KEGG ENZYME: 1.14.11.9

ENZYME: 1.14.11.9

Entry

EC 1.14.11.9                Enzyme

Name

flavanone 3-dioxygenase;
naringenin 3-hydroxylase;
flavanone 3-hydroxylase;
flavanone 3beta-hydroxylase;
flavanone synthase I;
(2S)-flavanone 3-hydroxylase;
naringenin,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating);
F3H;
flavanone,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)

Class

Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor

Sysname

(2S)-flavan-4-one,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)

Reaction(IUBMB)

a (2S)-flavan-4-one + 2-oxoglutarate + O2 = a (2R,3R)-dihydroflavonol + succinate + CO2 [RN:R07329]

Reaction(KEGG)

R07329 > R02444 R03640 R05039 R07993 R07996 R07997

Substrate

(2S)-flavan-4-one [CPD:C02099];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007]

Product

(2R,3R)-dihydroflavonol [CPD:C21417];
succinate [CPD:C00042];
CO2 [CPD:C00011]

Comment

Requires Fe2+ and ascorbate. This plant enzyme catalyses an early step in the flavonoid biosynthesis pathway, leading to the production of flavanols and anthocyanins. Substrates include (2S)-naringenin, (2S)-eriodictyol, (2S)-dihydrotricetin and (2S)-pinocembrin. Some enzymes are bifuctional and also catalyse EC 1.14.20.6, flavonol synthase.

History

EC 1.14.11.9 created 1983, modified 1989, modified 2004, modified 2016

Pathway

ec00941

Flavonoid biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K00475

naringenin 3-dioxygenase

Genes

ATH:	AT3G51240(F3H)

ALY:

9313862

CRB:

17885266

CSAT:

104711665 104780958 104791360

EUS:	EUTSA_v10010399mg

BRP:

103841041

BNA:	106367722 106444347 106449286 111197703

BOE:	106307555 106338655

RSZ:	108805892 108852668 130511095

THJ:

104821327

CPAP:

110822393

CIT:	102617426(CitF3H)

CIC:	CICLE_v10023305mg CICLE_v10025931mg

PVY:

116139362

MINC:

123194609 123199757

TCC:

18610772

GRA:	105763220 105803713

GHI:	107912810 107912992 107945804 121202986

GAB:	108474291 108479753

HSYR:

120127017 120152174 120153094

DZI:	111292793 111316263

EGR:

104422756

GMX:	100780057 100799462 100815441 100818312 732548(F3H)

GSJ:	114381549 114390422 114390424 114390425 114405690

PVU:	PHAVU_003G261900g

VRA:

106769061

VAR:

108323664

VUN:

114179503

VUM:

124822906

APRC:

113858951 113859370 113868659

MTR:	11408162 11443565 25489119

TPRA:

123923749

CAM:	101492596 101492925 101501974

PSAT:

127074683 127074684 127074686

VVO:	131608727 131640720

LJA:	130711196 130745193

ADU:	107476683 127743933

AIP:

107622822

AHF:	112719684 112796379

LANG:

109330585 109332349 109359463

PCIN:

129310468 129322959

QSA:	O6P43_033614

FVE:

101300182

RCN:

112186620

PPER:

18770366

PMUM:

103340206

PAVI:

110758277

PDUL:

117633678

MDM:	103400025 103436139

MSYL:

126604572 126611794

PXB:

103953484

ZJU:

107424368

MNT:

21409326

CSAV:

115702709 115712997

CSV:	101206443 101215613

CMO:	103491109 103498778

BHJ:	120068304 120069023

MCHA:

111014783 111023502 111024602

CMAX:

111465227 111498563

CMOS:

111430948 111445185

CPEP:

111800452 111809659

RCU:

8268714

MEAN:

126679253

JCU:

105629005

HBR:	110641151 110642838

MESC:

110609679

POP:	18099191 18099194 18099195

PEU:	105138720 105138722

PALZ:

118029845 118029846 118053245

PNZ:	133694454 133695417 133706043

JRE:

108997708

CILL:

122315855

CAVE:

132171639

QSU:

112035407

QLO:

115994995

TWL:	120012699 120015517

VVI:	100233079(F3H) 100253950 104879126

VRI:	117907342 117912217 117912816 117913309

SLY:	100736482(F3H)

SPEN:

107011910

SOT:

102577463

SDUL:

129872327

CANN:

