Naringenin

Manufactured by Thermo Fisher Scientific

Sourced in United Kingdom

Naringenin is a natural flavonoid compound found in various citrus fruits. It is a white to pale yellow crystalline solid. Naringenin serves as a reference standard for analytical and research applications in laboratories.

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Lab products found in correlation

7 protocols using naringenin

Comprehensive Wine Polyphenol Analysis

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All standards and reagents were LC-MS grade and were used without any further treatments. Authentic standards of 2,5-Dihydroxybenzoic acid (gentisic acid), 3,4-dihydroxybenzoic acid (protocatechuic acid), 4-hydroxybenzoic acid, cinnamic acid, epicatechin, eriodictyol, ferulic acid, gallic acid, myricetin, p-coumaric acid, pinoresinol, quercetin, resveratrol, rosmarinic acid, salicylic acid, syringic acid, taxifolin, and vanillic acid were purchased from Sigma-Aldrich (Stenheim, Germany). Apigenin, caffeic acid, catechin, ethyl vanillin (internal standard, IS), galangin, genistein, naringenin, tyrosol, and vanillin were acquired from Alfa Aesar (Karlsruche, Germany), whereas hydroxytyrosol and luteolin were obtained from Santa Cruz Biotechnology (Santa Cruz, CA, USA).
2-Propanol (LC–MS grade) and methanol (MeOH) (LC–MS grade) were purchased from Fisher Scientific (Geel, Belgium) and Merck (Darmstadt, Germany), respectively. Formic acid 99%, ammonium acetate and sodium hydroxide monohydrate for trace analysis ≥ 99.9995% were all obtained from Fluka (Buchs, Switzerland). Ultrapure water (18.2 MΩ resistivity) was provided by a Millipore Direct-Q UV purification System (Millipore, Bedford, MA, USA). The wine samples were filtered using regenerated cellulose syringe filters (RC filters, pore size 0.2 μm, diameter 15 mm) purchased from Phenomenex (Torrance, CA, USA).

Tzachristas A., Dasenaki M.E., Aalizadeh R., Thomaidis N.S, & Proestos C. (2021). Development of a Wine Metabolomics Approach for the Authenticity Assessment of Selected Greek Red Wines. Molecules, 26(10), 2837.

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Formulation and Characterization of Quercetin-Cyclodextrin Complexes

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Quercetin (Que, MW: 302.24 g/mol), Methyl-β-cyclodextrin (Me-β-CD, MW: 1310 g/mol) and Hydroxypropyl-β-cyclodextrin (HP-β-CD, MW: 1460 g/mol) were purchased from Sigma-Aldrich (St. Louis, MO, USA), Fluka Chemika (Buchs, Switzerland) and Ashland (Covington, KY, USA), respectively. Naringenin was supplied from Alfa Aesar (Ward Hill, MA, USA). Mannitol (Ph. Eur.) was obtained from Lisapharma S.p.A. (Erba (CO), Italy), and soybean lecithin (Lipoid^® S45) was obtained from Lipoid AG (Steinhausen, Switzerland). Potassium dihydrogen phosphate and sodium acetate were acquired from Merck KGaA (Darmstadt, Germany), while sodium hydroxide (1 mol/L) was acquired from Chem-Lab NV (Zedelgem, Belgium). Glacial acetic acid was purchased from PanReac AppliChem (Chicago, IL, USA). sodium acetate buffer solution (pH 5.0) was prepared using sodium acetate and Glacial acetic acid in HPLC-grade water. The β-glucuronidase enzyme solution (3000 units/mL) was freshly prepared using the sodium acetate buffer. HPLC-grade solvents (water, methanol, acetonitrile) and reagents were obtained from Fischer Scientific (Pittsburgh, PA, USA). Triple-deionized water purchased from Fischer Scientific was used for all preparations.

Manta K., Papakyriakopoulou P., Nikolidaki A., Balafas E., Kostomitsopoulos N., Banella S., Colombo G, & Valsami G. (2023). Comparative Serum and Brain Pharmacokinetics of Quercetin after Oral and Nasal Administration to Rats as Lyophilized Complexes with β-Cyclodextrin Derivatives and Their Blends with Mannitol/Lecithin Microparticles. Pharmaceutics, 15(8), 2036.

