BRENDA - Enzyme Database show
show all sequences of 1.14.14.126

Two CYP716A subfamily cytochrome P450 monooxygenases of sweet basil play similar but nonredundant roles in ursane- and oleanane-type pentacyclic triterpene biosynthesis

Misra, R.; Sharma, S.; Sandeep, S.; Garg, A.; Chanotiya, C.; Ghosh, S.; New Phytol. 214, 706-720 (2017)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
gene CYP716A253, semi-quantitative and quantitative RT-PCR enzyme expressison analysis, phylogenetic analysis, recombinant expression in Saccharomyces cerevisiae strain BY4741
Ocimum basilicum
Engineering
Amino acid exchange
Commentary
Organism
additional information
virus-induced gene silencing (VIGS) in Ocimum basilicum, plasmids are individually transformed into Agrobacterium tumefaciens strain GV3101 by the freeze-thaw method
Ocimum basilicum
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
beta-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
Ocimum basilicum
overall reaction
oleanolate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
Ocimum basilicum
-
erythrodiol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
erythrodiol + [reduced NADPH-hemoprotein reductase] + O2
Ocimum basilicum
-
oleanolic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
?
oleanolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
Ocimum basilicum
-
oleanolate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Ocimum basilicum
A0A161ABB0
-
-
Source Tissue
Source Tissue
Commentary
Organism
Textmining
leaf
-
Ocimum basilicum
-
additional information
spatiotemporal expression patterns of amyrin synthases and amyrin C-28 oxidases
Ocimum basilicum
-
seedling
-
Ocimum basilicum
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
beta-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
overall reaction
745906
Ocimum basilicum
oleanolate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
-
745906
Ocimum basilicum
erythrodiol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
erythrodiol + [reduced NADPH-hemoprotein reductase] + O2
-
745906
Ocimum basilicum
oleanolic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
additional information
GC-MS metabolite identification
745906
Ocimum basilicum
?
-
-
-
-
oleanolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
-
745906
Ocimum basilicum
oleanolate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
Cofactor
Cofactor
Commentary
Organism
Structure
cytochrome P450
-
Ocimum basilicum
heme
-
Ocimum basilicum
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._
Ocimum basilicum
Cloned(Commentary) (protein specific)
Commentary
Organism
gene CYP716A253, semi-quantitative and quantitative RT-PCR enzyme expressison analysis, phylogenetic analysis, recombinant expression in Saccharomyces cerevisiae strain BY4741
Ocimum basilicum
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
cytochrome P450
-
Ocimum basilicum
heme
-
Ocimum basilicum
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._
Ocimum basilicum
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
additional information
virus-induced gene silencing (VIGS) in Ocimum basilicum, plasmids are individually transformed into Agrobacterium tumefaciens strain GV3101 by the freeze-thaw method
Ocimum basilicum
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
beta-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
Ocimum basilicum
overall reaction
oleanolate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
Ocimum basilicum
-
erythrodiol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
erythrodiol + [reduced NADPH-hemoprotein reductase] + O2
Ocimum basilicum
-
oleanolic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
?
oleanolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
Ocimum basilicum
-
oleanolate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
leaf
-
Ocimum basilicum
-
additional information
spatiotemporal expression patterns of amyrin synthases and amyrin C-28 oxidases
Ocimum basilicum
-
seedling
-
Ocimum basilicum
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
beta-amyrin + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
overall reaction
745906
Ocimum basilicum
oleanolate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
-
745906
Ocimum basilicum
erythrodiol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
erythrodiol + [reduced NADPH-hemoprotein reductase] + O2
-
745906
Ocimum basilicum
oleanolic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
additional information
GC-MS metabolite identification
745906
Ocimum basilicum
?
