KEGG ORTHOLOGY: K13265

ORTHOLOGY: K13265

Entry

K13265                      KO

Symbol

Name

vestitone reductase [EC:1.1.1.348]

Pathway

map00943

Isoflavonoid biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Module

M00942

Pterocarpan biosynthesis, daidzein => medicarpin

Reaction

R07737

(3R,4R)-4'-methoxyisoflavan-2',4,7-triol:NADP+ 4-oxidoreductase

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00943 Isoflavonoid biosynthesis
    K13265  VR; vestitone reductase
Enzymes [BR:ko01000]
1. Oxidoreductases
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.348  (3R)-2'-hydroxyisoflavanone reductase
     K13265  VR; vestitone reductase

Genes

GMX:	100194416 100793687 100794209 547660

GSJ:	114394465 114394525 114425491 114425668

PVU:	PHAVU_008G076600g PHAVU_008G076700g

VRA:	106779595 106779598

VAR:	108327832 108328041

VUN:	114183399 114184905

VUM:	124826905 124835625

CCAJ:

APRC:

MTR:

TPRA:

CAM:

PSAT:

VVO:

LJA:	130728131 130728133

ADU:	107472037 107485391

AIP:	107624299 107638006

AHF:	112716970 112740569 112784826 112794395

AG:

AAB41550

» show all

Reference

PMID:7625843

Authors

Guo L, Paiva NL

Title

Molecular cloning and expression of alfalfa (Medicago sativa L.) vestitone reductase, the penultimate enzyme in medicarpin biosynthesis.

Journal

Arch Biochem Biophys 320:353-60 (1995)
DOI:10.1016/0003-9861(95)90019-5

Sequence

[ag:AAB41550]

LinkDB

ENZYME: 1.1.1.348

Entry

EC 1.1.1.348                Enzyme

Name

(3R)-2'-hydroxyisoflavanone reductase;
vestitone reductase;
pterocarpin synthase (incorrect);
pterocarpan synthase (incorrect)

Class

Oxidoreductases;
Acting on the CH-OH group of donors;
With NAD+ or NADP+ as acceptor

Sysname

(3R)-2'-hydroxyisoflavanone:NADP+ 4-oxidoreductase

Reaction(IUBMB)

a (4R)-4,2'-dihydroxyisoflavan + NADP+ = a (3R)-2'-hydroxyisoflavanone + NADPH + H+ [RN:R11877]

Reaction(KEGG)

R11877 > R07737

Substrate

(4R)-4,2'-dihydroxyisoflavan [CPD:C21738];
NADP+ [CPD:C00006]

Product

(3R)-2'-hydroxyisoflavanone [CPD:C21739];
NADPH [CPD:C00005];
H+ [CPD:C00080]

Comment

This plant enzyme participates in the biosynthesis of the pterocarpan phytoalexins medicarpin, maackiain, and several forms of glyceollin. The enzyme has a strict stereo specificity for the 3R-isoflavanones.

History

EC 1.1.1.348 created 1992 as EC 1.1.1.246, part transferred 2013 to EC 1.1.1.348

Pathway

ec00943

Isoflavonoid biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K13265

vestitone reductase

Genes

GMX:	100194416 100793687 100794209 547660

GSJ:	114394465 114394525 114425491 114425668

PVU:	PHAVU_008G076600g PHAVU_008G076700g

VRA:	106779595 106779598

VAR:	108327832 108328041

VUN:	114183399 114184905

VUM:	124826905 124835625

CCAJ:

109802944

APRC:

113866729

MTR:

11435356

TPRA:

123889339 123892808

CAM:

101514431

PSAT:

127127236

VVO:

131612054

LJA:	130728131 130728133

ADU:	107472037 107485391

AIP:	107624299 107638006

AHF:	112716970 112740569 112784826 112794395

» show all

Reference

Authors

Bless W, Barz W.

Title

Isolation of pterocarpan synthase, the terminal enzyme of pterocarpan phytoalexin biosynthesis in cell-suspension cultures of Cicer arietinum.

Journal

FEBS Lett 235:47-50 (1988)

Reference

2 [PMID:8071365]

Authors

Guo L, Dixon RA, Paiva NL.

Title

Conversion of vestitone to medicarpin in alfalfa (Medicago sativa L.) is catalyzed by two independent enzymes. Identification, purification, and characterization of vestitone reductase and 7,2'-dihydroxy-4'-methoxyisoflavanol dehydratase.

Journal

J Biol Chem 269:22372-8 (1994)

Sequence

[ag:AAB41550]

Reference

3 [PMID:7805842]

Authors

Guo L, Dixon RA, Paiva NL

Title

The 'pterocarpan synthase' of alfalfa: association and co-induction of vestitone reductase and 7,2'-dihydroxy-4'-methoxy-isoflavanol (DMI) dehydratase, the two final enzymes in medicarpin biosynthesis.

Journal

FEBS Lett 356:221-5 (1994)
DOI:10.1016/0014-5793(94)01267-9

Sequence

[ag:AAB41550]

Reference

4 [PMID:7625843]

Authors

Guo L, Paiva NL

Title

Molecular cloning and expression of alfalfa (Medicago sativa L.) vestitone reductase, the penultimate enzyme in medicarpin biosynthesis.

Journal

Arch Biochem Biophys 320:353-60 (1995)
DOI:10.1016/0003-9861(95)90019-5

Sequence

[ag:AAB41550]

Reference

5 [PMID:17433362]

Authors

Shao H, Dixon RA, Wang X

Title

Crystal structure of vestitone reductase from alfalfa (Medicago sativa L.).

Journal

J Mol Biol 369:265-76 (2007)
DOI:10.1016/j.jmb.2007.03.040

Other DBs

ExplorEnz - The Enzyme Database:

1.1.1.348

IUBMB Enzyme Nomenclature:

1.1.1.348

ExPASy - ENZYME nomenclature database:

1.1.1.348

BRENDA, the Enzyme Database:

1.1.1.348

CAS:	118477-70-6

LinkDB

REACTION: R07737

Entry

R07737                      Reaction

Name

(3R,4R)-4'-methoxyisoflavan-2',4,7-triol:NADP+ 4-oxidoreductase

Definition

(-)-Vestitone + NADPH + H+ <=> 7,2'-Dihydroxy-4'-methoxy-isoflavanol + NADP+

Equation

C00786 + C00005 + C00080 <=> C16187 + C00006

Comment

vestitione reductase

Reaction class

RC00001

C00005_C00006

RC00235

C00786_C16187

Enzyme

1.1.1.348

Pathway

rn00943

Isoflavonoid biosynthesis

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Module

M00942

Pterocarpan biosynthesis, daidzein => medicarpin

Brite

Enzymatic reactions [BR:br08201]
1. Oxidoreductase reactions
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.348
     R07737  (-)-Vestitone + NADPH + H+ <=> 7,2'-Dihydroxy-4'-methoxy-isoflavanol + NADP+
IUBMB reaction hierarchy [BR:br08202]
1. Oxidoreductase reactions
  1.1.1.348
   R11877  (4R)-4,2'-Dihydroxyisoflavan <=> (3R)-2'-Hydroxyisoflavanone
    R07737  7,2'-Dihydroxy-4'-methoxy-isoflavanol <=> (-)-Vestitone

Orthology

K13265

vestitone reductase [EC:1.1.1.348]

Other DBs

RHEA:

35406

LinkDB

DBGET integrated database retrieval system