Procyanidin c1

All chemicals, reagents, and standards used were either analytical or LC-MS grade reagents. The water was treated in a Milli-Q water purification system (Millipore, Bedford, MA, USA) before use. Gallic acid (purity ≥ 98% HPLC), procyanidin B1 (purity ≥ 90% HPLC), procyanidin B2 (purity ≥ 90% HPLC), procyanidin B3 (purity ≥ 95% HPLC), procyanidin C1 (purity ≥ 90% HPLC), catechin (purity ≥ 98% HPLC), chlorogenic acid (purity ≥ 95% HPLC), neochlorogenic acid (purity ≥ 98% HPLC), caffeic acid (purity ≥ 98% HPLC), vanillic acid (purity ≥ 97% HPLC), syringic acid (purity ≥ 98% HPLC), p-coumaric acid (purity ≥ 98% HPLC), epicatechin (purity ≥ 98% HPLC), ferulic acid (purity ≥ 99% HPLC), rutin (purity ≥ 94% HPLC), naringenin (purity ≥ 95% HPLC), quercetin 3-O-glucoside (purity ≥ 98% HPLC), kaempferol 3-O-glucoside (purity ≥ 90% HPLC), quercetin (purity ≥ 98% HPLC) and reagents for in vitro studies were purchased from Sigma-Aldrich (Milan, Italy).

Porcine pancreatic α-amylase, starch soluble from potato, α-glucosidase from Saccharomyces cerevisiae, p-nitrophenyl-α-D-glucopyranoside (PNPG), p-nitrophenol, maltose, acarbose, bovine serum albumin (BSA), fructose and aminoguanidine were purchased from Sigma-Aldrich (Seelze, Germany/St. Louis, MO, USA). The standard of chlorogenic acid hemihydrate (CHA), neochlorogenic acid (NCHA), cryptochlorogenic acid (CCHA), caffeic acid (CA), (–)-epicatechin (ECA), procyanidin C1 (PC1), isoquercitrin (IQ), rutin trihydrate (RT) were purchased from Sigma-Aldrich (St. Louis, MO, USA) or PhytoLab GmbH (Vestenbergsgreuth, Germany). The other standards of caffeoylmalic acid (CAD), procyanidin B2 (PB2), hyperoside (HP), quercitrin (QR), and quercetin 3-O-β-D-(2″-O-β-D-xylopyranosyl)galactopyranoside (QPH) were previously isolated form the leaves of C. bullatus or C. zabelii [50 (link)]. HPLC-grade solvents such as acetonitrile and phosphoric acid were from Avantor Performance Materials (Gliwice, Poland). All other reagents used in the quantitative study were of analytical grade and of the same origin as described elsewhere for the relevant tests [20 (link),21 (link)].

The following study analyzed the influence of the extracts obtained from raw and roasted cocoa beans (T. cacao L.) of Forastero variety harvested in Peru, added to the diet of laboratory rats. Cocoa beans were purchased from Barry Callebaut Polska Sp. z o.o. (Lodz, Poland). Standards of catechin (C), epicatechin (EC), epigallocatechin (EGC), gallic acid (GA), procyanidin B2 (PC B2), procyanidin C1 (PC C1), quercetin (Q), quercetin 3-O-glucoside (Q-Glu), quercetin 3-O-arabinoside (Q-Ara), quercetin 3-O-galactoside (Q-Gal), caffeine (CF), theobromine (TE), acetonitrile of HPLC grade (≥99.9 %), and formic acid for LC–MS (~98%) were all purchased from Sigma-Aldrich (St. Louis, MO, USA). All other chemicals were of analytical grade and reagents were prepared according to standard analytical procedures.

Phenolic compound standards: gallic acid, syringic acid, protocatechuic acid, caffeic acid, chlorogenic acid, naringenin, epicatechin, catechin, hesperetin, resveratrol, quercetin, rutin, ellagic acid, myricetin, kaempferol, luteolin, isorhamnetin, epigallocatechin, gallocatechin, gallocatechin gallate, epicatechin gallate, procyanidin A1, procyanidin A2, procyanidin B1, procyanidin B2, procyanidin C1, and corilagin were HPLC grade and purchased from Merck (St. Louis, MO, USA). Acetonitrile, formic acid, methanol, hexane, and water were HPLC/spectrum grade and purchased from Tedia (Fairfield, OH, USA). All other reagents and solvents used were analytical grade from Merck (St. Louis, MO, USA).

Commercial standards of derivatives of anthraquinones (aloe-emodin, aloe-emodin-8-Glu, emodin, emodin-8-Glu, rhein, rhein-8-Glu, chrysophanol, chrysophanol-8-Glu, physcion, sennoside-A, sennoside-B, sennoside-C, sennoside-D), stilbenes (resveratrol, pterostilbene, pinostilbene, piceatannol, astringin, polydatin, rhapontigenin, rhaponticin, isorhapontigenin, isorhaponticin, deoxyrhapontigenin, deoxyrhaponticin), phenolic acids (glucogallin, gallic-acid), flavones (vicenin-II, vicenin-III, apigenin-7-Glu), flavanones (pinocembrin, pinocembroside), chalcones (phloretin, phloridzin, trilobatin), and catechins (catechin, epicatechin, gallocatechin, procyanidin-B1, procyanidin-B2, procyanidin-B3, and procyanidin-C1), acetonitrile LC-MS grade, formic acid MS-grade, and tert-butanol were purchased from Merck (Darmstadt, Germany). Methanol, n-hexane, and n-butanol, all of analytical grade, were purchased from Fisher Chemical (Loughborough, UK). Ultrapure water was prepared using a Milli-Q water purification system (MerckMillipore). General reagents for bioassays were purchased from Sigma-Aldrich (a part of Merck KGaA, Darmstadt, Germany) and Cayman Chemicals (Ann Arbor, MI, USA). Reagents specific to cell culture, gene expression analyses, and cytokine profiling have been indicated below in the descriptions of the applied methods.