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Transit and Metabolic Pathways of Quercetin in Tubular Cells: Involvement of Its Antioxidant Properties in the Kidney

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Transit and Metabolic Pathways of Quercetin in Tubular Cells: Involvement of Its Antioxidant Properties in the Kidney antioxidants Review Transit and Metabolic Pathways of Quercetin in Tubular Cells: Involvement of Its Antioxidant Properties in the Kidney Daniel Muñoz-Reyes 1,2,3 , Ana I. Morales 1,2,3,4,5,* and Marta Prieto 1,2,3,4,5 1 Toxicology Unit, University of Salamanca, 37007 Salamanca, Spain; [email protected] (D.M.-R.); [email protected] (M.P.) 2 Department of Physiology and Pharmacology, University of Salamanca, 37007 Salamanca, Spain 3 Group of Translational Research on Renal and Cardiovascular Diseases (TRECARD), 37007 Salamanca, Spain 4 Institute of Biomedical Research of Salamanca (IBSAL), 37007 Salamanca, Spain 5 National Network for Kidney Research REDINREN, RD016/0009/0025, Instituto de Salud Carlos III, 28029 Madrid, Spain * Correspondence: [email protected]; Tel.: +34-677-555-055 Abstract: Quercetin is a flavonoid with antioxidant, antiviral, antimicrobial, and anti-inflammatory properties. Therefore, it has been postulated as a molecule with great therapeutic potential. The renoprotective capacity of quercetin against various toxins that produce oxidative stress, in both in vivo and in vitro models, has been shown. However, it is not clear whether quercetin itself or any of its metabolites are responsible for the protective effects on the kidney. Although the pharmacokinetics of quercetin have been widely studied and the complexity of its transit throughout the body is well known, the metabolic processes that occur in the kidney are less known. Because of that, the objective of this review was to delve into the molecular and cellular events triggered Citation: Muñoz-Reyes, D.; Morales, by quercetin and/or its metabolites in the tubular cells, which could explain some of the protective A.I.; Prieto, M. Transit and Metabolic properties of this flavonoid against oxidative stress produced by toxin administration. Thus, the Pathways of Quercetin in Tubular following are analyzed: (1) the transit of quercetin to the kidney; (2) the uptake mechanisms of Cells: Involvement of Its Antioxidant quercetin and its metabolites from plasma to the tubular cells; (3) the metabolic processes triggered Properties in the Kidney. Antioxidants 2021, 10, 909. https://doi.org/ in those cells, which affect the accumulation of metabolites in the intracellular space; and (4) the 10.3390/antiox10060909 efflux mechanisms of these compounds and their subsequent elimination through urine. Finally, it is discussed whether those processes that are mediated in the tubular cells and that give rise to Academic Editors: Luciano Saso, different metabolites are related to the antioxidant and renoprotective properties observed after the Ryszard Amarowicz and administration of quercetin. Jasmina Dimitri´cMarkovi´c Keywords: quercetin conjugates; renal intake; kidney metabolism; renal efflux; antioxidant; renoprotection Received: 18 May 2021 Accepted: 1 June 2021 Published: 3 June 2021 1. Introduction Publisher’s Note: MDPI stays neutral Quercetin is a flavonoid present in the diet in high proportions. Its main sources are with regard to jurisdictional