Beta-carotene 15,15'-dioxygenase

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β-carotene 15,15'-dioxygenase
Identifiers
EC no. 1.13.11.63
CAS no. 37256-60-3
Databases
IntEnz IntEnz view
BRENDA BRENDA entry
ExPASy NiceZyme view
KEGG KEGG entry
MetaCyc metabolic pathway
PRIAM profile
PDB structures RCSB PDB PDBe PDBsum
Gene Ontology AmiGO / QuickGO
Search
PMC articles
PubMed articles
NCBI proteins
BCO1
Identifiers
Aliases BCO1 , BCDO, BCDO1, BCMO, BCMO1, BCO, beta-carotene oxygenase 1
External IDs OMIM: 605748 MGI: 1926923 HomoloGene: 41172 GeneCards: BCO1
EC number 1.13.11.63
Orthologs
SpeciesHumanMouse
Entrez
Ensembl
UniProt
RefSeq (mRNA)

NM_017429

NM_001163028
NM_021486

RefSeq (protein)

NP_059125

NP_001156500
NP_067461

Location (UCSC) Chr 16: 81.24 – 81.29 Mb Chr 8: 117.82 – 117.86 Mb
PubMed search [3] [4]
Wikidata
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In enzymology, beta-carotene 15,15'-dioxygenase, (EC 1.13.11.63) is an enzyme with systematic name beta-carotene:oxygen 15,15'-dioxygenase (bond-cleaving). [5] [6] In human it is encoded by the BCO1 gene. This enzyme catalyses the following chemical reaction

beta-carotene + O2 → 2 all-trans-retinal

This is a cleavage reaction which cleaves β-carotene, utilizes molecular oxygen, is enhanced by the presence of bile salts and thyroxine, and generates two molecules of retinal. In humans, the enzyme is present in the small intestine and liver. [7] The dioxygenase also asymmetrically cleaves beta-cryptoxanthin, trans-β-apo-8'-carotenal, beta-4'-apo-β-carotenal, alpha-carotene and gamma-carotene in decreasing order, creating one retinal molecule, all of these being substrates with a carbon chain greater than C30, with at least one unsubstituted β-ionone ring. [8]

This enzyme belongs to the (enzymatically-defined) family of oxidoreductases, specifically those acting on paired donors, with O2 as oxidant and incorporation or reduction of oxygen. A related enzyme is β-carotene 15,15'-monooxygenase, coded for by the gene BCMO1, which symmetrically cleaves β-carotene into two retinal molecules. [9] [10]

In general, carnivores are poor converters of ionone-containing carotenoids, and pure carnivores such as felids (cats) lack beta-carotene 15,15'-dioxygenase and beta-carotene 15,15'-monooxygenase and cannot convert any carotenoids to retinal, resulting in none of the carotenoids being forms of vitamin A for these species. They must have preformed vitamin A in their diet. [11]

Beta-carotene 15,15'-dioxygenase belongs to the (similarity-defined) family of carotenoid oxygenases (InterPro :  IPR004294 ). Enzymes of this family contain a Fe2+ active site, coordinated usually by four His residues.[ citation needed ]

Related Research Articles

<span class="mw-page-title-main">Carotene</span> Class of compounds

The term carotene (also carotin, from the Latin carota, "carrot") is used for many related unsaturated hydrocarbon substances having the formula C40Hx, which are synthesized by plants but in general cannot be made by animals (with the exception of some aphids and spider mites which acquired the synthesizing genes from fungi). Carotenes are photosynthetic pigments important for photosynthesis. Carotenes contain no oxygen atoms. They absorb ultraviolet, violet, and blue light and scatter orange or red light, and (in low concentrations) yellow light.

