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Information on EC 1.13.11.51 - 9-cis-epoxycarotenoid dioxygenase and Organism(s) Arabidopsis thaliana and UniProt Accession Q9LRR7

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IUBMB Comments
Requires iron(II). Acts on 9-cis-violaxanthin and 9'-cis-neoxanthin but not on the all-trans isomers [2,3]. In vitro, it will cleave 9-cis-zeaxanthin. Catalyses the first step of abscisic-acid biosynthesis from carotenoids in chloroplasts, in response to water stress. The other enzymes involved in the abscisic-acid biosynthesis pathway are EC 1.1.1.288 (xanthoxin dehydrogenase), EC 1.2.3.14 (abscisic-aldehyde oxidase) and EC 1.14.13.93 [(+)-abscisic acid 8'-hydroxylase].
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Arabidopsis thaliana
UNIPROT: Q9LRR7
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The taxonomic range for the selected organisms is: Arabidopsis thaliana
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
9-cis-epoxycarotenoid dioxygenase, nced3, atnced3, nced1, nced2, nced5, nced9, lenced1, sgnced1, vvnced1, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
9-cis-epoxycarotenoid dioxygenase 3
nine-cis-epoxycarotenoid dioxygenase 3
-
9-cis epoxycarotenoid dioxygenase
-
-
9-cis-epoxicarotenoid dioxygenase
-
-
9-cis-epoxycarotenoid dioxygenase
-
key enzyme of abscisic acid biosynthesis
9-cis-epoxycarotenoid dioxygenase 3
-
-
9-cis-epoxycarotenoid dioxygenase 6
-
-
carotenoid cleavage dioxygenase 1
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C-C-bond cleavage
-
-
SYSTEMATIC NAME
IUBMB Comments
9-cis-epoxycarotenoid 11,12-dioxygenase
Requires iron(II). Acts on 9-cis-violaxanthin and 9'-cis-neoxanthin but not on the all-trans isomers [2,3]. In vitro, it will cleave 9-cis-zeaxanthin. Catalyses the first step of abscisic-acid biosynthesis from carotenoids in chloroplasts, in response to water stress. The other enzymes involved in the abscisic-acid biosynthesis pathway are EC 1.1.1.288 (xanthoxin dehydrogenase), EC 1.2.3.14 (abscisic-aldehyde oxidase) and EC 1.14.13.93 [(+)-abscisic acid 8'-hydroxylase].
CAS REGISTRY NUMBER
COMMENTARY hide
199877-10-6
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
9'-cis neoxanthin + O2
xanthoxin + ?
show the reaction diagram
-
-
-
-
?
9'-cis-neoxanthin + O2
2-cis,4-trans-xanthoxin + (3S,5R,6R)-5,6-dihydroxy-6,7-didehydro-5,6-dihydro-12'-apo-beta-caroten-12'-al
show the reaction diagram
-
-
-
-
?
9'-cis-neoxanthin + O2
5,6-epoxy-3-hydroxy-12'-apo-beta-caroten-12'-al + 3,5-dihydroxy-6,7-didehydro-12'-apo-beta-caroten-12'-al + ?
show the reaction diagram
-
-
-
-
?
9-cis violaxanthin + O2
2-cis,4-trans-xanthoxin + ?
show the reaction diagram
-
-
-
-
?
9-cis-neoxanthin + O2
xanthoxin + ?
show the reaction diagram
-
assay at pH 6.7, 22°C, 20 min, reaction stopped by adding 50 microl of 25% Triton X-100
-
-
?
9-cis-violaxanthin + O2
2-cis,4-trans-xanthoxin + (3S,5R,6S)-5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-beta-caroten-12'-al
show the reaction diagram
-
-
-
-
?
9-cis-violaxanthin + O2
5,6-epoxy-3-hydroxy-12'-apo-beta-caroten-12'-al + 5,6-epoxy-3-hydroxy-9-apo-beta-caroten-9-one + ?
show the reaction diagram
-
-
-
-
?
all-trans-violaxanthin + O2
4,9-dimethyldodeca-2,4,6,8,10-pentaene-1,12-dial + ?
show the reaction diagram
-
-
-
-
?
beta,beta-carotene + O2
4,9-dimethyldodeca-2,4,6,8,10-pentaene-1,12-dial + 3-hydroxy-9-apo-beta-caroten-9-one + ?
show the reaction diagram
-
-
-
-
?
beta-apo-8'-carotenal + O2
beta-ionone + ?
show the reaction diagram
-
-
-
-
?
beta-carotene + O2
?
show the reaction diagram
-
-
-
-
?
beta-carotene + O2
strigolactone + ?
show the reaction diagram
-
two cleavage steps by CCD7 and CCD8
-
-
?
lutein + O2
4,9-dimethyldodeca-2,4,6,8,10-pentaene-1,12-dial + ?
show the reaction diagram
-
-
-
-
?
zeaxanthin + O2
4,9-dimethyldodeca-2,4,6,8,10-pentaene-1,12-dial + ?
show the reaction diagram
-
-
-
-
?
zeaxanthin + O2
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
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
?
