Any feedback?
Information on EC 1.14.20.4 - anthocyanidin synthase
for references in articles please use BRENDA:EC1.14.20.4Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
1.14.20.4 anthocyanidin synthaseIUBMB Comments
The enzyme requires Fe(II) and ascorbate. It is involved in the pathway by which many flowering plants make anthocyanin flower pigments (glycosylated anthocyandins). The enzyme hydroxylates the C-3 carbon, followed by a trans diaxial elimination, forming a C-2,C-3 enol. The product loses a second water molecule to form anthocyanidins. When assayed in vitro, non-enzymic epimerization of the product can lead to formation of dihydroflavanols. Thus when the substrate is leucocyanidin, a mixture of (+)-taxifolin and (+)-epitaxifolin are formed. The enzyme can also oxidize the formed (+)-taxifolin to quercetin (cf. EC 1.14.20.6, flavonol synthase) [2,3].
Specify your search results
Word Map
- 1.14.20.4
- anthocyanins
- dihydroflavonol
- chalcone
-
4-reductase
- flavanone
- flavonols
-
leucoanthocyanidins
-
3-hydroxylase
-
ammonia-lyase
- 3-o-glucosyltransferase
- petal
- proanthocyanidins
- dihydroflavonol-4-reductase
-
3',5'-hydroxylase
-
udp-glucose:flavonoid
-
sarawak
-
r2r3-myb
-
2-oxoglutarate-dependent
- myrtillus
- 3-o-glucoside
- dihydroquercetin
- pelargonidin
-
3beta-hydroxylase
- agriculture
-
anthocyanin-related
- medicine
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
anthocyanidin synthase, mdans, leucoanthocyanidin dioxygenase, ibans, anthocyanin synthase, gbans, rtldox, ans-1, ans-2, anthocyanidin synthase 1, 
more
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
ANS
anthocyanidin synthase
anthocyanin synthase
-
-
-
-
GbANS
bifunctional enzyme within the anthocyanidin and flavonol biosynthetic pathway
LDOX
leucoanthocyanidin dioxygenase
leucocyanidin dioxygenase
-
-
-
-
leucocyanidin oxygenase
-
-
-
-
leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a (2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O2 = a (4S)- 2,3-dehydroflavan-3,4-diol + succinate + CO2 + H2O
(1a)
-
-
-
a (2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O2 = an anthocyanidin + succinate + CO2 + 2 H2O
a (4S)- 2,3-dehydroflavan-3,4-diol = an anthocyanidin + H2O
(1b)
-
-
-
a (2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O2 = an anthocyanidin + succinate + CO2 + 2 H2O
mechanism
-
a (2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O2 = an anthocyanidin + succinate + CO2 + 2 H2O
mechanism
-
a (2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O2 = an anthocyanidin + succinate + CO2 + 2 H2O
overall reaction
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PATHWAY SOURCE
PATHWAYS
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYSTEMATIC NAME
IUBMB Comments
(2R,3S,4S)-leucoanthocyanidin,2-oxoglutarate:oxygen oxidoreductase
The enzyme requires Fe(II) and ascorbate. It is involved in the pathway by which many flowering plants make anthocyanin flower pigments (glycosylated anthocyandins). The enzyme hydroxylates the C-3 carbon, followed by a trans diaxial elimination, forming a C-2,C-3 enol. The product loses a second water molecule to form anthocyanidins. When assayed in vitro, non-enzymic epimerization of the product can lead to formation of dihydroflavanols. Thus when the substrate is leucocyanidin, a mixture of (+)-taxifolin and (+)-epitaxifolin are formed. The enzyme can also oxidize the formed (+)-taxifolin to quercetin (cf. EC 1.14.20.6, flavonol synthase) [2,3].
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CAS REGISTRY NUMBER
COMMENTARY
180984-01-4
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(+)-catechin + 2-oxoglutarate + O2
cyanidin + succinate + CO2 + 2 H2O
-
-
-
?
(2R,3R)-trans-dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + O2
-
-
-
-
?
(2R,3S,4R)-trans-leucocyanidin + 2-oxoglutarate + O2
trans-dihydroquercetin + cis-dihydroquercetin + quercetin + succinate + CO2
-
-
-
-
?
