KEGG   ORTHOLOGY: K07382
Entry
K07382            Tight     KO                                     

Name
E1.14.14.52
Definition
(S)-limonene 7-monooxygenase [EC:1.14.14.52]
Pathway
ko00902  Monoterpenoid biosynthesis
ko00903  Limonene and pinene degradation
ko01110  Biosynthesis of secondary metabolites
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00902 Monoterpenoid biosynthesis
    K07382  E1.14.14.52; (S)-limonene 7-monooxygenase
   00903 Limonene and pinene degradation
    K07382  E1.14.14.52; (S)-limonene 7-monooxygenase
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
    1.14.14.52  (S)-limonene 7-monooxygenase
     K07382  E1.14.14.52; (S)-limonene 7-monooxygenase
Other DBs
RN: R02470
GO: 0018676
Genes
AG: ADC94830
Reference
  Authors
Mau CJ, Karp F, Ito M, Honda G, Croteau RB
  Title
A candidate cDNA clone for (-)-limonene-7-hydroxylase from Perilla frutescens.
  Journal
Phytochemistry 71:373-9 (2010)
DOI:10.1016/j.phytochem.2009.12.002
  Sequence
Reference
PMID:2297225
  Authors
Karp F, Mihaliak CA, Harris JL, Croteau R
  Title
Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves.
  Journal
Arch Biochem Biophys 276:219-26 (1990)
DOI:10.1016/0003-9861(90)90029-X

KEGG   ENZYME: 1.14.14.52
Entry
EC 1.14.14.52               Enzyme                                 

Name
(S)-limonene 7-monooxygenase;
(-)-limonene 7-monooxygenase;
(-)-limonene hydroxylase;
(-)-limonene monooxygenase;
(-)-limonene,NADPH:oxygen oxidoreductase (7-hydroxylating)
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
(S)-limonene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (7-hydroxylating)
Reaction(IUBMB)
(S)-limonene + [reduced NADPH---hemoprotein reductase] + O2 = (-)-perillyl alcohol + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R02470]
Reaction(KEGG)
R02470
Substrate
(S)-limonene [CPD:C00521];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
(-)-perillyl alcohol [CPD:C02452];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme thiolate) enzyme. The enzyme, characterized from the plant Perilla frutescens, participates in the biosynthesis of perillyl aldehyde, the major constituent of the essential oil that accumulates in the glandular trichomes of this plant. Some forms of the enzyme also catalyse the oxidation of (-)-perillyl alcohol to (-)-perillyl aldehyde.
History
EC 1.14.14.52 created 1992 as EC 1.14.13.49, modified 2003, transferred 2017 to EC 1.14.14.52
Pathway
ec00902  Monoterpenoid biosynthesis
ec00903  Limonene and pinene degradation
ec01110  Biosynthesis of secondary metabolites
Orthology
K07382  (S)-limonene 7-monooxygenase
K14732  limonene hydroxylase
K17719  cytochrome P450 family 2 subfamily C9
K17721  cytochrome P450 family 2 subfamily C19
Genes
HSA: 1557(CYP2C19) 1559(CYP2C9)
PTR: 100616515(CYP2C9) 740956(CYP2C19)
PPS: 100995695 100996034
GGO: 101126456 101151965
PON: 100439483 100450749
NLE: 100591471 100601437
MCC: 678686(CYP2C75) 678695(CYP2C9)
MCF: 102115450(CYP2C43) 102147103(CYP2C75)
CSAB: 103216299(CYP2C19) 103216301(CYP2C9)
RRO: 104665355 104666123
CJC: 100389947(CYP2C19)
SBQ: 101041912
 » show all
Reference
1  [PMID:2297225]
  Authors
Karp F, Mihaliak CA, Harris JL, Croteau R
  Title
Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves.
  Journal
Arch Biochem Biophys 276:219-26 (1990)
DOI:10.1016/0003-9861(90)90029-X
Reference
2  [PMID:20079506]
  Authors
Mau CJ, Karp F, Ito M, Honda G, Croteau RB
  Title
A candidate cDNA clone for (-)-limonene-7-hydroxylase from Perilla frutescens.
  Journal
Phytochemistry 71:373-9 (2010)
DOI:10.1016/j.phytochem.2009.12.002
  Sequence
Reference
3  [PMID:27890582]
  Authors
Fujiwara Y, Ito M
  Title
Molecular cloning and characterization of a Perilla frutescens cytochrome P450 enzyme that catalyzes the later steps of perillaldehyde biosynthesis.
  Journal
Phytochemistry 134:26-37 (2017)
DOI:10.1016/j.phytochem.2016.11.009
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.52
IUBMB Enzyme Nomenclature: 1.14.14.52
ExPASy - ENZYME nomenclature database: 1.14.14.52
BRENDA, the Enzyme Database: 1.14.14.52
CAS: 122653-75-2

KEGG   REACTION: R02470
Entry
R02470                      Reaction                               

Name
(S)-limonene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (7-hydroxylating)
Definition
(S)-Limonene + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (-)-Perillyl alcohol + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
Reaction class
RC00001  C00005_C00006
RC00724  C00521_C02452
Enzyme
Pathway
rn00902  Monoterpenoid biosynthesis
rn00903  Limonene and pinene degradation
rn01110  Biosynthesis of secondary metabolites
Orthology
K07382  (S)-limonene 7-monooxygenase [EC:1.14.14.52]
K14732  limonene hydroxylase [EC:1.14.14.51 1.14.14.52 1.1.1.243 1.1.1.144]
Other DBs
RHEA: 23435

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