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EC Tree
IUBMB Comments A cytochrome P-450 (heme thiolate) plant enzyme that catalyses the 2-hydroxylation of multiple flavanones such as (2S)-naringenin, (2S)-eriodictyol, (2S)-pinocembrin, and (2S)-liquiritigenin. The products are meta-stable and exist in an equilibrium with open forms such as 1-(4-hydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propane-1,3-dione.
The enzyme appears in viruses and cellular organisms
Synonyms
cyp93g2, flavanone 2-hydroxylase, (2s)-flavanone 2-hydroxylase, osf2h, os06g01250,
more
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(2S)-flavanone 2-hydroxylase
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EC 1.14.13.87
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formerly
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EC 1.14.14.140
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formerly
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licodione synthase
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liquiritigenin,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (licodione-forming)
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CYP93G2
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LS
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additional information
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LS is likely to be identical with flavone synthase II from soybean
additional information
CYP93B1 encodes (2S)-flavanone 2-hydroxylase, which has previously been designated to licodione synthase and flavone synthase II
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a flavanone + [reduced NADPH-hemoprotein reductase] + O2 = a 2-hydroxyflavanone + [oxidized NADPH-hemoprotein reductase] + H2O
a flavanone + [reduced NADPH-hemoprotein reductase] + O2 = a 2-hydroxyflavanone + [oxidized NADPH-hemoprotein reductase] + H2O
a heme-thiolate protein, P-450, it probably forms 2-hydroxyliquiritigenin which spontaneously forms licodione, NADH can act instead of NADPH, but more slowly, reaction mechanism
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a flavanone + [reduced NADPH-hemoprotein reductase] + O2 = a 2-hydroxyflavanone + [oxidized NADPH-hemoprotein reductase] + H2O
mechanism, stereoselectivity
a flavanone + [reduced NADPH-hemoprotein reductase] + O2 = a 2-hydroxyflavanone + [oxidized NADPH-hemoprotein reductase] + H2O
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flavanone,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (2-hydroxylating)
A cytochrome P-450 (heme thiolate) plant enzyme that catalyses the 2-hydroxylation of multiple flavanones such as (2S)-naringenin, (2S)-eriodictyol, (2S)-pinocembrin, and (2S)-liquiritigenin. The products are meta-stable and exist in an equilibrium with open forms such as 1-(4-hydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propane-1,3-dione.
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(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
(2S)-naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
luteolin + [oxidized NADPH-hemoprotein reductase] + H2O
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product is formed after acid treatment
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naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
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(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
hydroxylation of liquiritigenin at C-2 and formation of licodione as a result of non-enzymatic hemiacetal opening, selectivity towards (2S)-flavanone
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(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
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requires NAD(P)H and O2 for activity, the reaction mechanism is likely to be 2-hydroxylation of the flavanone molecule to yield 2-hydroxyliquiritigenin and the subsequent hemiacetal opening to give licodione, introduces one atom of oxygen into the substrate, NADH serves as hydride donor less effectively than NADPH
i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
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(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
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requires NAD(P)H and O2 for activity, the reaction mechanism is likely to be 2-hydroxylation of the flavanone molecule to yield 2-hydroxyliquiritigenin and the subsequent hemiacetal opening to give licodione, introduces one atom of oxygen into the substrate, NADPH serves as hydride donor more effectively than NADH
i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
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(2S)-naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
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the product is further converted into apigenin when treated with acid
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(2S)-naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
selectivity towards (2S)-flavanone
the product is further converted into apigenin when treated with HCl
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eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
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eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
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naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
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naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
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additional information
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flavone biosynthesis
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additional information
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involved in flavonoid biosynthesis, may play a role symbiotic plant-microbe interactions
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eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
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eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
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eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
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naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
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naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
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additional information
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flavone biosynthesis
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additional information
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involved in flavonoid biosynthesis, may play a role symbiotic plant-microbe interactions
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?
