Eriodictyol

Organic solvents such as methanol (MeOH), acetonitrile (ACN), dimethyl sulfoxide (DMSO) were obtained from J.T. Baker (Deventer, The Netherlands). Milli-Q system (Millipore Corp., Billerica, MA, USA) ultra-pure water was used throughout this experiment. All chemicals and reagents were of analytical grade. The following chemicals were purchased from Sigma-Aldrich (St. Louis, MO, USA): butylhydroxytoluene (BHT); ethylenediaminetetraacetic acid (EDTA); apigenin (≥97%); hesperidin; hesperetin and rutin (≥95%). The flavanone standards eriocitrin, eriodictyol, homoeriodictyol, and narigenin were purchased from Extrasynthese (Genay, France). The metabolites hesperetin 7-O-glucuronide, hesperetin 3′-O-glucuronide, hesperetin 3-O-sulfate were obtained from Villapharma Research S.L. (Fuente Alamo, Murcia, Spain), and naringenin 4′-O-glucuronide and naringenin 7′-O-glucuronide from Bertin Pharma (Montigny le Bretonneux, France).

The following materials were purchased from the suppliers indicated in parentheses: chlorogenic acid (MP Biomedicals); gossypetin (Indofine Chemical Company); butein, eriodictyol, formononetin, herbacetin, isorhamnetin, kaempferol, myricetin, and quercetin (Extrasynthèse); daidzein and genistein (LC Laboratories); vestitol (Plantech); apigenin, biochanin A, coniferyl alcohol, o-coumaric acid, m-coumaric acid, coumestrol, 5-hydroxyferulic acid, luteolin, naringenin, phloretic acid, sinapic acid, and umbelliferone (Merck); p-coumaric acid, erythronic acid, isoferulic acid, and succinic anhydride (TCI); caffeic acid, trans-cinnamic acid, 3,4-dimethoxycinnamic acid, ferulic acid, p-methoxycinnamic acid, phenylalanine, tetronic acid, and L-tyrosine (FUJIFILM Wako Pure Chemical). Umbellic acid was prepared from umbelliferone by a treatment with 1 M NaOH at 90°C for 1 h. Isoliquiritigenin was obtained from our laboratory stock (Shimamura et al., 2007 (link)).

The phytochemicals were obtained as follows. Chrysoeriol (1104S), 6-O-Me-luteolin (520-11-6), 7,4′-dihydroxyflavone (1259), datiscetin (1141S), eriodictyol (0056), flavonol (1026), homoeriodictyol (1118S), isorhamnetin-3G (1228), isorhamnetin (1120S), kaempferol-3G (1243G), luteolin-7G (1126S), quercetin-3G (0074), quercetagetin (1030), rhamnetin (1136S), tamarixetin (1140S), and tricetin (1335S) were obtained from Extrasynthese (Genay, France); 2,2′,4′-trihydroxychalcone (T502), 4,2′,5′-trihydroxychalcone (22-314), and gossypetin (G500) were purchased from INDOFINE Chemical Company Inc. (Hillsborough, NJ, USA). Flavone (16012-31), morin (23416-31), and pyrogallol (29703-52) were obtained from Nacalai Tesque Inc. (Kyoto, Japan). EGCG (E4268), hyperoside (00180585-25MG), and phloroglucinol (79330-25G) were purchased from Sigma-Aldrich (St. Louis, MO, USA); 1,2,4-trihydroxybenzene, daidzin, piceid, rutin, and tangeretin were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan); 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, cyanidin, hesperetin, and sudachitin were purchased from FUJIFILM Wako Pure Chemical Corporation. Zerumbone was obtained from Adipogen Life Sciences (San Diego, CA, USA). Other phytochemicals were from natural compound libraries (S990043-NAT1/NAT2) purchased from Sigma-Aldrich (St. Louis, MO, USA).

Isoliquiritigenin, butein, apigenin, luteolin, naringenin, eriodictyol, dihydrokaempferol, dihydroquercetin, marein, maritimein, peonidin and cyanidin were purchased from Extrasynthese (Genay, France). Okanin and maritimetin were obtained from marein and maritimein by enzymatic hydrolysis, as described previously [32 (link)]. Lutein (≥95%) and β-carotene (≥98%) were obtained from Extrasynthese (Genace, France). For HPLC mobile phases, acetonitrile hypergrade LC-MS (and formic acid 98–100% and ultra-pure water (Type 1, Direct-Q^® 3UV)) were purchased from Merck (Darmstadt, Germany). NADPH was purchased from LabConsulting (Vienna, Austria).