Revisiting the Oxidation of Flavonoids: Loss, Conservation or Enhancement of Their Antioxidant Properties
Abstract
:1. Introduction
2. Flavonoids as Antioxidants
3. Oxidation and Other Metabolic Reactions Capable of Affecting the Antioxidant Properties of Flavonoids
4. Oxidation of the Phenolic Moieties of Flavonoids and Its Consequences on Their Antioxidant Properties
5. Oxidation of Quercetin and Its Consequences on Its Antioxidant Properties
6. Onion Peel as a Natural Source of Q-BZF
7. Conclusions
Author Contributions
Funding
Conflicts of Interest
Abbreviations
ARE | antioxidant response elements |
BZF | 2-(benzoyl)-2-hydroxy-3(2H)-benzofuranone derivative(s) |
Caco-2 | human colonic adenocarcinoma |
CAT | catalase |
CYP | cytochrome P450 |
DPPH | 2,2-diphenyl-1-picrylhydrazyl |
EpRE | electrophile response elements |
FITC dextran | 3–5-kDa dextran conjugated with fluorescein isothiocyanate |
Ɣ-Glu–Cys ligase | gamma glutamate–cysteine ligase |
GI | gastrointestinal |
GSH | reduced glutathione |
GSHpx | glutathione peroxidase |
GSSGred | glutathione reductase |
HO-1 | heme oxygenase-1 |
Keap1 | Kelch-like ECH-associated protein 1 |
NF-κB | nuclear factor kappa B |
NQO1 | NAD(P)H:quinone oxidoreductase 1 |
Nrf2-Keap1 | nuclear factor (erythroid-derived 2)-like 2 |
NSAID | non-steroidal anti-inflammatory drugs |
OAE | onion peel aqueous extract |
PKC | protein kinase C |
PKCζ | protein kinase C zeta type |
Q-BZF | 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone |
Qox | quercetin oxidation mixture |
ROS | reactive oxygen species |
SOD | superoxide dismutase |
TEER | transepithelial electrical resistance |
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Phenol Compromising Reactions | Metabolites | Impact on Antioxidant Potency |
---|---|---|
O-Glycosylation (in plants) | Glycosides (e.g., Q-3-O-glucoside; Q-4′-O-glucoside; 3,4′-O-diglucoside; Q-5-O-glucoside and Q-7-O-glucoside) | In general, these metabolites have less ROS-scavenging potency than their corresponding aglycones |
O-Deglycosylation (in human intestine/colon) | Quercetin O-deglycosylated in C3, C4′, C5 or C7 | The ROS-scavenging potency of O-deglycosylated metabolites is, in most cases, considerably higher |
Biotransformation (in human intestine/liver/kidney) | Glucuronides (e.g., Q-3-O- and Q-7-O-glucuronides) Sulphates (e.g., Q-3-O-and Q-3′-O-sulphates) Methyl ethers (e.g., Q-3-O- and Q-3′-O-methyl) | These metabolites have, in general, less ROS scavenging/reduction potency but in some particular cases are able to up-regulate the endogenous antioxidant capacity |
Metabolic Degradation (in human microbiota) | Simple phenolics (e.g., 3,4-dihydroxy-benzoic and 3,4-dihydroxyphenylacetic acids) Deglycosylated flavonoids (e.g., quercetin aglycone) | In general, these metabolites maintain the original ROS-scavenging potency |
Oxidative Consumption (in plants/possibly in human) | Q-BZF as a mayor oxidation-derived metabolite | Q-BZF, and possibly other flavonol-derived BZF, maintain their ROS-scavenging potency and show a markedly higher capacity to upregulate the Nrf2-mediated endogenous antioxidant capacity |
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Speisky, H.; Shahidi, F.; Costa de Camargo, A.; Fuentes, J. Revisiting the Oxidation of Flavonoids: Loss, Conservation or Enhancement of Their Antioxidant Properties. Antioxidants 2022, 11, 133. https://doi.org/10.3390/antiox11010133
Speisky H, Shahidi F, Costa de Camargo A, Fuentes J. Revisiting the Oxidation of Flavonoids: Loss, Conservation or Enhancement of Their Antioxidant Properties. Antioxidants. 2022; 11(1):133. https://doi.org/10.3390/antiox11010133
Chicago/Turabian StyleSpeisky, Hernan, Fereidoon Shahidi, Adriano Costa de Camargo, and Jocelyn Fuentes. 2022. "Revisiting the Oxidation of Flavonoids: Loss, Conservation or Enhancement of Their Antioxidant Properties" Antioxidants 11, no. 1: 133. https://doi.org/10.3390/antiox11010133