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Information on EC 1.1.1.207 - (-)-menthol dehydrogenase
for references in articles please use BRENDA:EC1.1.1.207
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EC Tree 1 Oxidoreductases
1.1 Acting on the CH-OH group of donors
1.1.1 With NAD+ or NADP+ as acceptor
1.1.1.207 (-)-menthol dehydrogenase
IUBMB Comments
Not identical with EC 1.1.1.208 (+)-neomenthol dehydrogenase. Acts also on a number of other cyclohexanols and cyclohexenols.
The expected taxonomic range for this enzyme is: Mentha
showSynonyms
(-)-menthone:(3R)-menthol reductase, dehydrogenase, menthol, menthone:(-)-menthol reductase, MMR, monoterpenoid dehydrogenase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
dehydrogenase, menthol
-
-
-
-
MMR
monoterpenoid dehydrogenase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(-)-menthol + NADP+ = (-)-menthone + NADPH + H+
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
menthol biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(-)-menthol:NADP+ oxidoreductase
Not identical with EC 1.1.1.208 (+)-neomenthol dehydrogenase. Acts also on a number of other cyclohexanols and cyclohexenols.
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CAS REGISTRY NUMBER
COMMENTARY
81811-46-3
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(+)-isomenthone + NADPH
(+)-neoisomenthol + NADP+
-
Substrates: -
Products: -
Products: -
?
(2R,5R)-isomenthone + NADPH + H+
(-)-menthol + NADP+
Substrates: -
Products: -
Products: -
r
(2S,5R)-menthone + NADPH + H+
(-)-menthol + NADP+
Substrates: -
Products: -
Products: -
r
d-isomenthone + NADPH
d-neoisomenthol + NADP+
-
Substrates: ?
Products: -
Products: -
?
(-)-menthol + NADP+
(-)-menthone + NADPH + H+
Substrates: -
Products: -
Products: -
r
(-)-menthol + NADP+
(-)-menthone + NADPH + H+
Substrates: -
Products: -
Products: -
r
(-)-menthone + NADPH
(3R)-menthol + NADP+
-
Substrates: -
Products: (3R)-menthol is the main product, product determination by gas chromatography, overview
Products: (3R)-menthol is the main product, product determination by gas chromatography, overview
ir
(-)-menthone + NADPH + H+
(-)-menthol + NADP+
Substrates: -
Products: -
Products: -
r
(-)-menthone + NADPH + H+
(-)-menthol + NADP+
Substrates: menthone reduction is the physiological reaction of enzyme MMR
Products: -
Products: -
r
(-)-menthone + NADPH + H+
(-)-menthol + NADP+
Substrates: -
Products: -
Products: -
r
(-)-menthone + NADPH + H+
(-)-menthol + NADP+
Substrates: -
Products: -
Products: -
r
(1R)-menthone + NADPH + H+
(1R)-menthol + NADP+
-
Substrates: ir
Products: -
Products: -
?
(1R)-menthone + NADPH + H+
(1R)-menthol + NADP+
-
Substrates: ?
Products: -
Products: -
?
additional information
?
-
-
Substrates: primary monoterpene biosynthesis pathway, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: monoterpenol is no substrate
Products: -
Products: -
?
additional information
?
-
Substrates: enzyme MMR has a preference for menthol over neomenthol from menthone and neoisomenthol over isomenthol with isomenthone
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(+)-isomenthone + NADPH
(+)-neoisomenthol + NADP+
-
Substrates: -
Products: -
Products: -
?
(-)-menthone + NADPH + H+
(-)-menthol + NADP+
Substrates: menthone reduction is the physiological reaction of enzyme MMR
Products: -
Products: -
r
(1R)-menthone + NADPH + H+
(1R)-menthol + NADP+
-
Substrates: ?
Products: -
Products: -
?
additional information
?