-
-
-
-
oleanolic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
-
745906
Ocimum basilicum
oleanolate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
Expression
Organism
Commentary
Expression
Ocimum basilicum
infection with Sclerotinia sclerotiorum and treatement with methyljasmonate and ACC induce the enzyme up to 6.8, 4.3 and 91fold
up
General Information
General Information
Commentary
Organism
metabolism
enzymes CYP716A252 and CYP716A253 catalyze sequential three-step oxidation at the C-28 position of alpha-amyrin and beta-amyrin to produce ursolic acid and oleanolic acid, respectively, essential roles for both of these CYP716As in constitutive biosynthesis of ursolic acid and oleanolic acid in sweet basil leaves, similar as well as distinct roles of CYP716A252 and CYP716A253 for the spatio-temporal biosynthesis of pentacyclic triterpenes. The cyclization of 2,3-oxidosqualene into either of two structural isomers, alpha-amyrin or beta-amyrin is the initial diversifying step for ursolic acid and oleanolic acid biosynthesis, pathway overview
Ocimum basilicum
additional information
enzyme CYP716A253 contains conserved amino acid motifs characteristic of bona fide CYP450s includig the highly conserved heme-binding motif FxxGxRxCxG at the C-terminal end, an EXXR.-.R motif (ERR triad) that maintains protein tertiary structure and positioning of the heme pocket, an A/GGXD/ET motif that participates in oxygen binding and activation, and a proline-rich and a hydrophobic regions at the N-terminal end
Ocimum basilicum
physiological function
the medicinal plant sweet basil (Ocimum basilicum) accumulates bioactive ursane- and oleanane-type pentacyclic triterpenes (PCTs), ursolic acid and oleanolic acid, respectively, in a spatio-temporal manner. Major role for CYP716A253 and a minor role for CYP716A252 in determining elicitor-induced biosynthesis of ursolic acid and oleanolic acid
Ocimum basilicum
General Information (protein specific)
General Information
Commentary
Organism
metabolism
enzymes CYP716A252 and CYP716A253 catalyze sequential three-step oxidation at the C-28 position of alpha-amyrin and beta-amyrin to produce ursolic acid and oleanolic acid, respectively, essential roles for both of these CYP716As in constitutive biosynthesis of ursolic acid and oleanolic acid in sweet basil leaves, similar as well as distinct roles of CYP716A252 and CYP716A253 for the spatio-temporal biosynthesis of pentacyclic triterpenes. The cyclization of 2,3-oxidosqualene into either of two structural isomers, alpha-amyrin or beta-amyrin is the initial diversifying step for ursolic acid and oleanolic acid biosynthesis, pathway overview
Ocimum basilicum
additional information
enzyme CYP716A253 contains conserved amino acid motifs characteristic of bona fide CYP450s includig the highly conserved heme-binding motif FxxGxRxCxG at the C-terminal end, an EXXR.-.R motif (ERR triad) that maintains protein tertiary structure and positioning of the heme pocket, an A/GGXD/ET motif that participates in oxygen binding and activation, and a proline-rich and a hydrophobic regions at the N-terminal end
Ocimum basilicum
physiological function
the medicinal plant sweet basil (Ocimum basilicum) accumulates bioactive ursane- and oleanane-type pentacyclic triterpenes (PCTs), ursolic acid and oleanolic acid, respectively, in a spatio-temporal manner. Major role for CYP716A253 and a minor role for CYP716A252 in determining elicitor-induced biosynthesis of ursolic acid and oleanolic acid
Ocimum basilicum
Expression (protein specific)
Organism
Commentary
Expression
Ocimum basilicum
infection with Sclerotinia sclerotiorum and treatement with methyljasmonate and ACC induce the enzyme up to 6.8, 4.3 and 91fold
up
Other publictions for EC 1.14.14.126
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
744248
Zhan
Cytochrome P450 CYP716A254 ca ...
Anemone flaccida
Biochem. Biophys. Res. Commun.
495
1271-1277
2018
-
-
1
-
-
-
-
-
2
-
-
1
-
3
-
-
-
-
-
1
-
-
2
-
1
-
-
-
1
-
-
2
-
-
-
-
-
1
2
-
-
-
-
-
-
-
2
-
-
1
-
-
-
-
-
1
-
-
2
-
1
-
-
-
1
-
-
-
-
2
2
-
-
-
745002
Yasumoto
Functional characterization o ...
Solanum lycopersicum
Front. Plant Sci.
