Quercetin 3 o glucoside

Formic acid, methanol, AA (L(+) ascorbic acid), AAPH (2,2′-azobis(2-amidinopropane)hydrochloride), MC540 (merocyanine 540), and enzyme COX-2 (cyclo-oxygenase) were purchased from Sigma-Aldrich (Steinheim, Germany). Acetonitrile was purchased from Merck (Darmstadt, Germany). Quercetin-3-O-glucoside, quercetin 3-O-galactoside, quercetin-3-O-rutinoside, (+)catechin, (−)epicatechin, procyanidin B2-3-O-gallate, procyanidin B3, vitexin, and luteolin-3-O-glucoside were purchased from Extrasynthese (Lyon, France). The DPH-PA (3-(4-(6-phenyl)-1,3,5-hexatrienyl) phenylpropionic acid), Laurdan ((6-dodecanoyl-2-dimethylaminonaphthalene)), and DPH (1,6-diphenyl-1,3,5-hexatriene) fluorescence probes were purchased from Life Technologies (California, USA).

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.

Acetonitrile, formic acid, methanol, ABTS (2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), 2,4,6-tri(2-pyridyl)-s-triazine (TPTZ), 2,2-Di(4-tert-octylphenyl)-1-picrylhydrazyl (DPPH), methanol, acetic acid, phosphate buffered saline (pH 7.4), LOX Activity Assay kit, AChE Assay kit, α-amylase from porcine pancreas, α-glucoamylase from Rhizopus sp., lipase from porcine pancreas, trini-trobenzenesulfonic acid, NaH₂PO₄, and 3,5-dini-trosalicylic acid were purchased from Sigma-Aldrich (Steinheim, Germany). COX Inhibitor Screening Assay Kit was purchased from Cayman (No. 560131; Ann Arbor, MI, USA). (−)-Epicatechin, (+)-catechin, chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, dicaffeic acid, procyanidin A2, procyanidin B2, p-coumaric acid, caffeic acid, 4-caffeoylquinic, kampferol-3-O-galactoside, quercetin-3-O-rutinoside, quercetin-3-O-galactoside, quercetin-3-O-glucoside, cyanidin-3-O-arabinoside, cyanidin-3-O-xyloside, cyanidin-3-O-galactoside, and cyanidin-3-O-glucoside were purchased from Extrasynthese (Lyon, France). Acetonitrile for ultra-performance liquid chromatography (UPLC; gradient grade) and ascorbic acid were from Merck (Darmstadt, Germany). The carriers (30%) applied to produce powders were maltodextrin DE (20–40) and inulin (Beneo-Orafti, Belgium).

1,1-Diphenyl-2-picrylhydrazyl radical (DPPH); 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox); 2,4,6-tri(2-pyridyl)-s-triazine (TPTZ), dimethyl sulfoxide (DMSO), FeCl₃, acetonitrile, formic acid, sweroside (S), and secologanin (SLo) were acquired from Sigma-Aldrich (Steinheim, Germany). Acetic acid was obtained from Chempur (Piekary Śląskie, Poland). acetonitrile for LC–MS was purchased from POCh (Gliwice, Poland). Cyanidin 3-O-glucoside (Cy 3-glc) and p-coumaric acid (p-CuA), caffeic acid (CA), ferulic acid (FA), quercetin 3-O-glucoside, luteolin 7-O-glucoside (Lglc), luteolin 7-O-rutinoside, diosmin, hesperidin, naringin, rutin, (+)-catechin, (−)-epicatechin, procyanidin B1, loganic acid (LA), and loganin (Lo) were purchased from Extrasynthese (Lyon Nord, France). 5-O-caffeoylquinic acid (5-CQA, chlorogenic acid), 3-O-caffeoylquinic acid (3-CQA, neochlorogenic acid), and 4-O-caffeoylquinic acid (4-CQA, cryptochlorogenic acid) were purchased from TRANS MIT GmbH (Giessen, Germany). All reagents were of analytical grade.

All reagents and organic solvents were of analytical grade. Authentic standards of loganic acid, cyanidin 3-O-glucoside, p-coumaric acid, gallic acid, quercetin 3-O-glucoside, and kaempferol 3-O-glucoside were purchased from Extrasynthese (Genay Cedex, France). Trans-caftaric acid was purchased from the Cayman Chemical Company (Michigan, EUA, Ann Arbor, MI, USA). Trans-Coutaric acid was purchased from Merck (Darmstadt, Germany). Methanol, acetonitrile, and formic acid were obtained from POCh (Gliwice, Poland).

All reagents and organic solvents were of analytical grade. Authentic standards of loganic acid, cyanidin 3-O-glucoside, p-coumaric acid, gallic acid, quercetin 3-O-glucoside, kaempferol 3-O-glucoside were purchased from Extrasynthese (Genay, France). Trans-caftaric acid was purchased from Cayman Chemical Company (Michigan, EUA, Ann Arbor, MI, USA). Trans-coutaric acid was purchased from Merck (Darmstadt, Germany). Methanol, acetonitrile and formic acid were obtained from POCh (Gliwice, Poland).

Iridoids and anthocyanins were assayed using the method described earlier [18 (link)] with an HPLC system equipped with the UltiMate 3000 model photodiode array detector (Dionex, Germany). The Cadenza Imtakt column CD-C18 (75 4.6 mm, 5 μm) was used. The mobile phase was composed of solvents: A (4.5% aq. formic acid, v/v, Sigma-Aldrich, Germany) and B (100% acetonitrile, Sigma-Aldrich, Germany). Runs were monitored at wavelengths of 245 nm (iridoids and ellagic acid), 320 nm (phenolic acid), 360 nm (flavonols), and 520 nm (anthocyanins). Iridoids, phenolic acids, and anthocyanins were quantified as loganic acid, 5-caffeoylquinic acid, and cyanidin 3-O-glucoside, respectively. Flavonols were quantified as quercetin 3-O-glucoside and kaempferol 3-O-glucoside (Extrasynthese, France).