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Rationale on the High Radical Scavenging Capacity of Betalains

Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo, SP 05508-000, Brazil
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Author to whom correspondence should be addressed.
Current address: Institute for Molecules and Materials, Radboud University, 6525 XZ Nijmegen, The Netherlands.
Antioxidants 2019, 8(7), 222; https://doi.org/10.3390/antiox8070222
Received: 17 June 2019 / Revised: 1 July 2019 / Accepted: 11 July 2019 / Published: 13 July 2019
(This article belongs to the Section Natural and Synthetic Antioxidants)
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Abstract

Betalains are water-soluble natural pigments of increasing importance as antioxidants for pharmaceutical use. Although non-phenolic betalains have lower capacity to scavenge radicals compared to their phenolic analogues, both classes perform well as antioxidants and anti-inflammatory agents in vivo. Here we show that meta-hydroxyphenyl betalain (m-OH-pBeet) and phenylbetalain (pBeet) show higher radical scavenging capacity compared to their N-methyl iminium analogues, in which proton-coupled electron transfer (PCET) from the imine nitrogen atom is precluded. The 1,7-diazaheptamethinium system was found to be essential for the high radical scavenging capacity of betalains and concerted PCET is the most thermodynamically favorable pathway for their one-electron oxidation. The results provide useful insights for the design of nature-derived redox mediators based on the betalain scaffold. View Full-Text
Keywords: betalain; antioxidant; radical scavenger; natural pigments; redox mediator betalain; antioxidant; radical scavenger; natural pigments; redox mediator
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Nakashima, K.K.; Bastos, E.L. Rationale on the High Radical Scavenging Capacity of Betalains. Antioxidants 2019, 8, 222.

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