BRENDA - Enzyme Database show
show all sequences of 1.14.14.99

Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves

Karp, F.; Mihaliak, C.A.; Harris, J.L.; Croteau, R.; Arch. Biochem. Biophys. 276, 219-226 (1990)

Data extracted from this reference:

Activating Compound
Activating Compound
Commentary
Organism
Structure
FAD
plus FMN, 0.005 mM each, activation
Mentha x piperita
FMN
plus FAD, 0.005 mM each, activation
Mentha x piperita
Inhibitors
Inhibitors
Commentary
Organism
Structure
5,11-Dimethyl-6H-pyrido[4,3-b]carbazole
-
Mentha x piperita
clotrimazole
i.e. 1-[chloro-alpha,alpha-diphenyl]imidazole, mixed-type, strong
Mentha x piperita
CO
CO:O2 ratio of 9:1, photoreversible
Mentha x piperita
cytochrome c
strong
Mentha x piperita
Metyrapone
i.e. 2-methyl-1,2-di-3-pyridyl-1-propanone, inhibition
Mentha x piperita
miconazole
i.e. 1-[2,4-dichloro-beta-([2,4-di-chlorobenzyl]oxy)phenethyl]-imidazole, mixed-type, weak
Mentha x piperita
additional information
no inhibition: ancymidol, imidazole, up to 5 mM
Mentha x piperita
NADP+
2 mM
Mentha x piperita
SKF 525A
i.e. 2-diethylaminoethyl-2,2-diphenylvalerate, moderate
Mentha x piperita
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.018
-
(-)-limonene
-
Mentha x piperita
Localization
Localization
Commentary
Organism
GeneOntology No.
Textmining
microsome
-
Mentha x piperita
-
-
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(-)-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
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Mentha x piperita
-
peppermint
-
Reaction
Reaction
Commentary
Organism
(S)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
mixed-function oxygenase, ring-hydroxylation
Mentha x piperita
Source Tissue
Source Tissue
Commentary
Organism
Textmining
leaf epidermis
of both surfaces
Mentha x piperita
-
Specific Activity [micromol/min/mg]
Specific Activity Minimum [mol/min/mg]
Specific Activity Maximum [mol/min/mg]
Commentary
Organism
0.000685
-
-
Mentha x piperita
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(+)-limonene + [reduced NADPH-hemoprotein reductase] + O2
hydroxylation at 50%
390083
Mentha x piperita
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
390083
Mentha x piperita
?
(+)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
i.e. (+)-8,9-dihydro-limonene, hydroxylation at 37% the rate of (-)-limonene hydroxylation
390083
Mentha x piperita
(+)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
-
390083
Mentha x piperita
?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
highly specific, regiospecific and stereospecific reaction
390083
Mentha x piperita
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
390083
Mentha x piperita
?
(-)-limonene + [reduced NADPH-hemoprotein reductase] + O2
one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-menthone
390083
Mentha x piperita
(-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(-)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
i.e. (-)-8,9-dihydrolimonene, hydroxylation at 37% the rate of (-)-limonene hydroxylation
390083
Mentha x piperita
(-)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
-
390083
Mentha x piperita
?
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
390083
Mentha x piperita
?
-
-
-
-
Temperature Optimum [C]
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
32
-
-
Mentha x piperita
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.4
-
-
Mentha x piperita
pH Range
pH Minimum
pH Maximum
Commentary
Organism
6.9
7.9
about half-maximal activity at pH 6.9 and 7.9
Mentha x piperita
Cofactor
Cofactor
Commentary
Organism
Structure
cytochrome P450
heme-thiolate protein, 0.2-0.9 nmol per mg protein
Mentha x piperita
Activating Compound (protein specific)
Activating Compound
Commentary
Organism
Structure
FAD
plus FMN, 0.005 mM each, activation
Mentha x piperita
FMN
plus FAD, 0.005 mM each, activation
Mentha x piperita
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
cytochrome P450
heme-thiolate protein, 0.2-0.9 nmol per mg protein
Mentha x piperita
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
5,11-Dimethyl-6H-pyrido[4,3-b]carbazole
-
Mentha x piperita
clotrimazole
i.e. 1-[chloro-alpha,alpha-diphenyl]imidazole, mixed-type, strong
Mentha x piperita
CO
CO:O2 ratio of 9:1, photoreversible
Mentha x piperita
cytochrome c
strong
Mentha x piperita
Metyrapone
i.e. 2-methyl-1,2-di-3-pyridyl-1-propanone, inhibition
Mentha x piperita
miconazole
i.e. 1-[2,4-dichloro-beta-([2,4-di-chlorobenzyl]oxy)phenethyl]-imidazole, mixed-type, weak
Mentha x piperita
additional information
no inhibition: ancymidol, imidazole, up to 5 mM
Mentha x piperita
NADP+
2 mM
Mentha x piperita
SKF 525A
i.e. 2-diethylaminoethyl-2,2-diphenylvalerate, moderate
Mentha x piperita
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.018
-
(-)-limonene
-
Mentha x piperita
Localization (protein specific)
Localization
Commentary
Organism
GeneOntology No.
Textmining
microsome
-
Mentha x piperita
-
-
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(-)-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
-
-
?
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
leaf epidermis
of both surfaces
Mentha x piperita
-
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [mol/min/mg]
Specific Activity Maximum [mol/min/mg]
Commentary
Organism
0.000685
-
-
Mentha x piperita
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(+)-limonene + [reduced NADPH-hemoprotein reductase] + O2
hydroxylation at 50%
390083
Mentha x piperita
(+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
390083
Mentha x piperita
?
(+)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
i.e. (+)-8,9-dihydro-limonene, hydroxylation at 37% the rate of (-)-limonene hydroxylation
390083
Mentha x piperita
(+)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
-
390083
Mentha x piperita
?
(-)-(4S)-limonene + [reduced NADPH-hemoprotein reductase] + O2
highly specific, regiospecific and stereospecific reaction
390083
Mentha x piperita
(-)-trans-(3S,4R)-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
390083
Mentha x piperita
?
(-)-limonene + [reduced NADPH-hemoprotein reductase] + O2
one of the key reactions of oxygenated monoterpenes, biosynthesis of (-)-menthone
390083
Mentha x piperita
(-)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(-)-p-menth-1-ene + [reduced NADPH-hemoprotein reductase] + O2
i.e. (-)-8,9-dihydrolimonene, hydroxylation at 37% the rate of (-)-limonene hydroxylation
390083
Mentha x piperita
(-)-trans-piperitol + [oxidized NADPH-hemoprotein reductase] + H2O
-
390083
Mentha x piperita
?
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
390083
Mentha x piperita
?
-
-
-
-
Temperature Optimum [C] (protein specific)
Temperature Optimum [C]
Temperature Optimum Maximum [C]
Commentary
Organism
32
-
-
Mentha x piperita
