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8 protocols using procyanidin c1

1

Phenolic Compounds Analysis in Wines

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(−)-Epicatechin and (+)-catechin standards, and ascorbic acid were provided by Sigma Aldrich. (−)-Epigallocatechin, (−)-Epigallocatechin gallate, (−)-epicatechin gallate, procyanidin B1, procyanidin B2, and procyanidin C1 standards were purchased from Extrasynthese (Genay, France). Wine samples used in this study were provided by Sogrape Vinhos, SA. The eluents used in the LC–MS analysis were methanol and acetic acid (CH3COOH) at a concentration of 0.1%, both provided by Sigma Aldrich (St. Louis, MO, USA). Ultra-pure deionized water was obtained from a Milli-Q water purification system. Gelatin was supplied from Proenol (Vila Nova de Gaia, Portugal), and vegetable proteins were supplied by Agrovin (Ciudad Real, Spain) and SAI Enology (Penafiel, Portugal). One patatin and one pea protein from each manufacturer were used. Producers guaranteed that proteins were not from genetically modified organisms (GMOs).
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2

Quantification of Cranberry Polyphenols

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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.
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3

Characterization of Catechin Standards

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All chemicals were at least of analytical grade. Toluene, 1-propanol, formic acid, acetic acid, hydrochloric acid (37%) and 4-dimethylaminocinnamaldehyde (DMACA) were from Merck (Darmstadt, Germany). Ethanol, acetone, as well as HPLC grade acetonitrile and mEthanol were purchased from Sigma-Aldrich (St. Louis, MO, USA). LC-MS grade acetonitrile and mEthanol used for MS analyses were from Fluka (Buchs, Switzerland). MilliQ 18.2 MΩ water (Millipore, Bedford, MA, USA) was also used.
Standards of (−)-epicatechin gallate, (−)-epigallocatechin, (−)-epigallocatechin gallate, (−)-catechin gallate, (−)-gallocatechin, (−)-gallocatechin gallate, procyanidin B1, procyanidin B2, procyanidin B3 and procyanidin C1 were obtained from Extrasynthèse (Genay, France), while (−)-epicatechin was from Sigma-Aldrich and (+)-catechin from Carl Roth (Karlsruhe, Germany).
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4

Cultivation of Plant In Vitro Cultures

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Reagents needed for cultivation of in vitro cultures, e.g., MS and SH basal media, agar, PGRs, and sucrose were acquired from Duchefa Farma B.V. (Haarlem, The Netherlands).
Ultrapure water was obtained using Millipore Milli-Q system (Merck Millipore, Molsheim, France). Acetonitrile and methanol were purchased from Thermo Fisher Scientific (Illkirch-Graffenstaden, France). Standard compounds L-leucine, L-isoleucine, L-phenylalanine, L-tyrosine, L-tryptophan, L-proline, citric acid, gallic acid, coutaric acid, trans-resveratrol, cis-resveratrol, E-piceid, catechin, epicatechin, catechin gallate, tyrosinase, and L-DOPA were purchased from Sigma-Aldrich (St. Louis, MO, USA). Rhamnetin, E-ε-viniferin, quercetin 3-O-glucoside, quercetin 3-O-glucuronide, quercetin-3-O-galactoside, procyanidin B1, procyanidin B2, procyanidin B3, and procyanidin C1 were obtained from ExtraSynthèse (Genay, France); caftaric acid was delivered by Carbosynth (Compton, Berkshire, UK), while E-ε-viniferin, Z/E-vitisin B, ampelopsin A, and hopeaphenol were obtained by previous extraction from grape stems [50 (link)].
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5

Cultivation of Plant In Vitro Cultures

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Reagents needed for cultivation of in vitro cultures, e.g., MS and SH basal media, agar, PGRs, and sucrose were acquired from Duchefa Farma B.V. (Haarlem, The Netherlands).
Ultrapure water was obtained using Millipore Milli-Q system (Merck Millipore, Molsheim, France). Acetonitrile and methanol were purchased from Thermo Fisher Scientific (Illkirch-Graffenstaden, France). Standard compounds L-leucine, L-isoleucine, L-phenylalanine, L-tyrosine, L-tryptophan, L-proline, citric acid, gallic acid, coutaric acid, trans-resveratrol, cis-resveratrol, E-piceid, catechin, epicatechin, catechin gallate, tyrosinase, and L-DOPA were purchased from Sigma-Aldrich (St. Louis, MO, USA). Rhamnetin, E-ε-viniferin, quercetin 3-O-glucoside, quercetin 3-O-glucuronide, quercetin-3-O-galactoside, procyanidin B1, procyanidin B2, procyanidin B3, and procyanidin C1 were obtained from ExtraSynthèse (Genay, France); caftaric acid was delivered by Carbosynth (Compton, Berkshire, UK), while E-ε-viniferin, Z/E-vitisin B, ampelopsin A, and hopeaphenol were obtained by previous extraction from grape stems [50 (link)].
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6

Quantitative Analysis of Polyphenols

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All chemicals were at least of analytical grade. Acetic acid, formic acid, hydrochloric acid (37%), toluene, 1-propanol, and 4-dimethylaminocinnamaldehyde (DMACA) were from Merck (Darmstadt, Germany). Acetone, ethanol as well as HPLC grade acetonitrile and methanol were purchased from Sigma-Aldrich (St. Louis, MO, USA). LC–MS grade acetonitrile and methanol used for MS analyses were from Fluka (Buchs, Switzerland). MilliQ 18.2 MΩ water (Millipore, Bedford, MA, USA) was also used.
Standard of (−)-epicatechin was obtained from Sigma-Aldrich and (+)-catechin from Carl Roth (Karlsruhe, Germany). Standards of procyanidin B1, procyanidin B2, procyanidin B3, procyanidin C1, (−)-catechin gallate, (−)-gallocatechin, (−)-gallocatechin gallate, (−)-epicatechin gallate, (−)-epigallocatechin and (−)-epigallocatechin gallate were obtained from Extrasynthèse (Genay, France).
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7

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).
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8

Polyphenol Extraction and Characterization

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Chemicals: Anhydrous sodium carbonate, 37% hydrochloric acid, Folin and Ciocalteu's phenol reagent, DPPH (1,1-diphenyl-2picrylhydrazyl), Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2 -carboxylic acid) and toluene-a-thiol were purchased from Sigma-Aldrich (Saint-Quentin Fallavier, France). Polyphenol standards, gallic acid, chlorogenic acid, p-coumaric acid, (+)-catechin, (À)-epicatechin were from Sigma-Aldrich; quercetin-3-Oglucoside, quercetin-3-O-rhamnoside, quercetin-3-O-galactoside, procyanidin B2, procyanidin A2, (-)-epigallocatechin and cyanidin-3-O-galactoside were purchased from Extrasynthese (Genay, France); procyanidin C1 was extracted from apple fruits (Malus domestica Borkh.) of the Kermerrien variety as described previously (Watrelot, Renard, & Le Bourvellec, 2015) .
Solvents: 96% ethanol was purchased from S.C. Chemical Company (Iași, Romania), HPLC-MS grade methanol and acetonitrile from Fisher Scientific (Illkirch, France), formic acid from Merck (Darmstadt, Germany), and glacial acetic acid from Merck (Fontenay Sous Bois, France). Ultrapure water (resistivity 18.2 MX.cm À1 at 25 °C) was obtained with a Milli-Q water purification system (Millipore, Bedford, MA).
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