Isorhamnetin 3 o glucoside

Acetonitrile (hypergrade for LC–MS), formic acid (for LC–MS) and methanol (analytical grade) were purchased from Merck (Merck, Bulgaria). The reference standards used for compound identification were obtained from Extrasynthese (Genay, France) for p-coumaric, o-coumaric, ferulic acids, saponarin, homoorientin, orientin, rutin, isovitexin, isoquercitrin, luteolin 7-O-glucoside, kaempferol 3-O-rutinoside, kaempferol 3-O-glucoside, isorhamnetin 3-O-glucoside, apigenin 7-O-glucoside, quercetin, and apigenin. Chlorogenic and caffeic acids were supplied from Phytolab (Vestenbergsgreuth, Bavaria, Germany).

All the solvents, reagents, and standards used were of analytical grade and met all the set quality requirements. The following substances were used in the study: ethanol 96% (v/v) (AB “Stumbras”, Kaunas, Lithuania), the Folin–Ciocalteu reagent, sodium carbonate, gallic acid, acetic acid, ABTS (2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), Trolox (6-hydroxy-2,5,7,8-tetramethyl- chroman-2-carboxylic acid), potassium persulfate, copper (II) chloride, ammonia acetate, neocuproine, sodium acetate (Scharlau, Sentmenat, Spain), TPTZ (Carl Roth, Karlsruhe, Germany), iron (III) chloride hexahydrate (Vaseline-Fabrik Rhenania, Bonn, Germany), TFPH (trifluoperazine dihydrochloride), sulfuric acid, acetonitrile (Sigma-Aldrich, Steinheim, Germany), acetic acid (Lachner, Neratovice, Czech Republic); (+)-catechin, (-)-epicatechin, luteolin-7-o-glucoside, procyanidin C1, procyanidin A2, phloretin, kaempferol, rutin, hyperoside, quercitrin, phlorizin, avicularin, neochlorogenic acid, chlorogenic acid, isorhamnetin, ferulic acid, caffeic acid, gallic acid, vanillic acid, p-coumaric acid, hydrochloric acid, hexamethylentetramine, potassium chloride, aluminum chloride (Sigma-Aldrich), and isorhamnetin -3-O-glucoside (ExtraSynthese, Lyon, France).

Acetonitrile (hypergrade for LC–MS), formic acid (for LC–MS) and methanol (an-alytical grade) were purchased from Merck (Merck, Bulgaria). The reference standards used for compound identification were obtained from Extrasynthese (Genay, France) for gallic, protocatechuic, p-coumaric, m-coumaric, o-coumaric, vanillic, and salicylic acid, as well as luteolin 7-O-rutinoside, luteolin 7-O-glucoside, isorhamnetin 3-O-glucoside, apigenin 7-O-glucoside, and luteolin. Neochlorogenic, chlorogenic, caffeic, 3,4-dicaffeoylquinic, 3,5-dicaffeylquinic and 1,5-dicaffeoylquinic acids were supplied from Phytolab (Vesten-bergsgreuth, Bavaria, Germany).

Acetonitrile (hypergrade for LC–MS), formic acid (for LC-MS) and methanol (analytical grade) were purchased from Merck (Merck, Bulgaria). The authentic standards used for compound identification were obtained from Extrasynthese (Genay, France) for protocatechuic, syringic, vanillic gentisic, p-coumaric, m-coumaric, o-coumaric acid, quercetin, apigenin, luteolin, apigenin 7-O-glucoside, kaempferol 3-O-glucoside, isorhamnetin 3-O-glucoside, luteolin 7-O-glucoside and rutin, and kaempferol 3-O-rutinoside, homoorientin, isoquercitrin, hyperoside, nepetin. Caffeic acid, neoChlorogenic acid, 3,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, jaceosidin and hispidulin were supplied from Phytolab (Vestenbergsgreuth, Germany). Chlorogenic acid, isorhamnetin and cirsimaritin were purchased from Sigma-Aldrich (St. Louis, MO, USA).

Gallic (3), ellagic (38), protocatechuic (45), neochlorogenic (48), caffeic (49), chlorogenic (50), syringic acids (53), myricitrin (59), isoquercitrin (60), hyperoside (64), kaempferol 3-O-glucoside (67), quercitrin (68), isorhamnetin 3-O-glucoside (72), quercetin (77), myricetin (78), kaempferol (80), (+)-catechin (82), and prunin (87) were obtained from Extrasynthese (Genay, France). All reagents and solvents were of analytical grade.

Acetonitrile (hypergrade for LC-MS), formic acid (for LC-MS) and methanol (analytical grade) were purchased from Merck, Sofia, Bulgaria. The authentic standards used for compound identification were obtained from Extrasynthese (Genay, France) for protocatechuic, p-hydroxyphenylacetic, vanillic, gentisic, ferulic, p-coumaric, o-coumaric acid, rutin, hyperoside, luteolin 7-O-rutinoside, luteolin 7-O-glucoside, isoquercitrin, kaempferol 3-O-rutinoside, isorhamnetin 3-O-rutinoside, kaempferol 3-O-glucoside, isorhamnetin 3-O-glucoside, apigenin 7-O-glucoside, quercetin, apigenin, luteolin, chrysoeriolq eupatilin and genkwanin. Caffeic, 3,4-dicaffeoylquinic, 3,5-dicaffeoylquinic 1,5-dicaffeoylquinic, 4,5-dicaffeoylquinic and 3,4,5- tricaffeoylquinic acids were supplied by Phytolab (Vestenbergsgreuth, Germany). Chlorogenic acid and isorhamnetin were purchased from Sigma-Aldrich (St. Louis, MO, USA). Diclofenac, silymarin, collagenase, 1-chloro-2,4-dinitrobenzene, beta-nicotinamide adenine dinucleotide 2′-phosphate reduced tetrasodium salt (NADPH), ethylenediaminetetraacetic acid (EDTA), bovine serum albumin (fraction V) and 2,2′-dinitro-5,5′dithiodibenzoic acid (DTNB) were obtained from Merck (Darmstadt, Germany). Reduced glutathione (GSH), oxidized glutathione (GSSG), glutathionereductase (GR) and cumene hydroperoxide were purchased from Sigma Chemical Co. (Taufkirchen, Germany).

Low iron diet was obtained by Special Diet Service, UK. Pentobarbitone sodium (Pentoject) was obtained from Animalcare Ltd., UK. ⁵⁹Fe was obtained by PerkinElmer, USA. Quercetin-3,4′-di-O-glucoside, quercetin-3-O-glucuronide, isorhamnetin-3-O-glucoside and isorhamnetin were obtained by Extrasynthese, France. All other chemicals were purchased from Sigma-Aldrich, USA.