8
21
2017
-
-
1
-
-
-
-
-
-
-
-
6
-
2
-
-
-
-
-
4
-
-
6
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
6
-
-
-
-
-
6
-
-
6
-
-
-
-
-
-
-
-
-
-
2
4
-
-
-
745906
Misra
Two CYP716A subfamily cytochr ...
Ocimum basilicum
New Phytol.
214
706-720
2017
-
-
1
-
1
-
-
-
-
-
-
4
-
4
-
-
-
-
-
3
-
-
5
-
-
-
-
-
-
-
-
3
-
-
-
-
-
1
3
-
1
-
-
-
-
-
-
-
-
4
-
-
-
-
-
3
-
-
5
-
-
-
-
-
-
-
-
-
1
3
3
1
-
-
746004
Jo
beta-Amyrin synthase (EsBAS) ...
Eleutherococcus senticosus
Phytochemistry
135
53-63
2017
-
-
1
-
-
-
-
-
1
1
-
4
-
7
-
-
-
-
-
2
-
-
7
1
-
-
-
-
-
-
-
3
-
-
-
-
-
1
3
-
-
-
-
-
-
-
1
1
-
4
-
-
-
-
-
2
-
-
7
1
-
-
-
-
-
-
-
-
1
2
2
1
-
-
746048
Tamura
Cytochrome P450 monooxygenase ...
Platycodon grandiflorus
Plant Cell Physiol.
58
874-884
2017
-
-
1
-
-
-
-
-
-
-
-
4
-
5
-
-
-
-
-
4
-
-
11
-
1
-
-
-
-
-
-
2
-
-
-
-
-
2
4
-
-
-
-
-
-
-
-
-
-
4
-
-
-
-
-
8
-
-
11
-
2
-
-
-
-
-
-
-
-
2
3
-
-
-
746049
Han
Transcriptomic analysis of Ka ...
Kalopanax septemlobus
Plant Cell Physiol.
59
319-330
2017
-
-
1
-
-
-
-
-
2
1
-
1
-
7
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
3
-
-
-
-
-
1
3
-
-
-
-
-
-
-
2
1
-
1
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
2
2
-
-
-
746060
Tamura
CYP716A179 functions as a tri ...
Glycyrrhiza uralensis, Glycyrrhiza uralensis 308-19
Plant Cell Rep.
36
437-445
2017
-
-
1
-
-
-
-
-
-
-
-
16
-
6
-
-
-
-
-
6
-
-
18
-
-
-
-
-
-
-
-
2
-
-
-
-
-
1
2
-
-
-
-
-
-
-
-
-
-
16
-
-
-
-
-
6
-
-
18
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
748772
Andre
Multifunctional oxidosqualene ...
Malus domestica
New Phytol.
211
1279-1294
2016
-
-
1
-
-
-
-
-
-
-
-
5
-
2
-
-
-
-
-
1
-
-
6
-
-
-
-
-
-
-
-
1
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
-
-
5
-
-
-
-
-
1
-
-
6
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
732623
Han
The involvement of beta-amyrin ...
Panax ginseng
Plant Cell Physiol.
54
2034-2046
2013
-
-
1
-
-
-
-
-
-
-
1
1
-
5
-
-
-
-
-
2
-
-
2
1
1
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
-
-
2
-
-
2
1
1
-
-
-
1
-
-
-
1
1
1
1
-
-
732622
Fukushima
CYP716A subfamily members are ...
Medicago truncatula, Vitis vinifera
Plant Cell Physiol.
52
2050-2061
2011
-
-
2
-
-
-
-
-
-
-
-
7
-
6
-
-
-
4
-
2
-
-
19
-
-
-
-
-
-
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
-
7
-
-
-
-
-
4
-
-
19
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
732627
Carelli
Medicago truncatula CYP716A12 ...
Medicago truncatula
Plant Cell
23
3070-3081
2011
-
-
1
-
-
-
-
-
1
-
1
-
-
5
-
-
-
-
-
5
-
-
2
1
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
5
-
-
2
1
-
-
-
-
-
-
-
-
-
1
1
-
-
-