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In Vitro Antioxidant versus Metal Ion Chelating Properties of Flavonoids: A Structure-Activity Investigation.

ABSTRACT: Natural flavonoids such as quercetin, (+)catechin and rutin as well as four methoxylated derivatives of quercetin used as models were investigated to elucidate their impact on the oxidant and antioxidant status of human red blood cells (RBCs). The impact of these compounds against metal toxicity was studied as well as their antiradical activities with DPPH assay. Antihemolytic experiments were conducted on quercetin, (+)catechin and rutin with excess of Fe, Cu and Zn (400 ?M), and the oxidant (malondialdehyde, carbonyl proteins) and antioxidant (reduced glutathione, catalase activity) markers were evaluated. The results showed that Fe and Zn have the highest prooxidant effect (37 and 33% of hemolysis, respectively). Quercetin, rutin and (+)catechin exhibited strong antioxidant properties toward Fe, but this effect was decreased with respect to Zn ions. However, the Cu showed a weak antioxidant effect at the highest flavonoid concentration (200 ?M), while a prooxidant effect was observed at the lowest flavonoid concentration (100 ?M). These results are in agreement with the physico-chemical and antiradical data which demonstrated that binding of the metal ions (for FeNTA: (+)Catechin, KLFeNTA = 1.6(1) × 106 M-1 > Rutin, KLFeNTA = 2.0(9) × 105 M-1 > Quercetin, KLFeNTA = 1.0(7) × 105 M-1 > Q35OH, KLFeNTA = 6.3(8.7) × 104 M-1 > Quercetin3'4'OH and Quercetin 3OH, KLFeNTA ~ 2 × 104 M-1) reflects the (anti)oxidant status of the RBCs. This study reveals that flavonoids have both prooxidant and antioxidant activity depending on the nature and concentration of the flavonoids and metal ions.

SUBMITTER: Cherrak SA

PROVIDER: S-EPMC5082868 | biostudies-other | 2016

REPOSITORIES: biostudies-other

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In Vitro Antioxidant versus Metal Ion Chelating Properties of Flavonoids: A Structure-Activity Investigation.

Cherrak Sabri Ahmed SA Mokhtari-Soulimane Nassima N Berroukeche Farid F Bensenane Bachir B Cherbonnel Angéline A Merzouk Hafida H Elhabiri Mourad M

PloS one 20161027 10

Natural flavonoids such as quercetin, (+)catechin and rutin as well as four methoxylated derivatives of quercetin used as models were investigated to elucidate their impact on the oxidant and antioxidant status of human red blood cells (RBCs). The impact of these compounds against metal toxicity was studied as well as their antiradical activities with DPPH assay. Antihemolytic experiments were conducted on quercetin, (+)catechin and rutin with excess of Fe, Cu and Zn (400 μM), and the oxidant (m ...[more]

PMID: 27788249

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Project description:Metal-catalyzed lipid oxidation is a major factor in food waste, as it reduces shelf life. Addressing this issue, our study investigates the potential of hydrolysates derived from potato protein, a by-product of potato starch production, as metal chelating antioxidants. Through sequential en-zymatic hydrolysis using Alcalase or Trypsin combined with Flavourzyme, we produced various hydrolysates, which were then fractionated via ultrafiltration. Using a combination of peptidomics and bioinformatics, we predicted the presence of metal-chelating and free radical scavenging pep-tides across all hydrolysate fractions, with a trend indicating a higher content of antioxidant pep-tides in lower molecular weight fractions. To validate these predictions, we utilized Surface Plas-mon Resonance (SPR) and a 9-day emulsion storage experiment. While SPR demonstrated poten-tial in identifying antioxidant activity, it faced challenges in differentiating between hydrolysate fractions due to significant standard errors. In the storage experiment, all hydrolysates showed li-pid oxidation inhibition, though not as effectively as EDTA. Remarkably, one fraction (AF13) was not significantly different (p < 0.05) from EDTA in suppressing hexanal formation. These results highlight SPR and peptidomics/bioinformatics as promising yet limited methods for antioxidant screening. Importantly, this study reveals the potential of potato protein hydrolysates as antioxi-dants in food products, warranting further research. The aim of this study was to evaluate the potential of SPR as a screening technique for potato protein hydrolysates (PPH) as metal chelating antioxidants. More specifically, the goal was to correlate the KD of the hydrolysates, determined by SPR, with development of different oxidation markers obtained during a storage experiment where the PPHs were added as antioxidants to 5 % fish oil-in-water emulsions at pH 7. Additionally, the effect of using different combinations of enzymes on antioxidant activity of the hydrolysates was investigated and peptidomics was applied to characterize the composition of the hydroly-sates. With the aim of achieving shorter peptides through a high degree of hydrolysis (DH%), this study utilized sequential hydrolysis, where Trypsin (Try) or Alcalase (Alc) was paired with Flavourzyme (Fla). Owing to its broad specificity as a heterogeneous combination of various endo- and exopeptidases [20], Flavourzyme is known to facilitate high DH% and the production of short peptides [21]. However, it has been reported that when used solely with a denatured substrate protein of limited solubility, Flavourzyme can yield a significantly lower DH% than anticipated [19]. Consequently, this study was designed to include substrate pre-digestion prior to Flavourzyme addition.

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In Vitro Antioxidant versus Metal Ion Chelating Properties of Flavonoids: A Structure-Activity Investigation.

Publications

In Vitro Antioxidant versus Metal Ion Chelating Properties of Flavonoids: A Structure-Activity Investigation.

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