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Information on EC 1.14.14.162 - flavanone 2-hydroxylase and Organism(s) Glycyrrhiza echinata and UniProt Accession P93149

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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.
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Glycyrrhiza echinata
UNIPROT: P93149
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Word Map
The taxonomic range for the selected organisms is: Glycyrrhiza echinata
The enzyme appears in selected viruses and cellular organisms
Synonyms
cyp93g2, flavanone 2-hydroxylase, (2s)-flavanone 2-hydroxylase, osf2h, os06g01250, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
(2S)-flavanone 2-hydroxylase
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licodione synthase
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-
-
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liquiritigenin,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (licodione-forming)
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-
-
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additional information
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a flavanone + [reduced NADPH-hemoprotein reductase] + O2 = a 2-hydroxyflavanone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
mechanism, stereoselectivity
a flavanone + [reduced NADPH-hemoprotein reductase] + O2 = a 2-hydroxyflavanone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
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-
PATHWAY SOURCE
PATHWAYS
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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.
CAS REGISTRY NUMBER
COMMENTARY hide
157972-05-9
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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)-naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
selectivity towards (2S)-flavanone
the product is further converted into apigenin when treated with HCl
-
?
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
luteolin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
product is formed after acid treatment
-
?
(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(2S)-naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
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the product is further converted into apigenin when treated with acid
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?
additional information
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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-
cytochrome P450
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cytochrome P450-dependent, cytochrome P450 monooxygenase
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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yeast extract induces LS activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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yeast extract-induced
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
recombinant enzyme, expressed in Sf9 insect cells or yeast cells
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Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
C93B1_GLYEC
523
1
59496
Swiss-Prot
Secretory Pathway (Reliability: 4)
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
CYP Ge-5/CYP93B1, expression in Sf9 insect cells and in Saccharomyces cerevisiae BJ2168
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)
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team