Quercetin 3 o glucuronide

Manufactured by Merck Group

Sourced in United States, Germany, France

Quercetin-3-O-glucuronide is a flavonoid compound found in various plants. It is a water-soluble derivative of the flavonoid quercetin, formed by the addition of a glucuronic acid group. This compound is commonly used in research applications as a standard or reference material for analytical techniques.

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Lab products found in correlation

Epicatechin, by Merck Group (10 mentions) Quercetin 3 o glucoside, by Merck Group (9 mentions) Gallic acid, by Merck Group (9 mentions) Catechin, by Merck Group (8 mentions) Quercetin, by Merck Group (7 mentions) Caffeic acid, by Merck Group (6 mentions) Ferulic acid, by Merck Group (5 mentions) Kaempferol, by Merck Group (5 mentions) Syringic acid, by Merck Group (5 mentions) Chlorogenic acid, by Merck Group (4 mentions) Protocatechuic acid, by Merck Group (4 mentions) Formic acid, by Thermo Fisher Scientific (4 mentions) Methanol, by Thermo Fisher Scientific (4 mentions) Acetonitrile, by Thermo Fisher Scientific (4 mentions) Procyanidin b2, by Merck Group (4 mentions) E resveratrol, by Merck Group (4 mentions) E piceatannol, by Merck Group (4 mentions) Sodium carbonate, by Merck Group (4 mentions) P coumaric acid, by Merck Group (3 mentions) Myricetin, by Merck Group (3 mentions)

Spelling variants of this product

Quercetin (2803 citations) Quercetin 3-glucuronide (3 citations)

19 protocols using quercetin 3 o glucuronide

Preparation and Characterization of Grape Extract

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Food grade resveratrol was purchased from ChromaDex (Irvine, CA). GSE was purchased from supplement Warehouse (UPC: 603573579173). Only one lot of the resveratrol and one lot of the GSE were used for this particular study. Both resveratrol and GSE have been shown to be very stable when stored at 4°C in dark. Welch Concord purple grape juice was purchased at a local market and concentrated by solid phase extraction (SPE), as previously described, to produce Concord Grape Juice total polyphenol extract (Ho et al., 2009 (link)). The polyphenol profile of this juice extract was confirmed by LC-MS analysis and previously reported (Xu et al., 2011 (link)). Total polyphenol content was determined to be 62 mg of gallic acid equivalents per mL extract, with principal components including anthocyanins, PAC oligomers, phenolic acids, and quercetin glycosides. The juice extract was stored at −20°C in the dark and was diluted to the desired concentration once every 3 days. (+)-catechin, (−)-epicatechin, quercetin-3-O-glucoside, quercetin-3-O-glucuronide, and quercetin standards were purchased from Sigma Chemical Co. (St. Louis, MO). Malvidin-3-glucoside chloride and cyanidin-3-glucoside chloride were purchased from ChromaDex (Irvine, CA). All extraction and LC solvents were HPLC certified and were obtained from J.T. Baker (Phillipsburg, NJ).

Wang J., Bi W., Cheng A., Freire D., Vempati P., Zhao W., Gong B., Janle E.M., Chen T.Y., Ferruzzi M.G., Schmeidler J., Ho L, & Pasinetti G.M. (2014). Targeting multiple pathogenic mechanisms with polyphenols for the treatment of Alzheimer's disease-experimental approach and therapeutic implications. Frontiers in Aging Neuroscience, 6, 42.

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Grape Polyphenol Chemical Characterization

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Food grade resveratrol was purchased from ChromaDex (Irvine, CA). GSE was purchased from Supplement Warehouse (UPC: 603573579173). Only one lot of the resveratrol and one lot of the GSE were used for this particular study. Both resveratrol and GSE have been shown to be very stable when stored at 4 °C in the dark. Welch Concord purple grape juice was purchased at a local market. Quercetin-3-O-glucuronide was purchased from Sigma (St. Louis, MO). Malvidin-3-O-glucoside chloride, delphinidin-3-O-glucoside, and cyanidin-3-O-glucoside chloride were purchased from ChromaDex (Irvine, CA). 3′-O-methyl-epicatechin-5′-O-glucuronide was synthesized as previously described (Blount et al., 2012 (link); Wang et al., 2012 (link)). All extraction and LC solvents were HPLC certified and were obtained from J.T. Baker (Phillipsburg, NJ).

