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8 protocols using salicylic

1

Simulated Gastrointestinal Digestion

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Pepsin from porcine stomach mucosa (250 U/mg), pancreatin (8 × USP) from porcine pancreas, porcine bile extract, mucin from porcine stomach-type II, albumin, resazurin, cysteine, peptone, yeast extract, pectin, xylan, gum arabic, potato starch, casein, glucose, and inulin were purchased from Sigma-Aldrich Chemical Co. (St. Louis, MO, USA). Phenolic compounds standards (2,4 dihydroxybenzoic, 3,4 dihydroxybenzoic, gallic, benzoic, caffeic, ferulic, p-coumaric, salicylic, rosmarinic, and 5-caffeoylquinic acids) were purchased from Sigma-Aldrich Chemical Co. All solvents were HPLC grade from Tedia (Fairfield, OH, USA). HPLC grade water (Milli-Q system, Millipore, Bedford, MA, USA) was used throughout the experiments.
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2

Phenolic Compounds Quantification Protocol

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Ethanol and sodium carbonate were purchased from Avantor Performance Materials Poland (Gliwice, Poland). Gallic, m-coumaric, o-coumaric, p-coumaric, caffeic, 5-O-caffeoylqunic, ferulic, isoferulic, vanillic, salicylic, 3-hydroxybenzoic, 4-hydroxybenzoic, protocatechuic, syringic, rosmarinic acid, quercitrin, apigenin 7-O-glucoside, eriocitrin, taxifolin, 3-O-methylquercetin, isorhamnetin, isorhamnetin-3-O-glucoside, luteolin, kaempferol, rutin, hyperoside, isoquercetin, sakuranetin, aluminum chloride, and LC–MS grade acetonitrile were purchased from Sigma-Aldrich Chemical Co. (St. Louis, Mo, USA). Folin–Ciocalteu reagent was supplied by Chempur (Piekary Śląskie, Poland). Quercetin was purchased from Fluka (Buchs, Switzerland). Catechin, naringenin 7-O-glucoside, eriodictyol, luteolin-7-O-glucoside, naringenin 7-O-glucoside, luteolin 3,7-diglucoside, nicotiflorin, narcissoside, gentisic, sinapic acid, and myricetin were provided by ChromaDex (Irvine, CA, USA). Astragalin, apigenin, naringenin, kaempferol-3-rutinoside, and tiliroside were supplied by Roth (Karlsruhe, Germany). LC–MS grade water was prepared using a Millipore Direct-Q3 purification system (Bedford, MA, USA).
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3

Quantifying Polyphenol Standards Analysis

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Standards of caffeic, gallic, ferulic, isoferulic, protocatechuic, 4-OH-benzoic, vanillic, p-coumaric, salicylic, and LC grade acetonitrile were purchased from Sigma–Aldrich Fine Chemicals (St. Louis, MO, USA). Gentisic and sinapic acids were from ChromaDex (Irvine, CA, USA). The LC grade water was prepared using a Millipore Direct-Q3 purification system (Bedford, MA, USA). Ethanol and methanol (reagent grade purity), used for the preparation of extracts, Folin-Ciocalteu reagents, and all analytical grade reagents were obtained from Avantor Performance Materials (Center Valley, PA, USA).
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4

Preparation of Deep Eutectic Solvents

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The following reagents were used for the preparation of DESs: as HBA: TBAC and 16-BAC with purity greater than 97%—(Sigma Aldrich, Buchs, Switzerland) and as HBD acids: salicylic, 3,5-dinitrobenzoic, 3,5-dinitrosalicylic, 4-chlorosalicylic, acetylsalicylic, 4-tert-butylbenzoic, 4-methylbenzoic, and 5-sulfosalicylic with purity greater than 98%—(Sigma Aldrich, Buchs, Switzerland). Glass was used as the reference material for contact angle measurement.
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5

