Substrate Specificity of Purified Recombinant Chicken β-Carotene 9′,10′-Oxygenase (BCO2)

Seña, Carlo dela; Sun, Jun; Narayanasamy, Sureshbabu; Riedl, Ken M.; Yuan, Yan; Curley, Robert W.; Schwartz, Steven J.; Harrison, Earl H.

doi:10.1074/jbc.m116.723684

Cited by 69 publications

(54 citation statements)

References 36 publications

(55 reference statements)

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“…This is consistent with the relevant findings from other groups (Amengual et al, 2013; dela Sena et al, 2013; Dela Sena et al, 2016; Lindqvist and Andersson, 2002; Lindshield et al, 2008; Mein et al, 2011; Wang, 2012). Our feeding data also revealed that in bco1 −/− /bco2 −/− mice, the retinal accumulation of xanthophylls lutein and zeaxanthin is around six times higher than retinal accumulation of β-carotene, while the hepatic β-carotene is around twenty times as much as the hepatic xanthophyll.…”

Section: Discussionsupporting

confidence: 93%

“…The human macula is a yellow spot rich in carotenoids, and we and others have recently shown that human retinal BCO2 is a relatively inactive carotenoid cleavage enzyme in contrast to the very active cleavage enzymes found in most non-primate vertebrates such as chickens and mice (Li et al, 2014, Dela Sena et al, 2016). Human BCO2’s poor carotenoid cleavage activity appears to be important in facilitating carotenoid deposition in human ocular tissues (Li et al, 2014).…”

Section: Introductionmentioning

confidence: 84%

“…All- trans -retinal can be converted to all -trans -retinol which participates in the visual cycle as well as a variety biological processes in other tissues (Krinsky et al, 1993), or it can be oxidized to retinoic acid which is critical for various gene regulation pathways. BCO2 was previously called β, β-carotene 9′, 10′-dioxygenase, and it splits carotenoids, especially xanthophyll carotenoids, eccentrically at the 9′, 10′ double-carbon bond and yields apo-10′-carotenoid and ionone, or rosafluene (Amengual et al, 2011; Dela Sena et al, 2016; Mein et al, 2011). Nonsense mutations or single nucleotide polymorphisms (SNPs) in the promoter region of the bco2 gene may cause an accumulation of lutein or zeaxanthin in animals, turning their skin, meat, and fat a yellowish color (Berry et al, 2009; Vage and Boman, 2010).…”

Section: Introductionmentioning

confidence: 99%

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Retinal accumulation of zeaxanthin, lutein, and β-carotene in mice deficient in carotenoid cleavage enzymes

Vachali

Shen

et al. 2017

Experimental Eye Research

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Carotenoid supplementation can prevent and reduce the risk of age-related macular degeneration (AMD) and other ocular disease, but until now, there has been no validated and well-characterized mouse model which can be employed to investigate the protective mechanism and relevant metabolism of retinal carotenoids. β-Carotene oxygenases 1 and 2 (BCO1 and BCO2) are the only two carotenoid cleavage enzymes found in animals. Mutations of the bco2 gene may cause accumulation of xanthophyll carotenoids in animal tissues, and BCO1 is involved in regulation of the intestinal absorption of carotenoids. To determine whether or not mice deficient in BCO1 and/or BCO2 can serve as a macular pigment mouse model, we investigated the retinal accumulation of carotenoids in these mice when fed with zeaxanthin, lutein, or β-carotene using an optimized carotenoid feeding method. HPLC analysis revealed that all three carotenoids were detected in sera, livers, retinal pigment epithelium (RPE)/choroids, and retinas of all of the mice, except that no carotenoid was detectable in the retinas of wild type (WT) mice. Significantly higher amounts of zeaxanthin and lutein accumulated in the retinas of BCO2 knockout (bco2−/−) mice and BCO1/BCO2 double knockout (bco1−/−/bco2−/−) mice relative to BCO1 knockout (bco1−/−) mice, while bco1−/− mice preferred to take up β-carotene. The levels of zeaxanthin and lutein were higher than β-carotene levels in the bco1−/−/bco2−/− retina, consistent with preferential uptake of xanthophyll carotenoids by retina. Oxidative metabolites were detected in mice fed with lutein or zeaxanthin but not in mice fed with β-carotene. These results indicate that bco2−/− and bco1−/−/bco2−/− mice could serve as reasonable non-primate models for macular pigment function in the vertebrate eye, while bco1−/− mice may be more useful for studies related to β-carotene.

