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14 protocols using hesperetin

1

Flavonoid Extraction and Analysis

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All of the solvents used for the solid phase extraction and HPLC-DAD analysis were LC-MS (liquid chromatography-mass spectroscopy) grade from Sigma-Aldrich (Madrid, Spain) or VWR Chemicals (Barcelona, Spain). Naringenin, eriodictyol, hesperetin, and homoeriodictyol were provided by Extrasynthese (Genay, France), while l-tyrosine (dissolved in distilled water and filtered using 0.2 μm nylon filters, VWR, Barcelona, Spain) was provided by Sigma-Aldrich (Madrid, Spain). PCRBIO Ladder II (Sursee, Switzerland) was used in the agarose gels for the PCR experiments.
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2

Citrus Flavonoid Quantification Protocol

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Dulbecco’s modified eagle medium (DMEM), phosphate buffered saline (PBS) pH 7.4, and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) were purchased from VWR (Milan, Italy). Nimesulide, trolox, 2′,7′-dichlorofluorescin diacetate (DCF-DA), and lucifer yellow (LY) CH dilithium salt were purchased from Merck KGaA (Darmstadt, Germany). HPLC-grade standards (purity ≥ 98%) of eriocitrin (ERI), neoeriocitrin (NER), hesperidin (HED), neohesperidin (NHE), and hesperetin (HET) were purchased from Extrasynthese (Genay, France).
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3

Intestinal Epithelium Differentiation Protocol

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MEM with Earle's salts, DMEM, fetal bovine serum (FBS), trypsin‐EDTA, and antibiotics were purchased from Biochrom GmbH (Berlin, Germany). Entero‐STIM Intestinal Epithelium Differentiation Medium and MITO+ Serum Extender were purchased from Corning (Wiesbaden, Germany). Hesperetin, peltatoside, hyperoside, kaempferol, ellagic acid, isoquercitrin, quercitrin, phloretin, (−)‐epicatechin, epigallocatechin, epicatechin gallate, procyanidin B1, procyanidin B2, epigallocatechin gallate, gallocatechin, and morine were obtained from Extrasynthese (Genay Cedex, France). Phloridzin, chlorogenic acid, caffeic acid, quercetin, (+)‐catechin, gallic acid, 2‐mercaptoethanol, NaCl, MgSO4, KCl, CaCl2, HEPES, and xylitol were purchased from Sigma‐Aldrich (Schnelldorf, Germany). Guaijaverin and avicularin were obtained from Glentham Life Sciences (Corsham, United Kingdom). Purified and concentrated GLE (cGLE) was provided by Belan GmbH (Wels, Austria).30 Guava fruit puree for preparation of fruit extracts was obtained from Tradework BV (Rotterdam, The Netherlands), commercially available GLE and apple extract (AE) were purchased from Pfannenschmidt (Hamburg, Germany). Transwell inserts (12 mm, collagen‐treated, 0.4 μm pore size) and 12‐well plates were obtained from Corning (Wiesbaden, Germany).
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4

Modulation of IL-2 Production in Activated T Cells

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In total, 1 × 105 clone 1C116 or 2C21 cells, were cultured with each material (concentration ranges are described below) or vehicle control (dimethyl sulfoxide: DMSO) and 20 ng/mL PMA in 96-well U-bottom tissue culture plates in 200 μL of CCM for 24 h. The materials were 0–100 μg/mL flavonoids (quercetin, isoquercitrin, hyperoside, galangin, kaempferol, morin, myricetin, hesperetin, hesperidin, acacetin, linarin, isorhoifolin, (all purchased from Extrasynthese, Lyon, France)), 0–1000 μM IPP (Sigma-Aldrich), 0–2000 μM risedronate, 0–33.5 μM methylamine (Sigma-Aldrich), 0–33.5 μM ethylamine (Sigma-Aldrich) and 1 μg/mL purified anti-human CD3 mAb (OKT3: Thermo Fisher Scientific). After the incubation, the culture supernatant was corrected, and the concentration of IL-2 was analyzed using an ELISA kit (BD Biosciense).
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5

Flavonoid Extraction and Analysis

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All solvents used for solid-phase extraction and HPLC-DAD analysis were LC-MS grade from either Sigma-Aldrich (Madrid, Spain) or VWR Chemicals (Barcelona, Spain). Luteolin, diosmetin, chrysoeriol, eriodictyol, hesperetin, homoeriodictyol, and homohesperetin were provided by Extrasynthese (Genay, France).
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6