Zhao W., Wang J., Bi W., Ferruzzi M., Yemul S., Freire D., Mazzola P., Ho L., Dubner L, & Pasinetti G.M. (2015). Novel application of brain-targeting polyphenol compounds in sleep deprivation-induced cognitive dysfunction. Neurochemistry international, 89, 191-197.

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Quercetin Compound Standards Characterization

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Standards of rutin trihydrate, quercetin 3,7,3,4 tetramethylether, peltatoside (3-arabinoglucosylquercetin), quercetin, hyperoside (quercetin 3-O-galactoside), quercitrin (quercetin 3-O-rhamnoside), isorhamnetin, myricetin, peonidin 3-O-glucoside, kuromanin (cyanidin 3-O-glucoside) chloride, ideanin (cyanidin 3-O-galactoside) chloride, Quercetin 3-O-glucoside, quercetin 3,4”di-O-glucoside and proanthocyanidin dimer A2 were purchased from Indofine Chemicals Inc. (Hillsborough, NJ, USA). Quercetin 3-O-glucuronide was purchased from Sigma Aldrich (St. Louis, MO). High Performance Liquid Chromatography (HPLC) solvents (methanol, and acetonitrile) and reagents were purchased from Fisher (Norcross, GA, USA) and were of HPLC grade.

Prasain J.K., Rajbhandari R., Keeton A.B., Piazza G.A, & Barnes S. (2016). Metabolism and growth inhibitory activity of cranberry derived flavonoids in bladder cancer cells. Food & function, 7(9), 4012-4019.

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Bioactive Compound Standards for Antioxidant Analysis

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Catechin hydrate (>98%), trans-resveratrol (>99%), quercetin 3-O-glucuronide (≥95%), cyanin chloride (≥90%), ferulic acid (99%), kaempferol, p-coumaric acid, kaempferol 3-O-rutinoside (98%), myricetin, isorhamnetin and rutin (quercetin 3-O-rutinoside) hydrate (>94%) were obtained from Sigma-Aldrich (Darmstadt, Germany). Sodium carbonate anhydrous (99%), Folin–Ciocalteu reagent, and glycerol anhydrous (99%) were purchased from Penta (Praha, Czechia). Formic acid (99%), L-ascorbic acid and citric acid (≥99.5%) were from Carlo Erba (Milan, Italy). All solvents used for chromatography were of appropriate (HPLC) grade. The radical probe 2,2-diphenyl-1-picrylhydrazyl (DPPH), quercetin hydrate (97%) and caffeic acid (99%) were from Alfa Aesar (Karlsruhe, Germany). Iron chloride hexahydrate (FeCl₃ • 6H₂O) was purchased from Merck (Darmstadt, Germany). 2,4,6-Tris(2-pyridyl)-s-triazine (TPTZ) was from Fluka (Steinheim, Germany).

Geropoulou M., Yiagtzi E., Chatzimitakos T., Palaiogiannis D, & Makris D.P. (2024). Organosolv Treatment of Red Grape Pomace for Effective Recovery of Antioxidant Polyphenols and Pigments Using a Ternary Glycerol/Ethanol/Water System under Mild Acidic Conditions. Molecules, 29(3), 563.

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Comprehensive Phytochemical Analysis

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This investigation utilized analytical‐grade chemicals. Sigma‐Aldrich Corporation (Castle Hill, NSW, Australia) was the primary supplier, providing substances that included aluminum chloride hexahydrate, potassium persulfate, and the Folin–Ciocalteu's phenol reagent. Additionally, the free radical scavengers 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) and 2,4,6‐tripyridyl‐s‐triazine (TPTZ), along with 2,20‐azino‐bis‐(3‐ethylbenzothiazoline‐6‐sulfonic acid), and a suite of standard compounds such as quercetin, vanillin, and catechin, were acquired. Supplies of acetic acid, ethanol, sulfuric acid, sodium acetate, sodium carbonate, and ferric chloride hexahydrate (FeCl₃·6H₂O) were procured from Thermo Fisher Scientific (Scoresby, Melbourne, VIC, Australia). Sigma‐Aldrich (St. Louis, MO, USA) provided additional standards, which encompassed protocatechuic acid, syringic acid, chlorogenic acid, caftaric acid, caffeic acid, p‐hydroxybenzoic acid, coumaric acid, gallic acid, epicatechin gallate, catechin, kaempferol, quercetin‐3‐galactoside, kaempferol‐3‐O‐glucoside, quercetin‐3‐O‐glucuronide, and quercetin standards.

