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IUBMB Comments A cytochrome P-450 (heme-thiolate) protein. Kinetic studies suggest that 1beta-hydroxyepiaristolochene is mainly formed first followed by hydroxylation at C-3. However the reverse order via 3alpha-hydroxyepiaristolochene does occur.
The enzyme appears in viruses and cellular organisms
Synonyms
5-epi-aristolochene-1,3-dihydroxylase, 5-epi-aristolochene dihydroxylase, ca01g05990,
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5-epi-aristolochene dihydroxylase
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5-epi-aristolochene-1,3-dihydroxylase
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EC 1.14.13.119
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formerly
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epi-aristolochene-1,3-dihydroxylase
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EAH
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5-epiaristolochene + 2 [reduced NADPH-hemoprotein reductase] + 2 O2 = capsidiol + 2 [oxidized NADPH-hemoprotein reductase] + 2 H2O
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5-epiaristolochene,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (1- and 3-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein. Kinetic studies suggest that 1beta-hydroxyepiaristolochene is mainly formed first followed by hydroxylation at C-3. However the reverse order via 3alpha-hydroxyepiaristolochene does occur.
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1-deoxycapsidiol + [reduced NADPH-hemoprotein reductase] + O2
capsidiol + [oxidized NADPH-hemoprotein reductase] + H2O
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1beta-hydroxy-5-epiaristolochene + [reduced NADPH-hemoprotein reductase] + O2
capsidiol + [oxidized NADPH-hemoprotein reductase] + H2O
the catalytic efficiency for 1beta-hydroxy-5-epiaristolochene is about 10times greater than that for 3alpha-hydroxy-5-epiaristolochene
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3-deoxycapsidiol + [reduced NADPH-hemoprotein reductase] + O2
capsidiol + [oxidized NADPH-hemoprotein reductase] + H2O
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3alpha-hydroxy-5-epiaristolochene + [reduced NADPH-hemoprotein reductase] + O2
capsidiol + [oxidized NADPH-hemoprotein reductase] + H2O
the catalytic efficiency for 3alpha-hydroxy-5-epiaristolochene is about 10times lower than that for 1beta-hydroxy-5-epiaristolochene
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5-epiaristolochene + 2 [reduced NADPH-hemoprotein reductase] + 2 O2
capsidiol + 2 [oxidized NADPH-hemoprotein reductase] + 2 H2O
5-epiaristolochene + [reduced NADPH-hemoprotein reductase] + O2
1-deoxycapsidiol + [oxidized NADPH-hemoprotein reductase] + H2O
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5-epiaristolochene + [reduced NADPH-hemoprotein reductase] + O2
1beta-hydroxy-5-epiaristolochene + [oxidized NADPH-hemoprotein reductase] + H2O
the release of an 1beta-hydroxy-5-epiaristolochene intermediate at high 5-epiaristolochene concentrations and a 10fold catalytic preference for 1beta-hydroxy-5-epiaristolochene versus 3alpha-hydroxy-5-epiaristolochene is indicative of a preferred reaction order of hydroxylation at C-1, followed by that at C-3
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5-epiaristolochene + [reduced NADPH-hemoprotein reductase] + O2
3-deoxycapsidiol + [oxidized NADPH-hemoprotein reductase] + H2O
premnaspirodiene + [reduced NADPH-hemoprotein reductase] + O2
solavetivone + [oxidized NADPH-hemoprotein reductase] + H2O
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5-epiaristolochene + 2 [reduced NADPH-hemoprotein reductase] + 2 O2
capsidiol + 2 [oxidized NADPH-hemoprotein reductase] + 2 H2O
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5-epiaristolochene + 2 [reduced NADPH-hemoprotein reductase] + 2 O2
capsidiol + 2 [oxidized NADPH-hemoprotein reductase] + 2 H2O
EAH mediates regio- and stereospecific hydroxylations at the C1 and C3 positions of 5-epi-aristolochene
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5-epiaristolochene + [reduced NADPH-hemoprotein reductase] + O2
3-deoxycapsidiol + [oxidized NADPH-hemoprotein reductase] + H2O
