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Literature summary extracted from

  • Karp, F.; Mihaliak, C.A.; Harris, J.L.; Croteau, R.
    Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves (1990), Arch. Biochem. Biophys., 276, 219-226.
    View publication on PubMed

Activating Compound

EC Number Activating Compound Comment Organism Structure
1.14.14.52 FAD plus FMN, 0.005 mM each, activation Perilla frutescens
1.14.14.52 FMN plus FAD, 0.005 mM each, activation Perilla frutescens
1.14.14.99 FAD plus FMN, 0.005 mM each, activation Mentha x piperita
1.14.14.99 FMN plus FAD, 0.005 mM each, activation Mentha x piperita

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.14.51 5,11-Dimethyl-6H-pyrido[4,3-b]-carbazole
-
Mentha spicata
1.14.14.51 clotrimazole i.e. 1-[chloro-alpha,alpha-diphenyl]imidazole, mixed-type, strong Mentha spicata
1.14.14.51 CO CO:O2 ratio of 9:1, photoreversible Mentha spicata
1.14.14.51 cytochrome c strong Mentha spicata
1.14.14.51 Metyrapone i.e. 2-methyl-1,2-di-3-pyridyl-1-propanone, moderate Mentha spicata
1.14.14.51 miconazole i.e. 1-[2,4-dichloro-beta-([2,4-di-chlorobenzyl]oxy)phenethyl]-imidazole, mixed-type, strong Mentha spicata
1.14.14.51 additional information no inhibition: ancymidol, imidazole, up to 5 mM Mentha spicata
1.14.14.51 NADP+ 2 mM Mentha spicata
1.14.14.51 SKF 525A i.e. 2-diethylaminoethyl-2,2-diphenylvalerate, moderate Mentha spicata
1.14.14.52 5,11-Dimethyl-6H-pyrido[4,3-b]carbazole
-
Perilla frutescens
1.14.14.52 clotrimazole i.e. 1-[chloro-alpha,alpha-diphenyl]imidazole, mixed-type, weak Perilla frutescens
1.14.14.52 CO CO:O2 ratio of 9:1, photoreversible Perilla frutescens
1.14.14.52 cytochrome c strong Perilla frutescens
1.14.14.52 Metyrapone i.e. 2-methyl-1,2-di-3-pyridyl-1-propanone, moderate Perilla frutescens
1.14.14.52 miconazole i.e. 1-[2,4-dichloro-beta-([2,4-di-chlorobenzyl]oxy)phenethyl]-imidazole, mixed-type, weak Perilla frutescens
1.14.14.52 additional information no inhibition: ancymidol, imidazole, up to 5 mM Perilla frutescens
1.14.14.52 NADP+ 2 mM Perilla frutescens
1.14.14.52 SKF 525A i.e. 2-diethyl-aminoethyl-2,2-diphenylvalerate, moderate Perilla frutescens
1.14.14.99 5,11-Dimethyl-6H-pyrido[4,3-b]carbazole
-
Mentha x piperita
1.14.14.99 clotrimazole i.e. 1-[chloro-alpha,alpha-diphenyl]imidazole, mixed-type, strong Mentha x piperita
1.14.14.99 CO CO:O2 ratio of 9:1, photoreversible Mentha x piperita
1.14.14.99 cytochrome c strong Mentha x piperita
1.14.14.99 Metyrapone i.e. 2-methyl-1,2-di-3-pyridyl-1-propanone, inhibition Mentha x piperita
1.14.14.99 miconazole i.e. 1-[2,4-dichloro-beta-([2,4-di-chlorobenzyl]oxy)phenethyl]-imidazole, mixed-type, weak Mentha x piperita
1.14.14.99 additional information no inhibition: ancymidol, imidazole, up to 5 mM Mentha x piperita
1.14.14.99 NADP+ 2 mM Mentha x piperita
1.14.14.99 SKF 525A i.e. 2-diethylaminoethyl-2,2-diphenylvalerate, moderate Mentha x piperita

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.14.14.51 0.02
-
(-)-limonene
-
Mentha spicata
1.14.14.52 0.021
-
(-)-limonene
-
Perilla frutescens
1.14.14.99 0.018
-
(-)-limonene
-
Mentha x piperita

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.14.14.51 microsome
-
Mentha spicata
-
-
1.14.14.99 microsome
-
Mentha x piperita
-
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.14.51 (-)-limonene + NADPH + O2 Mentha spicata one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-carvone (-)-trans-carveol + NADP+ + H2O
-
?
1.14.14.52 (-)-limonene + NADPH + O2 Perilla frutescens one of the key reactions of oxygenated monoterpenes, perillyl aldehyde biosynthesis perillyl alcohol + NADP+ + H2O
-
?
1.14.14.99 (-)-limonene + [reduced NADPH-hemoprotein reductase] + O2 Mentha x piperita one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-menthone (-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.51 Mentha spicata
-
spearmint
-
1.14.14.52 Perilla frutescens
-
-
-
1.14.14.99 Mentha x piperita
-
peppermint
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.14.14.51 partial Mentha spicata