-
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R,3S,6R)-(3'Z)-1,5,5-trimethyl-6-(3'-methyl-5'-(phenylamino)-pent-3'-en-1'-ynyl)-7-oxabicyclo[4.1.0]heptan-3-ol
-
1 mM, complete inhibition of enzyme activity
(1R,3S,6R)-(3'Z)-1,5,5-trimethyl-6-(3'-methyl-5'-(phenylthio)-pent-3'-en-1'-ynyl)-7-oxa-bicyclo[4.1.0]heptan-3-ol
-
1 mM, complete inhibition of enzyme activity
(1R,4R,6R)-(3'Z)-1-(5'-(ethylthio)-3'-methylpent-3'-en-1'-ynyl)-2,2,6-trimethylcyclohexane-1,4-diol
-
1 mM, about 25% inhibition of enzyme activity
(1S,4R,6R)-(3'Z)-1-(5'-(ethylthio)-3'-methylpent-3'-en-1'-ynyl)-2,2,6-trimethylcyclohexane-1,4-diol
-
1 mM, about 65% inhibition of enzyme activity
(2Z,4E)-5-(1'-hydroxy-2',2',6'-trimethyl-4'-oxocyclohexyl)-3-methylpenta-2,4-dienyl 2-(thiophen-2''-yl)acetate
-
1 mM, about 70% inhibition of enzyme activity
(4R,5S)-(3'Z)-4-(5'-(ethylthio)-3'-methylpent-3'-en-1'-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexanone
-
1 mM, complete inhibition of enzyme activity
(4S,5R)-(3'Z)-4-(5'-(ethylthio)-3'-methylpent-3'-en-1'-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexanone
-
1 mM, about 55% inhibition of enzyme activity
(4S,5R/4R,5S)-(3'Z)-4-(5'-(ethylthio)-3'-methylpent-3'-en-1'-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexanone
-
1 mM, 75% inhibition of enzyme activity
abamine
-
1 mM, about 70% inhibition of enzyme activity
abamine SG
-
1 mM, about 80% inhibition of enzyme activity
additional information
-
identification of the lenc1, i.e. low expression of NCED3 1, mutation, the mutant shows lower AtNCED3 promoter activity after dehydration treatment compared to the wild-type. The lenc1 mutant is hypersensitive to methyl viologen, LiCl, NaCl, and high light
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.024
9-cis-neoxanthin
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.7
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
drought-induced expression of AtNCED3 is restricted to the vascular parenchyma cells
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
CCDI, CCD7
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
the lenc1, i.e. for low expression of NCED3 1, mutant shows reduced AtNCED3 promoter activity after dehydration treatment compared to the wild-type. The lenc1 mutation is recessive and is located on chromosome 4. Both the AtNCED3 transcripts and endogenous abscisic acid levels in lenc1 mutant plants are less abundant than in wild-type plants under dehydration treatments. The mutant is hypersensitive to methyl viologen, LiCl, NaCl and high light, phenotype, overview
metabolism
physiological function
-
NCED3 is the rate-limiting enzyme responsible for abscisic acid biosynthesis under osmotic stress, regulatory mechanisms of NCED3 expression, overview
additional information
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
NCED3_ARATH
599
0
65857
Swiss-Prot
Chloroplast (Reliability: 3)
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
glutathione sepharose 4 fast flow resin
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli JM109 cells
-
expression in Escherichia coli as a fusion to glutathione S-transferase
-
expression in Escherichia coli BL21
-
gene NCED6, transgenic expression in Arabidopsis thaliana by Agrobacterium tumefaciens transfection method, expression analysis
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NCED3 quantitative RT-PCR expression analysis
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quantitative RT-PCR expression analysis of wild-type enzyme and lenc1 mutant, overview
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
identification of the lenc1, i.e. low expression of NCED3 1, mutation, the mutant shows lower AtNCED3 promoter activity after dehydration treatment compared to the wild-type. The lenc1 mutant is hypersensitive to methyl viologen, LiCl, NaCl, and high light
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Schwartz, S.H.; Qin, X.; Zeevaart, J.A.D.
Characterization of a novel carotenoid cleavage dioxygenase from plants
J. Biol. Chem.
276
25208-25211
2001
Arabidopsis thaliana
Manually annotated by BRENDA team
Ruggiero, B.; Koiwa, H.; Manabe, Y.; Quist, T.M.; Inan, G.; Saccardo, F.; Joly, R.J.; Hasegawa, P.M.; Bressan, R.A.; Maggio, A.
Uncoupling the effects of abscisic acid on plant growth and water relations. Analysis of sto1/nced3, an abscisic acid-deficient but salt stress-tolerant mutant in Arabidopsis
Plant Physiol.
136
3134-3147
2004
Arabidopsis thaliana
Manually annotated by BRENDA team
Guerrini, I.A.; Trigueiro, R.M.; Leite, R.M.; Wilcken, C.F.; Velini, E.D.; Mori, E.S.; Furtado, E.L.; Marino, C.L.; Maia, I.G.
