Coumestrol

Manufactured by Merck Group

Sourced in United States

Coumestrol is a laboratory equipment product manufactured by Merck Group. It is a phytoestrogen compound that can be used as a standard reference material in various analytical applications.

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Lab products found in correlation

Genistein, by Merck Group (6 mentions) Daidzein, by Merck Group (5 mentions) Formononetin, by Merck Group (5 mentions) Methanol, by Merck Group (3 mentions) Quercetin, by Merck Group (3 mentions) Rutin, by Merck Group (3 mentions) Naringenin, by Merck Group (3 mentions) Luteolin, by Merck Group (2 mentions) Kaempferol, by Merck Group (2 mentions) Daidzin, by Merck Group (2 mentions) Genistin, by Merck Group (2 mentions) Biochanin a, by Merck Group (2 mentions) Formic acid, by Merck Group (2 mentions) Dimethyl sulfoxide (dmso), by Merck Group (2 mentions) Reduced nicotinamide adenine dinucleotide phosphate, by Merck Group (1 mentions) Phosphate buffered saline (pbs), by Thermo Fisher Scientific (1 mentions) Dimethyl sulfoxide (dmso), by Thermo Fisher Scientific (1 mentions) Sodium chloride (nacl), by Merck Group (1 mentions) Rat serum, by Merck Group (1 mentions) Sealing tape, by Thermo Fisher Scientific (1 mentions)

17 protocols using coumestrol

Rat Liver Metabolism Assay

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Diethylstilbestrol (DES, CAS 56-53-1), 17α-ethinylestradiol (EE2, CAS 57-63-6), genistein (GEN, CAS 446-72-0), coumestrol (COU, CAS 479-13-0), methoxychlor (MXC, CAS 72-43-5), reduced nicotinamide adenine dinucleotide phosphate (NADPH), uridine 5ʹ-diphosphoglucurnic acid (UDPGA), adenosine 3ʹ-phosphate 5ʹ-phosphosulfate (PAPS), lithium salt hydrate, acetyl coenzyme A (acetyl CoA) sodium salt, alamethicin, magnesium chloride, sodium phosphate, sodium chloride, and rat serum were purchased from Sigma-Aldrich (Zwijndrecht, the Netherlands). Dimethyl sulfoxide (DMSO) was purchased from Acros Organics (Geel, Belgium) and phosphate-buffered saline was purchased from Invitrogen (Breda, the Netherlands). Pooled liver S9 fractions from male and female Sprague-Dawley rats were obtained from Tebu-bio (Heerhugowaard, the Netherlands). Rapid equilibrium dialysis (RED) devices, including RED inserts, RED base plate and sealing tape, were purchased from Fisher (Landsmeer, the Netherlands).

Zhang M., van Ravenzwaay B, & Rietjens I.M. (2019). Development of a Generic Physiologically Based Kinetic Model to Predict In Vivo Uterotrophic Responses Induced by Estrogenic Chemicals in Rats Based on In Vitro Bioassays. Toxicological Sciences, 173(1), 19-31.

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Analytical Standards for Chromatographic Analysis

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Ultra-pure water (18 mΩ) was obtained from a Milli-Q water purification system (Millipore Co., Ltd., Milford, MA, USA). High-performance liquid chromatography (HPLC)-grade methanol, acetic acid, and 56 analytical standards, including catechinic, scopolin, chlorogenic acid, epicatechinic, vanillic acid, caffeic acid, purerarin, syringic acid, daidzin, glycitin, scopoletin, eriocitrin, umbelliferone, p-coumaric acid, dihydro quercetin, sinapic acid, genistin, liquiritin, ferulic acid, salicylic acid, rutin, isoferulic acid, m-coumaric acid, naringin, hesperidin, resveratrol, xanthotoxol, silydianin, sinapyl alcohol, o-coumaric acid, liquiritigenin, kaempferol, 2’-hydroxygenistein, eriodictyol, daidzein, psoralen, glycitein, quercetin, didymin, bergaptol, naringenin, luteolin, cinnamic_acid, hesperetin, genistein, bergapten, diosmetin, isoliquiritigenin, coumestrol, sinensetin, formononetin, medicarpin, imperatorin, biochanin A, tangeretin, and rotenone (displayed in Table S2), were purchased from Sigma-Aldrich Co., Ltd. The stock solutions of these authentic standards were 10.0 mg of each standard dissolved in 10 mL methanol. Then, the stock solutions were diluted to various concentrations before analysis. All stock solutions were sealed with Parafilm^® and stored in a −20 °C freezer.

