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Information on EC 1.14.14.115 - 11-oxo-beta-amyrin 30-oxidase for references in articles please use BRENDA:EC1.14.14.115
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IUBMB Comments A cytochrome P-450 (heme-thiolate) protein. The enzyme from the plant Glycyrrhiza uralensis (licorice) is involved in the biosynthesis of the triterpenoid saponin glycyrrhizin. The enzyme from the plant Medicago truncatula can also hydroxylate beta-amyrin.
The enzyme appears in viruses and cellular organisms
Synonyms
beta-amyrin C-16beta oxidase, C-16beta oxidase, CYP716A141, CYP72A, CYP72A154, CYP88D6, More,
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beta-amyrin C-16beta oxidase
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additional information
cf. EC 1.14.13.201, beta-amyrin C-28 oxidase
CYP72A154
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11-oxo-beta-amyrin + 3 O2 + 3 [reduced NADPH-hemoprotein reductase] = glycyrrhetinate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
overall reaction
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11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase] = 30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
(1a)
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30-hydroxy-11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase] = glycyrrhetaldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
(1b)
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glycyrrhetaldehyde + O2 + [reduced NADPH-hemoprotein reductase] = glycyrrhetinate + [oxidized NADPH-hemoprotein reductase] + H2O
(1c)
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11-oxo-beta-amyrin,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (30-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein. The enzyme from the plant Glycyrrhiza uralensis (licorice) is involved in the biosynthesis of the triterpenoid saponin glycyrrhizin. The enzyme from the plant Medicago truncatula can also hydroxylate beta-amyrin.
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11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
30-hydroxy-11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
glycyrrhetaldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
maniladiol + [oxidized NADPH-hemoprotein reductase] + H2O
hydroxylation at C-16beta, main activity of enzyme CYP716A141
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beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
oleanolic acid + [oxidized NADPH-hemoprotein reductase] + H2O
hydroxylation at C-28, reaction of EC 1.14.13.201
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glycyrrhetaldehyde + O2 + [reduced NADPH-hemoprotein reductase]
glycyrrhetinate + [oxidized NADPH-hemoprotein reductase] + H2O
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maniladiol + [reduced NADPH-hemoprotein reductase] + O2
cochalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
hydroxylation at C-28
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oleanolic acid + [reduced NADPH-hemoprotein reductase] + O2
cochalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
hydroxylation at C-16beta
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additional information
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CYP716A141 is capable of catalyzing oxidation at both C-16beta and C-28, metabolites analysis by mass spectrometry
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11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
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single oxidation reaction catalyzed by CYP72A154
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11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
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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
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30-hydroxy-11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
glycyrrhetaldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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30-hydroxy-11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
glycyrrhetaldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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single oxidation reaction catalyzed by CYP72A154
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11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
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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
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beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
maniladiol + [oxidized NADPH-hemoprotein reductase] + H2O
hydroxylation at C-16beta, main activity of enzyme CYP716A141
-
-
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
oleanolic acid + [oxidized NADPH-hemoprotein reductase] + H2O
hydroxylation at C-28, reaction of EC 1.14.13.201
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-
?
maniladiol + [reduced NADPH-hemoprotein reductase] + O2
cochalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
hydroxylation at C-28
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-
?
oleanolic acid + [reduced NADPH-hemoprotein reductase] + O2
cochalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
hydroxylation at C-16beta
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?
