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Oxidation of Quercetin and Kaempferol Markedly Amplifies Their Antioxidant, Cytoprotective, and Anti-Inflammatory Properties

The contention that flavonoids’ oxidation would necessarily lead to a loss of their antioxidant properties was recently challenged by the demonstration that quercetin oxidation leads to the formation of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (Que-BZF), a metabolite whose antio...

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Autores principales: Speisky, Hernán, Arias-Santé, María Fernanda, Fuentes, Jocelyn
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9854986/
https://www.ncbi.nlm.nih.gov/pubmed/36671017
http://dx.doi.org/10.3390/antiox12010155
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author Speisky, Hernán
Arias-Santé, María Fernanda
Fuentes, Jocelyn
author_facet Speisky, Hernán
Arias-Santé, María Fernanda
Fuentes, Jocelyn
author_sort Speisky, Hernán
collection PubMed
description The contention that flavonoids’ oxidation would necessarily lead to a loss of their antioxidant properties was recently challenged by the demonstration that quercetin oxidation leads to the formation of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (Que-BZF), a metabolite whose antioxidant potency was notably higher than that of its precursor. Here, we compared and expanded the former observation to that of the quercetin analogue kaempferol. Oxidation of kaempferol led to the formation of a mixture of metabolites that included the 2-(4-hydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (Kae-BZF). Following the chromatographic isolation of Kae-BZF from such a mixture, its antioxidant, mitochondria- and cell-protecting, and NF-kB-inhibiting effects were assessed, and compared with those of Que-BZF, in Caco-2 cells exposed to indomethacin as a source of ROS. The concentrations of Que-BZF (100 nm) and Kae-BZF (1 nm) needed to attain their maximal protection effects were 50- and 5000-fold lower than those of their respective precursors. The former differences in concentrations were also seen when the abilities of Que-BZF and Kae-BZF to inhibit the indomethacin-induced activation of NF-kB were compared. These data not only reveal that the oxidative conversion of quercetin and kaempferol into their respective 2-benzoyl-2-hydroxy-3(2H)-benzofuranones (BZF) results in a considerable amplification of their original antioxidant properties, but also that the in the case of kaempferol, such amplification is 100-fold greater than that of quercetin.
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spelling pubmed-98549862023-01-21 Oxidation of Quercetin and Kaempferol Markedly Amplifies Their Antioxidant, Cytoprotective, and Anti-Inflammatory Properties Speisky, Hernán Arias-Santé, María Fernanda Fuentes, Jocelyn Antioxidants (Basel) Article The contention that flavonoids’ oxidation would necessarily lead to a loss of their antioxidant properties was recently challenged by the demonstration that quercetin oxidation leads to the formation of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (Que-BZF), a metabolite whose antioxidant potency was notably higher than that of its precursor. Here, we compared and expanded the former observation to that of the quercetin analogue kaempferol. Oxidation of kaempferol led to the formation of a mixture of metabolites that included the 2-(4-hydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (Kae-BZF). Following the chromatographic isolation of Kae-BZF from such a mixture, its antioxidant, mitochondria- and cell-protecting, and NF-kB-inhibiting effects were assessed, and compared with those of Que-BZF, in Caco-2 cells exposed to indomethacin as a source of ROS. The concentrations of Que-BZF (100 nm) and Kae-BZF (1 nm) needed to attain their maximal protection effects were 50- and 5000-fold lower than those of their respective precursors. The former differences in concentrations were also seen when the abilities of Que-BZF and Kae-BZF to inhibit the indomethacin-induced activation of NF-kB were compared. These data not only reveal that the oxidative conversion of quercetin and kaempferol into their respective 2-benzoyl-2-hydroxy-3(2H)-benzofuranones (BZF) results in a considerable amplification of their original antioxidant properties, but also that the in the case of kaempferol, such amplification is 100-fold greater than that of quercetin. MDPI 2023-01-09 /pmc/articles/PMC9854986/ /pubmed/36671017 http://dx.doi.org/10.3390/antiox12010155 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Speisky, Hernán
Arias-Santé, María Fernanda
Fuentes, Jocelyn
Oxidation of Quercetin and Kaempferol Markedly Amplifies Their Antioxidant, Cytoprotective, and Anti-Inflammatory Properties
title Oxidation of Quercetin and Kaempferol Markedly Amplifies Their Antioxidant, Cytoprotective, and Anti-Inflammatory Properties
title_full Oxidation of Quercetin and Kaempferol Markedly Amplifies Their Antioxidant, Cytoprotective, and Anti-Inflammatory Properties
title_fullStr Oxidation of Quercetin and Kaempferol Markedly Amplifies Their Antioxidant, Cytoprotective, and Anti-Inflammatory Properties
title_full_unstemmed Oxidation of Quercetin and Kaempferol Markedly Amplifies Their Antioxidant, Cytoprotective, and Anti-Inflammatory Properties
title_short Oxidation of Quercetin and Kaempferol Markedly Amplifies Their Antioxidant, Cytoprotective, and Anti-Inflammatory Properties
title_sort oxidation of quercetin and kaempferol markedly amplifies their antioxidant, cytoprotective, and anti-inflammatory properties
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9854986/
https://www.ncbi.nlm.nih.gov/pubmed/36671017
http://dx.doi.org/10.3390/antiox12010155
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