Reaction and Scavenging Mechanism of β-Carotene and Zeaxanthin with Reactive Oxygen Species

Nishino, Azusa; Yasui, Hiroyuki; Maoka, Takashi

doi:10.5650/jos.ess16107

Cited by 49 publications

(34 citation statements)

References 15 publications

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“…15) [38]. Similar results were also obtained in the case of β-carotene, zeaxanthin, and capsanthin [39,40]. These results suggest that carotenoids could take up singlet oxygen, superoxide anion radicals and hydroxyl radicals by the formation of endoperoxide or epoxide.…”

Section: Chemical Mechanism Of Scavenging Of Active Oxygen Species Bysupporting

confidence: 74%

Carotenoids as natural functional pigments

2019

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Carotenoids are tetraterpene pigments that are distributed in photosynthetic bacteria, some species of archaea and fungi, algae, plants, and animals. About 850 naturally occurring carotenoids had been reported up until 2018. Photosynthetic bacteria, fungi, algae, and plants can synthesize carotenoids de novo. Carotenoids are essential pigments in photosynthetic organs along with chlorophylls. Carotenoids also act as photo-protectors, antioxidants, color attractants, and precursors of plant hormones in non-photosynthetic organs of plants. Animals cannot synthesize carotenoids de novo, and so those found in animals are either directly accumulated from food or partly modified through metabolic reactions. So, animal carotenoids show structural diversity. Carotenoids in animals play important roles such precursors of vitamin A, photo-protectors, antioxidants, enhancers of immunity, and contributors to reproduction. In the present review, I describe the structural diversity, function, biosyntheses, and metabolism of natural carotenoids.

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Section: Chemical Mechanism Of Scavenging Of Active Oxygen Species Bysupporting

confidence: 74%

Carotenoids as natural functional pigments

2019

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“…β-Carotene scavenges various ROS, including singlet oxygen ( 1 O 2 ), the superoxide anion radical ( • O 2 − ), the hydroxy radical ( • OH), the peroxyl radical (RCOO • ) and nitric oxide (NO) (24)(25)(26). The antioxidant activity of β-carotene as well as lycopene may be attributable to their high number of conjugated dienes, which act as potent ROS quenchers.…”

Section: Discussionmentioning

confidence: 99%

“…The radical-scavenging activity of carotenoids, characterized by a small n value and a large k inh value, may be attributable to their high number of conjugated dienes (Figure 1), which act as potent singlet oxygen quenchers and ROS scavengers; radicals are trapped by the unsaturated polyene chain of carotenoids (20). β-Carotene also yields reaction products such as epoxide or endoperoxide when it reacts with • O 2 − and • OH (24,28). Epoxides of lycopene have been found after photochemical and chemical reactions with ROS (29); the initiator radicals induce newly formed β-carotene radical products, which in turn undergo further transformation leading to a variety of secondary β-carotene derivatives.…”

Section: Discussionmentioning

confidence: 99%

“…Adducts are formed by reaction of β-carotene with alkoxy and alkylperoxy free radicals through thermolysis of azo-initiators that are utilized in industrial processes such as benzene polymer synthesis (32). The products of the reaction between β-carotene and ROS, such as epoxides and endoperoxides, may be produced more preferentially than is the case for lycopene (24). Our data for the pro-oxidant activity of 20 mM β-carotene with both the AIBN and BPO radicals were strongly suggestive of the molecular difference between β-carotene and lycopene.…”

Section: Discussionmentioning

confidence: 99%

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Anti-inflammatory Activity of β-Carotene, Lycopene and Tri-n-butylborane, a Scavenger of Reactive Oxygen Species

Kawata

Murakami

Suzuki

et al. 2018

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“…4A-C) implies that EuCBPs function as ROS scavengers instead of excitation energy quenchers in Euhalothece cells. Like other carotenoids, Zea and β-Car are strong ROS scavengers 38 , and OCP and HCP exhibit antioxidant properties 9,39 . Thus, we hypothesized that E. coli producing both carotenoids and CBPs would show better survival under ROS stress than wild-type cells.…”