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.4
-
-
Mentha x piperita
pH Range (protein specific)
pH Minimum
pH Maximum
Commentary
Organism
6.9
7.9
about half-maximal activity at pH 6.9 and 7.9
Mentha x piperita
Other publictions for EC 1.14.14.99
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
745019
Wriessnegger
Enhancing cytochrome P450-med ...
Mentha x piperita
Fungal Genet. Biol.
89
114-125
2016
1
-
1
-
-
-
-
-
-
-
-
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-
4
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1
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2
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1
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1
2
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1
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-
-
-
-
-
-
-
-
-
712853
Dolzhenko
UV-B modulates the interplay b ...
Mentha x piperita
J. Photochem. Photobiol. B Biol.
100
67-75
2010
-
-
-
-
-
-
-
-
-
-
-
1
-
2
-
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-
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1
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1
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1
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1
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1
-
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-
-
-
-
-
-
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1
-
-
1
-
-
713236
Mau
A candidate cDNA clone for (-) ...
Perilla frutescens
Phytochemistry
71
373-379
2010
-
-
1
-
1
-
-
-
-
-
-
1
-
5
-
-
-
-
-
-
-
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2
-
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1
1
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1
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1
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1
-
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-
-
-
-
-
2
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
660103
Mahmoud
Cosuppression of limonene-3-hy ...
Mentha x piperita
Phytochemistry
65
547-554
2004
-
1
-
-
-
-
-
-
-
-
-
1
-
3
-
-
-
-
-
2
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
2
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
660093
Bertea
Molecular evaluation of a spea ...
Mentha x gracilis
Phytochemistry
64
1203-1211
2003
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
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1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
390089
Wust
Hydroxylation of limonene enan ...
Mentha x piperita
Arch. Biochem. Biophys.
387
125-136
2001
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
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-
-
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-
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2
-
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-
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-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
390086
Schalk
A single amino acid substituti ...
Mentha spicata
Proc. Natl. Acad. Sci. USA
97
11948-11953
2000
-
-
-
-
-
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
1
-
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-
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-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
390088
Haudenschild
Functional expression of regio ...
Mentha x piperita
Arch. Biochem. Biophys.
379
127-136
2000
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
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1
-
-
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-
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1
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1
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1
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1
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-
-
-
-
-
-
-
-
-
-
-
-
390087
Lupien
Regiospecific cytochrome P450 ...
Mentha x piperita
Arch. Biochem. Biophys.
368
181-192
1999
-
-
1
-
-
-
-
-
-
-
-
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-
3
-
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-
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1
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-
-
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-
390085
Gershenzon
Isolation of secretory cells f ...
Mentha x piperita
Anal. Biochem.
200
130-138
1992
-
-
-
-
-
3
-
-
1
-
-
-
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1
-
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1
-
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1
1
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1
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1
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1
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1
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3
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1
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1
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1
1
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1
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1
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-
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-
-
-
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-
390084
Croteau
Biochemical characterization o ...
Mentha x gracilis, Mentha x piperita
Plant Physiol.
96
744-752
1991
-
-
-
-
-
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2
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2
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2
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8
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2
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2
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2
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2
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8
-
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-
390083
Karp
Monoterpene biosynthesis: spec ...
Mentha x piperita
Arch. Biochem. Biophys.
276
219-226
1990
2
-
-
-
-
-
9
1
1
-
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1
-
1
-
-
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1
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1
1
-
6
-
1
-
-
-
1
1
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1
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-
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2
-
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1
-
-
-
-
9
-
1
1
-
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1
-
-
-
-
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1
1
-
6
-
1
-
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1
1
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