107859880

LBB:

132621943

NTA:	107770893(NtF3H) 107806462

NSY:

104217085

NTO:

104098512

NAU:

109242464

INI:	109167724(F3H) 109167725 109177773

ITR:	115998797 116011765

SIND:

105166042

OEU:

111401282

EGT:	105956424 105959582

SSPL:

121759171 121773225

SMIL:

130985418 131011084

SHIS:

125216273 125219987

APAN:

127246896

HAN:

110915473

ECAD:

122610074

LSV:

111897600

CCAV:

112512382

DCR:	108211971 108213382

CSIN:

114305452 114306386

RVL:	131298380 131334463

AEW:	130783998 130785573 130786885 130786914

BVG:	104895196 104905115 104905116 104905117 104905155

SOE:	110799526 110799527 110800737

CQI:	110686439 110686440 110694697 110724781 110733452 110733463 110733489

ATRI:

130824193

MOF:	131149037 131161421

NNU:	104587834 104588723 104605233 104605566

MING:

122072758 122073762 122073763 122084606

TSS:	122658733 122661380 122661381

PSOM:

113288864 113290254

OSA:

9270463

OBR:

102719670

OGL:

127770046

BDI:

100823527

ATS:

109770765

TDC:	119356708 119365932 119366543

TAES:

100192198 123042301 123042899 123186261

TUA:

125539912

LPER:

127336783

LRD:

124677615

ZMA:

542712

MFLO:

136473396 136493985 136493986 136493989 136494229 136494286 136497056 136497399 136497660

SITA:

101777126

SVS:

117847667

PVIR:

120642073 120683857

PHAI:

112900936

PDA:	103697163 103708217 120108474

EGU:	105054663 105059410

MUS:	103970367 103992006

ZOF:	122032774 122034319

DCT:	110097388 110106800

PEQ:	110032785 110037298

AOF:

109848156

MSIN:

131237355

NCOL:

116245897 116246718 116247898 116253956 116263301

ATR:	18441761 18441765

» show all

Reference

Authors

Forkmann G, Heller W, Grisebach H.

Title

Anthocyanin biosynthesis in flowers of Matthiola incana flavanone 3- and flavonoid 3'-hydroxylases.

Journal

Z Naturforsch C: Biosci 35:691-695 (1980)

Reference

2 [PMID:8541503]

Authors

Charrier B, Coronado C, Kondorosi A, Ratet P

Title

Molecular characterization and expression of alfalfa (Medicago sativa L.) flavanone-3-hydroxylase and dihydroflavonol-4-reductase encoding genes.

Journal

Plant Mol Biol 29:773-86 (1995)
DOI:10.1007/bf00041167

Sequence

[ag:CAA55628]

Reference

3 [PMID:8685272]

Authors

Pelletier MK, Shirley BW

Title

Analysis of flavanone 3-hydroxylase in Arabidopsis seedlings. Coordinate regulation with chalcone synthase and chalcone isomerase.

Journal

Plant Physiol 111:339-45 (1996)
DOI:10.1104/pp.111.1.339

Reference

4 [PMID:15013767]

Authors

Wellmann F, Matern U, Lukacin R.

Title

Significance of C-terminal sequence elements for Petunia flavanone 3beta-hydroxylase activity.

Journal

FEBS Lett 561:149-54 (2004)
DOI:10.1016/S0014-5793(04)00159-0

Reference

5 [PMID:16147863]

Authors

Jin Z, Grotewold E, Qu W, Fu G, Zhao D

Title

Cloning and characterization of a flavanone 3-hydroxylase gene from Saussurea medusa.

Journal

DNA Seq 16:121-9 (2005)
DOI:10.1080/10425170500050742

Reference

6 [PMID:16779664]

Authors

Shen G, Pang Y, Wu W, Deng Z, Zhao L, Cao Y, Sun X, Tang K

Title

Cloning and characterization of a flavanone 3-hydroxylase gene from Ginkgo biloba.

Journal

Biosci Rep 26:19-29 (2006)
DOI:10.1007/s10540-006-9007-y

Other DBs

ExplorEnz - The Enzyme Database:

1.14.11.9

IUBMB Enzyme Nomenclature:

1.14.11.9

ExPASy - ENZYME nomenclature database:

1.14.11.9

BRENDA, the Enzyme Database:

1.14.11.9

CAS:	75991-43-4

DBGET integrated database retrieval system