Dou X., Zhang L., Wang X., Yang R., Wang X., Ma F., Yu L., Mao J., Li H., Wang X, & Li P. (2020). Identification and Validation of Metabolic Markers for Adulteration Detection of Edible Oils Using Metabolic Networks. Metabolites, 10(3), 85.

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Characterization of hMAO Isozymes

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Human monoamine oxidase (hMAO) isozymes, robinin, rutin, nicotiflorin, daidzin, genistin, coumestrol, daidzein, genistein, curcumin, amyloid β peptide 25–35 (Aβ_25–35), hexafluoroisopropanol (HFIP), and selegiline hydrochloride were purchased from Sigma-Aldrich (St. Louis, MO, USA). All solvents used for high pressure liquid chromatography coupled to quadrupole time-of-flight mass spectrometry (HPLC–Q-TOF–MS) were liquid chromatography–mass spectrometry grade and purchased from Merck (Darmstadt, Germany).

Seong S.H., Kim B.R., Cho M.L., Kim T.S., Im S., Han S., Jeong J.W., Jung H.A, & Choi J.S. (2022). Phytoestrogen Coumestrol Selectively Inhibits Monoamine Oxidase-A and Amyloid β Self-Aggregation. Nutrients, 14(18), 3822.

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Competitive Fluorometric Binding Assay for ER

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Relative binding affinities were determined by a competitive fluorometric binding assay as previously described. Briefly, 40 nM fluorescence tracer (coumestrol, Sigma-Aldrich, MO) and 0.8 μM purified human ERα or ERβ ligand binding domain (LBD) were diluted in 100 mM potassium phosphate buffer (pH 7.4), containing 100 μg/mL bovine gamma globulin (Sigma-Aldrich, MO). Incubations were for 2h at room temperature (25 °C). Fluorescence polarization values were then measured. The binding affinities are expressed as relative binding affinity (RBA) values with the RBA of 17-β estradiol set to 100%. The values given are the average ± range of two independent determinations. IC₅₀ values were calculated according to equations described previously.^{[50 (link)]}

Zhang S., Wang Z., Hu Z., Li C., Tang C., Carlson K.E., Luo J., Dong C., Katzenellenbogen J.A., Huang J, & Zhou H.B. (2017). Selenophenes: Introducing a New Element into the Core of Non-Steroidal Estrogen Receptor Ligands. ChemMedChem, 12(3), 235-249.

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Cell Culture and Reagent Sourcing

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Coumestrol and anti-β-actin were obtained from Sigma-Aldrich. McCoy’s 5A, DMEM and RPMI 1640 medium were purchased from Thermo Fisher Scientific (Carlsbad, CA, USA)). Basal Medium Eagle (BME), gentamicin, penicillin/streptomycin, and L-glutamine were purchased from Invitrogen (Carlsbad, CA, USA). [γ-32P]-ATP and the chemiluminescence detection kit were obtained from Amersham Pharmacia Biotech (Piscataway, NJ, USA). CNBr-Sepharose 4B beads were purchased from GE Healthcare (Pittsburgh, PA, USA). The MTS solution was purchased from Promega (Madison, WI, USA). Antibodies against phospho-histone H3 (Thr-3), histone H3 and haspin were obtained from Cell Signaling Technology (Danvers, MA, USA).

Kim J.E., Lee S.Y., Jang M., Choi H.K., Kim J.H., Chen H., Lim T.G., Dong Z, & Lee K.W. (2017). Coumestrol Epigenetically Suppresses Cancer Cell Proliferation: Coumestrol Is a Natural Haspin Kinase Inhibitor. International Journal of Molecular Sciences, 18(10), 2228.

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Antioxidant Compounds and Activity Assays

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Coumestrol, α-Tocopherol, BHA, BHT, Trolox, DPPH^•, ABTS and DMPD were commercially obtained from Sigma-Aldrich GmbH (Steinheim, Germany).

Durmaz L., Erturk A., Akyüz M., Polat Kose L., Uc E.M., Bingol Z., Saglamtas R., Alwasel S, & Gulcin İ. (2022). Screening of Carbonic Anhydrase, Acetylcholinesterase, Butyrylcholinesterase, and α-Glycosidase Enzyme Inhibition Effects and Antioxidant Activity of Coumestrol. Molecules, 27(10), 3091.