(2R,3S,4S)-cis-leucocyanidin + 2-oxoglutarate + O2
quercetin + succinate + CO2
-
-
-
-
?
(2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O2
anthocyanidin + succinate + CO2 + 2 H2O
-
-
-
-
r
2R,3S,4R-trans-leucocyanidin + 2-oxoglutarate + O2
2R,3S-cis-dihydroquercetin + 2R,3R-trans-dihydroquercetin + cyanidin + quercetin
-
-
55% 2R,3S-cis-dihydroquercetin + 11% 2R,3R-trans-dihydroquercetin + 4% cyanidin + 30% quercetin
-
?
2R,3S,4S-cis-leucoanthocyanidin + 2-oxoglutarate + O2
cis- and trans-dihydroquercetins + succinate + CO2 + 2 H2O
-
catalyses the penultimate step in anthocyanin biosynthesis by oxidation of the 2R,3S,4S-cis-leucoanthocyanidins
both quercetin and dihydroquercetin are products with the distribution being dependent on the C-4 stereochemistry of the leucocyanidin substrates
-
?
2R,3S,4S-cis-leucocyanidin + 2-oxoglutarate + O2
2R,3S-cis-dihydroquercetin + 2R,3R-trans-dihydroquercetin + cyanidin + quercetin
-
-
10% 2R,3S-cis-dihydroquercetin + 2% 2R,3R-trans-dihydroquercetin + 3% cyanidin + 85% quercetin
-
?
2R-naringenin + 2-oxoglutarate + O2
apigenin + succinate + CO2 + 2 H2O
-
-
-
?
2S-naringenin + 2-oxoglutarate + O2
apigenin + succinate + CO2 + 2 H2O
-
-
-
?
3,4-cis-leucocyanidin + 2-oxoglutarate + O2
cyanidin + succinate + CO2
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
dihydroquercetin + luteolin + succinate + CO2 + 2 H2O
-
-
-
?
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
naringenin + 2-oxoglutarate + O2
apigenin + 2R,3R-trans-dihydrokaempferol + succinate + CO2 + 2 H2O
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2
-
-
-
?
dihydroquercetin + 2-oxoglutarate + O2
quercetin + succinate + CO2
-
-
-
?
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
-
using (2R,3S,4R)-leucocyanidin or (2R,3S,4R)-leucopelargonidin as substrates
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
-
-
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
-
-
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
-
more detail to stereochemistry
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
-
-
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
-
more detail to stereochemistry
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
-
using (2R,3S,4R)-leucocyanidin or (2R,3S,4R)-leucopelargonidin as substrates
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
-
using (2R,3S,4R)-leucocyanidin or (2R,3S,4R)-leucopelargonidin as substrates
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
-
using (2R,3S,4R)-leucocyanidin or (2R,3S,4R)-leucopelargonidin as substrates
-
ir
leucocyanidin + 2-oxoglutarate + O2
cis-dihydroquercetin + trans-dihydroquercetin + succinate + CO2
-
using (2R,3S,4R)-leucocyanidin or (2R,3S,4R)-leucopelargonidin as substrates
-
ir
leucocyanidin + 2-oxoglutarate + O2 + H+
cyanidin + succinate + CO2 + 2 H2O
-
-
-
?
leucocyanidin + 2-oxoglutarate + O2 + H+
cyanidin + succinate + CO2 + 2 H2O
-
-
-
?
trans-leucocyanidin + 2-oxoglutarate + O2
cyanidin + succinate + CO2 + 2 H2O
-
-
-
?
trans-leucocyanidin + 2-oxoglutarate + O2
cyanidin + succinate + CO2 + 2 H2O
-
-
-
?
additional information
?
-
product formation is essentially dependent on the presence of ferrous ions and 2-oxoglutarate. No substrates: ent(-)-catechin (2S,3R-trans-catechin), (-)-epicatechin, ent(+)-epicatechin (2S,3S-cis-epicatechin) and (-)-gallocatechin
-
-
?
additional information
?
