Information on EC 1.14.14.115 - 11-oxo-beta-amyrin 30-oxidase

for references in articles please use BRENDA:EC1.14.14.115
Word Map on EC 1.14.14.115
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.14.115
-
RECOMMENDED NAME
GeneOntology No.
11-oxo-beta-amyrin 30-oxidase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
11-oxo-beta-amyrin + 3 O2 + 3 [reduced NADPH-hemoprotein reductase] = glycyrrhetinate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
show the reaction diagram
overall reaction
-
-
-
11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase] = 30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1a)
-
-
-
30-hydroxy-11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase] = glycyrrhetaldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
(1b)
-
-
-
glycyrrhetaldehyde + O2 + [reduced NADPH-hemoprotein reductase] = glycyrrhetinate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1c)
-
-
-
SYSTEMATIC NAME
IUBMB Comments
11-oxo-beta-amyrin,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (30-hydroxylating)
A heme-thiolate protein (cytochrome P-450). The enzyme is involved in the biosynthesis of the triterpenoid saponin glycyrrhizin in the plant Glycyrrhiza uralensis (licorice). The enzyme from the plant Medicago truncatula can also hydroxylate beta-amyrin.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
the enzyme belongs to the CYP716A subfamily of cytochrome P450 monooxygenases
metabolism
-
the beta-amyrin 11-oxidase gene CYP88D6 is the initial P450 gene in glycyrrhizin biosynthesis. CYP72A154 is responsible for C-30 oxidation of beta-amyrin in the glycyrrhizin pathway; the enzyme is involved in the biosynthesis of glycyrrhizin
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
30-hydroxy-11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
glycyrrhetaldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
maniladiol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
hydroxylation at C-16beta, main activity of enzyme CYP716A141
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
oleanolic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
hydroxylation at C-28, reaction of EC 1.14.13.201
-
-
?
glycyrrhetaldehyde + O2 + [reduced NADPH-hemoprotein reductase]
glycyrrhetinate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
maniladiol + [reduced NADPH-hemoprotein reductase] + O2
cochalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
hydroxylation at C-28
-
-
?
oleanolic acid + [reduced NADPH-hemoprotein reductase] + O2
cochalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
hydroxylation at C-16beta
-
-
?
additional information
?
-
CYP716A141 is capable of catalyzing oxidation at both C-16beta and C-28, metabolites analysis by mass spectrometry
-
-
-
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
11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
the enzyme mainly catalyzes the C-30 hydroxylation of 11-oxo-beta-amyrin to yield 30-hydroxy-11-oxo-beta-amyrin as the major product, accompanied by its isomers as minor products
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
maniladiol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
A0A1I9Q5Z0
hydroxylation at C-16beta, main activity of enzyme CYP716A141
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
oleanolic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
A0A1I9Q5Z0
hydroxylation at C-28, reaction of EC 1.14.13.201
-
-
?
maniladiol + [reduced NADPH-hemoprotein reductase] + O2
cochalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
A0A1I9Q5Z0
hydroxylation at C-28
-
-
?
oleanolic acid + [reduced NADPH-hemoprotein reductase] + O2
cochalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
A0A1I9Q5Z0
hydroxylation at C-16beta
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH-hemoprotein reductase
A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli DH10Bac cells and in Saccharomyces cerevisiae strain BJ2168; expressed in Saccharomyces cerevisiae strain BJ2168 that endogenously produces 11-oxo-beta-amyrin
-
gene CYP716A141, DNA and amino acid sequence determination and analysis, phylogenetic tree, quantitative real-time PCR enzyme expression analysis, recombinant coexpression of genes CYP716A140v2 and CYP716A141 in Saccharomyces cerevisiae strain 10, that shows increased cochalic acid levels