Information on EC 1.3.1.81 - (+)-pulegone reductase

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The expected taxonomic range for this enzyme is: Mentha

EC NUMBER
COMMENTARY hide
1.3.1.81
-
RECOMMENDED NAME
GeneOntology No.
(+)-pulegone reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(+)-isomenthone + NADP+ = (+)-pulegone + NADPH + H+
show the reaction diagram
-
-
-
-
(-)-menthone + NADP+ = (+)-pulegone + NADPH + H+
show the reaction diagram
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
menthol biosynthesis
-
-
Monoterpenoid biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
(-)-menthone:NADP+ oxidoreductase
NADH cannot replace NADPH as reductant. The Delta8,9-double bond of (+)-cis-isopulegone and the Delta1,2-double bond of (±)-piperitone are not substrates. The enzyme from peppermint (Mentha x piperita) converts (+)-pulegone into both (-)-menthone and (+)-isomenthone at a ratio of 70:30 for native enzyme but it does not catalyse the reverse reaction. This enzyme is a member of the medium-chain dehydrogenase/reductase superfamily.
CAS REGISTRY NUMBER
COMMENTARY hide
138066-95-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
-
p-menthane monoterpene biosynthesis in peppermint glandular trichomes, generation of a mathematical model of peppermint essential oil biosynthesis, monoterpene contents in the essential oil, overview
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-pulegone + NADPH + H+
(-)-menthone + NADP+
show the reaction diagram
-
-
-
r
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(+)-pulegone + NADPH + H+
(-)-menthone + NADP+
show the reaction diagram
Q6WAU0
-
-
-
r
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-menthofuran
-
weak competitive inhibition, in peppermint plants grown under low-light conditions, (+)-menthofuran is selectively retained in secretory cells and accumulated to very high levels of up to 20 mM, whereas under regular growth conditions, (+)-menthofuran levels remain very low, below 0.4 mM
menthofuran
-
-
additional information
-
although (+)-menthofuran does not inhibit (+)-pulegone reductase activity, stem feeding with menthofuran selectively decreases enzyme transcript levels in immature leaves, thereby accounting for decreased reductase activity and increased pulegone content, overview, the flux of (+)-pulegone through pulegone reductase correlates negatively with the essential oil content of menthofuran, such that menthofuran, and pulegone increase, or decrease, in concert, overview
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0023 - 0.04
(+)-pulegone
0.0069
NADPH
-
pH 5.0, recombinant enzyme
additional information
additional information
-
kinetic data analysis, overview
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.8
(+)-pulegone
Mentha x piperita
-
pH 5.0, recombinant enzyme
1.8
NADPH
Mentha x piperita
-
pH 5.0, recombinant enzyme
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.3
(+)-menthofuran
-
pH 6.6
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.15
(+)-menthofuran
Mentha x piperita
-
pH 6.6
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
essential oil composition of wild-type peppermint
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.6
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 6.5
-
70% of maximal activity within this range
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.2
-
about, isoelectric focusing
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
secretory cells of peltate glandular trichomes with abundant labeling corresponding to the secretory phase of gland development
Manually annotated by BRENDA team
-
glandular
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37914
-
1 x * 43000, SDS-PAGE, 1 * 37914, sequence calculation
38000
-
x * 38000
43000
-
1 x * 43000, SDS-PAGE, 1 * 37914, sequence calculation
45000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 38000
monomer
-
1 x * 43000, SDS-PAGE, 1 * 37914, sequence calculation
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
neither protease inhibitors nor flavins improve the activity or stability of the purified native enzyme, and the addition of glycerol to the buffers leads to rapid loss of activity upon storage
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme partially by isolation of secretory cells from leaves
-
recombinant enzyme from Escherichia coli by anion exchange and hydrophobic interaction chromatography followed by SDS-PAGE and gel excision
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recombinant enzyme from Escherichia coli strain BL21(DE3), native enzyme by oil gland secretory cell isolation procedure, two steps of anion exchange chromatography, hydroxyapatite chromatography, and beta-NADPH affinity chromatography, the activity is rapidly lost during purification on each matrix, 10fold purification accompanied by loss of over 98% of starting activity
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, functional expression in Escherichia coli strain BL21(DE3)
-
expression analysis with and without UV-B irradiation
-
expression in Escherichia coli strain BL21(DE3)
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
UV-B irradiation does not affect the enzyme expression neither in field plants not in growth chamber plants, overview
-
UV-B irradiation does not cause any significant variation in expression
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