-
-
product formation is essentially dependent on the presence of ferrous ions and 2-oxoglutarate. No substrates: ent(-)-catechin (2S,3R-trans-catechin), (-)-epicatechin, ent(+)-epicatechin (2S,3S-cis-epicatechin) and (-)-gallocatechin
-
-
?
additional information
?
-
catalyzes the penultimate step in the biosynthesis of the anthocyanin class of flavonoids, from the colorless leucoanthocyanidins to the colored anthocyanidins
-
-
?
additional information
?
-
-
catalyzes the penultimate step in the biosynthesis of the anthocyanin class of flavonoids, from the colorless leucoanthocyanidins to the colored anthocyanidins
-
-
?
additional information
?
-
expression in abiotic stress responses. Up-regulated by all of the six tested abiotic stresses, UV-B, abscisic acid, sucrose, salicylic acid, cold and ethylene, consistent with the promoter region analysis of GbANS
-
-
?
additional information
?
-
-
expression in abiotic stress responses. Up-regulated by all of the six tested abiotic stresses, UV-B, abscisic acid, sucrose, salicylic acid, cold and ethylene, consistent with the promoter region analysis of GbANS
-
-
?
additional information
?
-
-
catalyzes the penultimate step in the biosynthesis of anthocyanin. This reaction is responsible for the formation of the colored anthocyanidins from the colorless leucoanthocyanidins
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2R,3S,4S-cis-leucoanthocyanidin + 2-oxoglutarate + O2
cis- and trans-dihydroquercetins + succinate + CO2 + 2 H2O
-
catalyses the penultimate step in anthocyanin biosynthesis by oxidation of the 2R,3S,4S-cis-leucoanthocyanidins
both quercetin and dihydroquercetin are products with the distribution being dependent on the C-4 stereochemistry of the leucocyanidin substrates
-
?
additional information
?
-
catalyzes the penultimate step in the biosynthesis of the anthocyanin class of flavonoids, from the colorless leucoanthocyanidins to the colored anthocyanidins
-
-
?
additional information
?
-
-
catalyzes the penultimate step in the biosynthesis of the anthocyanin class of flavonoids, from the colorless leucoanthocyanidins to the colored anthocyanidins
-
-
?
additional information
?
-
expression in abiotic stress responses. Up-regulated by all of the six tested abiotic stresses, UV-B, abscisic acid, sucrose, salicylic acid, cold and ethylene, consistent with the promoter region analysis of GbANS
-
-
?
additional information
?
-
-
expression in abiotic stress responses. Up-regulated by all of the six tested abiotic stresses, UV-B, abscisic acid, sucrose, salicylic acid, cold and ethylene, consistent with the promoter region analysis of GbANS
-
-
?
additional information
?
-
-
catalyzes the penultimate step in the biosynthesis of anthocyanin. This reaction is responsible for the formation of the colored anthocyanidins from the colorless leucoanthocyanidins
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
ascorbate
maximal activity requires the addition of 0.3 mM ascorbate
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Liver Neoplasms
Overexpression of the Anthocyanidin Synthase Gene in Strawberry Enhances Antioxidant Capacity and Cytotoxic Effects on Human Hepatic Cancer Cells.
Lymphoma, B-Cell
Real-Time Analysis of Polyphenol-Protein Interactions by Surface Plasmon Resonance Using Surface-Bound Polyphenols.