claims in fruits, vegetables, and teas [1]. High concentrations of this flavonoid have been described published maps and institutional affil- in kale, onions, berries, apples, red grapes, black tea, etc. Incorporation of quercetin in iations. different commercial food supplements is also common [2]. From a chemical point of view, the nomenclature for quercetin is 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4- one. It is a flavonol with a hydroxyl group in position 3, typical of flavonoids, and four additional hydroxyl groups, in positions 5, 7, 30, and 40 (Table1)[3]. Copyright: © 2021 by the authors. In nature, quercetin can be found free as quercetin aglycone or conjugated as a Licensee MDPI, Basel, Switzerland. quercetin derivative, the latter being the predominant form. Among the most abundant This article is an open access article quercetin derivatives in the diet are quercetin glycosides and ethers, while prenylated, distributed under the terms and sulfated, and glucuronide derivatives are found in smaller proportions (Table1)[ 4]. The conditions of the Creative Commons Attribution (CC BY) license (https:// presence of different groups attached to quercetin changes the biochemical activity and creativecommons.org/licenses/by/ bioavailability of the molecules when compared to aglycone [5]. Quercetin can also be 4.0/). Antioxidants 2021, 10, 909. https://doi.org/10.3390/antiox10060909 https://www.mdpi.com/journal/antioxidants Antioxidants 2021, 10, x FOR PEER REVIEW 2 of 16 Antioxidants 2021, 10, 909 presence of different groups attached to quercetin changes the biochemical2 of 16 activity and bioavailability of the molecules when compared to aglycone [5]. Quercetin can also be found as dihydroquercetin (taxifolin) in nature, the reduced form of quercetin, which has found as dihydroquercetintwo stereocenters (taxifolin) on the C in ring, nature, as theopposed reduced to form quercetin, of quercetin, which which has none has (Table 1) [6]. two stereocenters on the C ring, as opposed to quercetin, which has none (Table1)[6]. Table 1. Main derivatives and metabolites of quercetin. Table 1. Main derivatives and metabolites of quercetin. Radicals Radicals QuercetinQuercetin Derivatives Derivatives R1R1 R2R2 R3R3 R4R4 R5 R6R5 R7R6 R8 R7 R8 AglyconeAglycone QuercetinQuercetin OHOH HH OHOH OHOH HOH OHH H OH H 1 ReducedReduced aglycone aglycone Dihydroquercetin Dihydroquercetin (taxifolin) (taxifolin) (OH)(OH)1 HH OHOH OHOH HOH OHH H OH H QuercetinQuercetin 3-O-rhamnoside 3-O-rhamnoside (quercitrin) O-Rham2 H OH OH OH H OH H O-Rham2 H OH OH OH H OH H Quercetin 7-O-rhamnoside(quercitrin) (Vincetoxicoside B) OH H OH OH OH H O-Rham H Glycosides QuercetinQuercetin 3-O-rhamnoglucoside 7-O-rhamnoside (rutin) O-RG3 H OH OH OH H OH H OH H OH OH OH H O-Rham H Quercetin 3-O-glucoside(Vincetoxicoside (isoquercetin) B) O-Gls4 H OH OH OH H OH H QuercetinQuercetin 3-O-galactoside 3-O- (hyperoside)rhamnoglu- O-Gal5 H OH OH OH H OH H Glycosides O-RG3 H OH OH OH H OH H Quercetin 30-methylethercoside (isorhamnetin)(rutin) OH H OH O-Met6 OH H OH H Quercetin0 3-O-glucoside Ethers Quercetin 4 -methylether (tamarixetin)O OH-Gls4 HH O-MetOH OH OH HOH OHH H OH H Quercetin 7-methylether(isoquercetin) (rhamnetin) OH H OH OH OH H O-Met H Quercetin 3-O-galactoside 8-prenylquercetinO OH-Gal5 HH OHOH OH OH HOH OH H Pren7 OH H Prenylated (hyperoside) 6,50-di-C-prenylquercetin OH H OH