Reaction

EC Number Reaction Comment Organism Reaction ID
1.14.14.52 (S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-perillyl alcohol + [oxidized NADPH-hemoprotein reductase] + H2O side-chain hydroxylation, mixed-function oxygenase Perilla frutescens
1.14.14.99 (S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O mixed-function oxygenase, ring-hydroxylation Mentha x piperita

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.14.14.51 leaf epidermis oil glands on upper and lower surface Mentha spicata
-
1.14.14.52 leaf epidermis oil glands on abaxial surface Perilla frutescens
-
1.14.14.99 leaf epidermis of both surfaces Mentha x piperita
-

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
1.14.14.51 0.00068
-
-
Mentha spicata
1.14.14.52 0.0001567
-
-
Perilla frutescens
1.14.14.99 0.000685
-
-
Mentha x piperita

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.51 (+)-limonene + NADPH + O2 hydroxylation at 25% the rate of (-)-limonene Mentha spicata (+)-cis-carveol + NADP+ + H2O
-
?
1.14.14.51 (+)-p-menth-1-ene + NADPH + O2 i.e. (+)-8,9-dihydrolimonene, hydroxylation at 30% the rate of (-)-limonene Mentha spicata (+)-cis-carvotanacetol + NADP+ + H2O
-
?
1.14.14.51 (-)-(4S)-limonene + NADPH + O2 highly specific Mentha spicata (-)-(4R,6S)-trans-carveol + NADP+ + H2O
-
?
1.14.14.51 (-)-limonene + NADPH + O2 one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-carvone Mentha spicata (-)-trans-carveol + NADP+ + H2O
-
?
1.14.14.51 (-)-p-menth-1-ene + NADPH + O2 i.e. (-)-8,9-dihydrolimonene, hydroxylation at 74% the rate of (-)-limonene Mentha spicata (-)-trans-carvotanacetol + NADP+ + H2O
-
?
1.14.14.51 additional information 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, NADH can replace NADPH, but more slowly Mentha spicata ?
-
?
1.14.14.52 (+)-limonene + NADPH + O2 hydroxylation at the same rate as (-)-limonene Perilla frutescens perillyl alcohol + NADP+ + H2O
-
?
1.14.14.52 (-)-limonene + NADPH + O2 highly specific Perilla frutescens perillyl alcohol + NADP+ + H2O
-
?
1.14.14.52 (-)-limonene + NADPH + O2 one of the key reactions of oxygenated monoterpenes, perillyl aldehyde biosynthesis Perilla frutescens perillyl alcohol + NADP+ + H2O
-
?
1.14.14.52 additional information 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 Perilla frutescens ?
-
?
1.14.14.99 (+)-limonene + [reduced NADPH-hemoprotein reductase] + O2 hydroxylation at 50% Mentha x piperita (+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.99 (+)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2 i.e. (+)-8,9-dihydro-limonene, hydroxylation at 37% the rate of (-)-limonene hydroxylation Mentha x piperita (+)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.99 (-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 highly specific, regiospecific and stereospecific reaction Mentha x piperita (-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.99 (-)-limonene + [reduced NADPH-hemoprotein reductase] + O2 one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-menthone Mentha x piperita (-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.99 (-)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2 i.e. (-)-8,9-dihydrolimonene, hydroxylation at 37% the rate of (-)-limonene hydroxylation Mentha x piperita (-)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.99 additional information 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, highly specific, absolute requirement for a reduced pyridine nucleotide and molecular oxygen Mentha x piperita ?
-
?

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.14.51 32
-
-
Mentha spicata
1.14.14.52 32
-
-
Perilla frutescens
1.14.14.99 32
-
-
Mentha x piperita

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.14.51 7.4
-
-
Mentha spicata
1.14.14.52 7.8
-
-
Perilla frutescens
1.14.14.99 7.4
-
-
Mentha x piperita

pH Range

EC Number pH Minimum pH Maximum Comment Organism
1.14.14.51 6.9 7.9 about half-maximal activity at pH 6.9 and 7.9 Mentha spicata
1.14.14.52 7.3 8.3 about half-maximal activity at pH 7.3 and 8.3 Perilla frutescens
1.14.14.99 6.9 7.9 about half-maximal activity at pH 6.9 and 7.9 Mentha x piperita

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.14.51 cytochrome P450 average content of 0.0005 mmol/mg protein Mentha spicata
1.14.14.52 cytochrome P450 heme-thiolate protein, 0.2-0.9 nmol per mg protein Perilla frutescens
1.14.14.52 NADH 5.3% as effective as NADPH Perilla frutescens
1.14.14.52 NADPH
-
Perilla frutescens
1.14.14.99 cytochrome P450 heme-thiolate protein, 0.2-0.9 nmol per mg protein Mentha x piperita