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Information on EC 1.14.14.52 - (S)-limonene 7-monooxygenase

for references in articles please use BRENDA:EC1.14.14.52

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EC Tree

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

IUBMB Comments

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.

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

Reaction Schemes

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(S)-limonene

[reduced NADPH-hemoprotein reductase]

(-)-perillyl alcohol

[oxidized NADPH-hemoprotein reductase]

H2O

Synonyms

(-)-limonene hydroxylase, show all synonyms

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

(-)-limonene 7-monooxygenase

(-)-limonene hydroxylase

(-)-limonene,NADPH:oxygen oxidoreductase (7-hydroxylating

(-)-limonene-7-hydroxylase

Perilla frutescens

713236

oxygenase, (-)-limonene mono-

additional information

Perilla frutescens

the enzyme is a cytochrome P450 limonene hydroxylase

713236

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-perillyl alcohol + [oxidized NADPH-hemoprotein reductase] + H2O

2 entries

(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-perillyl alcohol + [oxidized NADPH-hemoprotein reductase] + H2O

side-chain hydroxylation, mixed-function oxygenase

Perilla frutescens

390083

(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-perillyl alcohol + [oxidized NADPH-hemoprotein reductase] + H2O

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REACTION TYPE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

oxidation

redox reaction

reduction

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Go to Pathway Search

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PATHWAY SOURCE

PATHWAYS

KEGG

Biosynthesis of secondary metabolites, Limonene and pinene degradation, Monoterpenoid biosynthesis

MetaCyc

perillyl aldehyde biosynthesis

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SYSTEMATIC NAME

IUBMB Comments

(S)-limonene,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (7-hydroxylating)

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CAS REGISTRY NUMBER

COMMENTARY

122653-75-2

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

(+)-limonene + NADPH + O2

perillyl alcohol + NADP+ + H2O

Perilla frutescens

hydroxylation at the same rate as (-)-limonene

390083

(-)-(S)-limonene + NADPH + O2

(-)-perillyl alcohol + NADP+ + H2O

2 entries

(-)-limonene + NADPH + O2

perillyl alcohol + NADP+ + H2O

2 entries

(S)-limonene + NADPH + H+ + O2

(-)-perillyl alcohol + NADP+ + H2O

Perilla frutescens

713236

additional information

2 entries

(-)-(S)-limonene + NADPH + O2

(-)-perillyl alcohol + NADP+ + H2O

Mycobacterium sp.

657606

(-)-(S)-limonene + NADPH + O2

(-)-perillyl alcohol + NADP+ + H2O

Mycobacterium sp. HXN-1500

657606

(-)-limonene + NADPH + O2

perillyl alcohol + NADP+ + H2O

Perilla frutescens

highly specific

390083

(-)-limonene + NADPH + O2

perillyl alcohol + NADP+ + H2O

Perilla frutescens

one of the key reactions of oxygenated monoterpenes, perillyl aldehyde biosynthesis

390083

additional information

Perilla frutescens

no substrates: isolimonenes, terpinolene, alpha- or beta-phellandrene, alpha- or beta-terpinene, bicyclic monoterpenes: pinene, sabinene, alpha-thujene, p-cymene, cis- or trans-p-menthane, p-menth-1-ene, i.e. 8,9-dihydrolimonene

390083

additional information

Perilla frutescens

the kinetically competent recombinant protein produces a mixture of C3-, C6- and C7-hydroxylated limonene derivatives, i.e. (-)-perillyl alcohol, (-)-trans-isopiperitenol, and (-)-trans-carveol, with a distribution of 33%, 14% and 53%, respectively, thus it performs the reaction of EC 1.14.13.47 and 1.14.13.48, overview

713236

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

(-)-(S)-limonene + NADPH + O2

(-)-perillyl alcohol + NADP+ + H2O

2 entries

(-)-limonene + NADPH + O2

perillyl alcohol + NADP+ + H2O

Perilla frutescens

one of the key reactions of oxygenated monoterpenes, perillyl aldehyde biosynthesis

390083

(S)-limonene + NADPH + H+ + O2

(-)-perillyl alcohol + NADP+ + H2O

Perilla frutescens

713236

(-)-(S)-limonene + NADPH + O2

(-)-perillyl alcohol + NADP+ + H2O

Mycobacterium sp.

657606

(-)-(S)-limonene + NADPH + O2

(-)-perillyl alcohol + NADP+ + H2O

Mycobacterium sp. HXN-1500

657606

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COFACTOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

cytochrome P450

Perilla frutescens

heme-thiolate protein, 0.2-0.9 nmol per mg protein

390083

NADH

Perilla frutescens

5.3% as effective as NADPH

NADPH

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INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

5,11-Dimethyl-6H-pyrido[4,3-b]carbazole

Perilla frutescens

390083

clotrimazole

Perilla frutescens

i.e. 1-[chloro-alpha,alpha-diphenyl]imidazole, mixed-type, weak

390083

Perilla frutescens

CO:O2 ratio of 9:1, photoreversible

cytochrome c

strong

Metyrapone

i.e. 2-methyl-1,2-di-3-pyridyl-1-propanone, moderate

390083

miconazole

Perilla frutescens

i.e. 1-[2,4-dichloro-beta-([2,4-di-chlorobenzyl]oxy)phenethyl]-imidazole, mixed-type, weak

NADP+

2 mM

SKF 525A

i.e. 2-diethyl-aminoethyl-2,2-diphenylvalerate, moderate

390083

additional information

Perilla frutescens

no inhibition: ancymidol, imidazole, up to 5 mM

390083

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ACTIVATING COMPOUND

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

FAD

Perilla frutescens

plus FMN, 0.005 mM each, activation

390083

FMN

Perilla frutescens

plus FAD, 0.005 mM each, activation

390083

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KM VALUE [mM]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.021

(-)-limonene

Perilla frutescens

390083

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SPECIFIC ACTIVITY [µmol/min/mg]

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

0.0001567

Perilla frutescens

390083

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pH OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

Mycobacterium sp.

657606

7.6

Perilla frutescens

recombinant chimeric mutant enzyme

7.8

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pH RANGE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

5.5 - 8

Mycobacterium sp.

almost no activity at pH 5.5 and pH 8.0, respectively

657606

6.75 - 8.5

Perilla frutescens

half-maximal activity at pH 6.75 and 8.5, recombinant chimeric mutant enzyme

713236

7.3 - 8.3

Perilla frutescens

about half-maximal activity at pH 7.3 and 8.3

390083

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TEMPERATURE OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

Perilla frutescens

390083

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

Mycobacterium sp.

HXN-1500

657606

brenda

Mycobacterium sp. HXN-1500

HXN-1500

brenda

brenda

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

brenda

oil glands on abaxial surface

brenda

brenda

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LOCALIZATION

ORGANISM

UNIPROT

COMMENTARY

GeneOntology No.

LITERATURE

SOURCE

brenda

brenda

Mycobacterium sp. HXN-1500

brenda

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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).

O85057 pBLAST

LIHY_GEOSE

Geobacillus stearothermophilus

543

61569

Swiss-Prot