Diosmetin

Manufactured by Merck Group

Sourced in United States, Germany

Diosmetin is a chemical compound used in laboratory equipment and research applications. It is a flavonoid with antioxidant properties. Diosmetin is primarily used as a reference standard and analytical tool in various scientific investigations.

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Lab products found in correlation

26 protocols using diosmetin

Quantification of Phenolic Compounds

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The 2,5-dihydroxybenzoic acid (2,5-DHBA), 3,4-dihydroxybenzoic acid (3,4-DHBA), 4-hydroxybenzoic acid (pHBA), 3-hydroxy tyrosol, apigenin, caffeic acid, chrysin, quercetin, naringenin, diosmetin, rutin, luteolin, luteolin-7-O-glucoside, p-coumaric acid, oleuropein and tyrosol were all from Sigma-Aldrich (Merck, St. Louis, MO, USA). Ferulic acid was purchased from Extrasynthese (Genay, France). apigenin-7-O-glucoside and verbascoside were obtained from HWI Analytik GmbH (Rülzheim, Germany). Gallic acid was obtained from Alfa Aesar (Thermo Fisher Scientific, Waltham, MA, USA).
Chemical reagents methanol (LC-MS purity) and acetonitrile (LC-MS purity) were purchased from Honeywell Research Chemicals (Bucharest, Romania). Formic acid (LC-MS purity) was obtained from Sigma-Aldrich, Merck. Milli-Q water was obtained using a Milli-Q water purification system (<0.058 μS/cm, Mili-Q model Pacific TII 12; Barnstead™, Thermo Fisher Scientific).

Peršurić Ž., Saftić L., Klisović D, & Pavelić S.K. (2019). Polyphenol-Based Design of Functional Olive Leaf Infusions§. Food Technology and Biotechnology, 57(2), 171-182.

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Diosmetin Modulates Inflammatory Pathways

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Diosmetin was purchased from Sigma-Aldrich (St. Louis, MO, USA). The enzyme-linked immunosorbent assay (ELISA) kits for interleukin (IL)-6, IL-1β, and tumor necrosis factor-α (TNF-α) were obtained from Abcam (Cambridge, UK). Akt, PI3K, and MyD88 were purchased from Cell Signaling Technology (Danvers, MA, USA) and NF-κB, nucleolin and β-actin antibodies were purchased from Santa Cruz Biotechnology (Santa Cruz, CA, USA).

Zhang Y., Jiang Y, & Lu D. (2019). Diosmetin Suppresses Neuronal Apoptosis and Inflammation by Modulating the Phosphoinositide 3-Kinase (PI3K)/AKT/Nuclear Factor-κB (NF-κB) Signaling Pathway in a Rat Model of Pneumococcal Meningitis. Medical Science Monitor : International Medical Journal of Experimental and Clinical Research, 25, 2238-2245.

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HPLC Standards for Biochemical Analysis

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All solvents used were of HPLC grade and supplied by Fisher Scientific. Canavanine sulfate salt, quercetin-3-glucoside, quercetin dihydrate, hyperoside, luteoloside, stachydrine (hydrochloride), trigonelline chloride, diosmetin, H-Glu-Tyr-OH and H-Phe-Glu-OH standards were purchased from the Sigma-Aldrich (Munich, Germany), Thermo scientific, Carl Roth (Karlsruhe, Germany), Chemodex (St. Gallen, Switzerland), Cayman (Düsseldorf, Germany) and Adipogen life sciences (San Diego, CA, USA) companies.

Abouzeid S., Beutling U., Elekhnawy E, & Selmar D. (2023). Antibacterial and Antibiofilm Effects of Allelopathic Compounds Identified in Medicago sativa L. Seedling Exudate against Escherichia coli. Molecules, 28(6), 2645.

