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Information on EC 1.1.1.208 - (+)-neomenthol dehydrogenase
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EC Tree
1.1.1.208 (+)-neomenthol dehydrogenaseIUBMB Comments
Not identical with EC 1.1.1.207 (-)-menthol dehydrogenase. Acts also on a number of other cyclohexanols and cyclohexenols.
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
menthone:(+)-(3s)-neomenthol reductase, (-)-menthone:(+)-neomenthol reductase, (+)-neomenthol dehydrogenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
dehydrogenase, neomenthol
-
-
-
-
menthone:(+)-(3S)-neomenthol reductase
monoterpenoid dehydrogenase
-
-
-
-
additional information
additional information
the enzyme is a member of the short chain dehydrogenase/reductase, SDR, superfamily
additional information
the enzyme is a member of the short chain dehydrogenase/reductase, SDR, superfamily, which adopts a unique alpha/beta structure known as the Rossmann fold
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(+)-neomenthol + NADP+ = (-)-menthone + NADPH + H+
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
(+)-neomenthol:NADP+ oxidoreductase
Not identical with EC 1.1.1.207 (-)-menthol dehydrogenase. Acts also on a number of other cyclohexanols and cyclohexenols.
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CAS REGISTRY NUMBER
COMMENTARY
81811-47-4
-
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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
(+)-neomenthol + NADP+
(-)-menthone + NADPH + H+
reaction proceeds via (-)-menthone
-
-
r
(-)-menthone + NADPH + H+
(+)-neomenthol + NADP+
-
main product, plus some (-)-menthol
-
r
(-)-menthone + NADPH + H+
(+)-neomenthol + NADP+
-
-
-
r
(-)-menthone + NADPH + H+
(+)-neomenthol + NADP+
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-
-
r
(-)-menthone + NADPH + H+
(+)-neomenthol + NADP+
menthone reduction is the physiological reaction of enzyme MNMR
-
-
r
(-)-menthone + NADPH + H+
(3S)-neomenthol + NADP+
in vitro antimicrobial activities of menthone, neomenthol and menthol, overview
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-
r
(-)-menthone + NADPH + H+
(3S)-neomenthol + NADP+
CaMNR1 converts (-)-menthone to 93% (3S)-neomenthol and 7% (3R)-menthol at pH 7.5, and to 72% (3S)-neomenthol and 28% (3R)-menthol at pH 9.0 with NADPH as a cofactor
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-
r
(-)-menthone + NADPH + H+
(3S)-neomenthol + NADP+
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low activity in the reverse reaction
(3S)-neomenthol is the main product, product determination by gas chromatography, overview
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r
additional information
?
-
the menthone reductase gene CaMNR1 positively regulates plant defenses against a broad spectrum of pathogens, overview
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-
?
additional information
?
-
no substrates for reduction: carvone and isopiperitenone. No substrates in dehydrogenase reaction: (+)-borneol, (-)-borneol, (+)-menthol and (-)-neomenthol
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-
?
additional information
?
-
CaMNR1 gene plays a role in regulating the resistance of pepper plants at the mRNA and protein levels, the menthone reductase gene CaMNR1 positively regulates plant defenses against a broad spectrum of pathogens, overview
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-
?
additional information
?
-
-
primary monoterpene biosynthesis pathway, overview
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-
?
additional information
?
-
enzyme MNMR has a preference for menthone over isomenthone
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-
?
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NATURAL SUBSTRATE
NATURAL 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
(-)-menthone + NADPH + H+
(+)-neomenthol + NADP+
menthone reduction is the physiological reaction of enzyme MNMR
-
-
r
(-)-menthone + NADPH + H+
(3S)-neomenthol + NADP+
in vitro antimicrobial activities of menthone, neomenthol and menthol, overview
-
-
r
additional information
?
-
the menthone reductase gene CaMNR1 positively regulates plant defenses against a broad spectrum of pathogens, overview
-
-
?
additional information
?
-
CaMNR1 gene plays a role in regulating the resistance of pepper plants at the mRNA and protein levels, the menthone reductase gene CaMNR1 positively regulates plant defenses against a broad spectrum of pathogens, overview
-
-
?
additional information
?
