Phytochemicals (purity > 95%): (-)-epigallocatechin gallate (AA blocks, San Diego, CA, USA), quercetin (Sigma-Aldrich Chemie GmbH, Steinheim, Germany), hyperoside, isoquercetin, ellagic acid (Carl Roth GmbH + Co. KG, Karlsruhe, Germany), plumbagin (Acros Organics, Morris Plains, NJ, USA), gallic acid (Merck Schuchardt OHG, Hohenbrunn, Germany); HPLC solvents LC-MS grade: water, acetonitrile, methanol (VWR BDH Chemicals International S.A.S., Rosny-sous-Bios, France).
Hyperoside
Manufactured by Carl Roth
Sourced in Germany
Hyperoside is a flavonoid compound derived from various plant sources. It is commonly used as a standard reference material in analytical chemistry and biochemical research. Hyperoside serves as a marker compound for quality control and identification purposes in the analysis of herbal and botanical materials.
Automatically generated - may contain errors
Lab products found in correlation
Isoquercitrin, by Carl Roth (5 mentions)
Quercetin, by Merck Group (4 mentions)
Rutin, by Carl Roth (4 mentions)
Chlorogenic acid, by Carl Roth (3 mentions)
2 2 azino bis, by Merck Group (2 mentions)
Acetonitrile, by Merck Group (2 mentions)
Malic acid, by Merck Group (2 mentions)
Potassium persulfate, by Merck Group (2 mentions)
Gallic acid, by Carl Roth (2 mentions)
Chlorogenic acid, by Merck Group (2 mentions)
Acetonitrile, by Avantor (2 mentions)
Ellagic acid, by Carl Roth (1 mentions)
Gallic acid, by Merck Group (1 mentions)
Daidzin, by Extrasynthese (1 mentions)
Apigenin, by Extrasynthese (1 mentions)
Naringenin, by Extrasynthese (1 mentions)
Astragalin, by Merck Group (1 mentions)
Genistin, by Merck Group (1 mentions)
Biochanin a, by Merck Group (1 mentions)
Nicotiflorin, by Merck Group (1 mentions)
11 protocols using hyperoside
1
Phytochemical Standards Characterization
2
Quantitative Analysis of Flavonoids
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Kaempferol (96%) and formononetin (99%) were
purchased from Fluka(Brøndby, Denmark). Biochanin A (97%), genistin
(95%), nicotiflorin (98%), and astragalin (99%) were purchased from
Sigma-Aldrich (Brøndby, Denmark). Hyperoside (99%) was purchased
from Roth (Karlsruhe, Germany). Daidzein (97%) and genistein (97%)
were purchased from Lancaster (Brønshøj, Denmark). Rutin
(99%), apigenin (99%), naringenin (99%), and daidzin (90%) were purchased
from Extrasynthese (Genay, France). Medicarpin was obtained from Dr.
Paul M. Dewick at the University of Nottingham, UK. Quercetin-rha-xyl-gal
was isolated from white clover, purified, and identified by its UV,
mass, and nuclear magnetic resonance spectra as part of a previous
study.14 (link)Stock flavonoid solutions
of 1 g·l–1 were prepared by dissolution in
methanol. Working standard solutions of the compounds were obtained
by serial dilution of the stock standard solutions in 35% MeOH and
65% Milli-Q water (v/v) containing 0.2% formic acid. Mixed standard
curves for the negative and positive modes were generated from 10
concentrations of each standard and used for quantification.
purchased from Fluka(Brøndby, Denmark). Biochanin A (97%), genistin
(95%), nicotiflorin (98%), and astragalin (99%) were purchased from
Sigma-Aldrich (Brøndby, Denmark). Hyperoside (99%) was purchased
from Roth (Karlsruhe, Germany). Daidzein (97%) and genistein (97%)
were purchased from Lancaster (Brønshøj, Denmark). Rutin
(99%), apigenin (99%), naringenin (99%), and daidzin (90%) were purchased
from Extrasynthese (Genay, France). Medicarpin was obtained from Dr.
