Metabolites of dietary quercetin: Profile, isolation, identification, and antioxidant capacity

Wiczkowski, Wiesław; Szawara-Nowak, Dorota; Topolska, Joanna; Olejarz, Katarzyna; Zieliński, Henryk; Piskuła, Mariusz K.

doi:10.1016/j.jff.2014.09.013

Cited by 33 publications

(16 citation statements)

References 35 publications

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“…In contrast, the results of individual tests for quercetin agree with our previously published data [ 19 ]. On the other hand, antioxidant activity (ABTS +• , DPPH and superoxide radical scavenging) of a mixture of 12 quercetin metabolites from pig urine was significantly stronger compared to quercetin [ 20 ].…”

Section: Resultsmentioning

confidence: 99%

“…Particular attention was paid to the free-radical-scavenging active groups [ 20 , 24 ], namely 3′-OH, 4′-OH, and 3-OH (see Table 6 and Figure 6 ), and their depth of insertion. The closer the distance to lipid unsaturation (where peroxy radicals are formed), the higher is the capacity to inhibit the propagation stage of lipid peroxidation.…”

Section: Resultsmentioning

confidence: 99%

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Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites

Valentová

Káňová

Meo

et al. 2017

IJMS

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Sulfated quercetin derivatives are important authentic standards for metabolic studies. Quercetin-3′-O-sulfate, quercetin-4′-O-sulfate, and quercetin-3-O-sulfate as well as quercetin-di-O-sulfate mixture (quercetin-7,3′-di-O-sulfate, quercetin-7,4′-di-O-sulfate, and quercetin-3′,4′-di-O-sulfate) were synthetized by arylsulfotransferase from Desulfitobacterium hafniense. Purified monosulfates and disulfates were fully characterized using MS and NMR and tested for their 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS+) and N,N-dimethyl-p-phenylenediamine (DMPD) radical scavenging, Folin-Ciocalteau reduction (FCR), ferric reducing antioxidant power (FRAP), and anti-lipoperoxidant activities in rat liver microsomes damaged by tert-butylhydroperoxide. Although, as expected, the sulfated metabolites were usually less active than quercetin, they remained still effective antiradical and reducing agents. Quercetin-3′-O-sulfate was more efficient than quercetin-4′-O-sulfate in DPPH and FCR assays. In contrast, quercetin-4′-O-sulfate was the best ferric reductant and lipoperoxidation inhibitor. The capacity to scavenge ABTS+• and DMPD was comparable for all substances, except for disulfates, which were the most efficient. Quantum calculations and molecular dynamics simulations on membrane models supported rationalization of free radical scavenging and lipid peroxidation inhibition. These results clearly showed that individual metabolites of food bioactives can markedly differ in their biological activity. Therefore, a systematic and thorough investigation of all bioavailable metabolites with respect to native compounds is needed when evaluating food health benefits.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites

Valentová

Káňová

Meo

et al. 2017

IJMS

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“…Nevertheless, it is necessary to take into account that in vivo situations a mixture of metabolites would exist and that the behavior of such a combination might differ from that of the individual compounds. In a recent study on the conjugated metabolites of quercetin detected in pig urine following intake of quercetin-rich onion dry skin, Wiczkowski et al [ 59 ] found that, whereas, quercetin aglycone possessed higher antioxidant activity than each of the individual conjugated metabolites, the pool of metabolites showed higher antioxidant capacity than that of the individual metabolites or quercetin, isorhamnetin, and their glycosides. On the other hand, different cells, including liver, blood, and kidney cells, contain enzymes capable of deconjugating the sulphated and glucuronidated forms of polyphenols [ 60 ].…”

Section: Effects and Mechanisms Of The Action Of Wine Polyphenols mentioning

confidence: 99%

An Integrated View of the Effects of Wine Polyphenols and Their Relevant Metabolites on Gut and Host Health

et al. 2017

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Over the last few decades, polyphenols, and flavonoids in particular, have attracted the interest of researchers, as they have been associated with the health-promoting effects derived from diets rich in vegetables and fruits, including moderate wine consumption. Recent scientific evidence suggests that wine polyphenols exert their effects through interactions with the gut microbiota, as they seem to modulate microbiota and, at the same time, are metabolized by intestinal bacteria into specific bioavailable metabolites. Microbial metabolites are better absorbed than their precursors and may be responsible for positive health activities in the digestive system (local effects) and, after being absorbed, in tissues and organs (systemic effects). Differences in gut microbiota composition and functionality among individuals can affect polyphenol activity and, therefore, their health effects. The aim of this review is to integrate the understanding of the metabolism and mechanisms of action of wine polyphenols at both local and systemic levels, underlining their impact on the gut microbiome and the inter-individual variability associated with polyphenols’ metabolism and further physiological effects. The advent of promising dietary approaches linked to wine polyphenols beyond the gut microbiota community and metabolism are also discussed.

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“…The result was identical to the one for myricetin and lower than that for the other compounds: fisetin (22.5 μM), catechin (32.5 μM), resveratrol (62.5 μM), α-tocopherol (60.0 μM), kaempferol (117 μM) and naringenin (> 250 μM). The antioxidative quercetin derivatives capacity was analysed in the research of Wiczkowski et al (2014), who proved the capability of the described compounds (quercetin aglycon, isorhamnetin, 3,4-diglucoside of quercetin, 4--glucoside of quercetin, 3-glucoside of isorhamnetin, 3-glucoside of quercetin) of DPPH radicals scavenging and ABTS cation-radicals reducing. Moreover, the same authors presented superoxide anion-radicals scavenging capacity of selected flavonoids in their photochemiluminescence assay (PCL).…”

Section: Antioxidative Activitymentioning

confidence: 99%

Quercetin – a flavonoid with a high health-promoting potential

Kulczyński¹,

Gramza‐Michałowska²,

Sidor³

2016

Nauka Przyr. Technol.

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Summary.Flavonoids are an important group of bioactive compounds with a high antioxidant potential. Among them, one of the most common components is quercetin, belonging to the flavonols group. The main sources of quercetin are: capers, chokeberries, onions, chia seeds, honey and elderberries. This flavonoid shows a number of health-promoting properties, such as lowering blood sugar level, improving blood lipid profile, lowering blood pressure, and antimicrobial and antiplatelet activity.

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Metabolites of dietary quercetin: Profile, isolation, identification, and antioxidant capacity

Cited by 33 publications

References 35 publications

Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites

Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites

An Integrated View of the Effects of Wine Polyphenols and Their Relevant Metabolites on Gut and Host Health

Quercetin – a flavonoid with a high health-promoting potential

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