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Section: Discussionsupporting

confidence: 93%

Section: Introductionmentioning

confidence: 84%

Section: Introductionmentioning

confidence: 99%

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Retinal accumulation of zeaxanthin, lutein, and β-carotene in mice deficient in carotenoid cleavage enzymes

Vachali

Shen

et al. 2017

Experimental Eye Research

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“…lutein, zeaxanthin, canthaxanthin). In fact, several lines of evidence suggest that BCO2 preferentially cleaves carotenoids containing 3-hydroxy-ionone ring, and β-carotene has been shown to be a generally poor substrate for BCO2 (Mein et al, 2011; De la Seña, 2014 and De la Seña et al, 2016). To date, no study has directly evaluated either BCO subtype with respect to the xanthophyll glycosides, although cleavage of myxoxanthophyll by both other CCE (e.g., ACO) from cyanobacteria has been demonstrated (Scherzinger et al, 2006; Scherzinger and Al-Babili, 2008).…”

Section: Discussionmentioning

confidence: 99%

Carotenoid glycosides from cyanobacteria are teratogenic in the zebrafish (Danio rerio) embryo model

et al. 2017

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Toxigenicity of cyanobacteria is widely associated with production of several well-described toxins that pose recognized threats to human and ecosystem health as part of both freshwater eutrophication, and episodic blooms in freshwater and coastal habitats. However, a preponderance of evidence indicates contribution of additional bioactive, and potentially toxic, metabolites. In the present study, the zebrafish (Danio rerio) embryo was used as a model of vertebrate development to identify, and subsequently isolate and characterize, teratogenic metabolites from two representative strains of C. raciborskii. Using this approach, three chemically related carotenoids - and specifically the xanthophyll glycosides, myxol 2′-glycoside (1), 4-ketomyxol 2′-glycoside (2) and 4-hydroxymyxol 2′-glycoside (3) - which are, otherwise, well known pigment molecules from cyanobacteria were isolated as potently teratogenic compounds. Carotenoids are recognized “pro-retinoids” with retinoic acid, as a metabolic product of the oxidative cleavage of carotenoids, established as both key mediator of embryo development and, consequently, a potent teratogen. Accordingly, a comparative toxicological study of chemically diverse carotenoids, as well as apocarotenoids and retinoids, was undertaken. Based on this, a working model of the developmental toxicity of carotenoids as pro-retinoids is proposed, and the teratogenicity of these widespread metabolites is discussed in relation to possible impacts on aquatic vertebrate populations.

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“…Human BCO1 appears to be the primary enzyme to cleave carotenes [12]. BCO2 isolated from ferret and chicken cleaves a variety of carotenoids including xanthophylls [13, 14]. Interestingly, Li et al [15] suggested that the inactivity of primate BCO2 due to the loss of an alternative splicing site contributes to selective accumulation of lutein and zeaxanthin in primate retina.…”

Section: Introductionmentioning

confidence: 99%

Relationships of carotenoid-related gene expression and serum cholesterol and lipoprotein levels to retina and brain lutein deposition in infant rhesus macaques following 6 months of breastfeeding or formula feeding

Jeon

Neuringer

Kuchan

et al. 2018

Archives of Biochemistry and Biophysics

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The purpose of this study was to investigate if the enhanced bioaccumulation of lutein in retina and brain of breastfed, compared to formula-fed, infant monkeys was associated with higher levels of serum total and HDL cholesterol, apolipoproteins, or mRNA/protein expression of carotenoid-related genes. Newborn rhesus macaques were either breastfed, fed a carotenoid-supplemented formula, or fed an unsupplemented formula for 6 months (n = 8, 8, 7). Real-time qPCR and western blotting were performed in two brain regions (occipital cortex and cerebellum) and two retina regions (macular and peripheral retina). Breastfed infants had higher serum total cholesterol, HDL cholesterol, apoA-I, and apoB-100 levels than the combined formula-fed groups (P < 0.05). Breast milk or infant formulas did not alter expression of the nine genes (CD36, SCARB1, SCARB2, LDLR, STARD3, GSTP1, BCO1, BCO2, RPE65) examined except for SCARB2 in the retina and brain regions. In conclusion, dietary regimen did not impact the expression of carotenoid-related genes except for SCARB2. However, carotenoid-related genes were differentially expressed across brain and retina regions. Breastfed infants had higher serum total and HDL cholesterol, and apolipoproteins, suggesting that lipoprotein levels might be important for delivering lutein to tissues, especially the macular retina, during infancy.

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Substrate Specificity of Purified Recombinant Chicken β-Carotene 9′,10′-Oxygenase (BCO2)

Cited by 69 publications

References 36 publications

Retinal accumulation of zeaxanthin, lutein, and β-carotene in mice deficient in carotenoid cleavage enzymes

Retinal accumulation of zeaxanthin, lutein, and β-carotene in mice deficient in carotenoid cleavage enzymes

Carotenoid glycosides from cyanobacteria are teratogenic in the zebrafish (Danio rerio) embryo model

Relationships of carotenoid-related gene expression and serum cholesterol and lipoprotein levels to retina and brain lutein deposition in infant rhesus macaques following 6 months of breastfeeding or formula feeding

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