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Information on EC 1.13.11.71 - carotenoid-9',10'-cleaving dioxygenase
for references in articles please use BRENDA:EC1.13.11.71
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EC Tree 1 Oxidoreductases
1.13 Acting on single donors with incorporation of molecular oxygen (oxygenases)
1.13.11 With incorporation of two atoms of oxygen
1.13.11.71 carotenoid-9',10'-cleaving dioxygenase
IUBMB Comments
Requires Fe2+. The enzyme catalyses the asymmetric oxidative cleavage of carotenoids. The mammalian enzyme can also cleave all-trans-lycopene.
The enzyme appears in viruses and cellular organisms
- 1.13.11.71
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retinoids
- lutein
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grey
- all-trans-retinal
- zeaxanthin
-
15,15'-monooxygenase
- lycopene
-
oviparous
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ornamental
- hamilton
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captive
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vitellogenesis
- loach
-
queen
- strigolactone
- synthesis
- csf1r
- junglefowl
- agriculture
Reaction Schemes
showSynonyms
bcdo2, scbco2, beta-carotene-9',10'-oxygenase, beta-carotene 9',10'-oxygenase, xanthophyll cleavage enzyme, ljccd7, bc-9',10'-oxygenase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Bcdo2
BCO2
beta,beta-carotene-9',10'-dioxygenase
beta-carotene 9',10'-oxygenase
beta-carotene-9',10'-oxygenase
beta-carotene-9,10'-oxygenase
CCD7
ScBCO2
xanthophyll cleavage enzyme
BCO2
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
all-trans-beta-carotene + O2 = all-trans-10'-apo-beta-carotenal + beta-ionone
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-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
carotenoid cleavage
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SYSTEMATIC NAME
IUBMB Comments
all-trans-beta-carotene:O2 oxidoreductase (9',10'-cleaving)
Requires Fe2+. The enzyme catalyses the asymmetric oxidative cleavage of carotenoids. The mammalian enzyme can also cleave all-trans-lycopene.
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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
9-cis-beta-carotene + O2
9-cis-beta-apo-10'-carotenal + beta-ionone
Substrates: -
Products: -
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beta-carotene + O2
10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
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beta-carotene + O2
beta-cyclocitral + beta-ionone
Substrates: the enzyme is able to break the 9,10 (9',10') and 7,8 (7',8') double-bonds of beta-carotene
Products: -
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beta-cryptoxanthin + O2
3-hydroxy-beta-apo-10'-carotenal + beta-ionone
Substrates: -
Products: -
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?
beta-cryptoxanthin + O2
3-hydroxy-beta-apo-8'-carotenal + beta-cyclocitral
Substrates: -
Products: -
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?
beta-cryptoxanthin + O2
beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
Substrates: -
Products: -
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beta-cryptoxanthin + O2
beta-apo-10'-carotenal + ?
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Substrates: main clevage product is beta-apo-10'-carotenal only small amounts of 3-OH-beta-apocarotenal are formed
Products: -
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lutein + O2
3-hydroxy-alpha-apo-10'-carotenal + 3-hydroxy-beta-ionone
Substrates: -
Products: -
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lutein + O2
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-alpha-ionone
Substrates: -
Products: -
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lycopene + O2
6-methyl-5-hepten-2-one + ?
Substrates: the enzyme also possesses oxidative cleavage activity at the 5,6 (5',6') positions of lycopene
Products: -
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all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
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all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
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all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
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Substrates: -
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all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
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all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
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all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
-
Substrates: -
Products: -
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all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
Products: -
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all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
Products: -
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all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
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all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
Products: -
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all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
-
Substrates: -
Products: -
Products: -
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all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
-
Substrates: -
Products: -
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alpha-carotene + O2
beta-apo-10'-carotenal + alpha-apo-10'-carotenal
Substrates: -
Products: -
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alpha-carotene + O2
beta-apo-10'-carotenal + alpha-apo-10'-carotenal
-
Substrates: -
Products: -
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alpha-carotene + O2
beta-apo-10'-carotenal + alpha-apo-10'-carotenal
-
Substrates: -
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beta-carotene + O2
10'-apo-carotenal + beta-ionone
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Substrates: -
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beta-carotene + O2
10'-apo-carotenal + beta-ionone
Substrates: -
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beta-carotene + O2
10'-apo-carotenal + beta-ionone
Substrates: -
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zeaxanthin + O2
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
Substrates: -
Products: -
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zeaxanthin + O2
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
Substrates: -
Products: -
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zeaxanthin + O2
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
Substrates: -
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?