Paul M. Dewick at the University of Nottingham, UK. Quercetin-rha-xyl-gal
was isolated from white clover, purified, and identified by its UV,
mass, and nuclear magnetic resonance spectra as part of a previous
study.14 (link)Stock flavonoid solutions
of 1 g·l–1 were prepared by dissolution in
methanol. Working standard solutions of the compounds were obtained
by serial dilution of the stock standard solutions in 35% MeOH and
65% Milli-Q water (v/v) containing 0.2% formic acid. Mixed standard
curves for the negative and positive modes were generated from 10
concentrations of each standard and used for quantification.
3
Phytochemical Analysis of Drosera rotundifolia
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Solvents were of analytical quality and obtained from VWR International (Darmstadt, Germany). Acetylcholine chloride (purity >99%), quercetin (purity >95%) and 8MmIBMX (purity >98%) were purchased from Sigma-Aldrich (Steinheim, Germany). The 2″-O-galloylHyperoside used for contraction experiments and measurements of ciliary beating (purity >98%) was isolated from D. rotundifolia as described below. The 2″-O-galloylHyperoside (purity >98%) tested in the PDE assays and used for quantification was purchased from Biopurify Phytochemicals (Chengdu, China). Hyperoside (purity >95%) was purchased from Carl Roth (Karlsruhe, Germany). Rolipram (purity >98%) was obtained from Biotrend (Cologne, Germany).
4
Mitochondrial Bioenergetics and Antioxidant Analysis
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Glutamic acid, succinic acid, adenosine-5′-diphosphate sodium salt (ADP), cytochrome c from bovine heart, malic acid, ethylene glycol-bis-(b-aminoethylether)-N,N,N′N′-tetra acetic acid (EGTA), KH2PO4, TrisHCl, ethylenediamine tetra-acetic acid (EDTA), amytal, carboxyatractyloside (CAT), guanosine triphosphate (GTP)quercetin, acetonitrile, 2,2-azinobis (ethyl-2,3-dihydrobenzothiazoline-6-sulphonic acid) diammonium salt (ABTS), potassium persulfate, iron(III) chloride hexahydrate (FeCl3·6H2O), 2,4,6-tripyridyl-s-triazine (TPTZ), hydrochloric acid, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox) were obtained from “Sigma–Aldrich GmbH”, Steinheim, Germany. Sucrose, mannitol, HEPES, KCl, MgCl2, trifluoroacetic acid, hyperoside, isoquercitrin, rutin were obtained from “Carl Roth Gmbh”, Karlsruhe, Germany.
5
Comprehensive Analysis of Bioactive Compounds in Plant Extracts
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Analytical and chromatographic grade reagents were used for this study: acetonitrile, neochlorogenic acid, cryptochlorogenic acid, quercetin 3-O-(6″-O-malonyl)-β-d -glucoside (quercetin malonylglucoside in text), isorhamnetin 3-O-rutinoside, cyanidin 3-O-galactoside, cyanidin 3-O-glucoside, cyanidin 3-O-arabinoside, β-carotene, ascorbic acid, malic acid, fructose, glucose, sorbitol, sucrose, xylose, calcium carbonate, BHT, hexane, potassium persulfate, 2,2-azinobis (ethyl-2,3-dihydrobenzothiazoline-6-sulphonic acid) diammonium salt (ABTS), Trolox were purchased from Sigma–Aldrich GmbH (Steinheim, Germany); 99.8% trifluoracetic acid, chlorogenic acid, hyperoside, isoquercitrin, rutin, astragalin were purchased from Carl Roth GmbH (Karlsruhe, Germany); 96.3% ethanol was purchased from Stumbras SC (Kaunas, Lithuania). Purified deionized water (18.2 mΩ/cm) was produced using the Millipore (Burlington, MA., USA) water purification system.
6
HPLC Purification and Characterization of Polyphenols
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Quercetin (12 , >98%) was purchased from Sigma-Aldrich. Gallic acid (1 , >98%), hyperoside (8 , >95%), isoquercitrin (10 , >95%), and polyamide (particle size: 0.05–0.16 mm) were from Carl Roth. HPLC-grade acetonitrile and methanol (Reuss Chemie AG), and distilled water were used for HPLC separations.
