KEGG ENZYME: 1.14.14.52

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 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(CYP2C19) 100996034(CYP2C9)

GGO:	101126456 101151965

PON:	100439483(CYP2C19) 100450749(CYP2C9)

PPYG:

129006337 129006530

NLE:	100591471 100601437

HMH:	116457268 116457271

SSYN:

129468897 129468985

MCC:	678686(CYP2C75) 678695(CYP2C9)

MCF:	102115450(CYP2C9) 102147103(CYP2C19)

MTHB:

126962028 126962032

MNI:	105479916 105479949

CSAB:

103216299(CYP2C19) 103216301(CYP2C9)

CATY:

105575618 105581138 105586929 105586938

PANU:

100997824 101012978

TGE:	112631549 112631550

MLEU:

105534699 105534700 105535382 105536626

RRO:	104665355 104666123

TFN:	117083900 117092015

PTEH:

111531037 111552212

CANG:

105501587 105504516 105504517

CJC:	100389947(CYP2C19)

SBQ:

101041912

CIMI:

108281686(CYP2C19)

ANAN:

110568730 135273997

CSYR:

103277060

PCOQ:

105822723

OGA:

100950266

DORD:

106001520

NCAR:

124985776

MMMA:

107149734

GAS:	123236335 123238232

TVP:	118828297 118828298 118828299 118828301 118828302

» 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

[ag:ADC94830]