Standards of catechin (CAT), epicatechin (EC), myricetin-3-O-glucoside, quercetin-3-O-glucoside, quercetin, procyanidin C1 (PC1), and procyanidin A2 (PA2) were purchased from Extrasynthese (Genay, France). Methanol, acetonitrile, 4-dimethylammino-cinnamaldehyde (DMAC), and acetic acid were from Sigma-Aldrich (St. Louis, MO, USA). Amicon ultra-4 centrifugal filter units of 3, 10, 30, 50, and 100 nominal molecular weight limits (NMWL) were supplied from Merck Millipore (Milan, Italy). Water was from a Milli-Q apparatus (Millipore, Milford, CT, USA). Commercial dried cranberry extracts (A1, A2, and A3) were obtained from different manufacturers. Notably, A1 and A3 were obtained from an industrial producer of natural ingredients starting from whole berry. On the contrary, A2 was produced by a small company through a proprietary purification and concentration process starting from cranberry commercial extracts. Details regarding the plant origins and manufacturing processes of the extracts are not available.
Myricetin 3 o glucoside
Manufactured by Extrasynthese
Sourced in France
Myricetin-3-O-glucoside is a naturally occurring flavonoid compound. It is a glycoside formed by the attachment of a glucose molecule to the myricetin aglycone. Myricetin-3-O-glucoside is commonly found in various plant species.
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Lab products found in correlation
Quercetin 3 o glucoside, by Extrasynthese (9 mentions)
Isorhamnetin 3 o glucoside, by Extrasynthese (5 mentions)
Kaempferol 3 o glucoside, by Extrasynthese (5 mentions)
Formic acid, by Merck Group (5 mentions)
Methanol, by Merck Group (4 mentions)
Quercetin 3 o rutinoside, by Extrasynthese (4 mentions)
Epicatechin, by Extrasynthese (3 mentions)
Catechin, by Extrasynthese (3 mentions)
Gallic acid, by Extrasynthese (3 mentions)
Procyanidin b1, by Extrasynthese (3 mentions)
Procyanidin b2, by Extrasynthese (3 mentions)
Gallic acid, by Merck Group (3 mentions)
Quercetin, by Extrasynthese (2 mentions)
Procyanidin c1, by Extrasynthese (2 mentions)
Cyanidin 3 o glucoside, by Extrasynthese (2 mentions)
Peonidin 3 o glucoside, by Extrasynthese (2 mentions)
Malvidin 3 o glucoside, by Extrasynthese (2 mentions)
Epicatechin gallate, by Merck Group (2 mentions)
Quercetin, by Merck Group (2 mentions)
Caffeic acid, by Merck Group (2 mentions)
12 protocols using myricetin 3 o glucoside
1
Quantification of Cranberry Polyphenols
2
Analytical Standards for Polyphenol Analysis
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Formic acid and methanol were purchased from Sigma-Aldrich (Steinheim, Germany). Acetonitrile was purchased from Merck (Darmstadt, Germany). Quercetin-3-O-glucoside, quercetin-3-O-rutinoside, kaempferol-3-O-glucoside, myricetin-3-O-glucoside, isorhamnetin-3-O-glucoside, cyanidin-3-O-glucoside, peonidin-3-O-glucoside, (−)-epicatechin, (+)-catechin, procyanidins, gallic acid were purchased from Extrasynthese (Lyon, France).
3
Analytical Standards for Polyphenol Analysis
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Sodium hydroxide solution (0.1 mol/L) was purchased from Sigma-Aldrich (Poznań, Poland). Buffer solutions of pH 2, 4 and 7 were purchased from POCH (Gliwice, Poland). Sucrose, glucose, fructose, tartaric, malic, lactic, acetic, citric and succinic acids were obtained from Sigma-Aldrich (Poznań, Poland), all with a purity level of ≥98%. Analytical standards of cyanidin-3-O-glucoside, peonidin-3-Oglucoside, petunidin-3-O-glucoside, malvidin-3-O-glucoside, delphinidin-3-O-glucoside, myricetin-3-O-glucoside, quercetin-3-O-rutinoside, quercetin-4′-O-glucoside, quercetin-3-O-glucoside, kaempferol-3-O-glucoside, isorhamnetin-3-O-glucoside, (+)-catechin, (−)-epicatechin, (−)-epicatechin-3-gallate, procyanidin A1 and A2, trans-resveratrol, and trans-piceid, were purchased from Extrasynthese (Lyon, France). The analytic standards of gallic acid, caftaric acid, protocatechuic acid, coutaric acid, caffeic acid, p-coumaric acid, and ferulic acid were purchased from PhytoLab (Vestenbergsgreuth, Germany). Acetonitrile (HPLC gradient grade) was purchased from POCH (Gliwice, Poland). Formic acid (LC–MS grade) was purchased from Fischer Scientific (Schwerte, Germany).
