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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 + 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
Substrates: hydroxylation at C-16beta, main activity of enzyme CYP716A141
Products: -
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
oleanolic acid + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: hydroxylation at C-28, reaction of EC 1.14.13.201
Products: -
?
glycyrrhetaldehyde + O2 + [reduced NADPH-hemoprotein reductase]
glycyrrhetinate + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: -
Products: -
?
maniladiol + [reduced NADPH-hemoprotein reductase] + O2
cochalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: hydroxylation at C-28
Products: -
?
oleanolic acid + [reduced NADPH-hemoprotein reductase] + O2
cochalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: hydroxylation at C-16beta
Products: -
?
additional information
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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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Substrates: single oxidation reaction catalyzed by CYP72A154
Products: -
?
11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: 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
Products: -
?
11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
?
11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
?
30-hydroxy-11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
glycyrrhetaldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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Substrates: single oxidation reaction catalyzed by CYP72A154
Products: -
?
30-hydroxy-11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
glycyrrhetaldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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Substrates: -
Products: -
?
additional information
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Substrates: CYP716A141 is capable of catalyzing oxidation at both C-16beta and C-28, metabolites analysis by mass spectrometry
Products: -
?
additional information
?
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Substrates: CYP716A141 is capable of catalyzing oxidation at both C-16beta and C-28, metabolites analysis by mass spectrometry
Products: -
?
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11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
maniladiol + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: hydroxylation at C-16beta, main activity of enzyme CYP716A141
Products: -
?
beta-amyrin + [reduced NADPH-hemoprotein reductase] + O2
oleanolic acid + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: hydroxylation at C-28, reaction of EC 1.14.13.201
Products: -
?
maniladiol + [reduced NADPH-hemoprotein reductase] + O2
cochalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: hydroxylation at C-28
Products: -
?
oleanolic acid + [reduced NADPH-hemoprotein reductase] + O2
cochalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: hydroxylation at C-16beta
Products: -
?
11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: 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
Products: -
?
11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
?
11-oxo-beta-amyrin + O2 + [reduced NADPH-hemoprotein reductase]
30-hydroxy-11-oxo-beta-amyrin + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
?
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expressed in Escherichia coli DH10Bac cells and in Saccharomyces cerevisiae strain BJ2168
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expressed in Saccharomyces cerevisiae strain BJ2168 that endogenously produces 11-oxo-beta-amyrin
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expression in Saccharomyces cerevisiae
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
expression in Saccharomyces cerevisiae
expression in Saccharomyces cerevisiae
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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
Istiandari, P.; Yasumoto, S.; Srisawat, P.; Tamura, K.; Chikugo, A.; Suzuki, H.; Seki, H.; Fukushima, E.O.; Muranaka, T.
Comparative analysis of NADPH-cytochrome P450 reductases from legumes for heterologous production of triterpenoids in transgenic Saccharomyces cerevisiae
Front. Plant Sci.
12
762546
2021
Glycyrrhiza uralensis (H1A988), Medicago truncatula (H1A981)
brenda
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