Chelation of Iron and Copper by Quercetin B-Ring Methyl Metabolites, Isorhamnetin and Tamarixetin, and Their Effect on Metal-Based Fenton Chemistry

Lomozová, Zuzana; Catapano, Maria Carmen; Hrubša, Marcel; Karlíčková, Jana; Macáková, Kateřina; Kučera, Radim

doi:10.1021/acs.jafc.1c01729

Cited by 19 publications

(10 citation statements)

References 41 publications

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“…Third, other antioxidant pathways attributed to flavonoids are inhibition or xanthine-oxidase (source of highly toxic hydroxyl radicals) enzymes or iron-chelating capacity. The key role of quercetin (one of the most powerful bioflavonoids) as an inhibitor of NO synthase ( 53 ), xanthine oxidase ( 54 ), and iron-chelator ( 55 ) is noticeable.…”

Section: Resultsmentioning

confidence: 99%

Neuroprotective Potential of Tamarillo (Cyphomandra betacea) Epicarp Extracts Obtained by Sustainable Extraction Process

et al. 2021

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Tamarillo (Cyphomandra betacea (Cav.) Sendt.), or tree tomato, is a tropical fruit from the Andean region of South America; it is highly rich in vitamins, minerals, and polyphenolic compounds. In this study, extracts from tamarillo epicarp (TE) were obtained by pressurized liquid extraction (PLE), and their in-vitro neuroprotective potential was assessed. A central composite design with response surface methodology was performed to optimize PLE as a function of solvent composition and temperature. Selected response variables were extraction yield, total phenolic content (TPC), total flavonoid content (TFC), total carotenoid content (TCC), antioxidant (ABTS), and anti-inflammatory (LOX) activities, and anti-acetylcholinesterase (AChE) inhibitory capacity. According to the desirability function, the optimal conditions were 100% ethanol and 180°C with a 0.87 desirability value. Next, the anti-butyrylcholinesterase enzyme (BChE), reactive oxygen species (ROS), and reactive nitrogen species (RNS) inhibition as well as cytotoxicity in HK-2, THP-1 monocytes, and SH-5YSY neuroblastoma cell lines were studied for the TE extract obtained under optimized conditions. The optimum TE extract provided the following results: extraction yield (36.25%), TPC (92.09 mg GAE/g extract), TFC (4.4 mg QE/g extract), TCC (107.15 mg CE/g extract), antioxidant capacity (ABTS, IC50 = 6.33 mg/ml extract), LOX (IC50 = 48.3 mg/ml extract), and AChE (IC50 = 97.46 mg/ml extract), and showed no toxicity at concentration up to 120 μg/ml extract for all the tested cell lines. Finally, chemical characterization by liquid chromatography-tandem mass spectrometry (UHPLC-q-TOF-MS/MS) of the optimum TE extract exhibited an important presence of hydroxycinnamic acid derivatives and other phenolic acids as well as quercetin hexoside and rutin, as main metabolites responsible for the observed biological properties. All these results suggested that TE, which represents between 8 and 15% of the total fruit, could become a promising natural by-product with a potential “multitarget” activity against Alzheimer's disease.

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Section: Resultsmentioning

confidence: 99%

Neuroprotective Potential of Tamarillo (Cyphomandra betacea) Epicarp Extracts Obtained by Sustainable Extraction Process

et al. 2021

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“…Following this first process of absorption, the polyphenols are transported through the portal vein to the liver, where they undergo phase I metabolism, which implies hydrolysis and oxidation reactions, and phase II metabolism, prevalently including glucuronidation, methylation, and sulfonation reactions [ 77 , 78 ]. Such metabolites can have markedly changed iron-chelating and anti/pro-oxidant properties [ 79 , 80 ]. They can be detected in systemic circulation; however, such modifications (in particular, sulfation and glucuronidation) also facilitate their efflux into the intestinal lumen.…”