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5-epiaristolochene + [reduced NADPH-hemoprotein reductase] + O2
3-deoxycapsidiol + [oxidized NADPH-hemoprotein reductase] + H2O
3-deoxycapsidiol is a reaction product when EAH is incubated with high concentrations (above 0.4 mM) of the 5-epiaristolochene substrate
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1-deoxycapsidiol + [reduced NADPH-hemoprotein reductase] + O2
capsidiol + [oxidized NADPH-hemoprotein reductase] + H2O
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3-deoxycapsidiol + [reduced NADPH-hemoprotein reductase] + O2
capsidiol + [oxidized NADPH-hemoprotein reductase] + H2O
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5-epiaristolochene + 2 [reduced NADPH-hemoprotein reductase] + 2 O2
capsidiol + 2 [oxidized NADPH-hemoprotein reductase] + 2 H2O
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5-epiaristolochene + [reduced NADPH-hemoprotein reductase] + O2
1-deoxycapsidiol + [oxidized NADPH-hemoprotein reductase] + H2O
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5-epiaristolochene + [reduced NADPH-hemoprotein reductase] + O2
3-deoxycapsidiol + [oxidized NADPH-hemoprotein reductase] + H2O
3-deoxycapsidiol is a reaction product when EAH is incubated with high concentrations (above 0.4 mM) of the 5-epiaristolochene substrate
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premnaspirodiene + [reduced NADPH-hemoprotein reductase] + O2
solavetivone + [oxidized NADPH-hemoprotein reductase] + H2O
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Ancymidol
dose-dependent inhibition with more than 80% by 0.075 mM ancymidol
dimethyl sulfoxide
conversion of 5-epiaristolochene to capsidiol activity is inhibited at concentrations above 10% (v/v) dimethyl sulfoxide
ketoconazole
dose-dependent inhibition with 95% inhibition at 0.1 mM ketoconazole
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dimethyl sulfoxide
maximum conversion of 5-epiaristolochene to capsidiol activity is observed at final concentrations of 2-5% (v/v) dimethyl sulfoxide
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Mycoses
Capsidiol-related genes are highly expressed in response to Colletotrichum scovillei during Capsicum annuum fruit development stages.
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0.00174 - 0.02124
1beta-hydroxy-5-epiaristolochene
0.01518 - 0.0688
5-epiaristolochene
0.00174
1beta-hydroxy-5-epiaristolochene
wild type enzyme, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.0062
1beta-hydroxy-5-epiaristolochene
mutant enzyme S368A, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.00997
1beta-hydroxy-5-epiaristolochene
mutant enzyme S368T, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.02124
1beta-hydroxy-5-epiaristolochene
mutant enzyme I486A, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.01518
5-epiaristolochene
mutant enzyme S368T, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.01672
5-epiaristolochene
mutant enzyme S386V, the reaction product is 1beta-hydroxy-5-epiaristolochene, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.01918
5-epiaristolochene
wild type enzyme, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.02267
5-epiaristolochene
mutant enzyme S368A, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.03863
5-epiaristolochene
mutant enzyme S386C, the reaction product is 1beta-hydroxy-5-epiaristolochene, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.0688
5-epiaristolochene
mutant enzyme I486A, the reaction product is 1beta-hydroxy-5-epiaristolochene, in 100 mM Tris-HCl (pH 7.5), at 30°C
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0.132 - 0.582
1beta-hydroxy-5-epiaristolochene
0.037 - 0.553
5-epiaristolochene
0.132
1beta-hydroxy-5-epiaristolochene
mutant enzyme I486A, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.482
1beta-hydroxy-5-epiaristolochene
mutant enzyme S368T, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.581
1beta-hydroxy-5-epiaristolochene
mutant enzyme S368A, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.582
1beta-hydroxy-5-epiaristolochene
wild type enzyme, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.037
5-epiaristolochene
mutant enzyme S368T, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.154