-
-
primary monoterpene biosynthesis pathway, overview
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH
the enzyme contains the coenzyme binding domain motif I: GxxxGxG
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
CaMNR1 is induced in leaves by bacterial infection and abiotic elicitor treatments. Under drought conditions, the CaMNR1 transcript is rapidly induced within 1 h and thereafter gradually increased to 25 h, while H2O2, cold and mechanical wounding treatment do not induce CaMNR1 expression in pepper leaves
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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
0.2
(2R,5R)-isomenthone
recombinant His6-tagged enzyme, pH 7.0, 30°C
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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
additional information
the pH alters the stereospecificity of the enzyme
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
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
additional information
CaMNR1 is expressed in an organ-specific manner, no activity in uninduced leaves, stems, roots, or green fruits
brenda
the enzyme is induced in pepper leaves during compatible and incompatible interactions with Xcv, and by bacterial infection and abiotic elicitor treatments
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
the enzyme is involved in neomenthol 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). SDR1_ARATH
296
0
32803
Swiss-Prot
other Location (Reliability: 3)
MNR1_CAPAN
314
0
34758
Swiss-Prot
other Location (Reliability: 3)
A0A0N1NQL5_9ACTN
243
0
25029
TrEMBL
-
A0A2I0BGM1_9ASPA
158
0
16872
TrEMBL
other Location (Reliability: 4)
A0A5B6ZUN3_DAVIN
264
4
29787
TrEMBL
Secretory Pathway (Reliability: 2)
A0A0N1FSA2_9ACTN
245
0
25502
TrEMBL
-
A0A2I0BGM6_9ASPA
307
0
33097
TrEMBL
Chloroplast (Reliability: 5)
A0A0N1GCL6_9ACTN
231
0
24275
TrEMBL
-
A0A2I0BGR1_9ASPA
307
0
33371
TrEMBL
Chloroplast (Reliability: 3)
A0A0N1GIC1_9ACTN
253
0
26474
TrEMBL
-
A0A396I9J0_MEDTR
120
0
13279
TrEMBL
other Location (Reliability: 3)
A0A2I0B2E8_9ASPA
319
0
35242
TrEMBL
Mitochondrion (Reliability: 2)
G8NSX7_GRAMM
Granulicella mallensis (strain ATCC BAA-1857 / DSM 23137 / MP5ACTX8)
243
0
25639
TrEMBL
-
A0A0N1NN49_9ACTN
272
0
28285
TrEMBL
-
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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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
additional information
AtSDR1 virus-induced gene silencing and ectopic overexpression in Arabidopsis thaliana plants leads to significantly more susceptible to Xanthomonas campestris pv. vesicatoria and Colletotrichum coccodes infection, and lower expression levels of salicylic acidresponsive CaBPR1 and CaPR10 and jasmonic acid-responsive CaDEF1 compared to wild-type plants, phenotype, overview
additional information
CaMNR1 tobacco rattle virus-mediated virus-induced gene silencing and ectopic overexpression in pepper and Arabidopsis thaliana plants, transgenic CaMNR1-silenced pepper plants are significantly more susceptible to Xanthomonas campestris pv. vesicatoria and Colletotrichum coccodes infection, and express lower levels of salicylic acidresponsive CaBPR1 and CaPR10 and jasmonic acid-responsive CaDEF1 compared to wild-type plants, while CaMNR1-overexpression transgenic Arabidopsis thaliana plants exhibit enhanced resistance to the hemi-biotrophic pathogen Pseudomonas syringae pv. tomato DC3000 and the biotrophic pathogen Hyaloperonospora parasitica isolate Noco2, accompanied by induction of AtPR1 and AtPDF1.2, phenotypes, overview
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 enzyme from Escherichia coli to homogeneity
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
gene CaMNR1, DNA and amino acid sequence determination and analysis, phylogenetic tree, overexpression in Escherichia coli and in transgenic Arabidopsis thaliana plants
recombinant expression of codon-optimized, C- and N-terminally double-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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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
the enzyme is useful, together with menthone:(-)-menthol reductase (EC 1.1.1.207), 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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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
Choi, H.W.; Lee, B.G.; Kim, N.H.; Park, Y.; Lim, C.W.; Song, H.K.; Hwang, B.K.
A role for a menthone reductase in resistance against microbial pathogens in plants
Plant Physiol.
148
383-401
2008
Capsicum annuum (B2X050), Arabidopsis thaliana (Q9M2E2)
brenda
Ryden, A.; Ruyter-Spira, C.; Litjens, R.; Takahashi, S.; Quax, W.; Osada, H.; Bouwmeester, H.; Kayser, O.
Molecular cloning and characterization of a broad substrate terpenoid oxidoreductase from Artemisia annua
Plant Cell Physiol.
51
1219-1228
2010
Artemisia annua (D1MI43)
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 (Q06ZW2)
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 x piperita (A0A1S5R238), Mentha x piperita (A0A1S5R263), Mentha arvensis (A0A1S5R240), Mentha arvensis (A0A1S5R244)
brenda
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Release 2023.1 (January 2023)
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