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Information on EC 1.14.14.162 - flavanone 2-hydroxylase
for references in articles please use BRENDA:EC1.14.14.162
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
1.14.14.162 flavanone 2-hydroxylase
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
- 1.14.14.162
- flavone
- flavanones
- flavonoid
-
c-glycosides
- naringenin
- 2-hydroxyflavanone
- sativa
- apigenin
-
c-glycosylation
- eriodictyol
-
2s-flavanone
- luteolin
- tricin
- grasses
- echinata
- glycyrrhiza
-
b-ring
-
today
-
c-glucosyltransferase
- licorice
- chrysoeriol
- 7,4'-dihydroxyflavone
-
5'-hydroxylase
-
o-glycosylate
- synthesis
Reaction Schemes
showSynonyms
cyp93g2, flavanone 2-hydroxylase, (2s)-flavanone 2-hydroxylase, osf2h, os06g01250, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CYP93G15
CYP93G2
EC 1.14.13.87
-
-
formerly
-
EC 1.14.14.140
-
-
formerly
-
F2H2
licodione synthase
-
-
-
-
liquiritigenin,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (licodione-forming)
-
-
-
-
LS
additional information
additional information
-
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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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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
-
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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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PATHWAY SOURCE
PATHWAYS
MetaCyc
echinatin biosynthesis, flavonoid di-C-glucosylation, naringenin C-glucosylation, orientin and isoorientin biosynthesis I, pinocembrin C-glucosylation
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SYSTEMATIC NAME
IUBMB Comments
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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CAS REGISTRY NUMBER
COMMENTARY
157972-05-9
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(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
a 2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
luteolin + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: product is formed after acid treatment
Products: product is formed after acid treatment
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
naringenin + [reduced NADPH-hemoprotein reductase] + O2
a 2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: 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
Products: i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
Products: i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
?
(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: 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
Products: i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
Products: i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
?
(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: hydroxylation of liquiritigenin at C-2 and formation of licodione as a result of non-enzymatic hemiacetal opening, selectivity towards (2S)-flavanone
Products: -
Products: -
?
(2S)-naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: the product is further converted into apigenin when treated with acid
Products: the product is further converted into apigenin when treated with acid
?
(2S)-naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: selectivity towards (2S)-flavanone
Products: the product is further converted into apigenin when treated with HCl
Products: the product is further converted into apigenin when treated with HCl
?
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
a 2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
a 2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
a 2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
Zea mays W22
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: involved in flavonoid biosynthesis, may play a role symbiotic plant-microbe interactions
Products: -
Products: -
?
additional information
?
-
Substrates: flavone biosynthesis
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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
naringenin + [reduced NADPH-hemoprotein reductase] + O2
a 2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
a 2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
a 2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
a 2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
Zea mays W22
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: involved in flavonoid biosynthesis, may play a role symbiotic plant-microbe interactions
Products: -
Products: -
?
additional information
?
-
Substrates: flavone biosynthesis
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome P-450
a cytochrome P-450 (heme thiolate) enzyme
-
cytochrome P450
-
cytochrome P450-dependent, cytochrome P450 monooxygenase
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ancymidol
-
0.001 mM: 33% inhibition, 0.01 mM: 68% inhibition, 0.1 mM: 81% inhibition
ketoconazole
-
0.001 mM: 44% inhibition, 0.01 mM: 86% inhibition, 0.1 mM: 72% inhibition
Metyrapone
-
0.001 mM: 23% inhibition, 0.01 mM: 57% inhibition, 0.1 mM: 74% inhibition
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
OsF3H, CYP93G1, and CYP93G2 are entry enzymes for the production of flavonols, flavones, and flavone C-conjugates, respectively, and the corresponding genes together with OsCHS1 display high expression levels in the late developmental stages of the anthers
brenda
-
f transcriptomic and metabolomic analysis of fungus-infected and noninfected leaves, enzyme F2H2 is induced
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
recombinant enzyme, expressed in Sf9 insect cells or yeast cells
-
brenda
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
malfunction
metabolism
physiological function
evolution
-
flavanone hydroxylases belong to the CYP93G subfamily that clusters with characterized monocot F2Hs or FNSIIs in the phylogenetic tree, but are only distantly related to dicot F2H/FNSII enzymes belonging to the CYP93B subfamily
evolution
Zea mays W22
-