-
-
Substrates: primary monoterpene biosynthesis pathway, overview
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
the enzyme is involved in menthol biosynthesis in the peppermint pathway, overview
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). A0A1S5R243_MENAR
253
0
27710
TrEMBL
Secretory Pathway (Reliability: 1)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
development of a one-pot (bio)synthesis of (1R,2S,5R)-(-)-menthol and (1S,2S,5R)-(+)-neomenthol from pulegone, using recombinant Escherichia coli extracts that contain the biosynthetic genes for an ene-reductase NtDBR from Nicotiana tabacum and two menthone dehydrogenases, MMR and MNMR from Mentha piperita, a modular engineering strategy to improve the final production level. Multigene-construct-derived enzyme mixtures production of menthone, isomenthone, menthol, and neomenthol, but no or poor production of neoisomenthol and isomenthol, overview
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His6-tagged enzyme from Escherichia coli strain NiCO2(DE3) by nickel affinity chromatography and gel filtration
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, expression in Escherichia coli
-
expression in Escherichia coli
recombinant expression of codon-optimized, C-terminally His6-tagged enzyme in Escherichia coli strain BL21(DE3)pLysS, recombinant expression of three multigene constructs: (i) NtDBR-His6-SD-MMRHis6-SD-His6-MNMR (DMN), (ii) NtDBR-His6-SD-MMRHis6 (DM), and (iii) NtDBR-His6-SD-His6-MNMR in Escherichia coli strain NiCO2(DE3), optimization of multigene expression
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
transcript level of menthol dehydrogenase/menthone reductase is highly upregulated in plants treated with calliterpenone, leading to increased content of menthone and menthol in oil
-
water stress decreases the gene expression levels of pulegone reductase and menthol dehydrogenase
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
synthesis
the enzyme is useful, together with menthone:(+)-neomenthol reductase (EC 1.1.1.208), for production of (1R,2S,5R)-(-)-menthol and (1S,2S,5R)-(+)-neomenthol from pulegone, development of a one-pot synthesis method, overview. Menthol isomers, (1R,2S,5R)-(-)-menthol, (1R,2S,5S)-(+)-isomenthol, (1S,2S,5R)-(+)-neomenthol, and (1R,2R,5R)-(+)-neoisomenthol, and carvone are used as additives in oral hygiene products and flavors in food and beverages, or cosmetics
agriculture
-
transcript level of menthol dehydrogenase/menthone reductase is highly upregulated in plants treated with calliterpenone, leading to increased content of menthone and menthol in oil
agriculture
-
water stress decreases the gene expression levels of pulegone reductase and menthol dehydrogenase, but increases the expression of trans-isopiperitenol dehydrogenase, isopiperitenone reductase and menthofuran synthase. The most of essential oil components (menthol, menthofuran, and plugene) are positively correlated with genes expression. Drought stress induces increasing contents of pulegone and menthofuran and reduces menthol percentages
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Kjonaas, R.; Martinkus-Taylor, C.; Croteau, R.
Metabolism of monoterpenes: Conversion of l-menthone tol-menthole and d-neomenthol by stereospecific dehydrogenases from peppermint (Mentha piperita) leaves
Plant Physiol.
69
1013-1017
1982
Mentha x piperita
brenda
Croteau, R.; Winters, J.N.
Demonstration of the intercellular compartmentation of l-menthone metabolism in peppermint (Mentha piperita) leaves
Plant Physiol.
69
975-977
1982
Mentha x piperita
brenda
Davis, E.M.; Ringer, K.L.; McConkey, M.E.; Croteau, R.
Monoterpene metabolism. Cloning, expression, and characterization of menthone reductases from peppermint
Plant Physiol.
137
873-881
2005
Mentha x piperita
brenda
Bose, S.K.; Yadav, R.K.; Mishra, S.; Sangwan, R.S.; Singh, A.K.; Mishra, B.; Srivastava, A.K.; Sangwan, N.S.
Effect of gibberellic acid and calliterpenone on plant growth attributes, trichomes, essential oil biosynthesis and pathway gene expression in differential manner in Mentha arvensis L
Plant Physiol. Biochem.
66
150-158
2013
Mentha arvensis
brenda
Toogood, H.; Cheallaigh, A.; Tait, S.; Mansell, D.; Jervis, A.; Lygidakis, A.; Humphreys, L.; Takano, E.; Gardiner, J.; Scrutton, N.
Enzymatic menthol production: one-pot approach using engineered Escherichia coli
ACS Synth. Biol.
4
1112-1123
2015
Mentha x piperita (Q5CAF4)
brenda
Rahimi, Y.; Taleei, A.; Ranjbar, M.
Changes in the expression of key genes involved in the biosynthesis of menthol and menthofuran in Mentha piperita L. under drought stress
Acta Physiol. Plant.
39
203
2017
Mentha x piperita
-
brenda
Akhtar, M.; Qamar, N.; Yadav, P.; Kulkarni, P.; Kumar, A.; Shasany, A.
Comparative glandular trichome transcriptome-based gene characterization reveals reasons for differential (-)-menthol biosynthesis in Mentha species
Physiol. Plant.
160
128-141
2017
Mentha arvensis (A0A1S5R244), Mentha arvensis (A0A1S5R243), Mentha arvensis (A0A1S5R240), Mentha x piperita (Q5CAF4), Mentha x piperita (A0A1S5R263), Mentha x piperita (A0A1S5R238)
brenda
EXTERNAL LINKS (specific for EC-Number 1.1.1.207)
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