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Comprehensive Flavonoid Compound Library

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The compounds kaempferol, acacetin, galangin, chrysin, homoeriodictyol were obtained from Carl Roth GmbH (Karlsruhe, Germany), apigenin, nargingenin, hispidulin, scutellarein, baicalein, quercetin, wogonin, and diosmetin from Sigma-Aldrich (Vienna, Austria), herbacetin, pinocembrin, luteolin, eriodictyol, norwogonin from Extrasynthése (Genay, France) and nepetin as well as oroxylin A from Phytolab (Vestenbergsgreuth, Germany). All stock solutions were prepared in dimethylsulfoxide (DMSO; 99.7% cell culture grade, Sigma-Aldrich (Vienna, Austria).

Berenda J., Smöch C., Stadlbauer C., Mittermair E., Taxauer K., Huttary N., Krupitza G, & Krenn L. (2020). Flavonoids Distinctly Stabilize Lymph Endothelial- or Blood Endothelial Disintegration Induced by Colon Cancer Spheroids SW620. Molecules, 25(9), 2066.

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Diosmetin Modulates Cancer Cell Behavior

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Diosmetin (Sigma-Aldrich, St. Louis, MO, USA) was dissolved in dimethyl sulfoxide (DMSO; MP Biomedicals, Santa Ana, CA, USA) at a stock solution concentration of 5 mg/ml, and was diluted as a working fluid for cell culture medium prior to use. Concentrations of DIOS used in the MTT assay were 0, 2, 5, 10, 20, 30, 40, 50 and 100 µg/ml; whereas 0, 10, 20 and 40 µg/ml DIOS was used in the other assays. The 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) was purchased from Sigma-Aldrich. Matrigel was purchased from BD Biosciences (Franklin Lakes, NJ, USA). SYBR Premix Ex Taq™ II kits were purchased from Takara Bio, Inc. (Shiga, Japan). Antibodies against GAPDH, MMP-2, MMP-9, c-Jun N-terminal kinase (JNK), phosphorylated (p)-JNK, extracellular signal-regulated kinase (ERK)1/2, p-ERK1/2 and protein kinase C (PKC)-δ were purchased from Cell Signal Technology, Inc. (Boston, MA, USA). Horseradish peroxidase-(HRP) conjugated goat anti-rabbit immunoglobulin G secondary antibody was purchased from EarthOx Life Sciences (Millibrae, CA, USA).

LIU J., WEN X., LIU B., ZHANG Q., ZHANG J., MIAO H, & ZHU R. (2016). Diosmetin inhibits the metastasis of hepatocellular carcinoma cells by downregulating the expression levels of MMP-2 and MMP-9. Molecular Medicine Reports, 13(3), 2401-2408.

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Diosmetin-Mediated Prostate Cancer Inhibition

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Diosmetin (>99% purity; chemical structure shown in Fig. 1), 3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) and propidium iodide (PI) were obtained from Sigma-Aldrich; Merck KGaA (Darmstadt, Germany). The prostate cancer cells (LNCaP and PC-3) were purchased from the American Type Culture Collection (Manassas, VA, USA). The RPMI-1640 medium used to culture the cells, phosphate-buffered saline (PBS) and trypsin were purchased from Thermo Fisher Scientific (Waltham, MA, USA). The reagents used for western blot analysis were purchased from Bio-Rad Laboratories (Hercules, CA, USA).

Oak C., Khalifa A.O., Isali I., Bhaskaran N., Walker E, & Shukla S. (2018). Diosmetin suppresses human prostate cancer cell proliferation through the induction of apoptosis and cell cycle arrest. International Journal of Oncology, 53(2), 835-843.

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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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Comprehensive Phytochemical Analysis Protocol

