Eriodictyol

The 3T3-L1 preadipocytes were purchased from American Type Culture Collection (Manassas, VA, USA). Antibodies for C/EBPα (#8178), PPARγ (#2435), FAS (#3180), adiponectin (#2789), perilipin (#9349), p-AKT (#4060), AKT (#4691), Bim (#2933), β-catenin (#9582), pERK (#9101), ERK (#9102), p-p38 (#9211), p38(#9212), p-JNK (#9251), JNK (#9258), pAMPK (#2535), AMPK (#5831), IRS-1 (#3407), PARP (#9542), and β-actin (#5125) were purchased from Cell Signaling (Danvers, MA, USA), Antibodies for Bak (sc-832) was purchased from Santa Cruz Biotechnology (Santa Cruz, CA, USA). All chemicals including cell culture media were purchased from Fisher Scientific (Waltham, MA, USA), unless otherwise specified.
For the HPLC, the solvents (analytical grade) ethanol, methanol, acetonitrile, and glacial acetic acid were obtained from Fisher Scientific (Waltham, MA, USA). The analytical standards of luteolin, luteolinidin, apigenin, kaempferol, catechin, and epicatechin were obtained from Indofine Chemical Company (Hillsborough, NJ, USA); eriodictyol and apigenidin were obtained from Sigma-Aldrich (St. Louis, MO, USA); 7-methoxy apigenidin was obtained from Cayman Chemicals (Ann Harbor, MI, USA); naringenin was obtained from SAFC (Lenexa, KS, USA); the p-coumaric acid, caffeic acid, ferulic acid, vanillic acid, and chlorogenic acid were obtained from MP (Santa Ana, CA, USA).

The chemicals and reagents used in this study were of analytical grade (purity >99.8%) and were used as obtained. HPLC-grade water, acetonitrile, methanol, and sulfuric acid were purchased from Fisher Scientific (Pittsburgh, PA, United States). The remaining chemicals and reagents, including luteolin, apigenin, luteolinidin, apigeninidin, eriodictyol, catechin, gallic acid, L-ascorbic acid, formic acid, anhydrous sodium carbonate (Na₂CO₃), vanillin, Folin–Ciocalteu phenol reagent, potassium ferricyanide, trichloroacetic acid, ferric chloride, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS), and 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid were ordered from Sigma-Aldrich (St. Louis, MO, United States).

All standards and reagents were LC-MS grade and were used without any further treatments. Authentic standards of 2,5-Dihydroxybenzoic acid (gentisic acid), 3,4-dihydroxybenzoic acid (protocatechuic acid), 4-hydroxybenzoic acid, cinnamic acid, epicatechin, eriodictyol, ferulic acid, gallic acid, myricetin, p-coumaric acid, pinoresinol, quercetin, resveratrol, rosmarinic acid, salicylic acid, syringic acid, taxifolin, and vanillic acid were purchased from Sigma-Aldrich (Stenheim, Germany). Apigenin, caffeic acid, catechin, ethyl vanillin (internal standard, IS), galangin, genistein, naringenin, tyrosol, and vanillin were acquired from Alfa Aesar (Karlsruche, Germany), whereas hydroxytyrosol and luteolin were obtained from Santa Cruz Biotechnology (Santa Cruz, CA, USA).
2-Propanol (LC–MS grade) and methanol (MeOH) (LC–MS grade) were purchased from Fisher Scientific (Geel, Belgium) and Merck (Darmstadt, Germany), respectively. Formic acid 99%, ammonium acetate and sodium hydroxide monohydrate for trace analysis ≥ 99.9995% were all obtained from Fluka (Buchs, Switzerland). Ultrapure water (18.2 MΩ resistivity) was provided by a Millipore Direct-Q UV purification System (Millipore, Bedford, MA, USA). The wine samples were filtered using regenerated cellulose syringe filters (RC filters, pore size 0.2 μm, diameter 15 mm) purchased from Phenomenex (Torrance, CA, USA).

