
Reaction(IUBMB)
a flavanone + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = a 3',5'-dihydroxyflavanone + 2 [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:R10069];
(1a) a flavanone + [reduced NADPH---hemoprotein reductase] + O2 = a 3'-hydroxyflavanone + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R07369];
(1b) a 3'-hydroxyflavanone + [reduced NADPH---hemoprotein reductase] + O2 = a 3',5'-dihydroxyflavanone + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R07370]
Reaction(KEGG)
Substrate
flavanone [CPD:C00766];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
3'-hydroxyflavanone [CPD:C15204]
Product
3',5'-dihydroxyflavanone [CPD:C15609];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
3'-hydroxyflavanone [CPD:C15204]
Comment
A cytochrome P-450 (heme-thiolate) protein found in plants. 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.
History
EC 1.14.14.81 created 2004 as EC 1.14.13.88, transferred 2018 to EC 1.14.14.81
Pathway
ec00941  Flavonoid biosynthesis
ec00944  Flavone and flavonol biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K13083  flavonoid 3',5'-hydroxylase
Genes
CPAP: 110807940
CIT: 102627616
CIC: CICLE_v10018289mg
TCC: 18589969
GRA: 105793944
GHI: 107937772 107952239 107953185 107953189 107954320 107963683
GAB: 108453491 108459521
DZI: 111285769 111302423 111304415
EGR: 104421458 104433881 104433882 104433887
GMX: 547705(W1)
GSJ: 114381448
CAM: 101503703
LJA: Lj0g3v0262779.1(Lj0g3v0262779.1) Lj2g3v2084440.1(Lj2g3v2084440.1) Lj6g3v1008110.1(Lj6g3v1008110.1)
LANG: 109335187
JCU: 105628967
MESC: 110629198
JRE: 109000585
SLY: 100736504
SPEN: 107005054
SOT: 102577676(P)
CANN: 107847144 107848667(F3'5'H)
NTA: 107777127
NSY: 104236486
NTO: 104111783
NAU: 109209238
DOSA: Os03t0367101-00(Os03g0367101)
OBR: 102721818
ATS: 109731523(LOC109731523) 109740351(LOC109740351) 109774860(LOC109774860) 109782004(LOC109782004) 109785547(LOC109785547)
SITA: 101754995
DCT: 110103762
PEQ: 110026775
 » show all
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: 1.14.14.81
IUBMB Enzyme Nomenclature: 1.14.14.81
ExPASy - ENZYME nomenclature database: 1.14.14.81
BRENDA, the Enzyme Database: 1.14.14.81
CAS: 94047-23-1

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