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Enzyme Nomenclature
Information on EC 1.14.13.158 - amorpha-4,11-diene 12-monooxygenase
for references in articles please use BRENDA:EC1.14.13.158transferred to EC 1.14.14.114
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1.14.13.158 amorpha-4,11-diene 12-monooxygenase
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CYP71AV1
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
amorpha-4,11-diene + O2 + NADPH + H+
artemisinic alcohol + NADP+ + H2O
-
-
-
?
artemisinic alcohol + O2 + NADPH + H+
artemisinic aldehyde + NADP+ + 2 H2O
-
-
-
?
artemisinic aldehyde + O2 + NADPH + H+
artemisinate + NADP+ + H2O
-
-
-
?
additional information
?
-
conversion of dihydroartemsinic aldehyde to artemisinate is nonenzymatic in trichomes by nonenzymatic autoxidation of dihydroartemsinic aldehyde to dihydroartemsinic acid tertiary hydroperoxide and subsequent nonenzymatic rearrangement to artemisinin
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
-
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
-
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
-
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
overall reaction via artemsinic alcohol and artemsinic aldehyde, multistep process
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
overall reaction, multistep process
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
overall reactionvia artemsinic alcohol and artemsinic aldehyde, multistep process
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
-
-
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
amorpha-4,11-diene + O2 + NADPH + H+
artemisinic alcohol + NADP+ + H2O
-
-
-
?
artemisinic alcohol + O2 + NADPH + H+
artemisinic aldehyde + NADP+ + 2 H2O
-
-
-
?
artemisinic aldehyde + O2 + NADPH + H+
artemisinate + NADP+ + H2O
-
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
-
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
-
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
-
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
overall reaction via artemsinic alcohol and artemsinic aldehyde, multistep process
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
overall reaction, multistep process
-
-
?
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
-
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
artemisinin production in Artemisia annua is localized in glandular trichomes on the surface of leaves, shoots and flowers
brenda
of stems, old and young leaves, and flower buds gathered 5-20 d after budding
brenda
the production of artemisinin occurs in specialized 10-cell biseriate glandular trichomes present on the leaves, stems, and inflorescences of Artemisia annua
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
metabolism
physiological function
malfunction
abolished activation of AabHLH1 by mutated E-boxes of the CYP71AV1 promoter
malfunction
the enzyme knockout mutant cyp71av1-1 reveals that the consequence of blocking the artemisinin biosynthetic pathway is the redirection of sesquiterpene metabolism to a sesquiterpene epoxide, termed arteannuin X. Disruption of CYP71AV1 results in the accumulation of a sesquiterpene epoxide at the expense of artemisinin
metabolism
amorpha-4,11-diene synthase (ADS) and Cyt P450 monooxygenase CYP71AV1 in Artemisia annua are two key enzymes involved in the biosynthesis of artemisinin. The promoters of ADS and CYP71AV1 contain E-box elements, which are putative binding sites for basic helix-loop-helix (bHLH) transcription factors. The E-box is important for the CYP71AV1 promoter activity. AabHLH1 can positively regulate the biosynthesis of artemisinin. AabHLH1 protein is capable of binding to the E-box cis-elements, present in both ADS and CYP71AV1 promoters, and possesses transactivation activity in yeast
metabolism
the amorpha-4,11-diene C-12 oxidase (CYP71AV1) enzyme, responsible for a series of oxidation reactions in the artemisinin biosynthetic pathway, overview
metabolism
the enzyme is involved in the artemisinin biosynthesis
metabolism
the first oxidation step by cytochrome P450 (CYP71AV1) is the main rate-limiting step in the dihydroartemisinic acid (DHAA) pathway
physiological function
amorpha-4,11-diene 12-monooxygenase (CYP71AV1) catalyzes the multistep oxidation of amorpha-4,11-diene to artemisinic alcohol and artemisinic aldehyde
physiological function
amorpha-4,11-diene 12-monooxygenase (CYP71AV1) catalyzes the multistep oxidation of amorpha-4,11-diene to artemisinic alcohol and artemisinic aldehyde
physiological function
amorpha-4,11-diene 12-monooxygenase (CYP71AV1) catalyzes the multistep oxidation of amorpha-4,11-diene to artemisinic alcohol and artemisinic aldehyde
physiological function
-
amorpha-4,11-diene 12-monooxygenase (CYP71AV1) catalyzes the multistep oxidation of amorpha-4,11-diene to artemisinic alcohol and artemisinic aldehyde
physiological function
enzyme CYP71AV1 is the critical enzyme that is capable of catalyzing three consecutive oxidation reactions at C-12 position of amorpha-4,11-diene to artemisinate. The heme catalytic site is situated at the C-terminal domain
physiological function
the antimalarial artemisinin is a sesquiterpene lactone produced by glandular secretory trichomes on the leaves, stems, and inflorescences of Artemisia annua. Glandular secretory trichomes are able to redirect flux into a sesquiterpene epoxide. The amorpha-4,11-diene C-12 oxidase (CYP71AV1) enzyme, responsible for a series of oxidation reactions in the artemisinin biosynthetic pathway
physiological function