Phenolic Compound Analysis by HPLC

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Acetonitrile (99.9%) was of high-performance liquid chromatography (HPLC) grade from Fisher Scientific (Lisbon, Portugal). Phenolic compound standards (caffeic acid, ferulic acid, hesperetin, naringenin, quercetin-3-O-glucoside and quercetin-3-O-rutinoside) were from Extrasynthèse (Genay, France). Formic acid was purchased from Sigma-Aldrich (St. Louis, MO, USA). All other general laboratory reagents were from Panreac Química S.L.U. (Barcelona, Spain). Water was treated in a Milli-Q water purification system (TGI Pure Water Systems, Greenville, SC, USA).
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7

Characterizing Bioactive Phenolic Compounds

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Acetonitrile 99.9% was of HPLC grade from Fisher Scientific (Lisbon, Portugal). Phenolic compound standards (caffeic acid ≥ 99%, p-coumaric acid ≥ 90%; hesperetin ≥ 99%, luteolin-7-O-glucoside ≥ 99%, quercetin-3-O-glucoside ≥ 99%, rosmarinic acid ≥ 99% HPLC purity) were from Extrasynthese (Genay, France). Trypan blue, lipopolysaccharide (LPS), dexamethasone, acetic acid, formic acid, ellipticine, sulforhodamine B (SRB), trichloroacetic acid (TCA) and Tris were all purchased from Sigma-Aldrich (St. Louis, MO, USA). Dulbecco’s modified Eagle’s medium was purchased from HyClone. RAW264.7 cells were acquired from ECACC (‘‘European Collection of Animal Cell Culture”) (Salisburg, UK), Griess reagent system kit was purchased from Promega, Fetal bovine serum (FBS), L-glutamine, Hank’s balanced salt solution (HBSS), trypsin-EDTA (ethylenediaminetetraacetic acid), penicillin/streptomycin solution (100 U/mL and 100 mg/mL, respectively), RPMI-1640 and DMEM media were from Hyclone (Logan, UT, USA). Water was treated in Milli-Q water purification system (TGI Pure Water Systems, Greenville, SC, USA).
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8

Synthesis and Purification of Flavonoids

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Sterubin was synthesized by Kanto Chemical (Tokyo, Japan). Luteolin was purchased from LKT Laboratories (St. Paul, MN). HGK was purchased from PhytoLab (Vestenbergsgreuth, Germany). Eriodictyol, homoEriodictyol, hesperetin, and diosmetin were purchased from Extrasynthese (Lyon, France).
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9

Phytochemical Characterization and Antioxidant Evaluation

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All the solvents and chemicals used in this study were analytical grade. Methanol, ethanol, acetonitrile LC-MS grade, formic acid LC-MS grade, 85% phosphoric acid, and water LC-MS grade were purchased from Merck® (Darmstadt, Germany). Gallic acid, quinic acid, caffeic acid, ferulic acid, protocatechuic acid, neochlorogenic acid (3-O-caffeoylquinic acid), chlorogenic acid (5-O-caffeoylquinic acid), cynarin (1,3-dicaffeoylquinic acid), isochlorogenic acid, kaempferol-3-O-glucoside, quercetin-3-O-glucoside, ferrous sulfate, 1,1-diphenyl-2-picrylhydrazyl radical (DPPH), (±)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), 2,4,6-tris(2-pyridyl) -1,3,5-triazine (TPTZ), 2,2′-azino-bis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS), Folin–Ciocalteu reagent, sodium carbonate, ferric chloride, AlCl3, NaNO2, and CuSO4∙5H2O were purchased from Merck®, Sigma-Aldrich®, or Fluka™ (Milan, Italy). Flavonoid standards of apigenin, apigenin-7-O-glucoside, hesperidin, hesperetin, luteolin-7-O-glucoside, naringin, and naringenin were purchased from Extrasynthese (Genay, France). Ultrapure water (18 MΩ·cm) was obtained with a Milli-Q Advantage A10 System apparatus (Millipore, Milan, Italy).
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10

Quantification of Phenolic Compounds

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Standards of phenolics, including kaempferol, catechin, chrysin, hesperetin, isorhamentin, naringenin, and phenolic acids (gallic, chlorogenic, ellagic, gentisic, homogentisic, pcoumaric, protocatechuic, sinapic) were purchased from Extrasynthese (Genay, France). Methyl syringate, caffeic, ferulic, syringic, and vanillic acids were purchased from Sigma-Aldrich (Steinheim, Germany). The purities of the standards were 98-99%. The chemical structures are shown in Table S1. All solutions were prepared by dissolving the abovementioned phenolic compounds in MS-grade acetonitrile (0.01 mg/mL) (Sigma-Aldrich Merck KGaA, Darmstadt, Germany).
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