<span class="mw-page-title-main">Vitamin A</span> Essential nutrient

Vitamin A is a fat-soluble vitamin and an essential nutrient for animals. The term "vitamin A" encompasses a group of chemically related organic compounds that includes retinol, retinal, retinoic acid, and several provitamin (precursor) carotenoids, most notably beta-carotene. Vitamin A has multiple functions: it is essential for embryo development and growth, for maintenance of the immune system, and for vision, where it combines with the protein opsin to form rhodopsin – the light-absorbing molecule necessary for both low-light and color vision.

<span class="mw-page-title-main">Retinol</span> Chemical compound

Retinol, also called vitamin A1, is a fat-soluble vitamin in the vitamin A family that is found in food and used as a dietary supplement. Retinol or other forms of vitamin A are needed for vision, cellular development, maintenance of skin and mucous membranes, immune function and reproductive development. Dietary sources include fish, dairy products, and meat. As a supplement it is used to treat and prevent vitamin A deficiency, especially that which results in xerophthalmia. It is taken by mouth or by injection into a muscle. As an ingredient in skin-care products, it is used to reduce wrinkles and other effects of skin aging.

<span class="mw-page-title-main">Carotenoid</span> Class of chemical compounds; yellow, orange or red plant pigments

Carotenoids are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, archaea, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, corn, tomatoes, canaries, flamingos, salmon, lobster, shrimp, and daffodils. Over 1,100 identified carotenoids can be further categorized into two classes – xanthophylls and carotenes.

β-Carotene Red-orange pigment of the terpenoids class

β-Carotene (beta-carotene) is an organic, strongly colored red-orange pigment abundant in fungi, plants, and fruits. It is a member of the carotenes, which are terpenoids (isoprenoids), synthesized biochemically from eight isoprene units and thus having 40 carbons.

<span class="mw-page-title-main">Xanthophyll</span> Chemical compounds subclass

Xanthophylls are yellow pigments that occur widely in nature and form one of two major divisions of the carotenoid group; the other division is formed by the carotenes. The name is from Greek: xanthos (ξανθός), meaning "yellow", and phyllon (φύλλον), meaning "leaf"), due to their formation of the yellow band seen in early chromatography of leaf pigments.

<span class="mw-page-title-main">Retinal</span> Chemical compound

Retinal is a polyene chromophore. Retinal, bound to proteins called opsins, is the chemical basis of visual phototransduction, the light-detection stage of visual perception (vision).

The ionones, from greek ἴον ion "violet", are a series of closely related chemical substances that are part of a group of compounds known as rose ketones, which also includes damascones and damascenones. Ionones are aroma compounds found in a variety of essential oils, including rose oil. β-Ionone is a significant contributor to the aroma of roses, despite its relatively low concentration, and is an important fragrance chemical used in perfumery. The ionones are derived from the degradation of carotenoids.

<span class="mw-page-title-main">Carotenoid oxygenase</span>

Carotenoid oxygenases are a family of enzymes involved in the cleavage of carotenoids to produce, for example, retinol, commonly known as vitamin A. This family includes an enzyme known as RPE65 which is abundantly expressed in the retinal pigment epithelium where it catalyzed the formation of 11-cis-retinol from all-trans-retinyl esters.

γ-Carotene (gamma-carotene) is a carotenoid, and is a biosynthetic intermediate for cyclized carotenoid synthesis in plants. It is formed from cyclization of lycopene by lycopene cyclase epsilon. Along with several other carotenoids, γ-carotene is a vitamer of vitamin A in herbivores and omnivores. Carotenoids with a cyclized, beta-ionone ring can be converted to vitamin A, also known as retinol, by the enzyme beta-carotene 15,15'-dioxygenase; however, the bioconversion of γ-carotene to retinol has not been well-characterized. γ-Carotene has tentatively been identified as a biomarker for green and purple sulfur bacteria in a sample from the 1.640 ± 0.003-Gyr-old Barney Creek Formation in Northern Australia which comprises marine sediments. Tentative discovery of γ-carotene in marine sediments implies a past euxinic environment, where water columns were anoxic and sulfidic. This is significant for reconstructing past oceanic conditions, but so far γ-carotene has only been potentially identified in the one measured sample.