the positive regulator and transcription factor, glandular trichome-specific WRKY 1, is involved in the regulatory network of the artemisinin biosynthetic pathway, overview. Both AaMYC2 and AabZIP1 form a feed-forward loop with AaGSW1 to regulate CYP71AV1
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
construction of enzyme knockout mutant cyp71av1-1, phenotype, overview
additional information
Saccharomyces cerevisiae expressing the native Artemisia annua cytochrome P450 monooxygenase (CYP71AV1) and artemisinic aldehyde D11(13) reductase (DBR2) is used as a whole-cell biocatalyst to produce the immediate artemisinin precursor, dihydroartemisinic acid (DHAA). Introducing artemisinic aldehyde dehydrogenase (ALDH1) from Artemisia annua, which recycles NADPH, results in a significant enhancement in artemisinate titer. Method optimization and evaluation, host screening and cofactor engineering, overview. The co-expression of DBR2 and modulation of abiotic conditions result in a higher yield. Optimal condition are 80 OD yeast cells in 0.05 ml reaction at pH 8.0. Growing the yeast cells at 20°C in galactose medium increases the dihydroartemisinate titer by 50%
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis
gene cyp71av1, recombinant expression of cytochrome P450 CYP71AV1 in Saccharomyces cerevisiae, coexpression with artemisinic aldehyde D11(13) reductase (DBR2), and artemisinic aldehyde dehydrogenase (ALDH1), which recycles NADPH
gene CYP71AV1, semi-quantitative RT-PCR enzyme expression analysis, the expression level of CYP71AV1 significantly increases with the overexpression of AabHLH1
DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis
DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis
DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
endophyte Penicillium oxalicum strain B4 induces the enzyme and leads to enhanced growth and artemisinin content of host plant in an in vitro dual culture of endophyte with regenerated plantlets via generation of reactive oxygen species (ROS) including superoxide ions and H2O2
the expression level of CYP71AV1 significantly increases with the overexpression of transcription factor AabHLH1. The promoters of ADS and CYP71AV1 contain E-box elements, which are putative binding sites for basic helix-loop-helix (bHLH) transcription factors. The E-box is important for the CYP71AV1 promoter activity. AabHLH1 can positively regulate the biosynthesis of artemisinin. AabHLH1 protein is capable of binding to the E-box cis-elements, present in both ADS and CYP71AV1 promoters, and possesses transactivation activity in yeast. Transient expression of AabHLH1 in Artemisia annua leaves increases transcript levels of the genes involved in artemisinin biosynthesis, such as ADS, CYP71AV1 and HMGR
transcription factor protein glandular trichome-specific WRKY 1, i.e. AaGSW1, promotes artemisinin biosynthesis in Artemisia annua by inducing CYP71AV1 expression. AaGSW1 positively regulates CYP71AV1 and AaORA expression by directly binding to the W-box motifs in their promoters. Overexpression of AaGSW1 in Artemisia annua (via Agrobacterium tumefaciens transformation method) significantly improves artemisinin and dihydroartemisinic acid contents. AaGSW1 can be directly regulated by AaMYC2 and AabZIP1, which are positive regulators of jasmonate- and abscisic acid-mediated artemisinin biosynthetic pathways, respectively. AaGSW1 binds to the W-box in the CYP71AV1 promoter in vitro and activates the transcription of CYP71AV1 in vivo. Global expression profile and phylogenetic analysis of WRKY transcription factors in Artemisia annua, overview
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
Saccharomyces cerevisiae expressing the native Artemisia annua cytochrome P450 monooxygenase (CYP71AV1) and artemisinic aldehyde D11(13) reductase (DBR2) is used as a whole-cell biocatalyst to produce the immediate artemisinin precursor, dihydroartemisinic acid (DHAA)
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Chen, X.; Zhang, C.; Too, H.
Multienzyme biosynthesis of dihydroartemisinic acid
Molecules
22
1422-1433
2017
Artemisia annua (Q1PS23)
brenda
Chen, M.; Yan, T.; Shen, Q.; Lu, X.; Pan, Q.; Huang, Y.; Tang, Y.; Fu, X.; Liu, M.; Jiang, W.; Lv, Z.; Shi, P.; Ma, Y.; Hao, X.; Zhang, L.; Li, L.; Tang, K.
Glandular trichome-specific WRKY 1 promotes artemisinin biosynthesis in Artemisia annua
New Phytol.
214
304-316
2017
Artemisia annua (Q1PS23)
brenda
Ji, Y.; Xiao, J.; Shen, Y.; Ma, D.; Li, Z.; Pu, G.; Li, X.; Huang, L.; Liu, B.; Ye, H.; Wang, H.
Cloning and characterization of AabHLH1, a bHLH transcription factor that positively regulates artemisinin biosynthesis in Artemisia annua
Plant Cell Physiol.
55
1592-1604
2014
Artemisia annua (Q1PS23)
brenda
Muangphrom, P.; Seki, H.; Suzuki, M.; Komori, A.; Nishiwaki, M.; Mikawa, R.; Fukushima, E.O.; Muranaka, T.
Functional analysis of amorpha-4,11-diene synthase (ADS) homologs from non-artemisinin-producing artemisia species the discovery of novel koidzumiol and (+)-alpha-bisabolol synthases
Plant Cell Physiol.
57
1678-1688
2016
Artemisia kurramensis, Artemisia absinthium (K7ZPJ9), Artemisia afra (K7ZR99), Artemisia annua (Q1PS23)
brenda
Zheng, L.; Tian, H.; Yuan, Y.; Wang, J.
The influence of endophytic Penicillium oxalicum B4 on growth and artemisinin biosynthesis of in vitro propagated plantlets of Artemisia annua L.
Plant Growth Regul.
80
93-102
2016
Artemisia annua (Q1PS23)
-
brenda
Czechowski, T.; Larson, T.R.; Catania, T.M.; Harvey, D.; Brown, G.D.; Graham, I.A.
Artemisia annua mutant impaired in artemisinin synthesis demonstrates importance of nonenzymatic conversion in terpenoid metabolism
Proc. Natl. Acad. Sci. USA
113
15150-15155
2016
Artemisia annua (Q1PS23)
brenda
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