3 5 di o caffeoyl quinic acid

Chicoric acid, chlorogenic acid, caffeic acid, catechin, epicatechin, rosmarinic acid, ferulic acid, rutin, vitexin, quercetin-3-O-glucoside, lutein, and β-carotene were obtained from Sigma (St. Louis, MO, USA). Quercetin-3-O-galactoside, kaempferol-7-O-glucoside, kaempferol-3-O-rutinoside, and 3,5-di-O-caffeoyl quinic acid were obtained from Extrasynthese (Genay, France). Methanol and formic acid (LC–MS grade) were obtained from Merck KGaA (Darmstadt, Germany). Ultrapure water was produced by a Milli-Q Gradient A10 water purification system. The purity of the standards was 98%, and all were prepared as initial stock solutions of 1 mg ml⁻¹ in Methanol. lutein and β-carotene stocks of 1 mg ml⁻¹ were prepared in chloroform. Multiple standards stock solutions were prepared as combinations of individual standard stock solutions with further dilutions made with Methanol to obtain standard calibration curves in the range of 0.01–5.0 mg L^-1.

HPLC grade acetonitrile, ethyl acetate, dichloromethane, hexane, and methanol were purchased from VWR International (Radnor, PA, USA). Kaempferol-3-O-rutinoside (35) and 3,5-di-O-caffeoylquinic acid (41) were purchased from Extrasynthèse (Genay, France). N-trans-p-coumaroyltyramine (48) was purchased from Phytolab GmbH & Co. KG (Vestenbergsgreuth, Germany). Chlorogenic acid (3-O-caffeoylquinic acid) (13), rutin (29), N-trans-feruloyltyramine (moupinamide) (49), dimethylsulfoxide (DMSO), camptothecin, (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), fetal bovine serum (FBS), and lipopolysaccharides (LPS from E. coli serotype O55:B5) were purchased from Sigma-Aldrich (Bornem, Belgium).

The reagents methanol and formic acid (LC-MS grade) were purchased from Merck KGaA (Darmstadt, Germany); β-carotene, chicoric acid, chlorogenic acid, caffeic acid, catechin, epicatechin, ferulic acid, lutein, quercetin-3-O-glucoside, rosmarinic acid, rutin and vitexin standards were purchased from Sigma (St. Louis, MO, USA) and 3,5-di-O-caffeoyl quinic acid, kaempferol-7-O-glucoside, kaempferol-3-O-rutinoside and quercetin-3-O-galactoside from Extrasynthese (Genay, France). A Milli-Q Gradient A10 water purification system (Merck Millipore, Darmstadt, Germany) was used to produce ultrapure water. The standards were 98% pure, prepared with methanol to form 1 mg mL⁻¹ initial stock solutions, while for lutein and β-carotene, chloroform was used to prepare the stocks of 1 mg mL⁻¹ as well. Then, in order to acquire standard calibration curves of 0.01–5.0 mg L⁻¹ span, individual standard stock solutions were combined to prepare multiple standards stock solutions by applying further dilutions made with methanol.