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cytochrome P-450
a cytochrome P-450 (heme thiolate) enzyme
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cytochrome P-450
a cytochrome P-450 (heme thiolate) enzyme
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cytochrome P450
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cytochrome P450
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cytochrome P450-dependent, cytochrome P450 monooxygenase
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Ancymidol
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0.001 mM: 33% inhibition, 0.01 mM: 68% inhibition, 0.1 mM: 81% inhibition
ketoconazole
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0.001 mM: 44% inhibition, 0.01 mM: 86% inhibition, 0.1 mM: 72% inhibition
Metyrapone
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0.001 mM: 23% inhibition, 0.01 mM: 57% inhibition, 0.1 mM: 74% inhibition
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additional information
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yeast extract induces LS activity
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25
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assay at
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subsp. japonica
SwissProt
brenda
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SwissProt
brenda
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SwissProt
brenda
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brenda
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yeast extract-induced
brenda
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brenda
recombinant enzyme, expressed in Sf9 insect cells or yeast cells
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brenda
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malfunction
knocking down Os06g01250 in rice (Oryza sativa subsp. japonica Zhonghua 11) preferentially depletes the accumulation of C-glycosylapigenin, C-glycosylluteolin, and C-glycosylchrysoeriol but does not affect the levels of tricin
metabolism
the enzyme channels flavanones to C-glycosylflavone biosynthesis in rice
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C93B1_GLYEC
523
1
59496
Swiss-Prot
Secretory Pathway (Reliability: 4 )
C93G2_ORYSJ
518
2
56681
Swiss-Prot
other Location (Reliability: 5 )
A0A396I5L9_MEDTR
148
0
16580
TrEMBL
Mitochondrion (Reliability: 4 )
D4Z854_SPHJU
Sphingobium japonicum (strain DSM 16413 / CCM 7287 / MTCC 6362 / UT26 / NBRC 101211 / UT26S)
354
0
36558
TrEMBL
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Q0ZM38_MEDTR
520
1
59170
TrEMBL
Secretory Pathway (Reliability: 3 )
A0A2P6QI77_ROSCH
523
1
59657
TrEMBL
Secretory Pathway (Reliability: 3 )
G7L269_MEDTR
520
2
59328
TrEMBL
Secretory Pathway (Reliability: 3 )
B9RHI5_RICCO
546
0
61856
TrEMBL
other Location (Reliability: 1 )
B9T2D2_RICCO
516
1
58822
TrEMBL
Secretory Pathway (Reliability: 2 )
A0A396I5M2_MEDTR
356
1
41287
TrEMBL
other Location (Reliability: 2 )
B9SYN2_RICCO
333
1
38483
TrEMBL
Secretory Pathway (Reliability: 4 )
B9T2D3_RICCO
513
1
57640
TrEMBL
Secretory Pathway (Reliability: 1 )
B9T2D1_RICCO
493
0
55731
TrEMBL
Secretory Pathway (Reliability: 2 )
B9SYN4_RICCO
506
1
57901
TrEMBL
Secretory Pathway (Reliability: 2 )
B9T2D0_RICCO
409
1
46189
TrEMBL
Secretory Pathway (Reliability: 2 )
A0A2P6QI69_ROSCH
265
0
30409
TrEMBL
other Location (Reliability: 5 )
A0A2P6QI75_ROSCH
527
1
60243
TrEMBL
Secretory Pathway (Reliability: 3 )
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CYP Ge-5/CYP93B1, expression in Sf9 insect cells and in Saccharomyces cerevisiae BJ2168
transgenic Arabidopsis overexpressing CYP93G2 or coexpressing CYP93G2 and OsCGT accumulates 2-hydroxyflavanone derivatives
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synthesis
two-step indirect glycosylation using combinations of flavanone 2-hydroxylase and C-glycosyltransferases, to convert 2-hydroxyflavanone intermediates into the 6C-glucoside flavones isovitexin and isoorientin, and the 8C-glucoside flavones vitexin and orientin. The ratio between 6C and 8C glycosylation depended on the C-glycosyltransferase used. The indirect route resuls in mixtures, similar to what has been reported for in vitro experiments
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Akashi, T.; Aoki, T.; Ayabe, S.
Identification of a cytochrome P450 cDNA encoding (2S)-flavanone 2-hydroxylase of licorice (Glycyrrhiza echinata L.; Fabaceae) which represents licodione synthase and flavone synthase II
FEBS Lett.
431
287-290
1998
Glycyrrhiza echinata (P93149)
brenda
Otani, K.; Takahashi, T.; Furuya, T.; Ayabe, S.
Licodione synthase, a cytochrome P450 monooxygenase catalyzing 2-hydroxylation of 5-deoxyflavanone, in cultured Glycyrrhiza echinata L. cells
Plant Physiol.
105
1427-1432
1994
Glycyrrhiza echinata
brenda
Vanegas, K.G.; Larsen, A.B.; Eichenberger, M.; Fischer, D.; Mortensen, U.H.; Naesby, M.
Indirect and direct routes to C-glycosylated flavones in Saccharomyces cerevisiae
Microb. Cell Fact.
17
107
2018
Oryza sativa Japonica Group (Q5VRI5)
brenda
Du, Y.; Chu, H.; Chu, I.K.; Lo, C.
CYP93G2 is a flavanone 2-hydroxylase required for C-glycosylflavone biosynthesis in rice
Plant Physiol.
154
324-333
2010
Oryza sativa (Q5VRI5), Oryza sativa
brenda
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