4
Antioxidant Compound Extraction and Analysis
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Gallic acid, caffeic acid, ellagic acid, quercetin, flavone, catechin, epicatechin, epigallocatechin, epicatechin gallate, epigallocatechin gallate, (±)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid (Trolox), 2,2′-diphenyl-1-picrylhydrazyl (DPPH), 2,4,6-tris(2-pyridyl)-s-triazine (TPTZ), and the Folin-Ciocalteu reagent were purchased from Sigma-Aldrich (St. Louis, MO, USA). quercetin-3-galactoside, quercetin-3-rhamnoside, myricetin-3-O-galactoside, myricetin-3-O-glucoside, procyanidin B1 and procyanidin B2 were supplied by Extrasynthese (Genay, France). All chemicals and reagents were of analytical grade unless specified.
5
Chromatographic Analysis of Antioxidants
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Acetonitrile for chromatography analysis and ascorbic acid were purchased from Merck (Darmstadt, Germany). Formic acid, methanol, 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), and 2,4,6-tri(2-pyridyl)striazine (TPTZ) were purchased from Sigma-Aldrich (Steinheim, Germany). Caftaric acid, (+)-catechin and procyanidin B2, quercetin-3-O-glucoside, myricetin-3-O-glucoside were purchased from Extrasynthese (Lyon, France). Divinylbenzene/carboxen/polydimethylsiloxane fiber ((DVB/CAR/PDMS), 50/30 μm, coating 2 cm) was purchased from Supelco (Bellafonte, PA, USA). K2S2O5, and NaOH were purchased from POCh (Gliwice, Poland). The yeast nutrient SIHA® Proferm Plus nutrient, commercially yeast S. cerevisiae as SIHA® Cryarome and S. bayanus as SIHA® Active Yeast 4 were purchased from Eaton (Langenlonsheim, Germany). S. cerevisiae as Challenge Aroma White was purchased from Enartis (San Martino-Trecate, Italy).
6
Characterization of Phenolic Compounds
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Acetonitrile and methanol were purchased from Thermo Fisher Scientific (France). A Millipore Milli-Q system (Merck Millipore, Molsheim, France) provided ultrapure water. L-leucine, L-isoleucine, L-phenylalanine, L-tyrosine, L-tryptophan, L-proline, citric acid, E-resveratrol, E-piceatannol, catechin, epicatechin, coutaric acid, fertaric acid, E-piceid, kaempferol 3-O-glucoside, and kaempferol 3-O-glucuronide were obtained from Sigma-Aldrich (St. Louis, MO, USA). Caftaric acid was purchased from Carbosynth (Compton, Berkshire, UK). Rhamnetin, E-ε-viniferin, kaempferol 3-O-rutinoside, quercetin 3-O-glucoside, quercetin 3-O-glucuronide, myricetin 3-O-glucoside, procyanidin B1, procyanidin B2, procyanidin B3, procyanidin C1, and kaempferol 3-O-rutinoside were purchased from Extrasynthèse (Genay, France). Pallidol and E-δ-viniferin were graciously provided by Dr. Mary-Lorène Goddard (EA-3991, Université de Haute-Alsace, Colmar, France). E-miyabenol C was obtained from Ambinter (Paris, France).
7
Phenolic Profile and Antioxidant Capacity
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Total Phenols (TP) was measured using the Folin-Ciocalteu method as described by Martín-Diana et al. (2017) . Results were expressed as μmol gallic acid equivalents (GAE) g−1 of sample using a calibration curve with gallic acid as standard (9.8–70 mM).
Phenolic compound profile was determined using HPLC-DAD-ESI/MS chromatography, as described in Dueñas et al. (2015) . The standards, gallic acid, quercetin 3-O-glucoside, kaempferol 3-O-glucoside, isorhamnetin 3-O-glucoside, myricetin 3-O-glucoside, apigenin 6-C-glucoside, were obtained from Extra synthese (Genay, France). Galloyl glucose derivatives were quantified using gallic acid standard curve; derivatives of apigenin, quercetin, kaempferol, isorhamnetin and myricetin were quantified using apigenin 6-C-glucoside, quercetin 3-O-glucoside, kaempferol 3-O-glucoside, isorhamnetin 3-O-glucoside and myricetin 3-O-glucoside standard curves, respectively. Results were expressed as μg g−1 sample (d.w.b.).