Section: Polyphenols’ Bioavailabilitymentioning

confidence: 99%

The Chelating Ability of Plant Polyphenols Can Affect Iron Homeostasis and Gut Microbiota

et al. 2023

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In the past decades, many studies have widely examined the effects of dietary polyphenols on human health. Polyphenols are well known for their antioxidant properties and for their chelating abilities, by which they can be potentially employed in cases of pathological conditions, such as iron overload. In this review, we have highlighted the chelating abilities of polyphenols, which are due to their structural specific sites, and the differences for each class of polyphenols. We have also explored how the dietary polyphenols and their iron-binding abilities can be important in inflammatory/immunomodulatory responses, with a special focus on the involvement of macrophages and dendritic cells, and how they might contribute to reshape the gut microbiota into a healthy profile. This review also provides evidence that the axes “polyphenol–iron metabolism–inflammatory responses” and “polyphenol–iron availability–gut microbiota” have not been very well explored so far, and the need for further investigation to exploit such a potential to prevent or counteract pathological conditions.

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“…In the correlation analysis, several compounds such as quercetin- O -deoxyhexoside- O -hexoside, esculetin- O -hexoside and hydroxytrimethoxyflavone were related to the observed metal chelating activities. These compounds have also been described in the literature as metal chelating agents [ 44 , 45 , 46 , 47 , 48 ]. Taken together, A. campestris subsp.…”

Section: Resultsmentioning

confidence: 99%

Exploring the Artemisia Genus: An Insight into the Phytochemical and Multi-Biological Potential of A. campestris subsp. lednicensis (Spreng.) Greuter & Raab-Straube

Trifan

Czerwińska

Mardari³

et al. 2022

Plants

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The Artemisia L. genus includes over five hundred species with great economic and medicinal properties. Our study aimed to provide a comprehensive metabolite and bioactivity profile of Artemisia campestris subsp. lednicensis (Spreng.) Greuter & Raab-Straube collected from north-eastern Romania. Liquid chromatography with tandem high-resolution mass spectrometry (LC-HRMS/MS) analysis of different polarity extracts obtained from the aerial parts led to the identification of twelve flavonoids, three phenolic acids, two sesquiterpene lactones, two fatty acids, one coumarin, and one lignan. The antioxidant and enzyme inhibitory properties were shown in the DPPH (0.71–213.68 mg TE/g) and ABTS (20.57–356.35 mg TE/g) radical scavenging, CUPRAC (38.56–311.21 mg TE/g), FRAP (121.68–202.34 mg TE/g), chelating (12.88–22.25 mg EDTAE/g), phosphomolybdenum (0.92–2.11 mmol TE/g), anti-acetylcholinesterase (0.15–3.64 mg GALAE/g), anti-butyrylcholinesterase (0–3.18 mg GALAE/g), anti-amylase (0.05–0.38 mmol ACAE/g), anti-glucosidase (0.43–2.21 mmol ACAE/g), and anti-tyrosinase (18.62–48.60 mg KAE/g) assays. At 100 μg/mL, Artemisia extracts downregulated the secretion of tumor necrosis factor (TNF)-α in a lipopolysaccharide (LPS)-stimulated human neutrophil model (29.05–53.08% of LPS+ control). Finally, the Artemisia samples showed moderate to weak activity (minimum inhibitory concentration (MIC) > 625 mg/L) against the seventeen tested microbial strains (bacteria, yeasts, and dermatophytes). Overall, our study shows that A. campestris subsp. lednicensis is a promising source of bioactives with putative use as food, pharmaceutical and cosmetic ingredients.

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Chelation of Iron and Copper by Quercetin B-Ring Methyl Metabolites, Isorhamnetin and Tamarixetin, and Their Effect on Metal-Based Fenton Chemistry

Cited by 19 publications

References 41 publications

Neuroprotective Potential of Tamarillo (Cyphomandra betacea) Epicarp Extracts Obtained by Sustainable Extraction Process

Neuroprotective Potential of Tamarillo (Cyphomandra betacea) Epicarp Extracts Obtained by Sustainable Extraction Process

The Chelating Ability of Plant Polyphenols Can Affect Iron Homeostasis and Gut Microbiota

Exploring the Artemisia Genus: An Insight into the Phytochemical and Multi-Biological Potential of A. campestris subsp. lednicensis (Spreng.) Greuter & Raab-Straube

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