flavanone hydroxylases belong to the CYP93G subfamily that clusters with characterized monocot F2Hs or FNSIIs in the phylogenetic tree, but are only distantly related to dicot F2H/FNSII enzymes belonging to the CYP93B subfamily
-
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
malfunction
detailed analysis of rice mutants for branch-point enzymes of the downstream flavonoid pathways, including flavanone 3-hydroxylase (OsF3H), flavone synthase II (CYP93G1), and flavanone 2-hydroxylase (CYP93G2). Rice osf3h and cyp93g1 cyp93g2 CRISPR/Cas9 mutants, and cyp93g1 and cyp93g2 T-DNA insertion mutants show altered flavonoid profiles in anthers, but only the osf3h and cyp93g1 cyp93g2 mutants display reduction in seed yield
metabolism
the enzyme channels flavanones to C-glycosylflavone biosynthesis in rice
metabolism
Proposed flavonoid biosynthetic pathway in rice, overview. Flavonoids are essential for complete male fertility in rice and a combination of different classes (flavanones, flavonols, flavones, and flavone C-glycosides) appears to be important, as opposed to the essential role played primarily by flavonols that has been previously reported in several plant species. Branch-point enzymes of the downstream flavonoid pathways include flavanone 3-hydroxylase (OsF3H), a flavonol pathway entry enzyme, also flavone synthase II (CYP93G1), a flavone pathway entry enzyme, aa well as flavanone 2-hydroxylase (CYP93G2), a flavone C-glycoside pathway entry enzyme
metabolism
-
upregulation of the flavonoid biosynthetic pathway by fungal infection, detailed overview
metabolism
Zea mays W22
-
upregulation of the flavonoid biosynthetic pathway by fungal infection, detailed overview
-
physiological function
flavanone 2-hydroxylase enzyme CYP93G2 produces 2-hydroxyflavanones from flavanones, followed by C-glycosylation and dehydration to generate flavone C-glycosides. OsF3H, CYP93G1, and CYP93G2 are entry enzymes for the production of flavonols, flavones, and flavone C-conjugates, respectively, and the corresponding genes together with OsCHS1 display high expression levels in the late developmental stages of the anthers. CYP93G2 channels the metabolite flux to flavone C-glycosides
physiological function
-
the enzyme F2H2 (CYP93G15) catalyzes the formation of 2-hydroxynaringenin. Two tautomers of a 2-hydroxynaringenin-derived compound termed xilonenin significantly inhibit the growth of two maize pathogens, e.g. Fusarium graminearum and Fusarium verticillioides. Induction of flavonoids is a general pathogen response. The non-O-methylated flavonoid naringenin also reduces the growth of all tested fungi, while its 5-O-methyl derivative shows no statistical effects at 48 h
physiological function
Zea mays W22
-
the enzyme F2H2 (CYP93G15) catalyzes the formation of 2-hydroxynaringenin. Two tautomers of a 2-hydroxynaringenin-derived compound termed xilonenin significantly inhibit the growth of two maize pathogens, e.g. Fusarium graminearum and Fusarium verticillioides. Induction of flavonoids is a general pathogen response. The non-O-methylated flavonoid naringenin also reduces the growth of all tested fungi, while its 5-O-methyl derivative shows no statistical effects at 48 h
-
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). C93B1_GLYEC
523
1
59496
Swiss-Prot
Secretory Pathway (Reliability: 3)
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
generation of osf3h and cyp93g1 cyp93g2 CRISPR/Cas9 mutants, and cyp93g1 and cyp93g2 T-DNA insertion mutants, analysis of fertility and the flavonoid profiles in the flavonoid mutants, phenotypes, overview. Double mutant cyp93g1 cyp93g2 shows highly reduced male fertility compared to wild-type while the single mutants cyp93g1 and cyp93g2 do not
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
CYP Ge-5/CYP93B1, expression in Sf9 insect cells and in Saccharomyces cerevisiae BJ2168
gene CYP93G15, DNA and amino acid sequence determination and analysis quantitative RT-PCR enzyme expression analysis
-
transgenic Arabidopsis overexpressing CYP93G2 or coexpressing CYP93G2 and OsCGT accumulates 2-hydroxyflavanone derivatives
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
fungal infection with maize pathogens, Fusarium graminearum and Fusarium verticillioides, induce enzyme F2H2 expression providing 2-hydroxynaringenin for the production of two open ring tautomeric di-O-methylated flavonoid derivatives termed xilonenin with antifungal activity. Induction of flavonoids is a general pathogen response. Upregulation of the flavonoid biosynthetic pathway by fungal infection, detailed overview
fungal infection with maize pathogens, Fusarium graminearum and Fusarium verticillioides, induce enzyme F2H2 expression providing 2-hydroxynaringenin for the production of two open ring tautomeric di-O-methylated flavonoid derivatives termed xilonenin with antifungal activity. Induction of flavonoids is a general pathogen response. Upregulation of the flavonoid biosynthetic pathway by fungal infection, detailed overview
-
fungal infection with maize pathogens, Fusarium graminearum and Fusarium verticillioides, induce enzyme F2H2 expression providing 2-hydroxynaringenin for the production of two open ring tautomeric di-O-methylated flavonoid derivatives termed xilonenin with antifungal activity. Induction of flavonoids is a general pathogen response. Upregulation of the flavonoid biosynthetic pathway by fungal infection, detailed overview
Zea mays W22
-
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
Wang, L.; Lam, P.Y.; Lui, A.C.W.; Zhu, F.Y.; Chen, M.X.; Liu, H.; Zhang, J.; Lo, C.
Flavonoids are indispensable for complete male fertility in rice
J. Exp. Bot.
71
4715-4728
2020
Oryza sativa Japonica Group (Q5VRI5)
brenda
Foerster, C.; Handrick, V.; Ding, Y.; Nakamura, Y.; Paetz, C.; Schneider, B.; Castro-Falcon, G.; Hughes, C.C.; Luck, K.; Poosapati, S.; Kunert, G.; Huffaker, A.; Gershenzon, J.; Schmelz, E.A.; Koellner, T.G.
Biosynthesis and antifungal activity of fungus-induced O-methylated flavonoids in maize
Plant Physiol.
188
167-190
2022
Zea mays, Zea mays W22
brenda
EXTERNAL LINKS (specific for EC-Number 1.14.14.162)
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