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The specific compounds, were: Caffeic acid, CAPE, chrysin, luteolin, daidzein, suberic acid, apigenin, (Alfa Aesar), pinocembrin, isorhamnetin, isosakuranetin, vitexin, orientin, rosmarinic acid, myricetin, vanillin, ursolic acid, hydroxytyrosol, tangeretin, chrysoeriol, betulinic acid, eriodictyol, sakuranetin, naringenin, t-cinnamic acid, genistein, diosmetin, resveratrol, galangin, pinocembrin 7-methyl ether, techtochrysin, (Extrasynthese) rutin, isoferulic acid, ellagic acid, kaempferol, quercetin, corosolic acid, acacetin, diosmin, protocatechuic acid ethyl ester, hesperetin, phloridzin, chlorogenic acid, p-coumaric acid, (±)catechin, maslinic acid, (Sigma Aldrich), rhamnetin, syringic acid, protocatechuic acid, ferulic acid, kaempferide, adipic acid, pinostrobin, gallic acid, pinobanksin (Fluka), naringin, hesperidin, (Acros Organics) pinobanksin-3O-acetate (Interchim Inc), cinnamylidenacetic acid, artepillin C (Wako Chemicals). o-Orselllinaldehyde was purchased from Santa Cruz Biotechnology (USA).
Water, acetonitrile, m Ethanol and formic acid were purchased from Fisher Scientific, UK and they were of LC-MS grade. Ethanol was purchased from Merck, Germany. PTFE filters (0.45 μm) were obtained from Macherey-Nagel, Germany.

Kasiotis K.M., Anastasiadou P., Papadopoulos A, & Machera K. (2017). Revisiting Greek Propolis: Chromatographic Analysis and Antioxidant Activity Study. PLoS ONE, 12(1), e0170077.

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Olive Root Extraction and Phytochemical Analysis

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O. europaea L. olive root cv. Chemlali (3 kg) was
taken from two olive trees cultivated in the region of Sfax (Tunisia).
The olive trees were about 45 years old. Olive root samples were picked
in the late February of 2017. The samples were dried for 90 days at
room temperature in a dark and airy room, and then, the root was scraped
in a local sawmill to separate the bark from the root wood. Subsequently,
all samples were ground into fine powder using a home mill before
extraction.
All phenolic standards used in this work (tyrosol,
caffeic, p-coumaric, ferulic acid, luteolin, apigenin,
diosmetin) were purchased from Sigma-Aldrich (Saint-Louis-Missouri).
The degree of purity of the standards was around 95% (w/w). All solvents
used for HPLC-MS analysis were delivered by J.T. Baker (Phillipsburg)
as used in the HPLC mobile phase. 2,2-Diphenyl-1-picrylhydrazyl (DPPH)
and the Folin–Ciocalteu reagents were purchased from Sigma-Aldrich
(Chemie Gmbh, Taufkirchen, Germany). Ultrapure water was used in all
analyses.

Ben Brahim S., Priego-Capote F, & Bouaziz M. (2022). Use of High-Performance Liquid Chromatography/Electrospray Ionization Mass Spectrometry for Structural Characterization of Bioactive Compounds in the Olive Root Bark and Wood of Chemlali Cultivar. ACS Omega, 7(38), 33873-33883.

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Quantitative and Qualitative Analysis of Flavonoids

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Ultra-pure water (H₂O) was obtained by a Milli-Q Direct 8 system (Millipore, Milan, Italy), methanol, acetonitrile (ACN) and formic acid (HCOOH) LC-MS grade were purchased from Sigma Aldrich (Milan, Italy). For the quantitative and qualitative analysis of flavonoids two columns were employed respectively: a Kinetex C18 150 × 4.6 mm (100 Å), packed with 2.6 µm particles, and a Kinetex C18 150 × 2.1 mm, 2.6 µm column (Phenomenex, Bologna, Italy). Both columns were protected with C18 precolumns (Phenomenex).
Flavonoids standards (diosmetin 6,8 di C-glucoside, neohesperidin, eriocitrin, isoquercetin, narirutin, diosmetin, hesperetin) and polymetoxyflavones (tangeretin) were purchased from Sigma Aldrich. For cell culture unless stated otherwise, all reagents and compounds were purchased from Sigma Chemicals Company (Milan, Italy).

Pepe G., Pagano F., Adesso S., Sommella E., Ostacolo C., Manfra M., Chieppa M., Sala M., Russo M., Marzocco S, & Campiglia P. (2017). Bioavailable Citrus sinensis Extract: Polyphenolic Composition and Biological Activity. Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry, 22(4), 623.

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