Preparative HPLC was carried out on an LC 8A preparative liquid chromatograph equipped with a SPD-M10A VP PDA detector (all Shimadzu). A SunFire C18 column (150 × 30 mm i.d., 5 μm; Waters) connected to a pre-column (10 × 10 mm) was used, at a flow rate of 20 mL/min. HPLC-based activity profiling was performed on an Agilent 1100 system equipped with a PDA detector. A SunFire C18 column (150 × 10 mm i.d., 5 μm; Waters) connected to a pre-column (10 × 10 mm) was used. The flow rate was 4 mL/min. Time-based fractions were collected with a Gilson FC204 fraction collector. ESI-MS spectra were obtained on an Esquire 3000 Plus ion trap mass spectrometer (Bruker Daltonics). NMR spectra were recorded on an Avance III 500 MHz spectrometer (Bruker BioSpin) equipped with a 1-mm TXI microprobe.
Preparative HPLC was carried out on an LC 8A preparative liquid chromatograph equipped with a SPD-M10A VP PDA detector (all Shimadzu). A SunFire C18 column (150 × 30 mm i.d., 5 μm; Waters) connected to a pre-column (10 × 10 mm) was used, at a flow rate of 20 mL/min. HPLC-based activity profiling was performed on an Agilent 1100 system equipped with a PDA detector. A SunFire C18 column (150 × 10 mm i.d., 5 μm; Waters) connected to a pre-column (10 × 10 mm) was used. The flow rate was 4 mL/min. Time-based fractions were collected with a Gilson FC204 fraction collector. ESI-MS spectra were obtained on an Esquire 3000 Plus ion trap mass spectrometer (Bruker Daltonics). NMR spectra were recorded on an Avance III 500 MHz spectrometer (Bruker BioSpin) equipped with a 1-mm TXI microprobe.
7
Extraction and Characterization of Bioactive Compounds from St. John's Wort
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Aerial parts (leaves, stem, petals, and flowers)
of H. perforatumL (St. John’s wort) were collected in July–August
2018 from the Ghab Plain in Syria (Google maps: 35.586856, 36.355724
and 180–200 m above sea level) and harvested during the flowering
season. Hypericin and quercetin were purchased from Cayman Pharma
(Neratovice, Czech Republic); hyperoside was purchased from Roth (Karlsruhe,
Germany); quercitrin hydrate, chlorogenic acid, 1,1-diphenyl-2-picrylhydrazyl
(DPPH), potassium persulfate, and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic
acid) (ABTS) were purchased from Sigma-Aldrich (Darmstadt, Germany);
Whatman 90 mm filter paper was purchased from GE Healthcare Life Sciences
(Freiburg Germany); a 0.22 μm nylon syringe filter, Sartolab
Vakuumfilter 180C5, 0.22 μm polyethersulfon, 500 mL, 25 mm syringe
filter, 0.45 μm RC with GF prefilter, and 0.45 μm PTFE
filter were purchased from Sartorius (Goettingen, Germany); and 0.45
μm prefilter was purchased from Wicom (Heppenheim, Germany).
Ethanol, mEthanol, and acetone were HPLC grade from Roth (Karlsruhe,
Germany); acetonitrile was obtained from VWR (Hannover, Germany),
and water was purified using a QM system from Sartorius (Goettingen,
Germany).
of H. perforatumL (St. John’s wort) were collected in July–August
2018 from the Ghab Plain in Syria (Google maps: 35.586856, 36.355724
and 180–200 m above sea level) and harvested during the flowering
season. Hypericin and quercetin were purchased from Cayman Pharma
(Neratovice, Czech Republic); hyperoside was purchased from Roth (Karlsruhe,
Germany); quercitrin hydrate, chlorogenic acid, 1,1-diphenyl-2-picrylhydrazyl
(DPPH), potassium persulfate, and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic
acid) (ABTS) were purchased from Sigma-Aldrich (Darmstadt, Germany);
Whatman 90 mm filter paper was purchased from GE Healthcare Life Sciences
(Freiburg Germany); a 0.22 μm nylon syringe filter, Sartolab
Vakuumfilter 180C5, 0.22 μm polyethersulfon, 500 mL, 25 mm syringe
filter, 0.45 μm RC with GF prefilter, and 0.45 μm PTFE
filter were purchased from Sartorius (Goettingen, Germany); and 0.45
μm prefilter was purchased from Wicom (Heppenheim, Germany).
