BRENDA - Enzyme Database show
show all sequences of 1.14.14.58

In planta variation of volatile biosynthesis an alternative biosynthetic route to the formation of the pathogen-induced volatile homoterpene DMNT via triterpene degradation in Arabidopsis roots

Sohrabi, R.; Huh, J.; Badieyan, S.; Rakotondraibe, L.; Kliebenstein, D.; Sobrado, P.; Tholl, D.; Plant Cell 27, 874-890 (2015)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
gene CYP705A1, the full-length CYP705A1 transcript is fused to the CaMV 35S promoter for ectopic expression in the cyp705a1-1 mutant background
Arabidopsis thaliana
Engineering
Amino acid exchange
Commentary
Organism
additional information
construction of the cyp705a1-1 null mutant, the mutant is complemented with a full-length CYP705A1 cDNA in C-terminal fusion to enhanced yellow fluorescent protein (eYFP)
Arabidopsis thaliana
Inhibitors
Inhibitors
Commentary
Organism
Structure
clotrimazole
-
Arabidopsis thaliana
miconazole
-
Arabidopsis thaliana
Localization
Localization
Commentary
Organism
GeneOntology No.
Textmining
membrane
-
Arabidopsis thaliana
16020
-
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
Arabidopsis thaliana
-
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
?
arabidiol + [reduced NADPH-hemoprotein reductase] + O2
Arabidopsis thaliana
-
(3E)-4,8-dimethylnona-1,3,7-triene + ? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
?
additional information
Arabidopsis thaliana
CYP705A1 cleaves the prenyl side chain of arabidiol to produce (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and a nonvolatile C19-ketone derivative
?
-
-
-
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Arabidopsis thaliana
-
-
-
Arabidopsis thaliana
Q0LSF8
-
-
Source Tissue
Source Tissue
Commentary
Organism
Textmining
flower
-
Arabidopsis thaliana
-
leaf
-
Arabidopsis thaliana
-
additional information
CYP705A1 clusters with the arabidiol synthase gene ABDS, and both genes are coexpressed constitutively in the root stele and meristematic tissue; CYP82G1 is not expressed in roots
Arabidopsis thaliana
-
root
-
Arabidopsis thaliana
-
root meristem
-
Arabidopsis thaliana
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
-
746029
Arabidopsis thaliana
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
major substrate
746029
Arabidopsis thaliana
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2
-
746029
Arabidopsis thaliana
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
arabidiol + [reduced NADPH-hemoprotein reductase] + O2
-
746029
Arabidopsis thaliana
(3E)-4,8-dimethylnona-1,3,7-triene + ? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
additional information
CYP705A1 cleaves the prenyl side chain of arabidiol to produce (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and a nonvolatile C19-ketone derivative
746029
Arabidopsis thaliana
?
-
-
-
-
Cofactor
Cofactor
Commentary
Organism
Structure
cytochrome P450
;
Arabidopsis thaliana
Cloned(Commentary) (protein specific)
Commentary
Organism
gene CYP705A1, the full-length CYP705A1 transcript is fused to the CaMV 35S promoter for ectopic expression in the cyp705a1-1 mutant background
Arabidopsis thaliana
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
cytochrome P450
-
Arabidopsis thaliana
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
additional information
construction of the cyp705a1-1 null mutant, the mutant is complemented with a full-length CYP705A1 cDNA in C-terminal fusion to enhanced yellow fluorescent protein (eYFP)
Arabidopsis thaliana
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
clotrimazole
-
Arabidopsis thaliana
miconazole
-
Arabidopsis thaliana
Localization (protein specific)
Localization
Commentary
Organism
GeneOntology No.
Textmining
membrane
-
Arabidopsis thaliana
16020
-
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
Arabidopsis thaliana
-
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
?
arabidiol + [reduced NADPH-hemoprotein reductase] + O2
Arabidopsis thaliana
-
(3E)-4,8-dimethylnona-1,3,7-triene + ? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
?
additional information
Arabidopsis thaliana
CYP705A1 cleaves the prenyl side chain of arabidiol to produce (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and a nonvolatile C19-ketone derivative
?
-
-
-
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
flower
-
Arabidopsis thaliana
-
leaf
-
Arabidopsis thaliana
-
additional information
CYP705A1 clusters with the arabidiol synthase gene ABDS, and both genes are coexpressed constitutively in the root stele and meristematic tissue
Arabidopsis thaliana
-
additional information
CYP82G1 is not expressed in roots
Arabidopsis thaliana
-
root
-
Arabidopsis thaliana
-
root meristem
-
Arabidopsis thaliana
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
-
746029
Arabidopsis thaliana
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
major substrate
746029
Arabidopsis thaliana
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2
-
746029
Arabidopsis thaliana
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
arabidiol + [reduced NADPH-hemoprotein reductase] + O2
-
746029
Arabidopsis thaliana
(3E)-4,8-dimethylnona-1,3,7-triene + ? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
additional information
CYP705A1 cleaves the prenyl side chain of arabidiol to produce (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and a nonvolatile C19-ketone derivative
746029
Arabidopsis thaliana
?
