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EC Tree
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
Synonyms
(-)-menthone:(3R)-menthol reductase, dehydrogenase, menthol, menthone:(-)-menthol reductase, MMR, monoterpenoid dehydrogenase,
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(-)-menthone:(3R)-menthol reductase
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dehydrogenase, menthol
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menthone:(-)-menthol reductase
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monoterpenoid dehydrogenase
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-
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MMR
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-
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(-)-menthol + NADP+ = (-)-menthone + NADPH + H+
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-
-
-
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(-)-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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(+)-isomenthone + NADPH
(+)-neoisomenthol + NADP+
-
-
-
-
?
(-)-menthone + NADPH
(3R)-menthol + NADP+
(-)-menthone + NADPH + H+
(-)-menthol + NADP+
(1R)-menthone + NADPH
(1R)-menthol + NADP+
(1R)-menthone + NADPH
(1R)-menthole + NADP+
(2R,5R)-isomenthone + NADPH + H+
(-)-menthol + NADP+
-
-
-
r
(2S,5R)-menthone + NADPH + H+
(-)-menthol + NADP+
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-
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r
d-isomenthone + NADPH
d-neoisomenthol + NADP+
additional information
?
-
(-)-menthone + NADPH
(3R)-menthol + NADP+
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-
-
?
(-)-menthone + NADPH
(3R)-menthol + NADP+
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(3R)-menthol is the main product, product determination by gas chromatography, overview
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ir
(-)-menthone + NADPH + H+
(-)-menthol + NADP+
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r
(-)-menthone + NADPH + H+
(-)-menthol + NADP+
menthone reduction is the physiological reaction of enzyme MMR
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r
(1R)-menthone + NADPH
(1R)-menthol + NADP+
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ir
-
?
(1R)-menthone + NADPH
(1R)-menthol + NADP+
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?
-
?
(1R)-menthone + NADPH
(1R)-menthole + NADP+
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?
-
?
(1R)-menthone + NADPH
(1R)-menthole + NADP+
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?
-
?
d-isomenthone + NADPH
d-neoisomenthol + NADP+
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?
-
?
d-isomenthone + NADPH
d-neoisomenthol + NADP+
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?
-
-
?
additional information
?
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primary monoterpene biosynthesis pathway, overview
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-
?
additional information
?
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monoterpenol is no substrate
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?
additional information
?
-
enzyme MMR has a preference for menthol over neomenthol from menthone and neoisomenthol over isomenthol with isomenthone
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-
?
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(+)-isomenthone + NADPH
(+)-neoisomenthol + NADP+
-
-
-
-
?
(-)-menthone + NADPH
(3R)-menthol + NADP+
-
-
-
-
?
(-)-menthone + NADPH + H+
(-)-menthol + NADP+
menthone reduction is the physiological reaction of enzyme MMR
-
-
r
(1R)-menthone + NADPH
(1R)-menthole + NADP+
additional information
?
-
-
primary monoterpene biosynthesis pathway, overview
-
-
?
(1R)-menthone + NADPH
(1R)-menthole + NADP+
-
?
-
?
(1R)-menthone + NADPH
(1R)-menthole + NADP+
-
?
-
?
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NADPH
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-
NADPH
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NADH far less effective
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Hg2+
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almost complete inhibition at 0.25 mM
iodoacetamide
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almost complete inhibition at 0.25 mM
N-ethylmaleimide
-
almost complete inhibition at 0.25 mM
p-hydroxymercuribenzoate
-
almost complete inhibition at 0.05 mM
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0.041
(+)-isomenthone
-
pH 7.0, 31°C, recombinant enzyme
0.003 - 0.25
(-)-menthone
0.003
(-)-menthone
-
pH 7.0, 31°C, recombinant enzyme
0.00012
NADPH
-
pH 7.0, 31°C, recombinant enzyme
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0.6
(-)-menthone
-
pH 7.0, 31°C, recombinant enzyme
2
(2R,5R)-isomenthone
recombinant His6-tagged enzyme, pH 7.0, 30°C
1.63
(2S,5R)-menthone
recombinant His6-tagged enzyme, pH 7.0, 30°C
0.6
NADPH
-
pH 7.0, 31°C, recombinant enzyme
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7.5
-
(-)-menthone + NADPH
7
-
-
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4.5 - 8.5
-
50% of maximal activity at pH 4.5 and pH 8.5
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-
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brenda
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UniProt
brenda
cv. Black Mitchum
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brenda
peppermint
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brenda
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-
brenda
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brenda
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epidermis
brenda
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metabolism
the enzyme is involved in menthol biosynthesis in the peppermint pathway, overview
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A0A1S5R263_MENPI
315
0
34590
TrEMBL
other Location (Reliability: 4 )
Q5CAF4_MENPI
311
0
34071
TrEMBL
other Location (Reliability: 4 )
A0A1S5R243_MENAR
253
0
27710
TrEMBL
other Location (Reliability: 4 )
A0A1S5R240_MENAR
155
0
16919
TrEMBL
other Location (Reliability: 4 )
A0A1S5R244_MENAR
313
0
34375
TrEMBL
other Location (Reliability: 4 )
A0A1S5R238_MENPI
280
0
31095
TrEMBL
other Location (Reliability: 4 )
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34070
-
x * 34070, amino acid sequence calculation
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?
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x * 34070, amino acid sequence calculation
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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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recombinant enzyme partially
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recombinant His6-tagged enzyme from Escherichia coli strain NiCO2(DE3) by nickel affinity chromatography and gel filtration
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DNA and amino acid sequence determination and analysis, expression in Escherichia coli
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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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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
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agriculture
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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
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
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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
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1.1.1.207 (-)-menthol dehydrogenase
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