Ethanol, mEthanol, and acetone were HPLC grade from Roth (Karlsruhe,
Germany); acetonitrile was obtained from VWR (Hannover, Germany),
and water was purified using a QM system from Sartorius (Goettingen,
Germany).
8
Analytical Methods for Phytochemical Analysis
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Deionized water was produced using Millipore Simplicty UV station (Merck Millipore, Burlington, MA, USA). Acetonitrile, formic acid, ethanol was purchased from VWR (Radnor, PA, USA). Chlorogenic acid, hyperoside, rutin, gallic acid were purchased from Carl Roth (Karlsruhe, Germany). L-arginine, Tween-80 and aluminum chloride were purchased from Sigma-Aldrich (Sant Louis, MI, USA). Querectin was bought from Borschagovsky CPP (Kyiv, Ukraine) and fructose—from LLC Company ”Ukrhimsyre” (Kharkiv, Ukraine). Blood glucose, high-density lipoprotein cholesterol (Ch-HDL) and low-density lipoprotein cholesterol (Ch-LDL) (Felitis-Diagnostics, Ukraine) insulin (DRG, Germany) and triacylglycerols (TAG, Lachema, Czech Republic) were determined in blood serum using standard sets of reagents. Chemical standards used for HPLC analysis were previously isolated and identified in the Department of Pharmacognosy and Molecular Basis of Phytotherapy, Medical University of Warsaw.
9
HPLC Fingerprinting of Methanolic Extracts
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For further analysis, HPLC fingerprints of the methanol extracts were recorded. Extracts were dissolved in methanol to a final concentration of 1 mg mL−1 (injection volume 20 µL). The following standard substances were used (each 0.1 mg mL−1, injection volume 5 µL): hyperoside (CarlRoth, D), quercetin (Sigma-Aldrich/Merck, D), isoquercitrin (CarlRoth, D), rosmaric acid (Sigma-Aldrich/Merck, D), (+)-catechin (CarlRoth, D), rutoside (Acros Organics/Thermo Scientific, Branchburg, NJ, USA), gallic acid (Acros Organics/Thermo Scientific, Waltham, MA, USA), umbelliferone (Sigma-Aldrich/Merck, D), and ellagic acid (Acros Organics/Thermo Scientific, Branchburg, NJ, USA). The HPLC configurations (Shimadzu LC20-AHT) were as follows: A Phenomenex® Luna® C18(2) (5 µm, 100 Å, 250 mm × 4.6 mm) was used as stationary phase and the column oven was set to 45 °C. Mobile Phase A was water with 0.1% acetic acid. Mobile phase B was acetonitrile with 0.1% acetic acid. The total flow was set at 1.2 mL min−1 with the following gradient: t0min B14%, t15min B16%, t38min B80%, t42.5min B80%, t42.6min B14%, t46min B14%. Detection was performed with UV detector at 254 nm.
10
HPLC-MS Analysis of Polyphenolic Compounds
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References used for the HPLC-MS analysis were purchased from Sigma Aldrich (St. Louis, MO, USA): Chlorogenic acid, p-coumaric acid, caffeic acid, rutin, apigenin, quercetin, isoquercitrin, quercitrin, hyperoside, kaempferol, myricetol, and fisetin, Roth (Karlsruhe, Germany): Ferulic acid, sinapic acid, gentisic acid, gallic acid, patuletin, luteolin or from Dalton (Toronto, ON, Canada): cichoric acid, caftaric acid. HPLC grade solvents, analytical grade acids used for mobile phases and Folin-Ciocâlteu reagent were purchased from Merck (Darmstadt, Germany), together with sodium carbonate, dipotassium hydrogen phosphate, potassium dihydrogen phosphate and aluminium chloride used for antioxidant assays. ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt) ≥98% purity, potassium peroxodisulfate (≥99% purity), DPPH, and Trolox (6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid; ≥97% purity) also used in antioxidant tests were purchased from Sigma Aldrich (Schnelldorf, Germany). Gallic acid monohydrate (99.5%) was purchased from Serva, (Heidelberg, Germany).
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