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Information on EC 1.14.14.143 - (+)-menthofuran synthase
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1.14.14.143 (+)-menthofuran synthaseIUBMB Comments
A cytochrome P-450 (heme-thiolate) protein. The conversion of substrate into product involves the hydroxylation of the syn-methyl (C9), intramolecular cyclization to the hemiketal and dehydration to the furan . This is the second cytochrome P-450-mediated step of monoterpene metabolism in peppermint, with the other step being catalysed by EC 1.14.14.99, (S)-limonene 3-monooxygenase .
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Word Map
- 1.14.14.143
- mentha
-
+-menthofuran
- peppermint
- piperita
-
+-pulegone
-
terpenoids
-
undesirable
-
monoterpene
- gpp
- 1-deoxy-d-xylulose-5-phosphate
-
geranyl
- reductoisomerase
- aquatica
- menthone
-
cosuppression
-
isopentenyl
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
menthofuran synthase, (+)-menthofuran synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(+)-pulegone-9-hydroxylase
EC 1.14.13.104
-
-
formerly
-
menthofuran synthase
MFS
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2 = (+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
(+)-pulegone,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (9-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein. The conversion of substrate into product involves the hydroxylation of the syn-methyl (C9), intramolecular cyclization to the hemiketal and dehydration to the furan [1]. This is the second cytochrome P-450-mediated step of monoterpene metabolism in peppermint, with the other step being catalysed by EC 1.14.14.99, (S)-limonene 3-monooxygenase [1].
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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
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
?
-
-
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, 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
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
hydroxylation of the syn-methyl group of (+)-pulegone, spontaneous intramolecular cyclization to the hemiketal, and dehydration to the furan
GC-MS product analysis
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
pathways for monoterpene biosynthesis in peppermint, overview
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
the principal pathway for monoterpene biosynthesis in peppermint, overview
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
hydroxylation of the syn-methyl group of (+)-pulegone, spontaneous intramolecular cyclization to the hemiketal, and dehydration to the furan
-
-
?
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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
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
?
-
-
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, 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
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
pathways for monoterpene biosynthesis in peppermint, overview
-
-
?
(+)-pulegone + [reduced NADPH-hemoprotein reductase] + O2
(+)-menthofuran + [oxidized NADPH-hemoprotein reductase] + H2O
-
the principal pathway for monoterpene biosynthesis in peppermint, overview
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH-hemoprotein reductase
-
A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
-
NADPH-hemoprotein reductase
A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
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pH OPTIMUM
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
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
-
the enzyme is involved in the terpene biosynthesis pathway, overview
physiological function
Trichoderma viride Tv-1511-inoculated peppermint produces higher concentrations of menthone, menthol, and pulegone and lower concentrations of menthofuran than uninoculated seedlings. In T. viride Tv-1511-incubated peppermint, pretreatment with MAPK inhibitor PD98059 results in the marked increase in the transcript of menthofuran synthase
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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). MFS_MENPI
493
1
55360
Swiss-Prot
Chloroplast (Reliability: 3)
A0A2P6REK2_ROSCH
118
0
13652
TrEMBL
Mitochondrion (Reliability: 5)
A0A2P6P549_ROSCH
87
0
9638
TrEMBL
other Location (Reliability: 3)
A0A396ITH3_MEDTR
196
0
21903
TrEMBL
other Location (Reliability: 4)
A0A2G9FYR4_9LAMI
369
1
42158
TrEMBL
Mitochondrion (Reliability: 2)
A0A2G9HN86_9LAMI
362
0
41261
TrEMBL
other Location (Reliability: 5)
A0A2G9HNW3_9LAMI
431
0
49186
TrEMBL
other Location (Reliability: 4)
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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
-
