Quercetin 3 o rutinoside

The following HPLC- or LC-MS-grade reagents were used for analyses: acetonitrile, L-ascorbic acid, methanol (Sigma-Aldrich, Poland), acetic acid (Baker, Poland), and formic acid (VWR Int., Poland). The qualitative and quantitative content of polyphenolic compounds was determined with the following standards: 3,4-dihydroxybenzoic acid, 4-hydroxybenzoic acid, chlorogenic acid, caffeic acid, gallic acid, isovanilic acid, kaempferol, luteolin, neochlorogenic acid, orientin (luteolin-8-glucoside), p-coumaric acid, procyanidin B2, quercetin, quercetin-3-O-glucoside (Sigma-Aldrich, Poland), (+)-catechin, (–)-epicatechin, quercetin-3-O-galactoside, quercetin-3-O-rutinoside, quercetin-3-O-vicianoside (Extrasynthese, France), cyanidin-3-O-arabinoside, cyanidin-3-O-galactoside, cyanidin-3-O-glucoside (Polyphenols Laboratories AS, Norway) and cyanidin-3-O-xyloside (Toronto Research Chemicals, Canada).

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).

Chemical reagents (acetonitrile, L-ascorbic acid, methanol, acetic acid, and formic acid) were purchased from Sigma-Merck, Poznań, Poland. For the qualitative and quantitative content of polyphenols the following standards were used: gallic acid, caffeic acid, isovanilic acid, chlorogenic acid, neochlorogenic acid, p-coumaric acid, 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid, orientin (luteolin-8-glucoside), quercetin, quercetin-3-O-glucoside, procyanidin B2, luteolin, kaempferol (Sigma-Aldrich, Poznań, Poland), cyanidin-3-O-glucoside, cyanidin-3-O-galactoside, cyanidin-3-O-arabinoside (Polyphenols Laboratories AS, Sandnes, Norway), cyanidin-3-O-xyloside (Toronto Research Chemicals, North York, ON, Canada), quercetin-3-O-galactoside, quercetin-3-O-vicianoside, quercetin-3-O-rutinoside, (+)-catechin and (−)-epicatechin (Extrasynthese, Genay, France). All other chemicals were of analytical grade.

Water soluble samples of olive leaf extract (OLE) from Olea europaea L. standardized in 30% of ortho-diphenols by UV/Vis were provided by Pharmactive Biotech Products S.L. (Madrid, Spain). All of them were in powder form and were stored in darkness until their addition into the feeding bottles.
For High Performance Liquid Chromatography (HPLC) analysis, milli-Q grade water was produced in house by a Milli-Q purification system (Millipore Corp., Bedford, MA, USA). Acetonitrile and methanol (HPLC solvents) were purchased from Merck (Dramstadt, Germany), and acetic acid from Labbox Labware SL (Madrid, Spain). For peak identification, the following reference substances were used: the HPLC grade 3,4-DHBA (protocatechuic acid) (> 97%), 3,4-DHPE (hydroxytyrosol, > 98%), 4-HPE (tyrosol, 98%), 3,4-DHPE-EA-glucoside (oleuropein, > 98%), and verbascoside (> 99%) were from Merck (Dramstadt, Germany). The 3,4-DHPE-DA-EDA (oleacein), quercetin-3-O-rutinoside (rutin), quercetin-3-O-glucoside, apigenin-7-O-rutinoside, luteolin and apigenin were from Extrasynthèse (Genay, France).

Methanol and formic acid were from Sigma-Aldrich (Steinheim, Germany). Acetonitrile was from Merck (Darmstadt, Germany). (−)-Epicatechin, (+)-catechin, procyanidin B2 chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, di-caffeic quinic acid, p-coumaric acid, quercetin-3-O-galactoside, quercetin-3-O-glucoside, quercetin-3-O-rutinoside, isorhamnetion-3-O-rutinoside, isorhamnetion-3-O-glucoside, eriodictyol 7-O-glucuronide, cyanidin-3-O-galactoside, cyanidin-3-O-glucoside, cyanidin-3-O-arabinoside and cyanidin-3-O-xyloside were purchased from Extrasynthese (Lyon, France).

All solvents used (methanol, acetonitrile, acetic acid, water and ethyl acetate) were HPLC-grade and were purchased from Merck (Darmstadt, Germany). Protocatechuic acid, 4-hydroxybenzoic acid, vanillic acid, chlorogenic acid, trans-p-coumaric acid, eriodictyol-7-O-glucoside, eriodictyol, naringenin, naringenin-7-O-glucoside, kaempferol-3-O-rutinoside, kaempferol-3-O-glucoside, isorhamnetin-3-O-glucoside, quercetin, kaempferol, isorhamnetin, quercetin-3-O-rutinoside, quercetin-3-O-galactoside, quercetin-3-O-glucoside, isorhamnetin-3-O-rutinoside, catechin and epicatechin were purchased from Extrasynthese (Genay, France). Other chemicals were of analytical grade.

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).