Rationale on the High Radical Scavenging Capacity of Betalains

Nakashima, Karina K.; Bastos, E. L.

doi:10.3390/antiox8070222

Cited by 25 publications

(39 citation statements)

References 64 publications

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“…In addition, in the red varieties, betalains were present at much higher levels than the phenolic compounds. Betalains are molecules with a high antioxidant capacity comparable to epicatechin gallate, capable of donating electrons and protons due to the presence of a 5-O-glucosyl catechol and 1,7-diazaheptamethinium [34]. However, not all betalains have the same antioxidant capacity, and this will depend on the source and position of the hydroxyl/imino groups and the glycosylation of aglycone in the betalains structure [35].…”

Section: Introductionmentioning

confidence: 99%

Effect of Ultrafiltration of Pitaya Extract (Stenocereus thurberi) on Its Phytochemical Content, Antioxidant Capacity, and UPLC-DAD-MS Profile

et al. 2020

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Stenocereus thurberi is an endemic species in northwestern Mexico. It produces colorful fruits called pitayas that have an edible pulp. They have phytochemical compounds associated with biological activities. Ultrafiltration is a widely used method for the clarification of fruit juices and the recovery of phytochemicals. However, its effect has not been extensively studied in extracts. Therefore, the objective of this work is to study the effect of the ultrafiltration of pitaya extract (Stenocereus thurberi) on its phytochemical content, antioxidant capacity, and identification of phenolic compounds by UPLC-DAD-MS, providing greater knowledge about the pitaya. In this study, two extracts were analyzed, the unclarified extract (UE) and the clarified extract (CE). The antioxidant capacity was higher in the CE with 15.93 ± 0.42 mM TE/g, DPPH and 18.37 ± 0.016 mM TE/g, ABTS. The UPLC-MS analysis indicated the decrease in phenolic compounds in the CE and the presence of gallic acid and resorcinol, compounds that had not been identified in other species of Stenocereus spp. The correlation analysis indicated that all the phytochemicals present in the pitaya contribute significantly to the antioxidant capacity. The ultrafiltration process could be a viable option to improve the biological activity of the natural extracts.

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Section: Introductionmentioning

confidence: 99%

Effect of Ultrafiltration of Pitaya Extract (Stenocereus thurberi) on Its Phytochemical Content, Antioxidant Capacity, and UPLC-DAD-MS Profile

et al. 2020

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“…3a). However, the oxidation of the 1,7-diazaheptamethinium system of OxiBeet occurred at a much lower potential than those of other betalains, 14 including pBeet, 34 as evidenced by the intense irreversible anodic response at 357 mV vs. Ag|AgCl. Moreover, OxiBeet nitrone was reversibly oxidized to the corresponding nitroxide (Epa = 166 mV and Epc = 78 mV; E1/2 = 124 mV, Fig.…”

Section: Resultsmentioning

confidence: 93%

Design of an Antioxidant Nitrone Scaffold Based on Plant Pigments

Ac¹,

Rb²,

Lc³

et al. 2021

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Nitrones derived from natural antioxidants are emerging as highly specific therapeutics for the treatment of various human diseases, including stroke, neurodegenerative pathologies, and cancer. However, the development of useful pseudo-natural nitrones requires the judicious choice of a secondary metabolite as precursor. Betalains are nitrogen-containing natural pigments that exhibit marked antioxidant and pharmacological properties and, hence, are ideal candidates for the design of multifunctional nitrones. In this work, we describe the semisynthesis and properties of a biocompatible and antioxidant betalain-nitrone named OxiBeet. This bio-based compound is a better radical scavenger than ascorbic acid, gallic acid and most non-phenolic antioxidants and undergoes concerted proton-coupled electron transfer. The autoxidation of OxiBeet gives rise to a persistent nitroxide radical, which was studied by electron paramagnetic resonance spectroscopy. Femtosecond transient absorption spectroscopy reveals that excited state formation is not required for the oxidation of OxiBeet. The results are compared with those obtained using betanin, a natural betalain, and pBeet, the imine analogue of OxiBeet. The findings in this study will enable the development of antioxidant nitrones based on the novel <i>N</i>-oxide 1,7-diazaheptamethinium scaffold and betalain dyes with enhanced hydrolytic stability in aqueous alkaline media.

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“…The product was isolated in 70% yield, which is three times higher than that reported for the semisynthesis of betalains (21,22). Betalamic acid can be extracted from base-hydrolyzed beetroot juice (20,23) or prepared by the enzymatic oxidation of l-dopa (24)(25)(26)(27).…”

Section: Semisynthesis and Structural Characterization Of Beetbluementioning

confidence: 82%

A metal-free blue chromophore derived from plant pigments

et al. 2020

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Blue natural pigments are rare, especially among plants. However, flowering species that evolved to attract Hymenoptera pollinators are colored by blue anthocyanin-metal complexes. Plants lacking anthocyanins are pigmented by betalains but are unable to produce blue hues. By extending the π-system of betalains, we designed a photostable and metal-free blue dye named BeetBlue that did not show toxicity to human hepatic and retinal pigment epithelial cells and does not affect zebrafish embryonal development. This chiral dye can be conveniently synthesized from betalamic acid obtained from hydrolyzed red beetroot juice or by enzymatic oxidation of l-dopa. BeetBlue is blue in the solid form and in solution of acidified polar molecular solvents, including water. Its capacity to dye natural matrices makes BeetBlue the prototype of a new class of low-cost bioinspired chromophores suitable for a myriad of applications requiring a blue hue.

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Rationale on the High Radical Scavenging Capacity of Betalains

Cited by 25 publications

References 64 publications

Effect of Ultrafiltration of Pitaya Extract (Stenocereus thurberi) on Its Phytochemical Content, Antioxidant Capacity, and UPLC-DAD-MS Profile

Effect of Ultrafiltration of Pitaya Extract (Stenocereus thurberi) on Its Phytochemical Content, Antioxidant Capacity, and UPLC-DAD-MS Profile

Design of an Antioxidant Nitrone Scaffold Based on Plant Pigments

A metal-free blue chromophore derived from plant pigments

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