Eucalyptus ESTs involved in the production of 9-cis epoxycarotenoid dioxygenase, a regulatory enzyme of abscisic acid production
Genet. Mol. Biol.
28
640-643
2005
Arabidopsis thaliana, Eucalyptus globulus, Eucalyptus camaldulensis, Eucalyptus grandis, Eucalyptus saligna, Eucalyptus urophylla, Solanum lycopersicum (O24023), Zea mays (O24592), Persea americana (Q9AXZ3), Vigna unguiculata (Q9FS24), Solanum tuberosum (Q9M3Z9), Phaseolus vulgaris (Q9M6E8)
-
Manually annotated by BRENDA team
Schmidt, H.; Kurtzer, R.; Eisenreich, W.; Schwab, W.
The carotenase AtCCD1 from Arabidopsis thaliana is a dioxygenase
J. Biol. Chem.
281
9845-9851
2006
Arabidopsis thaliana
Manually annotated by BRENDA team
Lefebvre, V.; North, H.; Frey, A.; Sotta, B.; Seo, M.; Okamoto, M.; Nambara, E.; Marion-Poll, A.
Functional analysis of Arabidopsis NCED6 and NCED9 genes indicates that ABA synthesized in the endosperm is involved in the induction of seed dormancy
Plant J.
45
309-319
2006
Arabidopsis thaliana
Manually annotated by BRENDA team
Toh, S.; Imamura, A.; Watanabe, A.; Nakabayashi, K.; Okamoto, M.; Jikumaru, Y.; Hanada, A.; Aso, Y.; Ishiyama, K.; Tamura, N.; Iuchi, S.; Kobayashi, M.; Yamaguchi, S.; Kamiya, Y.; Nambara, E.; Kawakami, N.
High temperature-induced abscisic acid biosynthesis and its role in the inhibition of gibberellin action in Arabidopsis seeds
Plant Physiol.
146
1368-1385
2008
Arabidopsis thaliana (O49505), Arabidopsis thaliana (Q9C6Z1), Arabidopsis thaliana (Q9M9F5)
Manually annotated by BRENDA team
Endo, A.; Sawada, Y.; Takahashi, H.; Okamoto, M.; Ikegami, K.; Koiwai, H.; Seo, M.; Toyomasu, T.; Mitsuhashi, W.; Shinozaki, K.; Nakazono, M.; Kamiya, Y.; Koshiba, T.; Nambara, E.
Drought induction of Arabidopsis 9-cis-epoxycarotenoid dioxygenase occurs in vascular parenchyma cells
Plant Physiol.
147
1984-1993
2008
Arabidopsis thaliana (Q9LRR7)
Manually annotated by BRENDA team
Boyd, J.; Gai, Y.; Nelson, K.M.; Lukiwski, E.; Talbot, J.; Loewen, M.K.; Owen, S.; Zaharia, L.I.; Cutler, A.J.; Abrams, S.R.; Loewen, M.C.
Sesquiterpene-like inhibitors of a 9-cis-epoxycarotenoid dioxygenase regulating abscisic acid biosynthesis in higher plants
Bioorg. Med. Chem.
17
2902-2912
2009
Arabidopsis thaliana
Manually annotated by BRENDA team
Cheng, W.H.; Chiang, M.H.; Hwang, S.G.; Lin, P.C.
Antagonism between abscisic acid and ethylene in Arabidopsis acts in parallel with the reciprocal regulation of their metabolism and signaling pathways
Plant Mol. Biol.
71
61-80
2009
Arabidopsis thaliana (Q9LRR7), Arabidopsis thaliana
Manually annotated by BRENDA team
Floss, D.S.; Walter, M.H.
Role of carotenoid cleavage dioxygenase 1 (CCD1) in apocarotenoid biogenesis revisited
Plant Signal. Behav.
4
172-175
2009
Arabidopsis thaliana, Medicago truncatula
Manually annotated by BRENDA team
Woo, D.H.; Park, H.Y.; Kang, I.S.; Lee, S.Y.; Moon, B.Y.; Lee, C.B.; Moon, Y.H.
Arabidopsis lenc1 mutant displays reduced ABA accumulation by low AtNCED3 expression under osmotic stress
J. Plant Physiol.
168
140-147
2011
Arabidopsis thaliana, Arabidopsis thaliana Col-0, Arabidopsis thaliana Columbia
Manually annotated by BRENDA team
Martinez-Andujar, C.; Ordiz, M.I.; Huang, Z.; Nonogaki, M.; Beachy, R.N.; Nonogaki, H.
Induction of 9-cis-epoxycarotenoid dioxygenase in Arabidopsis thaliana seeds enhances seed dormancy
Proc. Natl. Acad. Sci. USA
108
17225-17229
2011
Arabidopsis thaliana, Arabidopsis thaliana Columbia-0
Manually annotated by BRENDA team