5-epiaristolochene
mutant enzyme S368A, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.278
5-epiaristolochene
mutant enzyme S386C, the reaction product is 1beta-hydroxy-5-epiaristolochene, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.293
5-epiaristolochene
mutant enzyme I486A, the reaction product is 1beta-hydroxy-5-epiaristolochene, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.493
5-epiaristolochene
wild type enzyme, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
0.553
5-epiaristolochene
mutant enzyme S386V, the reaction product is 1beta-hydroxy-5-epiaristolochene, in 100 mM Tris-HCl (pH 7.5), at 30°C
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6.2 - 334.4
1beta-hydroxy-5-epiaristolochene
2.4 - 33.1
5-epiaristolochene
6.2
1beta-hydroxy-5-epiaristolochene
mutant enzyme I486A, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
48.3
1beta-hydroxy-5-epiaristolochene
mutant enzyme S368T, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
93.7
1beta-hydroxy-5-epiaristolochene
mutant enzyme S368A, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
334.4
1beta-hydroxy-5-epiaristolochene
wild type enzyme, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
2.4
5-epiaristolochene
mutant enzyme S368T, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
4.3
5-epiaristolochene
mutant enzyme I486A, the reaction product is 1beta-hydroxy-5-epiaristolochene, in 100 mM Tris-HCl (pH 7.5), at 30°C
6.8
5-epiaristolochene
mutant enzyme S368A, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
7.2
5-epiaristolochene
mutant enzyme S386C, the reaction product is 1beta-hydroxy-5-epiaristolochene, in 100 mM Tris-HCl (pH 7.5), at 30°C
25.7
5-epiaristolochene
wild type enzyme, the reaction product is capsidiol, in 100 mM Tris-HCl (pH 7.5), at 30°C
33.1
5-epiaristolochene
mutant enzyme S386V, the reaction product is 1beta-hydroxy-5-epiaristolochene, in 100 mM Tris-HCl (pH 7.5), at 30°C
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0.025
Ancymidol
Nicotiana tabacum
pH and temperature not specified in the publication
0.025
ketoconazole
Nicotiana tabacum
pH and temperature not specified in the publication
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brenda
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UniProt
brenda
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brenda
cvs. CM334 and ECW30R
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brenda
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brenda
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evolution
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the enzyme is encoded by gene EAH which belongs to the multigene family EAS/EAH
metabolism
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the enzyme is involved in biosynthesis of capsidiol. Capsidiol accumulation is essential for nonhost resistance of pepper against Phytophthora infestans infection
physiological function
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CA01g05990 gene shows an early response to fungus infection in ripe fruit, being 53fold more expressed at 96 h post infection
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C71DK_TOBAC
504
0
57083
Swiss-Prot
Secretory Pathway (Reliability: 2 )
A0A2P6P5G4_ROSCH
64
0
7287
TrEMBL
Mitochondrion (Reliability: 3 )
A0A2P6SET6_ROSCH
150
0
17073
TrEMBL
Mitochondrion (Reliability: 3 )
A0A2P6R518_ROSCH
107
0
11989
TrEMBL
other Location (Reliability: 4 )
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I468A
the mutant produces significant amounts 1beta-hydroxy-5-epiaristolochene, but negligible amounts of capsidiol from 5-epiaristolochene
S368A
the mutant retains its ability to fully convert 5-epiaristolochene to capsidiol, but the turnover rates for capsidiol formation is 3-13times lower compared with that of the wild type enzyme and is also able to convert 1beta-hydroxy-5-epiaristolochene to capsidiol with kcat values comparable with that of wild type enzyme, but with Km values for 1beta-hydroxy-5-epiaristolochene 4-6times greater compared with that of wild type
S368C
the mutant exhibits wild type catalytic efficiency for 1beta-hydroxy-5-epiaristolochene biosynthesis, but is devoid of the successive hydroxylation activity for capsidiol biosynthesis