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Standardized Reagents for Spectrophotometric Assays

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Folin–Ciocalteu’s phenol reagent, ferric chloride hexahydrate (FeCl₃·6H₂O), ferrous sulfate heptahydrate (FeSO₄·7H₂O), and hydrogen chloride (hydrochloric acid ≥ 37% w/w) were purchased from Chem-Lab NV (Zedelgem, Belgium). Sodium carbonate was obtained from Carlo Erba Reagents (Cornaredo, Italy), and absolute ethanol and acetic acid from Merck KgaA (Darmstadt, Germany). Gallic acid (3,4,5-trihydroxybenzoic acid), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid ammonium salt) (ABTS non radical form) and 2,4,6-tris(2-pyridyl)-s-triazine (TPTZ) were bought from Alfa Aesar (Karlsruhe, Germany), while Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) and potassium persulfate were supplied from Sigma-Aldrich (St. Louis, MO, USA). Standard phenolic compound of chlorogenic acid (≥99%) was purchased from Extrasynthese (Genay, France), and naringenin (97%) and 4-chloro-4’-hydroxybenzophenone (97%) were from Alfa Aesar (Karlsruhe, Germany). Formic acid was bought from LGC Standards (Wesel, Germany). All reagents used for the spectrophotometric assays were of analytical grade (≥94%). Solvents used for all experimental analyses were of LC-MS grade and were purchased from Sigma Aldrich Co. (Gillingham, United Kingdom), Carlo Erba Reagents (Val de Reuil, France), Chem-Lab NV (Zedelgem, Belgium), Fischer-Scientific (Loughborough, UK), and Merck KGaA (Darmstadt, Germany).

Tsiaka T., Lantzouraki D.Z., Polychronaki G., Sotiroudis G., Kritsi E., Sinanoglou V.J., Kalogianni D.P, & Zoumpoulakis P. (2023). Optimization of Ultrasound- and Microwave-Assisted Extraction for the Determination of Phenolic Compounds in Peach Byproducts Using Experimental Design and Liquid Chromatography–Tandem Mass Spectrometry. Molecules, 28(2), 518.

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Tannin Extraction from Diverse Plants

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Arbutin, luteolin and taxifolin were purchased from Apin Chemicals Ltd (Abingdon, U.K.); vanillic acid and naringenin from Alfa Aesar (Blackpool, U.K.); gallocatechin and quercetin from Sigma–Aldrich (Gillingham, U.K.); phosphate buffered saline (PBS) from bioMerieux (Lyon, France), Milton solution, sodium hypochlorite 2% w/v and sodium chloride 16.5% w/v from Milton (Inibsa laboratorios, Barcelona, Spain). Goat willow (Salix caprea), black currant (Ribes nigrum) and red currant (Ribes rubrum) leaves were collected in July and August 2012. Tilia (Linden) flowers (Tilia × europaea) were purchased from Flos (Mokrsko, Poland). These plant samples were chosen as they allowed the testing of different tannin types, all of which are known to occur in willow.

Klongsiriwet C., Quijada J., Williams A.R., Mueller-Harvey I., Williamson E.M, & Hoste H. (2015). Synergistic inhibition of Haemonchus contortus exsheathment by flavonoid monomers and condensed tannins. International Journal for Parasitology: Drugs and Drug Resistance, 5(3), 127-134.