Liu H., Agar O.T., Imran A., Barrow C.J., Dunshea F.R, & Suleria H.A. (2024). LC‐ESI‐QTOF‐MS/MS characterization of phenolic compounds in Australian native passion fruits and their potential antioxidant activities. Food Science & Nutrition, 12(4), 2455-2472.

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Phytochemical Identification and Extraction

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E-Resveratrol, E-piceatannol, E-piceid, catechin, epicatechin, gallic acid, gallocatechin, astilbin, procyanidin B1, procyanidin B2, and quercetin-3-O-glucuronide were purchased from Sigma-Aldrich (St Louis, MI, USA). E-ε-viniferin, Z/E-vitisin B, ampelopsin A, E-miyabenol C, and hopeaphenol were obtained by previous extraction from grape stems (Houillé et al., 2014 (link)). Acetonitrile, methanol and formic acid were purchased from ThermoFisher Scientific (Courtaboeuf, France). Ultra-pure water was prepared with a Milli-Q water purification system (Millipore, USA).

Billet K., Houillé B., Dugé de Bernonville T., Besseau S., Oudin A., Courdavault V., Delanoue G., Guérin L., Clastre M., Giglioli-Guivarc'h N, & Lanoue A. (2018). Field-Based Metabolomics of Vitis vinifera L. Stems Provides New Insights for Genotype Discrimination and Polyphenol Metabolism Structuring. Frontiers in Plant Science, 9, 798.

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Analytical Determination of Polyphenols

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All reagents used for analytical determinations, (water, acetonitrile, methanol, formic acid and hydrochloric acid) were from VWR International (Fontenay-sous-Bois, France).
Hyperoside (purity > 98%), kaempferol-3-O-glucoside (purity > 99%), procyanidin B1 (purity ≥ 80%), procyanidin B2 (purity ≥ 90%), and catechin (purity ≥ 99%) were purchased from Extrasynthese (Genay, France); rutin (purity > 97%), quercetin-3-O-glucoside (purity ≥ 98%), quercetin-3-O-glucuronide (purity > 98%), epicatechin (purity > 90%), epicatechin-3-gallate (purity > 98%), epigallocatechin-3-gallate (purity > 95%), Gallic acid, sodium carbonate, and Folin–Ciocalteu’s reagent were from Sigma-Aldrich (St. Louis, MO, USA); caftaric acid (purity ≥ 95%) and procyanidin C1 (purity ≥ 80%) were from Phytolab GMBH & Co. (Vestenbergsgreuth, Germany); and procyanidin B3 (purity > 98%) was from Carbosynth Limited (Compton, Berkshire, UK).

Di Lorenzo C., Sangiovanni E., Fumagalli M., Colombo E., Frigerio G., Colombo F., Peres de Sousa L., Altindişli A., Restani P, & Dell’Agli M. (2016). Evaluation of the Anti-Inflammatory Activity of Raisins (Vitis vinifera L.) in Human Gastric Epithelial Cells: A Comparative Study. International Journal of Molecular Sciences, 17(7), 1156.

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Phytochemical Standard Characterization

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Gallic, 4-hydroxybenzoic, and ellagic acids, catechin, epicatechin, (E)-resveratrol, (E)-ε-viniferin, (E)-piceatannol, eriodictyol, taxifolin, quercetin, quercetin-3-O-glucoside, and quercetin-3-O-glucuronide were purchased from Sigma-Aldrich (St. Louis, MO, USA). Gallic acid and kaempferol-3-O-glucoside were acquired from Extrasynthèse (Genay, Auvergne-Rhône-Alpes, France). Isohopeaphenol and hopeaphenol were kindly given by the research group of Prof. Dr. Peter Winterhalter (Institute of Food Chemistry, Technical University Braunschweig, Lower Saxony, Germany). Light exposure was avoided when manipulating the standards.
HPLC-grade acetonitrile, formic acid, ethanol, and water were purchased from Merck (Darmstadt, Hesse, Germany). Ultrapure water was generated by a Milli-Q water purification system Millipore (Bedford, Massachusetts, USA). Potable ethanol (96%) from molasses employed for pilot-plant scale extraction was purchased from Oxiquim S.A. (Coronel, Concepción, Chile).
Hydroxypropyl beta-cyclodextrin (HP-β-CD, Kleptose^®, HP oral grade) was purchased from Roquette Frères (Lestrem, Lillers, France). Maltodextrin (MD) (dextrose equivalent 16.5–19.5) was obtained from Merck KGaA, (Darmstadt, Hesse, Germany).

