KEGG   ENZYME: 1.14.14.81
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
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
CPAP110807940
CIT102627616
CICCICLE_v10018289mg
PVY116110943 116110956 116126796 116126798 116126842
MINC123196758 123201698 123205864 123205865 123205875 123205879 123209637 123225242 123225291 123226250
TCC18589969
GRA105793944
GHI107953189 107954320
GAB108453491 108459521
DZI111285769 111302423 111304415
EGR104421458 104433881 104433882 104433887
GMX547705(W1)
GSJ114381448
PVUPHAVU_006G015400g PHAVU_006G018800g
VRA106774548 106775588
VAR108342643 108345990
VUN114186854 114187675
CCAJ109788818 109816205
APRC113854599 113856260
MTRMTR_3g436390 MTR_3g436540
CAM101503703
LJALj0g3v0262779.1(Lj0g3v0262779.1) Lj2g3v2084440.1(Lj2g3v2084440.1) Lj6g3v1008110.1(Lj6g3v1008110.1)
LANG109335187
ZJU107403962 107410717
JCU105628967
HBR110653348
MESC110629198
POP7463882 7475030
PEU105114298 105125989
PALZ118027605 118055534
JRE109000585 118344424
QSU111992819 112039568
QLO115981331
TWL119990945 119991612 119992132 120002289
VVI100232896(F3'5'H) 100242945 100243414 100246462 100247021 100248071 100251607 100256733 100261319(F3'5'H) 100266025 100267840 100852531 104877273(VvF3'5'h)
VRI117916337 117916343 117916516 117916517 117916518
SLY100736504
SPEN107005054
SOT102577676(P)
CANN107847144 107848667(F3'5'H)
NTA107777127
NSY104236486
NTO104111783
NAU109209238
SSPL121772475
CSIN114261298 114276755 114309335 114309343
NNU104590491 104590495
MING122063430 122071590 122083715
TSS122642056 122669460
NCOL116260989 116264364 116264369
OSA4332919
DOSAOs03t0367101-00(Os03g0367101)
OBR102721818
BDI100832240 100842616
ATS109731523 109740351 109774860 109782004 109785547
TDC119288140 119314882 119317373 119324785 119324825 119325713 119330628 119366002
TAES123047038 123054866 123088337 123098061 123129897 123131240 123133080 123133082 123139302 123139307 123140667 123145987 123151823 123168051 123170643
SBI8080780 8082602
ZMA100278079 103639113
SITA101754995
SVS117838872
PVIR120652259 120688288
PHAI112877217
PDA103706219 103706786 103713287 103719265 120110262
EGU105032764 105036168 105045491 105045492 105045493 105053152 105053154
MUS103970890 103971552 103973791 103974749 103993499 103993746 103998211 104000770 108951142
DCT110103762
PEQ110026775
 » show all
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)
DOI:10.1104/pp.106.2.633
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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