Reagents: Folin-Ciocalteu, sodium persulfate, gallic acid (GA), BHT, 2,2′-azinobis-3-ethylbenzothiazoline-6-sulphonic acid, diammonium salt (ABTS), Trolox, ferrous chloride, and 2,2-diphenyl-1-picrylhydrazyl (DPPH), were purchased from Sigma-Aldrich (Athens, Greece); 2,4,6-Tris (2-pyridyl)-s-triazine (TPTZ) was purchased from Fluka Chemica (Athens, Greece). Dimethylsulfoxide (DMSO), (Merck KGaA, Darmstaadt, Germany) was used as a solvent. Water was obtained from a Milli-Q water purification system (TGI Pure Water Systems, Topway Global, Greenville, SC, USA). Lichrosolv hypergrade for LC-MS acetonitrile was supplied by Merck (Darmstadt, Germany). Water (18.2 MΩ) was from a Milli-Q water system (Millipore, Bedford, MA, USA). Acetic acid was from LGC Standards (Middlesex, UK). Eighteen standard phenolic compounds were used (gallic acid, protocatechuic acid, HydroxyTyrosol, 4-hydroxybenzoic acid, chlorogenic acid, gentisic acid, caffeic acid, vanillic acid, syringic acid, p-coumaric acid, rutin, ferulic acid, trans-m-hydroxycinnamic acid, o-coumaric acid, salicylic acid, luteolin, eriodictyol and cinnamic acid) purchased from Sigma Aldrich.

Ultra-pure water (18 mΩ) was obtained from a Milli-Q water purification system (Millipore Co., Ltd., Milford, MA, USA). High-performance liquid chromatography (HPLC)-grade methanol, acetic acid, and 56 analytical standards, including catechinic, scopolin, chlorogenic acid, epicatechinic, vanillic acid, caffeic acid, purerarin, syringic acid, daidzin, glycitin, scopoletin, eriocitrin, umbelliferone, p-coumaric acid, dihydroquercetin, sinapic acid, genistin, liquiritin, ferulic acid, salicylic acid, rutin, isoferulic acid, m-coumaric acid, naringin, hesperidin, resveratrol, xanthotoxol, silydianin, sinapyl alcohol, o-coumaric acid, liquiritigenin, kaempferol, 2’-hydroxygenistein, eriodictyol, daidzein, psoralen, glycitein, quercetin, didymin, bergaptol, naringenin, luteolin, cinnamic_acid, hesperetin, genistein, bergapten, diosmetin, isoliquiritigenin, coumestrol, sinensetin, formononetin, medicarpin, imperatorin, biochanin A, tangeretin, and rotenone (displayed in Table S2), were purchased from Sigma-Aldrich Co., Ltd. The stock solutions of these authentic standards were 10.0 mg of each standard dissolved in 10 mL methanol. Then, the stock solutions were diluted to various concentrations before analysis. All stock solutions were sealed with Parafilm^® and stored in a −20 °C freezer.

Dulbecco's modified Eagle's medium (DMEM) was purchased from Gibco BRL. 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT) were obtained from AppliChem. PMA, LPS, DHR123, DMSO, Eriodictyol, Naringenin, and Pinocembrin were bought from Sigma‐Aldrich. Fetal bovine serum (FBS) and antibiotics were supplied by Biological Industries.

Bark of Brunfelsia grandiflora was collected from the native community of Canaán de Cachiyacú, Contamana district, Ucayali province, Loreto region (Peru). All solvents and reagents were of analytical grade unless otherwise stated. Gallic acid, 3,4-dihydroxyphenylpropionic acid, 4-hydroxy-3-methoxyphenylpropionic acid, 3- and 4-hydroxybenzoic acids, 4-hydroxyphenylacetic acid, protocatechuic acid, 4-hydroxyphenylpropionic acid, 4-hydroxy-3-methoxyacetic acid (homovanillic acid), 5-caffeoylquinic acid, caffeic acid, ferulic acid, p-coumaric acid, sinapic acid, gallocatechin, hesperetin, eriodictyol, naringenin, isorhamentin, 2,2-diphenyl-1-picrylhydrazyl (DPPH), and trolox (6-hydroxy-2,5,7,8-tetramethylchromo-2-carboxylic acid) (97%) were acquired from Sigma-Aldrich (Madrid, Spain). Formic acid and acetonitrile (HPLC grade) were acquired from Panreac (Madrid, Spain).