Information on EC 1.14.13.104 - (+)-menthofuran synthase

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The expected taxonomic range for this enzyme is: Mentha

EC NUMBER
COMMENTARY
1.14.13.104
-
RECOMMENDED NAME
GeneOntology No.
(+)-menthofuran synthase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(+)-pulegone + NADPH + H+ + O2 = (+)-menthofuran + NADP+ + H2O
show the reaction diagram
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
menthol biosynthesis
-
Monoterpenoid biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
(+)-pulegone,NADPH:oxygen oxidoreductase (9-hydroxylating)
A heme-thiolate protein (P-450). 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 1.14.13.47, (S)-limonene 3-monooxygenase [1].
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
(+)-pulegone-9-hydroxylase
Q947B7
-
(+)-pulegone-9-hydroxylase
-
-
menthofuran synthase
Q947B7
-
menthofuran synthase
-
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
cv. Black Mitcham
-
-
Manually annotated by BRENDA team
cv. Black Mitcham, gene mfs
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
show the reaction diagram
-, Q947B7
-
-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
show the reaction diagram
-
pathways for monoterpene biosynthesis in peppermint, overview
-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
show the reaction diagram
-
the principal pathway for monoterpene biosynthesis in peppermint, overview
-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
show the reaction diagram
-
hydroxylation of the syn-methyl group of (+)-pulegone, spontaneous intramolecular cyclization to the hemiketal, and dehydration to the furan
-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
show the reaction diagram
-, Q947B7
hydroxylation of the syn-methyl group of (+)-pulegone, spontaneous intramolecular cyclization to the hemiketal, and dehydration to the furan
GC-MS product analysis
-
?
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
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
show the reaction diagram
Q947B7
-
-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
show the reaction diagram
-
pathways for monoterpene biosynthesis in peppermint, overview
-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
show the reaction diagram
-
the principal pathway for monoterpene biosynthesis in peppermint, overview
-
-
?
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
-
-
-
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
cytochrome P450
-, Q947B7
a cytochrome P450 monooxygenase
-
cytochrome P450
-
a cytochrome P450 monooxygenase
-
NADPH
-, Q947B7
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Fe2+
-, Q947B7
-
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7.4
-
-, Q947B7
assay at
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
30
-
-, Q947B7
assay at
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-, Q947B7
secretory cells
Manually annotated by BRENDA team
-
secretory cells
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
-, Q947B7
x * 55360, sequence calculation
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
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
-, Q947B7
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
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
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