Neochlorogenic acid

The compounds 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), 2,4,6-tri(2-pyridyl)-s-triazine (TPTZ), methanol, malic acid, oxalic acid, citric acid, isocitric acid, quinic acid, ferulic acid, galacturonic acid, and succinic acid were purchased from Sigma-Aldrich (Steinheim, Germany). On the other hand, (−)-epicatechin, (+)-catechin, procyanidin B2, chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, caffeic acid, dicaffeoylquinic acid, p-coumaric acid, myricetin, isoquercitrin, 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).

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).

Acetonitrile, formic acid, methanol, betulinic, oleanolic and ursolic acid, ABTS (2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid), 6-hydroxy-2,5,7,8-tetramethylchroman -2-carboxylic acid (Trolox), acetic acid, and phloroglucinol were purchased from Sigma-Aldrich (Steinheim, Germany). (−)-Epicatechin, (+)-catechin, chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, dicaffeic acid, procyanidin B2, p-coumaric acid, quercetin-3-O-galactoside, quercetin-3-O-rhamnoside, caffeic acid, caftaric acid, galloyl acid, and luteolin-3-O-galactoside were purchased from Extrasynthese (Lyon, France).

Dairy proteins were obtained from Ingredia Functional (Arras, France). Methanol used for analysis was HPLC grade and it was obtained from J.T. Baker (Deventer, The Netherlands). Orthophosphoric acid was also HPLC grade (>85%) and it was purchased from Fisher Scientific (Loughborough, UK). 4-dimethyl-amino-cinnamaldehyd, trolox, 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt, 2,2-diphenyl-1-picrylhydrazil and standards for HPLC analysis (rutin, quercetin, chlorogenic acid, p-coumaric acid, (−)-epicatechin) were products of Sigma-Aldrich (St. Louis, MO, USA). The standard of cyanidin-3-rutinoside was from Phytolab GmbH (Vestenbergsgreuth, Germany) and the standard of neochlorogenic acid was the product of Extrasynthese (Genay, France). Folin-Ciocalteu reagent and potassium persulfate were products of Kemika (Zagreb, Croatia). Neocuproine, cupric chloride and 2,4,6-tri(2-pyridyl)-s-triazine (TPTZ) were products of Acros Organic (Geel, Belgium). Sodium carbonate was bought from T.T.T. (Sveta Nedelja, Croatia) and hydrochloric acid (37%) from Carlo Erba Reagents (Sabadell, Spain).

CMC was purchased from CP Kelco (Äänekoski, Finland). Sucrose was a product of Gram-mol (Zagreb, Croatia). Trehalose was obtained from Hayashibara doo (Nagase group, Tokyo, Japan). Hydrochloric acid was from Carlo Erba Reagents (Sabadell, Spain). Sodium carbonate was from T.T.T. (Sveta Nedelja, Croatia). Folin–Ciocalteu reagent and potassium persulfate were from Kemika (Zagreb, Croatia). Trolox, 2,2-diphenyl-1-picrylhydrazil, 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt, and most of the standards used (rutin, quercetin, quercetin-3-D-glucoside, chlorogenic acid) were products of Sigma-Aldrich (St. Louis, MO, USA), while the standards of cyanidin-3-glucoside, cyanidin-3-galactoside, cyanidin-3-arabinoside, neochlorogenic acid, and quercetin-3-D-galactoside were products of Extrasynthese (Genay, France). Cupric chloride, neocuproine, and 2,4,6-tri(2-pyridyl)-s-triazine (TPTZ) were purchased from Acros Organic (Geel, Belgium). Methanol (HPLC grade) was from J.T. Baker (Deventer, Netherlands) and orthophosphoric acid (HPLC grade, >85%) was from Fisher Scientific (Longhborough, UK).

Acetonitrile, formic acid, methanol, ABTS (2,2′-azinobis-(3-ethylbenzothiazoline-6-sulphonic acid), Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid), TPTZ (2,4,6-Tri(2-pyridyl)-s-triazine), acetic acid phloroglucinol and eriodictyol were purchased from Sigma-Aldrich (Steinheim, Germany). (−)-Epicatechin, (+)-catechin, isoquercitrin, quercetin 3-O-glucoside, quercetin 3-O-galactoside, isorhamnetin 3-O-glucoside, chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, di-caffeic quinic acid, procyanidin B2, p-coumaric acid, caffeic acid, cyanidin-3-O-galactoside and cyanidin-3-O-glucoside were purchased from Extrasynthese (Lyon, France).

Formic acid (LC-MS grade) was obtained from Merck KGaA (Darmstadt, Germany). Acetonitrile (LC-MS grade) and methanol (LC-MS grade) were purchased from VWR International Srl (Milan, Italy). Liquid nitrogen was purchased from Rivoira (Milan, Italy). Sodium fluoride, phosphoric acid, glacial acetic acid, TPTZ, ABTS, iron (III) chloride hexahydrate, Trolox, potassium chloride, (+)-catechin, sodium carbonate, F-C reagent, quercetin-3-xyloside, 3,4-dihydroxybenzoic acid, naringenin-7-glucoside, and phloridzin were purchased from Sigma–Aldrich (St. Louis, MO, USA). Quercetin-3-rutinoside and potassium peroxydisulfate were purchased from Roth (Karlsruhe, Germany). Quercetin-3-glucoside, neochlorogenic acid, cryptochlorogenic acid, cyanidin-3-galactoside chloride, and malvidin-3-glucoside chloride were purchased from Extrasynthese (Genay, France).
(−)-Epicatechin, procyanidin B1, procyanidin B2, procyanidin C1, chlorogenic acid, cyanidin-3-glucoside chloride, cyanidin-3-arabinoside chloride, phloretin, quercetin-3-arabinoside, quercetin-3-galactoside, quercetin-4’-glucoside, and quercetin-3-rhamnoside were purchased from Phytolab (Vestenbergsgreuth, Germany). Sodium acetate anhydrous was purchased from CHEMSOLUTE^® (Renningen, Germany). Hydrochloric acid from Fisher Chemical (Pittsburgh, UK). Deionized water was from MilliQ apparatus (Millipore Corp., Bedford, MA, USA).