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Phytochemical Characterization of Blackthorn Flowers

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Hydrochloric acid (37%, AR grade), butan-1-ol, acetic acid glacial (AR grade), acetone (AR grade), acetonitrile (HPLC grade), dichloromethane (LR grade), hexane (GLC, pesticide residue grade) and methanol (HPLC grade) were obtained from ThermoFisher Scientific (Loughborough, UK); benzyl mercaptan (99%), catechin hydrate (≥98%), epicatechin (90%), epi gallocatechin (95%), gallocatechin (≥97%), catechin gallate (≥98%), epicatechin gallate (≥98%), epi gallocatechin gallate (≥95%), gallocatechin gallate (≥98%), quercetin (≥99%), isoquercitrin (≥90%), rutin hydrate (≥95%), naringin (≥95%), (±)-eriodictyol (≥90%) from Sigma-Aldrich (Poole, UK); naringenin (97%) from Alfa Aesar (Lancashire, UK); (±)-taxifolin (98%) from Apin Chemicals (Abingdon, UK); procyanidin A2 (PC A2, ≥99%) and naringenin-7-O-glucoside ( ≥99%) from Extrasynthese (Genay Cedex, France); afzelechin (96-98%) from Plantech UK (Reading, UK) and Sephadex LH-20 from GE Healthcare (Little Chalfont, UK). 1). Details of other samples are in Table A1 and Appendix A.1.1. Plant materials were purchased in 2012/2013 and ground to pass a 1 mm sieve (impeller SM1 cutting mill, Retsch, Haan, Germany). Leaves and stalks were removed from blackthorn flowers and only flowers were used.

Ropiak H.M., Ramsay A, & Mueller-Harvey I. (2016). Condensed tannins in extracts from European medicinal plants and herbal products. Journal of pharmaceutical and biomedical analysis, 121.

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Screening of Carboxylesterase Inhibitors

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The recombinant purified CES2 and CES1 enzymes, and 4-NPA were purchased from Sigma-Aldrich with product IDs E0412, E0162, and N8130, respectively. Hesperetin, naringenin, and 2’, 4’-dihydroxychalcone were purchased form Fisher Scientific (>95% purity). All compounds were dissolved in DMSO at 10mM. In the screening assay, the compounds were diluted in 50mM HEPES and the final compound concentration in the reaction system was adjusted to 50μM. In the IC50 determination assay, selected compounds were diluted in 50mM HEPES to obtain ten final concentrations from 300μM to 0.005μM with 3 fold decrement. The assays were conducted at 300μl total volume in 96-well plates. Reactions consisted of the following: 100μL 50mM HEPES with 20 units of enzyme, 10μL compound solution (various concentrations), 2μL 300mM 4-NAP, and 188μL 50mM HEPES, pH 7.4. The compound and 4-NAP solution were added into the plate first and then the reaction was initiated by the addition of enzyme solution. After 15 minutes incubation at 25°C, absorbance was measured using a microplate reader at 405nm in FLUOstar Omega Microplate Reader. The CES1/CES2 inhibitor compound bis-(4-nitrophenyl) phosphate (BNPP) was used as positive control in all the assays.

Yu Y., Kong R., Cao H., Yin Z., Liu J., Nan X., Phan A.T., Ding T., Zhao H, & Wong S.T. (2018). Two birds, one stone: hesperetin alleviates chemotherapy-induced diarrhea and potentiates tumor inhibition. Oncotarget, 9(46), 27958-27973.

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Purification and Characterization of Flavonoids

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All chemicals were used as purchased without further purification. (-)-Epicatechin (EC), (-)-Epicatechin gallate (ECG), quercetin (QT), 3-hydroxyflavone (3-HF), hesperetin, ACES, tricine, and bathocuproine disulfonic acid disodium salt (BCS) were obtained from Sigma-Aldrich (St. Louis, MO). Catechin (Cat), luteolin (Lut), (-)-epigallocatechin (EGC), and biochanin A were purchased from VWR (Radnor, PA). (-)-Epigallocatechin gallate (EGCG), chrysin, naringenin, naringin, hesperidin, rutin, kaempferol, cyanidin, genistein, hematoxylin, coumarin-3-carboxylic acid (CCA), ascorbic acid, ethylenediaminetetraacetic acid (EDTA), tris(hydroxymethyl-d₃)amino-d₂-methane (deuterated Tris, Tris-d₁₁), MOPS, BisTris, and all solvents were obtained from Fisher Scientific (Waltham, MA).

Lee V.J, & Heffern M.C. (2022). Structure-activity assessment of flavonoids as modulators of copper transport. Frontiers in Chemistry, 10, 972198.

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