<i>Blakeslea trispora</i> Species of fungus

Blakeslea trispora is a mould and member of the division Zygomycota. This species has been well studied for its ability to produce carotenoids, particularly, β-carotene and lycopene. β-carotene is a vitamin A precursor and both of β-carotene and lycopene play a significant role in the inhibition of oxidative stress. Blakeslea trispora is commonly isolated from soil samples throughout the Southern United States and Southern Asia. B. trispora is a pathogen of tropical plants. In vivo pathogenicity testing using animal models suggests this fungus is not a cause of animal or human disease.

<span class="mw-page-title-main">Dopamine beta-hydroxylase</span> Mammalian protein found in Homo sapiens

Dopamine beta-hydroxylase (DBH), also known as dopamine beta-monooxygenase, is an enzyme that in humans is encoded by the DBH gene. Dopamine beta-hydroxylase catalyzes the conversion of dopamine to norepinephrine.

Apo-beta-carotenoid-14',13'-dioxygenase (EC 1.13.11.67 is an enzyme that catalyzes the chemical reaction

Carotenoid isomerooxygenase (EC 1.13.11.65, ninaB (gene)) is an enzyme with systematic name zeaxanthin:oxygen 15,15'-oxidoreductase (bond-cleaving, cis-isomerizing). This enzyme catalyses the following chemical reaction

8'-apo-beta-carotenoid 14',13'-cleaving dioxygenase (EC 1.13.11.67) is an enzyme with systematic name 8'-apo-beta-carotenol:O2 oxidoreductase (14',13'-cleaving). This enzyme catalyses the following chemical reaction

9-cis-beta-carotene 9',10'-cleaving dioxygenase (EC 1.13.11.68, CCD7 (gene), MAX3 (gene), NCED7 (gene)) is an enzyme with systematic name 9-cis-beta-carotene:O2 oxidoreductase (9',10'-cleaving). This enzyme catalyses the following chemical reaction

Carlactone synthase (EC 1.13.11.69, CCD8 (gene), MAX4 (gene), NCED8 (gene)) is an enzyme with systematic name 9-cis-10'-apo-beta-carotenal:O2 oxidoreductase (14,15-cleaving, carlactone-forming). This enzyme catalyses the following chemical reaction

Carotenoid-9',10'-cleaving dioxygenase (EC 1.13.11.71, BCO2 (gene), beta-carotene 9',10'-monooxygenase (misleading)) is an enzyme with systematic name all-trans-beta-carotene:O2 oxidoreductase (9',10'-cleaving). This enzyme catalyses the following chemical reaction

All-trans-8'-apo-beta-carotenal 15,15'-oxygenase (EC 1.14.99.41, Diox1, ACO, 8'-apo-beta-carotenal 15,15'-oxygenase) is an enzyme with systematic name all-trans-8'-apo-beta-carotenal:oxygen 15,15'-oxidoreductase (bond-cleaving). This enzyme catalyses the following chemical reaction

β-Cyclocitral Chemical compound

β-Cyclocitral (beta-cyclocitral) is an apocarotenoid derived from the C7 oxidation of β-carotene. This apocarotenoid has revived interest due to its roles in plant development. β-cyclocitral has been found endogenously in a variety of organisms including plants, cyanobacteria, fungi and animals. β-Cyclocitral is a volatile compound that contributes to the aroma of various fruits, vegetables and ornamental plants. In plants, β-cyclocitral was found to be an important regulator in root development.

References

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  8. Kim YS, Oh DK (March 2009). "Substrate specificity of a recombinant chicken beta-carotene 15,15'-monooxygenase that converts beta-carotene into retinal". Biotechnology Letters. 31 (3): 403–8. doi:10.1007/s10529-008-9873-4. PMID   18979213. S2CID   21220270.
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