Section: Salt Acclimation Genes Associated With Ion Homeostasis Compmentioning

confidence: 99%

Genomic Survey of Salt Acclimation-Related Genes in the Halophilic Cyanobacterium Euhalothece sp. Z-M001

Yang

Song

Cho

et al. 2020

Sci Rep

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, cheol-Ho pan 2 & Youn-il park 1* Like other halophilic cyanobacterial genomes, the de novo-assembled genome of Euhalothece sp. Z-M001 lacks genes encoding keto-carotenoid biosynthesis enzymes, despite the presence of genes encoding carotenoid-binding proteins (cBps). consistent with this, HpLc analysis of carotenoids identified β-carotene and zeaxanthin as the dominant carotenoids. CBPs coexpressed with the zeaxanthin biosynthesis gene increased the survival rates of Escherichia coli strains by preventing antibiotic-induced accumulation of reactive oxygen species (ROS). RNA-seq analysis of Euhalothece revealed that among various salt resistance-related genes, those encoding the na + transporting multiple resistance and pH adaptation (Mrp) systems, glycine betaine biosynthesis enzymes, exopolysaccharide metabolic enzymes, and CBPs were highly upregulated, suggesting their importance in hypersaline habitats. During the early phase of salt deprivation, the amounts of β-carotene and zeaxanthin showed a negative correlation with ROS content. Overall, we propose that in some halophilic cyanobacteria, β-carotene and zeaxanthin, rather than keto-carotenoids, serve as the major chromophores for CBPs, which in turn act as effective antioxidants. Cyanobacteria are photosynthetic prokaryotes that exhibit diverse protective mechanisms to cope with harsh environmental conditions. One of the protective mechanisms involves the use of carotenoids 1 and diverse carotenoid-binding proteins (CBPs) 2 , which play essential roles in protecting the photosynthetic apparatus from damage by both excess light energy and reactive oxygen species (ROS). Most cyanobacterial CBPs bind to β-carotene (β-Car) and its oxygenated derivatives, called xanthophylls (Xan), and are located in photosynthetic protein complexes such as photosystem I (PSI), PSII, and cytochrome b 6 f 3. By contrast, water soluble CBPs bind non-covalently to cyanobacterial keto-carotenoids, such as echinenone (Ech) and canthaxanthin (Can), and to glycosylated-carotenoids such as myxoxanthophyll (Myx) 4 ; CBPs then function as effective energy dissipaters by interacting with the light-harvesting antenna, phycobilisome (PBS) 5. CBPs also bind to zeaxanthin (Zea), albeit with low affinity 6. The orange carotenoid protein (OCP) and its two paralogs, helical carotenoid protein (HCP) and C-terminal domain homolog (CTDH), are the only known soluble CBPs 4. The OCP is composed of two globular domains (one each at the N-and C-terminal ends); a single carotenoid is embedded between the two domains via a hydrophobic interaction 7. Blue light absorption by a keto-carotenoid results in a conformational change in the OCP, from the orange inactive form (OCP°) to the red active form (OCP R). Binding of OCP R to PBS quenches PBS fluorescence, which is prevented by fluorescence recovery protein (FRP) 8. FRP prevents accumulation of the OCP R by interacting with the C-terminal domain of OCP 8. The biological functions of HCPs, which are grouped into nine distinct clades 7 , are largely unknow...

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Reaction and Scavenging Mechanism of β-Carotene and Zeaxanthin with Reactive Oxygen Species

Cited by 49 publications

References 15 publications

Carotenoids as natural functional pigments

Carotenoids as natural functional pigments

Anti-inflammatory Activity of β-Carotene, Lycopene and Tri-n-butylborane, a Scavenger of Reactive Oxygen Species

Genomic Survey of Salt Acclimation-Related Genes in the Halophilic Cyanobacterium Euhalothece sp. Z-M001

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