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Enzyme Nomenclature
Information on EC 1.3.1.81 - (+)-pulegone reductase
for references in articles please use BRENDA:EC1.3.1.81
Word Map on EC 1.3.1.81
- 1.3.1.81
- peppermint
-
monoterpene
- piperita
- mentha
-
+-menthofuran
-
terpenoids
- diphosphate
-
geranyl
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The expected taxonomic range for this enzyme is: Mentha
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EC NUMBER 
COMMENTARY 
1.3.1.81
-
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RECOMMENDED NAME
GeneOntology No.
(+)-pulegone reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(+)-isomenthone + NADP+ = (+)-pulegone + NADPH + H+
-
-
-
-
(-)-menthone + NADP+ = (+)-pulegone + NADPH + H+
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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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.
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CAS REGISTRY NUMBER
COMMENTARY
138066-95-2
-
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
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
additional information
-
UV-B irradiation does not affect the enzyme expression neither in field plants not in growth chamber plants, overview
additional information
-
simulation of the effects of environmental stress conditions on essential oil profiles, glandular trichome dynamics, overview. Substantially higher proportion of large-sized glandular trichomes, fewer medium-sized trichomes, and no small trichomes on plants lead to decreased (+)-pulegone and increased (-)-menthone contents
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
-
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
pathways of monoterpene biosynthesis, overview
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
-
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
-
ratio of 90% (-)-menthone and 10% (+)-isomenthone
-
r
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
branchpoint enzyme in essential oil biosynthesis
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
pathways of monoterpene biosynthesis, overview
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
regulation of pulegone metabolism involves menthofuran, 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
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
the enzyme is required for catalyzation of the reduction of the DELTA4,8 double bond to produce menthone on route to menthol, monoterpene biosynthetic pathways in peppermint, overview
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
the NADPH-dependent reductase reduces the conjugated double bond to yield both (-)-menthone and (+)-isomenthone
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
the reductase catalyzes the reduction of the 4(8)-double bond of (+)-pulegone to produce both (-)-menthone and (+)-isomenthone in a 70:30 ratio
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
the reductase catalyzes the reduction of the 4(8)-double bond of (+)-pulegone to produce both (-)-menthone and (+)-isomenthone in a 70:30 ratio, product analysis by GC-MS, stereospecific reductase
-
-
?
additional information
?
-
-
kinetic modeling and simulations of the developmental patterns of monoterpenoid essential oil accumulation in peppermint, overview
-
-
-
additional information
?
-
-
pathways for monoterpene biosynthesis in peppermint, overview
-
-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
pathways of monoterpene biosynthesis, overview
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
-
ratio of 90% (-)-menthone and 10% (+)-isomenthone
-
r
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
branchpoint enzyme in essential oil biosynthesis
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
pathways of monoterpene biosynthesis, overview
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
regulation of pulegone metabolism involves menthofuran, 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
-
-
?
2 (+)-pulegone + 2 NADPH + 2 H+
(-)-menthone + (+)-isomenthone + 2 NADP+
-
the enzyme is required for catalyzation of the reduction of the DELTA4,8 double bond to produce menthone on route to menthol, monoterpene biosynthetic pathways in peppermint, overview
-
-
?
additional information
?
-
-
kinetic modeling and simulations of the developmental patterns of monoterpenoid essential oil accumulation in peppermint, overview
-
-
-
additional information
?
-
-
pathways for monoterpene biosynthesis in peppermint, overview
-
-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
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
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
LITERATURE
IMAGE
additional information
additional information
-
kinetic data analysis, overview
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
secretory cells of peltate glandular trichomes with abundant labeling corresponding to the secretory phase of gland development
-
essential oil biosynthetic enzyme expression patterns, overview
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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
recombinant enzyme from Escherichia coli by anion exchange and hydrophobic interaction chromatography followed by SDS-PAGE and gel excision
-
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)
-
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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
-
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LINKS TO OTHER DATABASES (specific for EC-Number 1.3.1.81)
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