Quantification of Phenolic Compounds and Antioxidant Activity

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Standards of gallic, protocatechuic, gentisic, 4-OH-benzoic, vanillic, caffeic, syringic, p-coumaric, ferulic, salicylic, veratric, synapic, 3-OH-cinnamic, rosmarinic acid and Trolox, 2,2-diphenyl-1-picrylhydrazyl radical (DPPH), ascorbic acid were purchased from Sigma–Aldrich Fine Chemicals (St. Louis, MO, USA). Ethanol, methanol and the Folin–Ciocalteu reagent were from POCH (Gliwice, Poland). All the chemicals were of analytical grade. LC grade methanol (MeOH) was purchased from J.T. Baker (Phillipsburg, USA). LC grade water was prepared using a Millipore Direct-Q3 purification system (Bedford, MA, USA). All colorimetric measurements were conducted on 96-well transparent microplates (Nunclon, Nunc, Roskilde, Denmark) using an Elisa Reader Infinite Pro 200F (Tecan Group Ltd., Männedorf, Switzerland).
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6

Phenolic Compound Extraction and Analysis

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Methanol, water and acetonitrile (HPLC grade), 2,2-Diphenyl-1-picrylhydrazyl (DPPH), 2,2′-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS), 2,4,6-Tris(2-pyridyl)-s-triazine (TPTZ), gallic, α-resorcylic, tyrosol, gentisic, p-hydroybenzoic, 2,6-dihydroxybenzoic, m-hydroxybenzoic, vanillic, salicylic, syringic, homovanillic, p-coumaric, m-coumaric, o-coumaric, ferulic, sinapic, caffeic, and chlorogenic acid were purchased from Sigma-Aldrich (St. Louis, MO, USA). All other chemicals used were of analytical grade.
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7

Analytical Characterization of Phenolic Compounds

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Methanol, water, acetic acid, ethyl acetate, acetonitrile (HPLC grade), orthophosphoric acid, citric acid, sodium hydrogen phosphate, sodium hydroxide, sodium carbonate, Folin–Ciocalteu’s phenol reagent, 2,2-diphenyl-1-picrylhydrazyl-hydrate (DPPH), 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS), 2,4,6tris(2-pyridyl)-s-triazine (TPTZ), gallic, α-resorcylic, tyrosol, gentisic, p-hydroybenzoic, 2,6-dihydroxybenzoic, m-hydroxybenzoic, vanillic, salicylic, syringic, homovanillic, p-coumaric, m-coumaric, o-coumaric, ferulic, sinapic, caffeic, and chlorogenic acid were purchased from Sigma-Aldrich (St. Louis, MO, USA). All other chemicals used were of analytical grade.
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8

Analysis of Phenolic Compounds

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Analytical standards (all with purity ≥ 95%) of caffeic, 5-O-caffeoylqunic, gallic, ferulic, isoferulic, homoGentisic, protocatechuic, 3-hydroxybenzoic, 4-hydroxybenzoic, rosmarinic, 3,4-dihydroxyphenylacetic, vanillic, syringic, m-coumaric, o-coumaric, p-coumaric, salicylic, 3,4-dimethoxycinnamic, α-resorcylic, β-resorcylic, γ-resorcylic, 3,5-dimethoxybenzoic acid, 3-O-methylquercetin, chrysin, isorhamnetin, kaempferol, luteolin, morin, prunetin, rhamnetin, sakuranetin, taxifolin, and LC grade acetonitrile, methanol were purchased from Sigma-Aldrich Fine Chemicals (St. Louis, MO, USA). Gentisic, sinapic, veratric acids, eriodictyol, myricetin and rhamnazin were from ChromaDex (Irvine, USA). Apigenin and naringenin were from Roth (Karlsruhe, Germany) and quercetin was from Fluka (Buchs, Switzerland). LC grade water was prepared using a Millipore Direct-Q3 purification system (Bedford, MA, USA).
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