Information on EC 1.3.1.92 - artemisinic aldehyde DELTA11(13)-reductase

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The expected taxonomic range for this enzyme is: Artemisia annua

EC NUMBER
COMMENTARY hide
1.3.1.92
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RECOMMENDED NAME
GeneOntology No.
artemisinic aldehyde DELTA11(13)-reductase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(11R)-dihydroartemisinic aldehyde + NADP+ = artemisinic aldehyde + NADPH + H+
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
artemisinin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
artemisinic aldehyde:NADP+ oxidoreductase
Cloned from Artemisia annua. In addition to the reduction of artemisinic aldehyde it is also able to a lesser extent to reduce artemisinic alcohol and artemisinic acid. Part of the biosyntheis of artemisinin.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-carvone + NADH + H+
(1R,4S)-isodihydrocarvone + NAD+
show the reaction diagram
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plus about 20% of (1S,4S)-dihydrocarvone
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?
2-cyclohexen-1-one + NADH + H+
cyclohexanone + NAD+
show the reaction diagram
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-
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?
2E-nonenal + NADH + H+
nonanal + NAD+
show the reaction diagram
about 12% of the activity with artemisinic aldehyde
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-
?
artemisinic aldehyde + NADH + H+
(11R)-dihydroartemisinic aldehyde + NAD+
show the reaction diagram
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-
-
?
artemisinic aldehyde + NADPH + H+
(11R)-dihydroartemisinic aldehyde + NADP+
show the reaction diagram
artemisinic aldehyde + NADPH + H+
dihydroartemisinic aldehyde + NADP+
show the reaction diagram
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-
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
artemisinic aldehyde + NADPH + H+
(11R)-dihydroartemisinic aldehyde + NADP+
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
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NADPH is preferred over NADH
NADPH
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
miconazole
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0.2 mM miconazole induce a 2.5-fold increase of artemisinin production after 24 h, but have severe effects on cell viability
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.65
(+)-carvone
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30C, pH 7.5
0.79
2-cyclohexen-1-one
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30C, pH 7.5
0.019
artemisinic aldehyde
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30C, pH 7.5
0.77
NADH
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30C, pH 7.5
0.095
NADPH
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30C, pH 7.5
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.86
(+)-carvone
-
30C, pH 7.5
1.8
2-cyclohexen-1-one
-
30C, pH 7.5
2.6
artemisinic aldehyde
-
30C, pH 7.5
1.3
NADH
-
30C, pH 7.5
2.5
NADPH
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30C, pH 7.5
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.3
(+)-carvone
-
30C, pH 7.5
2.3
2-cyclohexen-1-one
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30C, pH 7.5
140
artemisinic aldehyde
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30C, pH 7.5
1.7
NADH
-
30C, pH 7.5
26
NADPH
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30C, pH 7.5
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5
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complete inhibition
9
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about 25% of maximum activity
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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flower bud, moderate expression
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
44000
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gel filtration
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Saccharomyces cerevisiae
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gene DBR2, cloning, sequencing, and analysis of the promoter of the DBR2 gene, detailed overview. The activity of the artemisinic aldehyde DELTA11(13) reductase promoter is important for artemisinin yield in different chemotypes of Artemisia annua, quantitative real-time PCR expression analysis, overview
gene DBR2, overexpression in Artemisia annua under control of the CaMV 35S promoter via transfecton through Agrobacterium tumefaciens strain LBA4404 mediated leaf disc transformation, quantitative real-time PCR expression analysis, method evaluation
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gene DBR2, quantitative real-time PCR expression analysis
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gene DBR2, recombinant expression of the enzyme in transgenic Nicotiana tabacum plant leaf chloroplasts via transfection with Agrobacterium tumefaciens strain EHA105, nuclear genome transformation of homoplastomic plant
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression levels of farnesyl diphosphate synthase (FPS), cytochrome P450-dependent hydroxylase CYP71AV1, and double bond reductase 2 (DBR2) are increased significantly in plants overexpressing Artemisia annua allene oxide cyclase, AaAOC. The product of AOC is jasmonate, that induces the expression of FPS, CYP71AV1, and DBR2
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methyljasmonate does not induce significant changes in the expression of DBR2
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the enzyme DBR2 is induced by 0.12 mmol/l of cadmium. Appropriate doses of cadmium can increase the concentrations of artemisinic metabolites at a certain time point by upregulating the relative expression levels of key enzyme genes involved in artemisinin biosynthesis, overview
three jasmonate-responsive transcription factors, ethylene response factor 1, ethylene response factor 2, and octadecanoidresponsive AP2/ERF, all transcriptionally activate the expression of artemisinin biosynthetic genes, such as amorpha-4,11-diene synthase (ADS), CYP71AV1, DBR2, and aldehyde dehydrogenase 1 (ALDH1). Cold stress indirectly activates the DBR2 expression by increasing the amount of jasmonate through upregulation of jasmonate biosynthetic genes (LOX1, LOX2, allene oxide cyclase [AOC], and jasmonate resistant 1 [JAR1]). Levels of artemisinin and related secondary metabolites, such as dihydroartemisinic acid, artemisinin B, and artemisinic acid, are increased in Artemisia annua under cold stress
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treatment for 30 min and 4 h with miconazole induces about four- und fivefold upregulation of the DBR2 gene, respectively
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
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oral feeding of whole intact plant cells bioencapsulating the artemisinin reduces the Plasmodium falciparum parasitemia levels in challenged mice in comparison with commercial drug. The synergistic approache may facilitate low-cost production and delivery of artemisinin and other drugs through metabolic engineering of edible plants
medicine
artemisinin is the main ingredient for malaria prevention. The World Health Organization recommends artemisinin combination therapies (ACT) as the first-line therapy for malaria worldwide
synthesis