Escobar-Avello D., Avendaño-Godoy J., Santos J., Lozano-Castellón J., Mardones C., von Baer D., Luengo J., Lamuela-Raventós R.M., Vallverdú-Queralt A, & Gómez-Gaete C. (2021). Encapsulation of Phenolic Compounds from a Grape Cane Pilot-Plant Extract in Hydroxypropyl Beta-Cyclodextrin and Maltodextrin by Spray Drying. Antioxidants, 10(7), 1130.

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Antioxidant Potential of Grape Phenolics

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Acetonitrile and ethanol were purchased from Thermo Fisher Scientific (Courtaboeuf, France). A Millipore Milli-Q system (Merck Millipore, Molsheim, Germany) provided ultrapure water. Gallic acid, caffeic acid, E-Resveratrol, E-piceatannol, catechin, epicatechin, gallocatechin, E-piceid, astilbin, quercetin-3-O-glucuronide, procyanidin B1 and procyanidin B2 were obtained from Sigma-Aldrich (St. Louis, MO, USA); E-ε-viniferin and quercetin-3-O-glucoside were purchased from Extrasynthèse (Genay, France) and E-miyabenol C from Ambinter (Paris, France). Pallidol and E-δ-viniferin were graciously provided by Mary-Lorène Goddard (EA-3991, Université de Haute-Alsace, Colmar, France). Z/E-vitisin B, ampelopsin A and hopeaphenol were purified from grape canes as previously described [37 (link)]. The 2,2′-Azo-bis-(2-amidinopropane) hydrochloride (ABAP), fluorescein, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS), potassium persulfate, 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,4,6-Tri(2-pyridyl)-s-triazine (TPTZ), Iron(III) chloride (FeCl₃), copper(II) chloride (CuCl₂), 2,9-Dimethyl-1,10-phenanthroline (neocuproine) and 3-(2-Pyridyl)-5,6-diphenyl-1,2,4-triazine-p,p′-disulfonic acid monosodium salt hydrate (ferrozine) were obtained from (Sigma-Aldrich, Saint-Quentin Fallavier, France).

Ferrier M., Billet K., Drouet S., Tungmunnithum D., Malinowska M.A., Marchal C., Dedet S., Giglioli-Guivarc’h N., Hano C, & Lanoue A. (2022). Identifying Major Drivers of Antioxidant Activities in Complex Polyphenol Mixtures from Grape Canes. Molecules, 27(13), 4029.

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Quantification of Polyphenol Standards

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Commercial standards of cyanidin-3-O-glucoside chloride, delphindin-3-O-glucoside chloride, malvidin-3-O-glucoside chloride, gallic acid, caffeic acid, ferulic acid, ethyl gallate, taxi Folin, chlorogenic acid, hippuric acid, 3-hydroxyhippuric acid, 4-hydroxybenzaldehyde, isovanillin, p-anisic acid, 4-hydroxyphenylacetic acid, 3-hydroxyphenylpropionic acid, 3-methoxyphenylacetic acid, isovanillic acid, homovanillic acid, 3-hydroxy-4-methoxyphenylpropionic acid, syringic acid, quercetin, myricetin, chlorogenic acid, quercetin-3-O-glucuronide, protocatechuic acid, p-coumaric acid, catechin, epicatechin, 4-methoxyquercetin, and quercetin-3-O-glucoside as well as sodium carbonate and Folin and Ciocalteu’s reagent (2N) were purchased from Sigma-Aldrich (St. Louis, MO, USA). caffeic acid glucuronide was supplied by Synthose (Concord, Ontario, Canada). LC-MS grade solvents, including methanol, water, ACN, and formic acid as well as trace metal grade concentrated nitric acid were purchased from Thermo Fisher Scientific (Waltham, MA, USA). ⁴⁵Ca was purchased from PerkinElmer (Waltham, MA, USA). EcoLite (+) scintillation cocktail was purchased from MP Biomedicals (Santa Ana, CA, USA).

Cladis D.P., Debelo H., Lachcik P.J., Ferruzzi M.G, & Weaver C.M. (2020). INCREASING DOSES OF BLUEBERRY POLYPHENOLS ALTERS COLONIC METABOLISM AND CALCIUM ABSORPTION IN OVARIECTOMIZED RATS. Molecular nutrition & food research, 64(12), e2000031.

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