Phenolic compound profile was determined using HPLC-DAD-ESI/MS chromatography, as described in Dueñas et al. (2015) . The standards, gallic acid, quercetin 3-O-glucoside, kaempferol 3-O-glucoside, isorhamnetin 3-O-glucoside, myricetin 3-O-glucoside, apigenin 6-C-glucoside, were obtained from Extra synthese (Genay, France). Galloyl glucose derivatives were quantified using gallic acid standard curve; derivatives of apigenin, quercetin, kaempferol, isorhamnetin and myricetin were quantified using apigenin 6-C-glucoside, quercetin 3-O-glucoside, kaempferol 3-O-glucoside, isorhamnetin 3-O-glucoside and myricetin 3-O-glucoside standard curves, respectively. Results were expressed as μg g−1 sample (d.w.b.).
8
Phenolic Compound Standards Characterization
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HPLC-grade acetonitrile was obtained from Merck KgaA (Darmstadt, Germany). Formic and acetic acids were purchased from Fisher Scientific (Waltham, MA USA). The phenolic compound standards (myricetin-3-O-glucoside, quercetin-3-O-rutinoside, kaempferol-3-O-rutinoside, quercetin 3-O-glucoside, isorhamnetin-3-O-rutinoside and isorhamnetin-3-O-glucoside) were from Extrasynthese (Genay, France). The cell lines HeLa, HEPG2, NCI-H460 and MCF-7 were purchased from Deutshe Sammlung von Mikroorganismen and Zellkulturen Gmbit (DSMZ, Braunschweig, Germany). Dulbecco’s modified Eagle’s medium (DMEM), hank’s balanced salt solution (HBSS), fetal bovine serum (FBS), l -glutamine, trypsin-EDTA, penicillin/streptomycin solution (100 U/mL and 100 mg/mL, respectively) were purchased from Gibco Invitrogen Life Technologies (Carlsbad, CA, USA). Water was treated in a Milli-Q water purification system (TGI Pure Water Systems, Greenville, SC, USA).
9
Polyphenol Extraction and Analysis
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Ethanol absolute was from VWR (Milan, Italy); methanol and 85% w/w phosphoric acid were from Sigma-Aldrich (Steinheim, Germany); LC–MS-grade acetonitrile, formic acid, and water were from Merck (Darmstadt, Germany). Standards of gallic acid, methyl gallate, ethyl gallate, myricetin 3-O-glucoside, quercetin, quercetin-3-O-rhamnoside, and kaempferol-3-O-glucoside were from Extrasynthese (Genay, France) and TransMIT (Giessen, Germany). Phospholipon90G (>94% phosphatidylcholine; P90G) was from Lipoid GmbH (Ludwigshafen, Germany). All the reagents for cell culture were provided by Lonza (Verviers, Belgium).
10
Phytochemical Screening and Bioactivity Assays
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All chemicals were obtained as pure commercial products and used without further purification. Acetylcholinesterase (AChE) from Electrophorus electricus, acetylthiocholine iodide, 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), aluminum nitrate, butyrylcholinesterase (BChE) from equine serum, S-butyrylthiocholine chloride, 3-O-caffeoylquinic acid (chlorogenic acid), catechin, 2,2-diphenyl-1-picrylhydrazyl radical (DPPH•), 5,5′-dithiobis(2-nitrobenzoic acid) (DTNB), ellagic acid, Folin-Ciocalteu phenol reagent, ferric chloride, galantamine hydrobromide, gallic acid, 4-hydroxybenzyl alcohol, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), myricetin, 2,4,6-tris(2-pyridyl)-1,3,5-triazine (TPTZ), and quercetin were purchased from Sigma Aldrich (Milan, Italy). LC-MS grade acetonitrile and formic acid were purchased from Merck (Darmstadt, Germany). Standards of myricetin-3-O-glucoside, quercetin-3-O-glucoside, and acacetin were purchased from Extrasynthese (Genay, France). HPLC grade water (18 MΩ·cm) was prepared by using a Millipore (Bedford, MA, USA) Milli-Q purification system.
Spectrophotometric determinations were obtained with an Ultrospec 2100 spectrophotometer (Biochrom Ltd., Cambridge, England) using cells with a 1 cm path length.
Spectrophotometric determinations were obtained with an Ultrospec 2100 spectrophotometer (Biochrom Ltd., Cambridge, England) using cells with a 1 cm path length.
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