KEGG   ORTHOLOGY: K15093
Entry
K15093            Tight     KO                                     

Name
E1.14.14.143
Definition
(+)-menthofuran synthase [EC:1.14.14.143]
Pathway
ko00902  Monoterpenoid biosynthesis
ko01110  Biosynthesis of secondary metabolites
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00902 Monoterpenoid biosynthesis
    K15093  E1.14.14.143; (+)-menthofuran synthase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.143  (+)-menthofuran synthase
     K15093  E1.14.14.143; (+)-menthofuran synthase
Other DBs
RN: R08923
GO: 0052582
Genes
AG: AAL06397
Reference
  Authors
Bertea CM, Schalk M, Karp F, Maffei M, Croteau R
  Title
Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene.
  Journal
Arch Biochem Biophys 390:279-86 (2001)
DOI:10.1006/abbi.2001.2378
  Sequence
Reference
  Authors
Mahmoud SS, Croteau RB
  Title
Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase.
  Journal
Proc Natl Acad Sci U S A 100:14481-6 (2003)
DOI:10.1073/pnas.2436325100
  Sequence

KEGG   ENZYME: 1.14.14.143
Entry
EC 1.14.14.143              Enzyme                                 

Name
(+)-menthofuran synthase;
menthofuran synthase;
(+)-pulegone 9-hydroxylase;
(+)-MFS;
cytochrome P450 menthofuran synthase
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
(+)-pulegone,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (9-hydroxylating)
Reaction(IUBMB)
(+)-pulegone + [reduced NADPH---hemoprotein reductase] + O2 = (+)-menthofuran + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R08923]
Reaction(KEGG)
R08923
Substrate
(+)-pulegone [CPD:C09893];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
(+)-menthofuran [CPD:C18025];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
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].
History
EC 1.14.14.143 created 2008 as EC 1.14.13.104, transferred 2018 to EC 1.14.14.143
Pathway
ec00902  Monoterpenoid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K15093  (+)-menthofuran synthase
Reference
1  [PMID:11396930]
  Authors
Bertea CM, Schalk M, Karp F, Maffei M, Croteau R
  Title
Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene.
  Journal
Arch Biochem Biophys 390:279-86 (2001)
DOI:10.1006/abbi.2001.2378
  Sequence
Reference
2  [PMID:14623962]
  Authors
Mahmoud SS, Croteau RB
  Title
Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase.
  Journal
Proc Natl Acad Sci U S A 100:14481-6 (2003)
DOI:10.1073/pnas.2436325100
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.143
IUBMB Enzyme Nomenclature: 1.14.14.143
ExPASy - ENZYME nomenclature database: 1.14.14.143
BRENDA, the Enzyme Database: 1.14.14.143

KEGG   REACTION: R08923
Entry
R08923                      Reaction                               

Name
(+)-pulegone,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (9-hydroxylating)
Definition
Pulegone + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (+)-Menthofuran + [Oxidized NADPH---hemoprotein reductase] + 2 H2O
Equation
Comment
multi-step reaction (9-hydroxylation, cyclization and dehydration)
Reaction class
RC02978  C09893_C18025
Enzyme
Pathway
rn00902  Monoterpenoid biosynthesis
rn01110  Biosynthesis of secondary metabolites
Orthology
K15093  (+)-menthofuran synthase [EC:1.14.14.143]
Other DBs
RHEA: 25661

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