additional information
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Substrates: no substrate: lycopene, lutein, zeaxanthin, violaxanthin, or neoxanthin
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additional information
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Substrates: like BCO1, EC 1.13.11.63, purified recombinant chicken BCO2 catalyzes the oxidative cleavage of the provitamin A carotenoids beta-carotene, alpha-carotene, and beta-cryptoxanthin. Its catalytic activity with beta-carotene as substrate is at least 10fold lower than that of BCO1. Purified recombinant chicken BCO2 also catalyzes the oxidative cleavage of 9-cis-beta-carotene and the non-provitamin A carotenoids zeaxanthin and lutein, and is inactive with all-trans-lycopene and beta-apo-carotenoids. Apo-10'-carotenoids are detected as enzymatic products by HPLC, and the identities are confirmed by LC-MS. Small amounts of 3-hydroxy-beta-apo-8'-carotenal are also consistently detected in BCO2-beta-cryptoxanthin reaction mixtures. With the exception of this activity with beta-cryptoxanthin, BCO2 cleaves specifically at the 9'-10'-bond to produce apo-10'-carotenoids. BCO2 is regioselective (or even regiospecific) for the trans 9'-10'-end of 9-cis-beta-carotene due to the size of the substrate tunnel. Unlike murine BCO2, chicken BCO2 cannot perform a second cleavage on beta-apo-10'-carotenal to yield rosafluene dialdehyde, and it has no activity with all-trans-lycopene, while it cleaves cis-lycopene isomers. Chicken BCO2 also does not have activity with the other beta-apocarotenals in the series (beta-apo-8'-carotenal, beta-apo-12'-carotenal, and beta-apo-14'-carotenal). Importance of the 3-hydroxy-beta-ionone ring for BCO2 cleavage, preference of BCO2 for substrates that contain a 3-hydroxy-beta-ionone ring
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additional information
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Substrates: inactivity of BCO2 with xanthophylls such as zeaxanthin
Products: -
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?
additional information
?
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Substrates: inactivity of BCO2 with xanthophylls such as zeaxanthin
Products: -
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additional information
?
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Substrates: human BCO2 isoform a (human BCO2a) fails to cleave zeaxanthin, retaining the yellow color
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additional information
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Substrates: human BCO2 isoform a (human BCO2a) fails to cleave zeaxanthin, retaining the yellow color
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additional information
?
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Substrates: ScBCO2-catalyzed conversion of beta-carotene to beta-apo-10'-carotenal is followed by HPLC and LC-MS
Products: -
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additional information
?
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Substrates: enzyme ScBCO2 only exhibits cleavage activity towards carotenoid substrates containing two beta-ionone rings and its catalytic efficiency (kcat/Km) follows the descending order beta-carotene, alpha-carotene, lutein
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additional information
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Substrates: ScBCO2-catalyzed conversion of beta-carotene to beta-apo-10'-carotenal is followed by HPLC and LC-MS
Products: -
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additional information
?
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Substrates: enzyme ScBCO2 only exhibits cleavage activity towards carotenoid substrates containing two beta-ionone rings and its catalytic efficiency (kcat/Km) follows the descending order beta-carotene, alpha-carotene, lutein
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
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
Products: -
?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
Products: -
?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
-
Substrates: -
Products: -
Products: -
?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
Products: -
?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
Products: -
?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
-
Substrates: -
Products: -
Products: -
?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
Products: -
?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
Products: -
?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
Products: -
?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
Substrates: -
Products: -
Products: -
?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
-
Substrates: -
Products: -
Products: -
?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
-
Substrates: -
Products: -
Products: -
?
alpha-carotene + O2
beta-apo-10'-carotenal + alpha-apo-10'-carotenal
-
Substrates: -
Products: -
Products: -
?
alpha-carotene + O2
beta-apo-10'-carotenal + alpha-apo-10'-carotenal
-
Substrates: -
Products: -
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?
zeaxanthin + O2
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
Substrates: -
Products: -
Products: -
?
zeaxanthin + O2
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: inactivity of BCO2 with xanthophylls such as zeaxanthin
Products: -
Products: -
?
additional information
?
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Substrates: inactivity of BCO2 with xanthophylls such as zeaxanthin
Products: -
Products: -
?
additional information
?
-
-
Substrates: ScBCO2-catalyzed conversion of beta-carotene to beta-apo-10'-carotenal is followed by HPLC and LC-MS
Products: -
Products: -
?
additional information
?
-
-
Substrates: ScBCO2-catalyzed conversion of beta-carotene to beta-apo-10'-carotenal is followed by HPLC and LC-MS
Products: -
Products: -
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
methanol
addition of methanol to in vitro assays has a stimulatory effect on activity at concentrations up to 25%
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Carcinogenesis
Lycopene attenuated hepatic tumorigenesis via differential mechanisms depending on carotenoid cleavage enzyme in mice.
Liver Diseases
Tomato Powder Inhibits Hepatic Steatosis and Inflammation Potentially Through Restoring SIRT1 Activity and Adiponectin Function Independent of Carotenoid Cleavage Enzymes in Mice.
Non-alcoholic Fatty Liver Disease
Tomato Powder Inhibits Hepatic Steatosis and Inflammation Potentially Through Restoring SIRT1 Activity and Adiponectin Function Independent of Carotenoid Cleavage Enzymes in Mice.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0152
beta-carotene
pH 7.0, temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.4
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7 - 9
-
50 % of the maximal activity at pH 7.0 and pH 9.0, 20% at pH 6.0 and pH 9.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
expression of the bco2 gene is dramatically decreased in prostate cancer tissue and in a range of prostate cancer cell lines as compared with nonneoplastic prostate tissue and normal prostatic epithelial cells, respectively. DNA methyltransferase inhibition induces bco2 expression in prostate cancer cells
brenda
additional information