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Standard Analytical Reagent Procurement

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Analytical grade acetone, acetic acid, anhydrous sodium acetate, ethanol, hexane, hydrochloric acid, potassium chloride, sodium carbonate, and sulfuric acid were obtained from Chem Supply (Port Adelaide, South Australia, Australia). High pressure liquid chromatography (HPLC) grade methanol, acetonitrile, formic acid, and ammonium acetate as well as analytical standards (Folin–Ciocalteu reagent, vanillin, gallic acid, cyanidin-3-O-glucoside, (+)-catechin, coumestrol, formononetin, genistein, and naringenin) were purchased from Sigma Aldrich (Australia).

Latif S., Weston P.A., Barrow R.A., Gurusinghe S., Piltz J.W, & Weston L.A. (2020). Metabolic Profiling Provides Unique Insights to Accumulation and Biosynthesis of Key Secondary Metabolites in Annual Pasture Legumes of Mediterranean Origin. Metabolites, 10(7), 267.

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Osteoclastogenesis Inhibition Bioactive Compounds

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OPG recombinant, expressed in E. coli ≥ 98%, sRANKL recombinant, expressed in E. coli ≥ 98%, daidzein ≥ 98%, biochanin A ≥ 95%, genistein ≥ 98% formononetin ≥ 99% coumestrol ≥ 97.5% and ITC reagents of LC/MS grade were obtained from Sigma Aldrich (St. Louis, MO, USA). All cell culture reagents were obtained from Life Technologies (Carlsbad, CA, USA). Tissue culture plastics were supplied by Greiner Bio-One GmbH (Frickenhausen, Austria). All the experimental measurements, if not stated otherwise, were performed using the Synergy 2 BioTek microplate reader (Winooski, VT, USA). Microscopic observations were performed using fluorescent microscope Nikon TS100 Eclipse (Tokyo, Japan) under 200× magnification if not stated otherwise.

Zakłos-Szyda M., Budryn G., Grzelczyk J., Pérez-Sánchez H, & Żyżelewicz D. (2020). Evaluation of Isoflavones as Bone Resorption Inhibitors upon Interactions with Receptor Activator of Nuclear Factor-κB Ligand (RANKL). Molecules, 25(1), 206.

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Phytoestrogen and Steroid Cytotoxicity Assay

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Coumestrol (Sigma), Daidzein, Genistein, (ChromaDex), Dexamethasone (CCM Duopharma, Malaysia), Estradiol (Sigma), Cyclophoshamide (Endoxan, Halle, Germany), BD Pharmingen™ Annexin V-FITC (BD Bioscience, CA,USA), Propidium Iodide, PI (Sigma, MO, USA), BD Cycletest™ Plus DNA Reagent Kit (Becton Dickinson, CA, USA), methyl thiazolyltetrazolium (Sigma, MO, USA), Dimethyl sulfoxide, DMSO (Merck, Darmstadt, Germany), ANXA1 ELISA kit (USCNK, Wuhan, China), haematoxylin (CLIN-TECH LIMITED, GU4 7BN, UK) eosin (HISTO-LINE, Selangor, Malaysia).

Sabran A., Kumolosasi E., Jantan I., Jamal J.A., Azmi N, & Jasamai M. (2020). Induction of cell death and modulation of Annexin A1 by phytoestrogens in human leukemic cell lines. Saudi Pharmaceutical Journal : SPJ, 29(1), 73-84.

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Identification of Phytochemical Standards

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Apigenin, Apigenin 7-O-glucoside, daidzein, daidzin, daidzin 6″-O-acetate, daidzin 6″-O-malonate, genistein, genistin, genistin 6″-O-acetate, genistin 6″-O-malonate, glycitein, glycitin, glycitin 6″-O-acetate, and glycitin 6″-O-malonate were purchased from Fujifilm Wako Pure Chemical Industries, Ltd. (Osaka, Japan). Coumestrol, dimethyl sulfoxide (DMSO), kaempferol, kaempferol 3-O-glucoside (astragalin), isoquercitrin, isorhamnetin, luteolin, quercetin, and rutin were purchased from Sigma-Aldrich Co., LLC (St. Louis, MO, USA). The purities of the authentic compounds are listed in Table S1. Two quercetin diglycosides, two quercetin triglycosides, two kaempferol diglycosides, and three kaempferol triglycosides were purified from SLs. Mass-grade formic acid, acetonitrile, methanol, and water were purchased from Thermo Fisher Scientific Inc. (Waltham, MA, USA). Other chemicals used were of American Chemical Society grade or higher.

Rha C.S., Jang E.K., Hong Y.D, & Park W.S. (2021). Supervised Statistical Learning Prediction of Soybean Varieties and Cultivation Sites Using Rapid UPLC-MS Separation, Method Validation, and Targeted Metabolomic Analysis of 31 Phenolic Compounds in the Leaves. Metabolites, 11(12), 884.

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