Fast Assembly and High-Throughput Screening of Structure and Antioxidant Relationship of Carotenoids

Kim, Dahye; Shi, Gaosheng; Kim, YunJi; Koo, Sangho

doi:10.1021/acs.orglett.8b03915

Cited by 10 publications

(11 citation statements)

References 35 publications

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“…Nevertheless, carotene 9e with ortho -phenyl substituent was not produced presumably due to the steric reason. Expeditious one-pot synthesis of carotene 9d was demonstrated by the double Wadsworth–Emmons olefination of C 20 polyene diphosphonate 10 with protected hydroxybenzaldehyde 4d . Carotenoids 9 were mostly obtained as all- E form (based on 1 H NMR spectra) and further purified by recrystallization with a mixed solvent of MeOH and THF.…”

Section: Resultsmentioning

confidence: 99%

Apocarotenals of Phenolic Carotenoids for Superior Antioxidant Activities

Shi

Jung

et al. 2021

ACS Omega

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A series of para-phenolic carotenes 1 with ortho- and meta-substitutions were respectively prepared utilizing the benzenesulfonyl protection method, which demonstrated the importance of the ring substituents on their effective conjugation, evaluated by their UV absorption values. The corresponding apo-12′-carotenals 2 were devised to improve the conjugation effect of the para-phenolic radical with the polyene chain by the conjugated aldehyde group. Apo-12′-carotenals 2b and 2c without ortho-substituents exhibited superior antioxidant activities to their corresponding symmetrical carotenes 1 as well as β-carotene and apo-12′-β-carotenal in 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging assays.

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Section: Resultsmentioning

confidence: 99%

Apocarotenals of Phenolic Carotenoids for Superior Antioxidant Activities

Shi

Jung

et al. 2021

ACS Omega

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“…Accordingly, a pharmacokinetic study showed that crocin was hydrolyzed to crocetin through the gastro-intestinal tract, and then absorbed and detected in plasma (Xi et al, 2007). In addition, the structure-activity relationship of carotenoids (including crocetin and crocin) suggested that diverse terminal structures, such as electron-rich aromatic methyl substituent and the polyene chain structures, were responsible for the antioxidant activity of carotenoids (Kim et al, 2019). These findings, together with the fact that crocetin is more effective than crocin, suggesting that crocetin may act as an active compound with a stronger anti-angiogenic effect.…”

Section: Discussionmentioning

confidence: 99%

Crocetin and Its Glycoside Crocin, Two Bioactive Constituents From Crocus sativus L. (Saffron), Differentially Inhibit Angiogenesis by Inhibiting Endothelial Cytoskeleton Organization and Cell Migration Through VEGFR2/SRC/FAK and VEGFR2/MEK/ERK Signaling Pathways

et al. 2021

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Crocetin and crocin are two important carotenoids isolated from saffron (Crocus sativus L.), which have been used as natural biomedicines with beneficial effects for improving the suboptimal health status associated with abnormal angiogenesis. However, the anti-angiogenic effects and underlying mechanisms of the effects of crocetin and crocin have not been investigated and compared. The anti-angiogenic effects of crocetin and crocin were tested on human umbilical vein endothelial cells (HUVECs) in vitro, and in zebrafish in vivo. In vivo, crocetin (20 μM) and crocin (50 and 100 μM) significantly inhibited subintestinal vein vessels formation, and a conversion process between them existed in zebrafish, resulting in a difference in their effective concentrations. In the HUVEC model, crocetin (10, 20 and 40 μM) and crocin (100, 200 and 400 μM) inhibited cell migration and tube formation, and inhibited the phosphorylation of VEGFR2 and its downstream pathway molecules. In silico analysis further showed that crocetin had a higher ability to bind with VEGFR2 than crocin. These results suggested that crocetin was more effective than crocin in inhibiting angiogenesis through regulation of the VEGF/VEGFR2 signaling pathway. These compounds, especially crocetin, are potential candidate natural biomedicines for the management of diseases associated with abnormal blood vessel growth, such as age-related macular degeneration.

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“…Quantitative measurements of the reduction in UV absorption for the above standard radicals by carotenoids represent the antioxidant activities of the carotenoids. These assays work very well for simple carotenoids such as β-carotene and lycopene [ 21 ]. However, antioxidant activities of oxo-carotenoids such as canthaxanthin, halocynthiaxanthin, and capsanthin as shown in Figure 1 may be underestimated by these standard radical assays [ 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Oxo-Carotenoids as Efficient Superoxide Radical Scavengers

2022

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Oxo-carotenoids containing conjugated carbonyl groups in their chains were designed to be more efficient superoxide radical scavengers than natural carotenoids, β-carotene and canthaxanthin. A practical chain-extension method for polyene dials (e.g., crocetin dial) was also proposed based on Horner–Wadsworth–Emmons olefination. Double aldol condensation between polyene dials and acetophenones with ring substituents produced oxo-carotenoids with substituted benzene rings. The antioxidant activity of oxo-carotenoids was measured using DPPH (radical) and ABTS (cationic radical) scavenging assays and compared with the analysis with the superoxide (anionic radical) probe. An effective conjugation length by carbon–carbon double bonds is important to provide superior antioxidant activity for oxo-carotenoids, regardless of the type of radical probe used in the assay. Increasing electron density is favorable to strong antioxidant activity in DPPH, and the phenol group is favored in ABTS, whereas electron deficient oxo-carotenoids are very potent in the superoxide radical assay. All oxo-carotenoids exhibited 105~151% better superoxide radical scavenging activity compared to beta-carotene (100%), whereas 38~155% in DPPH and 16~96% in ABTS radical scavenging activities were observed.

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Fast Assembly and High-Throughput Screening of Structure and Antioxidant Relationship of Carotenoids

Cited by 10 publications

References 35 publications

Apocarotenals of Phenolic Carotenoids for Superior Antioxidant Activities

Apocarotenals of Phenolic Carotenoids for Superior Antioxidant Activities

Crocetin and Its Glycoside Crocin, Two Bioactive Constituents From Crocus sativus L. (Saffron), Differentially Inhibit Angiogenesis by Inhibiting Endothelial Cytoskeleton Organization and Cell Migration Through VEGFR2/SRC/FAK and VEGFR2/MEK/ERK Signaling Pathways

Oxo-Carotenoids as Efficient Superoxide Radical Scavengers

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