-
-
-
-
Expression
Organism
Commentary
Expression
Arabidopsis thaliana
CYP705A1 is transiently induced in a jasmonate-dependent manner by infection with the root rot oomycete pathogen Pythium irregulare. DMNT is emitted from Arabidopsis thaliana roots upon infection with Pythium irregulare or treatment with jasmonic acid. ProCYP705A1:CYP705A1-eYFP lines, accumulation of the full-length CYP705A1 transcript is detected upon JA treatment, while only basal transcript levels of the gene are observed in ProCaMV35S-CYP705A1 lines with no jasmonate-dependent increase of transcript abundance; CYP82G1 is induced in Arabidopsis thaliana leaves upon insect feeding damage
up
General Information
General Information
Commentary
Organism
evolution
CYP705A1 is a member of the Brassicaceae-specific CYP705 family
Arabidopsis thaliana
malfunction
the null mutant cyp82g1-1 is not impaired in root-specific DMNT biosynthesis, indicating that enzyme Cyp82g1 is not involved in the formation of DMNT in Arabidopsis thaliana roots
Arabidopsis thaliana
metabolism
enzyme CYP705A1 is involved in DMNT biosynthesis in Arabidopsis thaliana roots. The formation of (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene, TMTT, in leaf or flower tissues usually occurs by the oxidative breakdown of (E)-nerolidol or (E,E)-geranyl linalool. Arabidiol Is the precursor in DMNT biosynthesis in Arabidopsis thaliana roots, it can be degraded by CYP705A1 to a C19 ketone product (14-apo-arabidiol). Role of the DMNT biosynthetic pathway in resistance against Pythium irregulare
Arabidopsis thaliana
physiological function
enzyme CYP82G1 produces (3E)-4,8-dimethylnona-1,3,7-triene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, in vitro but functions as a TMTT synthase in planta because of the presence of (E,E)-geranyllinalool but not of (E)-nerolidol in Arabidopsis thaliana leaves; while Arabidopsis thaliana and other angiosperms are known to produce the homoterpene (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, or its C16-analogue (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene, TMTT, by the breakdown of sesquiterpene and diterpene tertiary alcohols in aboveground tissues, Arabidopsis thaliana roots biosynthesize DMNT by the degradation of the C30 triterpene diol, arabidiol. The reaction is catalyzed by the Brassicaceae-specific cytochrome P450 monooxygenase CYP705A1. In volatile terpene biosynthesis, irregular homo/norterpenes can arise from different biosynthetic routes in a tissue-specific manner. DMNT negatively affects pathogen Pythium irregulare oospore germination and growth
Arabidopsis thaliana
General Information (protein specific)
General Information
Commentary
Organism
evolution
CYP705A1 is a member of the Brassicaceae-specific CYP705 family
Arabidopsis thaliana
malfunction
the null mutant cyp82g1-1 is not impaired in root-specific DMNT biosynthesis, indicating that enzyme Cyp82g1 is not involved in the formation of DMNT in Arabidopsis thaliana roots
Arabidopsis thaliana
metabolism
enzyme CYP705A1 is involved in DMNT biosynthesis in Arabidopsis thaliana roots. The formation of (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene, TMTT, in leaf or flower tissues usually occurs by the oxidative breakdown of (E)-nerolidol or (E,E)-geranyl linalool. Arabidiol Is the precursor in DMNT biosynthesis in Arabidopsis thaliana roots, it can be degraded by CYP705A1 to a C19 ketone product (14-apo-arabidiol). Role of the DMNT biosynthetic pathway in resistance against Pythium irregulare
Arabidopsis thaliana
physiological function
while Arabidopsis thaliana and other angiosperms are known to produce the homoterpene (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, or its C16-analogue (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene, TMTT, by the breakdown of sesquiterpene and diterpene tertiary alcohols in aboveground tissues, Arabidopsis thaliana roots biosynthesize DMNT by the degradation of the C30 triterpene diol, arabidiol. The reaction is catalyzed by the Brassicaceae-specific cytochrome P450 monooxygenase CYP705A1. In volatile terpene biosynthesis, irregular homo/norterpenes can arise from different biosynthetic routes in a tissue-specific manner. DMNT negatively affects pathogen Pythium irregulare oospore germination and growth
Arabidopsis thaliana
physiological function
enzyme CYP82G1 produces (3E)-4,8-dimethylnona-1,3,7-triene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, in vitro but functions as a TMTT synthase in planta because of the presence of (E,E)-geranyllinalool but not of (E)-nerolidol in Arabidopsis thaliana leaves
Arabidopsis thaliana
Expression (protein specific)
Organism
Commentary
Expression
Arabidopsis thaliana
CYP705A1 is transiently induced in a jasmonate-dependent manner by infection with the root rot oomycete pathogen Pythium irregulare. DMNT is emitted from Arabidopsis thaliana roots upon infection with Pythium irregulare or treatment with jasmonic acid. ProCYP705A1:CYP705A1-eYFP lines, accumulation of the full-length CYP705A1 transcript is detected upon JA treatment, while only basal transcript levels of the gene are observed in ProCaMV35S-CYP705A1 lines with no jasmonate-dependent increase of transcript abundance
up
Arabidopsis thaliana
CYP82G1 is induced in Arabidopsis thaliana leaves upon insect feeding damage
up
Other publictions for EC 1.14.14.58
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)
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Richter
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Zea mays
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2651-2665
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1
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5
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8
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2
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8
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1
3
6
2
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746029
Sohrabi
In planta variation of volati ...
Arabidopsis thaliana
Plant Cell
27
874-890
2015
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1
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1
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2
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1
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4
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2
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5
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1
4
5
2
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728442
Tholl
The biochemistry of homoterpen ...
Arabidopsis thaliana
Phytochemistry
72
1635-1646
2011
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1
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1
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713423
Lee
Herbivore-induced and floral h ...
Arabidopsis thaliana
Proc. Natl. Acad. Sci. USA
107
21205-21210
2010
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1
1
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4
1
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3
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1
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3
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2
746284
Lee
Herbivore-induced and floral ...
Arabidopsis thaliana
Proc. Natl. Acad. Sci. USA
107
21205-21210
2010
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1
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