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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._
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brenda
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UniProt
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the enzyme is highly expressed in roots
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additional information
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not detected in leaves
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additional information
transcriptome analysis in different tissues using RNA sequencing technology, overview
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evolution
the enzyme belongs to the CYP716A subfamily of cytochrome P450 monooxygenases
metabolism
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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
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C7254_GLYUR
523
1
59020
Swiss-Prot
C7263_MEDTR
524
1
59454
Swiss-Prot
A0A072VA38_MEDTR
523
1
60251
TrEMBL
A0A2P6QXV5_ROSCH
220
0
24785
TrEMBL
A0A2G9GCH4_9LAMI
635
1
73131
TrEMBL
A0A396JAV6_MEDTR
136
0
16080
TrEMBL
A0A072VAP5_MEDTR
518
1
59381
TrEMBL
A0A2P6RT69_ROSCH
99
0
11866
TrEMBL
A0A2P6R2D3_ROSCH
450
1
51218
TrEMBL
A0A2P6R2I5_ROSCH
169
1
19190
TrEMBL
A0A2P6Q9E6_ROSCH
523
1
59528
TrEMBL
A0A396GGV3_MEDTR
401
2
46002
TrEMBL
A0A396JEP9_MEDTR
545
2
62873
TrEMBL
A0A2P6R2E1_ROSCH
211
0
23546
TrEMBL
A0A2P6RPW3_ROSCH
93
0
10760
TrEMBL
A0A2P6P8Q9_ROSCH
531
1
60215
TrEMBL
A0A396JCZ5_MEDTR
520
1
59900
TrEMBL
G7LJ58_MEDTR
524
1
59642
TrEMBL
A0A2P6Q8N4_ROSCH
414
0
47123
TrEMBL
G7K4K9_MEDTR
516
1
59691
TrEMBL
Q2MJ17_MEDTR
524
1
59452
TrEMBL
A0A396GHE5_MEDTR
178
0
20207
TrEMBL
A0A072VK08_MEDTR
513
1
58961
TrEMBL
A0A2P6R2A8_ROSCH
105
0
12277
TrEMBL
A0A2P6SAL0_ROSCH
521
1
59505
TrEMBL
A0A072VK12_MEDTR
518
1
59142
TrEMBL
A0A2P6RPU1_ROSCH
58
0
6527
TrEMBL
A0A2P6R2C7_ROSCH
367
0
41889
TrEMBL
A0A2P6Q9F5_ROSCH
220
0
24719
TrEMBL
A0A2P6SAJ7_ROSCH
262
0
29636
TrEMBL
A0A2P6PYL1_ROSCH
257
0
28665
TrEMBL
A0A2G9FZ78_9LAMI
133
1
15916
TrEMBL
A0A396J914_MEDTR
530
1
60538
TrEMBL
Q2MJ08_MEDTR
528
1
60074
TrEMBL
A0A2G9FVW3_9LAMI
352
0
40114
TrEMBL
A0A396J916_MEDTR
530
1
60694
TrEMBL
A0A072V9E9_MEDTR
520
1
59807
TrEMBL
A0A2P6SD30_ROSCH
347
0
39506
TrEMBL
A0A2P6R2A7_ROSCH
58
0
6475
TrEMBL
A0A2G9G2A7_9LAMI
525
1
60734
TrEMBL
A0A2G9G7H3_9LAMI
417
1
49228
TrEMBL
A0A396JDQ8_MEDTR
518
1
59316
TrEMBL
A0A396JI51_MEDTR
513
1
58531
TrEMBL
A0A2G9G739_9LAMI
525
1
60606
TrEMBL
A0A2G9HQL8_9LAMI
164
1
19035
TrEMBL
A0A2P6QXY3_ROSCH
250
0
28265
TrEMBL
A0A2P6SAN6_ROSCH
250
1
28695
TrEMBL
A0A396IW59_MEDTR
43
0
4933
TrEMBL
A0A396J7L6_MEDTR
520
1
59880
TrEMBL
A0A2P6R285_ROSCH
92
0
10339
TrEMBL
A0A2P6Q9F9_ROSCH
330
0
37221
TrEMBL
A0A2P6SD78_ROSCH
66
0
7271
TrEMBL
A0A396GGT0_MEDTR
645
3
73757
TrEMBL
A0A2P6Q1G6_ROSCH
511
1
58629
TrEMBL
A0A411JJD7_GLYGL
523
0
59052
TrEMBL
A0A396JCJ6_MEDTR
111
0
12387
TrEMBL
A0A1I9Q5Z0_9ASTR
481
0
54169
TrEMBL
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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
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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
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Seki, H.; Sawai, S.; Ohyama, K.; Mizutani, M.; Ohnishi, T.; Sudo, H.; Fukushima, E.O.; Akashi, T.; Aoki, T.; Saito, K.; Muranaka, T.
Triterpene functional genomics in Licorice for identification of CYP72A154 involved in the biosynthesis of glycyrrhizin
Plant Cell
23
4112-4123
2011
Glycyrrhiza uralensis
brenda
Tamura, K.; Teranishi, Y.; Ueda, S.; Suzuki, H.; Kawano, N.; Yoshimatsu, K.; Saito, K.; Kawahara, N.; Muranaka, T.; Seki, H.
Cytochrome P450 monooxygenase CYP716A141 is a unique beta-amyrin C-16beta oxidase involved in triterpenoid saponin biosynthesis in Platycodon grandiflorus
Plant Cell Physiol.
58
874-884
2017
Platycodon grandiflorus (A0A1I9Q5Z0), Platycodon grandiflorus
brenda
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