expression of a homologous antisense version of the menthofuran synthase cDNA, both driven by the CaMV 35S promoter, in Mentha x piperita plants leads to altered essential oil composition very similar in composition to the DXR46 plant transformed with the sense version of the reductoisomerase, overview
additional information
-
overexpression and cosuppression of mfs results in the respective increase or decrease in the production of menthofuran
additional information
-
hybrid cross-breading of menthofuran-rich Mentha piperita cv. Kukrail with Mentha arvensis cv. Kosi, which does not produce menthofuran, leads to plants with altered oil quality, chemoprofiling of essential oil, altered phenotype of genotype CIMAP-Patra, overview
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determinationand analysis, functional expression in Saccharomyces cerevisiae strains WAT11U and WAT21U, which constitutively express two different isoforms of the Arabidposis thaliana NADPH-cytochrome P450 reductase, and in Escherichia coli strain JM109
-
expression of a homologous antisense version of the menthofuran synthase cDNA, both driven by the CaMV 35S promoter, in Mentha x piperita plants using Agrobacterium tumefaciens strain EHA105 transfection method
-
gene mfs, expression under control of the CaMV 35S promoter in transformed peppermint plants
-
real-time PCR-based transcript profiling of key terpenoid pathway genes, i.e. menthofuran synthase, pulegone reductase and menthol dehydrogenase, correlated with the menthofuran-rich phenotype in var. CIMAP-Patra
-
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
increasing Cd level in the soil is followed by a reduction in the expression of menthone reductase and pulegone reductase genes, while an increase in the expression of menthofuran synthase is observed
Mn2+ induces the enzyme pathway, the expression level of Mfs is significantly higher in the leaves of the 0.04 mM-treated plants than the control and other treatments groups, transcriptome analysis, detailed overview
Trichoderma viride Tv-1511-inoculated peppermint produces higher concentrations of menthone, menthol, and pulegone and lower concentrations of menthofuran than uninoculated seedlings. Menthofuran synthase is downregulated by Trichoderma viride Tv-1511
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
increasing Cd level in the soil is followed by a reduction in the expression of menthone reductase and pulegone reductase genes, while an increase in the expression of menthofuran synthase is observed
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Mahmoud, S.S.; Croteau, R.B.
Metabolic engineering of essential oil yield and composition in mint by altering expression of deoxyxylulose phosphate reductoisomerase and menthofuran synthase
Proc. Natl. Acad. Sci. USA
98
8915-8920
2001
Mentha x piperita
brenda
Bertea, C.M.; Schalk, M.; Karp, F.; Maffei, M.; Croteau, R.
Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene
Arch. Biochem. Biophys.
390
279-286
2001
Mentha x piperita, Mentha pulegium
brenda
Mahmoud, S.S.; Croteau, R.B.
Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase
Proc. Natl. Acad. Sci. USA
100
14481-14486
2003
Mentha x piperita
brenda
Atsbaha Zebelo, S.; Bertea, C.M.; Bossi, S.; Occhipinti, A.; Gnavi, G.; Maffei, M.E.
Chrysolina herbacea modulates terpenoid biosynthesis of Mentha aquatica L
PLoS ONE
6
e17195
2011
Mentha aquatica
brenda
Lange, B.M.; Mahmoud, S.S.; Wildung, M.R.; Turner, G.W.; Davis, E.M.; Lange, I.; Baker, R.C.; Boydston, R.A.; Croteau, R.B.
Improving peppermint essential oil yield and composition by metabolic engineering
Proc. Natl. Acad. Sci. USA
108
16944-16949
2011
Mentha x piperita (Q947B7), Mentha x piperita
brenda
Kumar, B.; Shukla, A.; Samad, A.
Development and characterization of the menthofuran-rich inter-specific hybrid peppermint variety CIMAP-Patra
Mol. Breed.
34
717-724
2014
Mentha x piperita, no activity in Mentha arvensis cv. Kosi
-
brenda
Nazari, M.; Zarinkamar, F.; Soltani, B.M.
Physiological, biochemical and molecular responses of Mentha aquatica L. to manganese
Plant Physiol. Biochem.
120
202-212
2017
Mentha x piperita (Q947B7)
brenda
Azimychetabi, Z.; Sabokdast Nodehi, M.; Karami Moghadam, T.; Motesharezadeh, B.
Cadmium stress alters the essential oil composition and the expression of genes involved in their synthesis in peppermint (Mentha piperita L.)
Ind. Crops Prod.
168
113602
2021
Mentha x piperita (Q947B7)
-
brenda
Guo, K.; Sui, Y.; Li, Z.; Huang, Y.; Zhang, H.; Wang, W.
Colonization of Trichoderma viride Tv-1511 in peppermint (Mentha x piperita L.) roots promotes essential oil production by triggering ROS-mediated MAPK activation
Plant Physiol. Biochem.
151
705-718
2020
Mentha x piperita (Q947B7)
brenda
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Release 2023.1 (January 2023)
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