S368F
devoid of any hydroxylase activity for 5-epiaristolochene or 1beta-hydroxy-5-epiaristolochene
S368I
devoid of any hydroxylase activity for 5-epiaristolochene or 1beta-hydroxy-5-epiaristolochene
S368T
the mutant retains its ability to fully convert 5-epiaristolochene to capsidiol, but the turnover rates for capsidiol formation is 3-13times lower compared with that of the wild type enzyme and is also able to convert 1beta-hydroxy-5-epiaristolochene to capsidiol with kcat values comparable with that of wild type enzyme, but with Km values for 1beta-hydroxy-5-epiaristolochene 4-6times greater compared with that of wild type
S368V
the mutant exhibits wild type catalytic efficiency for 1beta-hydroxy-5-epiaristolochene biosynthesis, but is devoid of the successive hydroxylation activity for capsidiol biosynthesis, the mutant catalyzes the relative equal biosynthesis of 1beta-hydroxy-5-epiaristolochene, 2beta-hydroxy-5-epiaristolochene, and 3beta-hydroxy-5-epiaristolochene from 5-epiaristolochene with wild type efficiency and converts about 1.5% of these monohydroxylated products to their respective ketone forms
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expressed in a WAT11 line of yeast
expressed in WAT11 yeast strain
gene EAH, quantitative RT-PCR enzyme expression analysis, phylogenetic analysis
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after an apparent lag phase of 8 h, a rapid induction of hydroxylase activity is observed 10 to 15 h after elicitor addition (cellulase or paraciticein) to the cell cultures, reaching a maximum by 18 h followed by a rather gradual decline of 10 to 20% over the next 8 h
expression is significantly upregulated after inoculation with Phytophthora infestans, or treatment with the INF1 elicitor of Phytophthora infestans. Wound-induced protein kinase WIPK and salicylic-acid-induced protein kinase SIPK and its homolog NTN4 are involved in transcriptional upregulation of 5-epi-aristolochene dihydroxylase genes
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gene is highly expressed in response to Colletotrichum scovillei during fruit development
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pathogen Phytophthora infestans isolates T30-4 and NL07434 highly induce the enzyme expression in Capsicum annuum, transcriptome analysis, overview
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Ralston, L.; Kwon, S.T.; Schoenbeck, M.; Ralston, J.; Schenk, D.J.; Coates, R.M.; Chappell, J.
Cloning, heterologous expression, and functional characterization of 5-epi-aristolochene-1,3-dihydroxylase from tobacco (Nicotiana tabacum)
Arch. Biochem. Biophys.
393
222-235
2001
Nicotiana tabacum (Q94FM7), Nicotiana tabacum
brenda
Greenhagen, B.T.; Griggs, P.; Takahashi, S.; Ralston, L.; Chappell, J.
Probing sesquiterpene hydroxylase activities in a coupled assay with terpene synthases
Arch. Biochem. Biophys.
409
385-394
2003
Nicotiana tabacum (Q94FM7)
brenda
Takahashi, S.; Zhao, Y.; O'Maille, P.E.; Greenhagen, B.T.; Noel, J.P.; Coates, R.M.; Chappell, J.
Kinetic and molecular analysis of 5-epiaristolochene 1,3-dihydroxylase, a cytochrome P450 enzyme catalyzing successive hydroxylations of sesquiterpenes
J. Biol. Chem.
280
3686-3696
2005
Nicotiana tabacum (Q94FM7)
brenda
Lee, H.A.; Kim, S.; Kim, S.; Choi, D.
Expansion of sesquiterpene biosynthetic gene clusters in pepper confers nonhost resistance to the Irish potato famine pathogen
New Phytol.
215
1132-1143
2017
Capsicum annuum
brenda
Rin, S.; Imano, S.; Camagna, M.; Suzuki, T.; Tanaka, A.; Sato, I.; Chiba, S.; Kawakita, K.; Takemoto, D.
Expression profiles of genes for enzymes involved in capsidiol production in Nicotiana benthamiana
J. Gen. Plant Pathol.
86
340-349
2020
Nicotiana benthamiana
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brenda
Baba, V.Y.; Powell, A.F.; Ivamoto-Suzuki, S.T.; Pereira, L.F.P.; Vanzela, A.L.L.; Giacomin, R.M.; Strickler, S.R.; Mueller, L.A.; Rodrigues, R.; Goncalves, L.S.A.
Capsidiol-related genes are highly expressed in response to Colletotrichum scovillei during Capsicum annuum fruit development stages
Sci. Rep.
10
12048
2020
Capsicum annuum
brenda
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