Pren OH Pren OH H Quercetin0 03′-methylether -8 - - 6 - Quercetin 3,7,3 ,4 -tetrasulfate OSOOH3 HH OSO3 OHOSO 3 O-OHMet HOH OSO3 H H OH H (isorhamnetin) Quercetin 3-O-sulfate OSO - H OH OH OH H OH H Quercetin 4′-methylether 3 Ethers Quercetin 30-O-sulfate OHOH HH OHO-Met OSO - OH HOH OHH H OH H Sulfated (tamarixetin) 3 Quercetin 40-O-sulfate OH H OSO - OH OH H OH H Quercetin 7-methylether 3 OH H OH OH OH - H O-Met H Quercetin(rhamnetin) 7-O-sulfate OH H OH OH OH H OSO3 H 9 Quercetin8-prenylquerce 3-O-glucuronidetin O-GlcOH HH OHOH OHOH HOH OHH H OH Pren7 Prenylated 0 Quercetin6,5′-di 3-C-O-glucuronide-prenylquercetin OHOH HH OHOH O-Glc Pren OH HOH OHPren H OH H 0 Glucuronides QuercetinQuercetin 4 -O-glucuronide 3,7,3′,4′-tetrasul- OH H O-Glc OH OH H OH H OSO3-8 H OSO3- OSO3- OH H OSO3- H Quercetin 7-O-glucuronidefate OH H OH OH OH H O-Glc H QuercetinQuercetin diglucuronide 3-O-sulfate O-GlcOSO3- HH OHOH OHOH HOH O-GlcH H OH H 1 Sulfated 2 3 4 5 6 7 () indicates stereocenter; Rham:Quercetin rhamnose; 3′-ORG:-sulfate rhamnosylglucose; OHGls: glucose;H Gal: galactoside;OH OSOMet: methyl;3- OHPren: 3-methyl-2-H OH H buten-1-il; 8 OSO3-: sulfate; 9 Glc: glucuronide acid. Quercetin 4′-O-sulfate OH H OSO3- OH OH H OH H - QuercetinQuercetin 7-O-sulfate glycosides areOH derivatives H of theOH flavonoid whereOH oneOH or more hydroxylH OSO3 H 9 Quercetingroups have3-O-glucuronide been replaced byO- differentGlc typesH of sugars,OH suchOH as glucose, OH rhamnose, H or ruti-OH H Quercetinnose. The 3′-O main-glucuronide glycosylated formsOH of quercetinH areOH O-glucosides, O-Glc which OH are formedH from an OH H Glucuronides QuercetinO-glycosidic 4′-O-glucuronide bond between theOH hydroxyl groupH inO position-Glc 3 ofOH quercetin (TableOH 1) andH the dif-OH H Quercetinferent carbohydrates. 7-O-glucuronide The presenceOH of theH carbohydrate OH increasesOH the solubilityOH of quercetin.H O-Glc H QuercetinMore than diglucuronide 20 quercetin glycosidesO-Glc haveH been described;OH amongOH theOH most commonH areO-Glc H 1 () indicates stereocenter;quercetin 2 3-O-glucosideRham: rhamnose; present 3 RG: in peasrhamnosylglucose; or sage, and quercetin 4 Gls: glucose; 3-O-rhamnoglycoside 5 Gal: galactoside; (rutin) 6 Met: methyl; 7 Pren: 3-methyl-2-butenin cherries,-1-il; 8 spinach,OSO3-: sulfate; or grapes 9 Glc: [7 ].glucuronide acid. Quercetin ethers are formed between a hydroxyl group on aglycone and an alcohol group on anotherQuercetin molecule. glycosides These derivatives are derivatives are very of abundant, the flavonoid and contain where sugarsone or more hydroxyl groups have been replaced by different types of sugars, such as glucose, rhamnose, or rutinose. The main glycosylated forms of quercetin are O-glucosides, which are formed Antioxidants 2021, 10, 909 3 of 16 present in great abundance in nature as substituents. Among the most common quercetin monoethers are isorhamnetin (3’-methyl ether) or tamarixetin (4’-methyl ether), present in onions and honey [8,9]. Prenylated quercetin derivatives are less common than the glycosylated and ether derivates in natural sources. Structurally, in C-prenylflavonols, the prenyl groups are attached to the carbon atom of the flavonol backbone [10]. The addition of a prenyl group increases the hydrophobicity of aglycone and enhances the biological function of quercetin [11].
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