Peripheral Nervous System Diseases
New method of sudomotor function measurement to detect microvascular disease and sweat gland nerve or unmyelinated C fiber dysfunction in adults with retinopathy.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Lam cultivar A5, A1, Yamakawamurasaki, and A3 and one of white-fleshed sweet potato cultivar Yubeibai
-
-
brenda
overexpression in rice mutant Nootripathu, which accumulates proanthocyanidins exclusively in pericarp
UniProt
brenda
wild-type and ldox/fls1-2 double mutant, lacking leucoanthocyanidin dioxygenase and functional flavonol synthase 1-2, EC 1.14.11.23
-
-
brenda
shoot cultures from TNR 31-35 (hybrid of Malus sieversii var. sieversii f. niedzwetzkyana)
UniProt
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
all lines and seed coats of the black-seeded lines, not in the yellow-seeded seed coats
brenda
-
exposure of shaded swollen hypocotyls to artificial light sources. Only UV-A light induces anthocyanin biosynthesis. During 24 h of exposure, expression of anthocyanidin synthase increases together with phenylalanine ammonia lyase EC 4.3.1.5, chalcone synthase EC 2.3.1.74, flavanone 3-hydroxylase EC 1.14.11.9, and dihydroflavonol 4-reductase EC 1.1.1.219
brenda
-
primarily distributed in the growth point and leaf primordium of the leaf buds
brenda
genes encoding anthocyanidin synthase, anthocyanidin reductase and leucoanthocyanidin reductase are abundantly expressed in pod exocarp
brenda
BjANS expressed in the seed coats of the black-seeded lines and in embryos of the all lines, but not in the yellow-seeded seed coats, RT-PCR expression analysis
brenda
additional information
-
primarily distributed in the exocarp, mesocarp, and seed of the fruit, developmentally dependent expression in skin and flesh
brenda
-
primarily distributed in the exocarp, mesocarp, and seed of the fruit, developmentally dependent expression in skin and flesh
-
brenda
genes encoding anthocyanidin synthase, anthocyanidin reductase and leucoanthocyanidin reductase are abundantly expressed
brenda
young and mature. Weakly expressed in young fruits, highest level of GbANS mRNA is observed in mature fruits
brenda
genotype SR-305 shows highest activity at 21 days after anthesis
brenda
analysis of activity in 14 genotypes. The activity of ANS in leaves of all genotypes and fruits of green and white colour progressively decreases from 7 to 21 days after anthesis while a progressive increase was observed in purple fruits during the same period
brenda
genotype BL-204 shows highest activity in leaves at 7 day after anthesis
brenda
analysis of activity in 14 genotypes. The activity of ANS in leaves of all genotypes and fruits of green and white colour progressively decreases from 7 to 21 days after anthesis while a progressive increase was observed in purple fruits during the same period
brenda
genes encoding anthocyanidin synthase, anthocyanidin reductase and leucoanthocyanidin reductase are abundantly expressed
brenda
-
primarily distributed in palisade and spongy tissues of the leaves
brenda
-
primarily distributed in palisade and spongy tissues of the leaves
-
brenda
-
fibrous, thick, and storage roots. IbANS is expressed most abundantly during the formation of storage roots
brenda
levels of transcripts encoding anthocyanidin synthase, dihydroflavonol reductase and anthocyanidin reductase parallel the accumulation of proanthocyanidins in developing seeds
brenda
genes encoding anthocyanidin synthase, anthocyanidin reductase and leucoanthocyanidin reductase are abundantly expressed
brenda
-
primarily distributed in the primary phloem and pith ray in the stems
brenda
-
primarily distributed in the primary phloem and pith ray in the stems
-
brenda
additional information
-
no expression in the mature stems, laminas or petioles
brenda
additional information
GbANS transcripts are not detected in the stems and roots
brenda
additional information
-
GbANS transcripts are not detected in the stems and roots
brenda
additional information
abundant expression in the red cell line, weak expression in the yellow cell line. No expression in root
brenda
additional information
dihydroflavonol 4-reductase and ANS are not expressed in most tissues and organs, except seeds
brenda
additional information
-
dihydroflavonol 4-reductase and ANS are not expressed in most tissues and organs, except seeds
brenda
additional information
-
expression and tissue localization of ANS in different Cabernet Sauvignon samples, overview
brenda
additional information
-
expression and tissue localization of ANS in different Cabernet Sauvignon samples, overview
-
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
additional information
-
in the mesocarp vascular bundle and leaf bud cells
-
brenda
additional information
-
subcellular localization of ANS in different Cabernet Sauvignon samples, overview
-
brenda
additional information
-
subcellular localization of ANS in different Cabernet Sauvignon samples, overview
-
-
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
metabolism
physiological function
malfunction
lack of enzyme encoding gene BjANS expression blocks biosynthesis of proanthocyanidins in the yellow seed coat, and therefore seeds appear yellow because of transparent testa
malfunction
an insertion in the PgLDOX gene (leucoanthocyanidin dioxygenase/anthocyanidin synthase) is responsible