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Information on EC 1.14.14.126 - beta-amyrin 28-monooxygenase and Organism(s) Solanum lycopersicum and UniProt Accession K4CEE8

for references in articles please use BRENDA:EC1.14.14.126
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IUBMB Comments
A cytochrome P-450 (heme-thiolate) protein found in plants. The enzyme is involved in the biosynthesis of oleanane-type triterpenoids, such as ginsenoside Ro. The enzyme from Medicago truncatula (barrel medic) (CYP716A12) can also convert alpha-amyrin and lupeol to ursolic acid and betulinic acid, respectively. The enzyme from Maesa lanceolata (false assegai) (CYP16A75) does not catalyse the reaction to completion, resulting in accumulation of both intermediates.
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Solanum lycopersicum
UNIPROT: K4CEE8
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Word Map
The taxonomic range for the selected organisms is: Solanum lycopersicum
The enzyme appears in selected viruses and cellular organisms
Synonyms
cyp716a12, multifunctional p450, multifunctional oxidase, cyp716a52v2, c-28 oxidase, cyp716a179, cyp716a253, triterpene c-28 oxidase, cyp716a94, cyp716a244, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
multifunctional triterpene C-28 oxidase
-
additional information
formerly EC 1.14.13.201
PATHWAY SOURCE
PATHWAYS
-
-
SYSTEMATIC NAME
IUBMB Comments
beta-amyrin,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (28-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein found in plants. The enzyme is involved in the biosynthesis of oleanane-type triterpenoids, such as ginsenoside Ro. The enzyme from Medicago truncatula (barrel medic) (CYP716A12) can also convert alpha-amyrin and lupeol to ursolic acid and betulinic acid, respectively. The enzyme from Maesa lanceolata (false assegai) (CYP16A75) does not catalyse the reaction to completion, resulting in accumulation of both intermediates.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
beta-amyrin + 3 O2 + 3 NADPH + 3 H+
oleanolate + 3 NADP+ + 4 H2O
show the reaction diagram
-
-
-
?
beta-amyrin + O2 + NADPH + H+
erythrodiol + NADP+ + H2O
show the reaction diagram
-
-
-
?
beta-amyrin + 3 O2 + 3 NADPH + 3 H+
oleanolate + 3 NADP+ + 4 H2O
show the reaction diagram
-
-
-
?
beta-amyrin + O2 + NADPH + H+
erythrodiol + NADP+ + H2O
show the reaction diagram
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
beta-amyrin + 3 O2 + 3 NADPH + 3 H+
oleanolate + 3 NADP+ + 4 H2O
show the reaction diagram
-
-
-
?
beta-amyrin + O2 + NADPH + H+
erythrodiol + NADP+ + H2O
show the reaction diagram
-
-
-
?
beta-amyrin + 3 O2 + 3 NADPH + 3 H+
oleanolate + 3 NADP+ + 4 H2O
show the reaction diagram
-
-
-
?
beta-amyrin + O2 + NADPH + H+
erythrodiol + NADP+ + H2O
show the reaction diagram
-
-
-
?
additional information
?
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cv. Heinz 1706
UniProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
exclusive expresion of CYP716A46 in flowers
Manually annotated by BRENDA team
very low expresion level
Manually annotated by BRENDA team
high enzyme level
Manually annotated by BRENDA team
very low expresion level
Manually annotated by BRENDA team
additional information
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
the enzyme belongs to the CYP716C subfamily, many CYP716 family P450 enzymes are characterized as multifunctional triterpene C-28 oxidases, which oxidize alpha-amyrin and beta-amyrin to the widely distributed triterpenoids ursolic and oleanolic acids, respectively. Isolation of all six CYP716 family genes from tomato, including CYP716A46, and sequence comparisons
metabolism
the enzyme is involved in the triterpenoid biosynthesis in tomato
evolution
the enzyme belongs to the CYP716C subfamily, many CYP716 family P450 enzymes are characterized as multifunctional triterpene C-28 oxidases, which oxidize alpha-amyrin and beta-amyrin to the widely distributed triterpenoids ursolic and oleanolic acids, respectively. Isolation of all six CYP716 family genes from tomato, including gene CYP716A44, and sequence comparisons
metabolism
the enzyme is involved in the triterpenoid biosynthesis in tomato
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
C7A46_SOLLC
482
1
54862
Swiss-Prot
Secretory Pathway (Reliability: 1)
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene CYP716A46, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, in beta-amyrin synthase (EC 5.4.99.39) and CYP716A46 co-expressing Saccharomyces cerevisiae strains SY57 and SY66, erythrodiol and oleanolic acid are detected as C-28 oxidation product of beta-amyrin
gene CYP716A44, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, in beta-amyrin synthase (EC 5.4.99.39) and CYP716A44 co-expressing Saccharomyces cerevisiae strains SY57 and SY66 erythrodiol and oleanolic acid are detected as C-28 oxidation product of beta-amyrin
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Yasumoto, S.; Seki, H.; Shimizu, Y.; Fukushima, E.O.; Muranaka, T.
Functional characterization of CYP716 family P450 enzymes in triterpenoid biosynthesis in tomato
Front. Plant Sci.
8
21
2017
Solanum lycopersicum (A0A3Q7HBJ5), Solanum lycopersicum (K4CEE8)
Manually annotated by BRENDA team