Eriocitrin

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).

HPLC-grade acetonitrile and DMSO were obtained by Sigma-Aldrich (St. Louis, MO, USA). Vicenin-2, hesperidin, eriocitrin, narirutin, sinensetin, nobiletin, and tangeretin were supplied from Extrasynthèse (Genay, France). Lucenin-2 4′-methylether and orientin 4′-methyl ether were separated from Citrus limetta and Citrus bergamia [14 (link),15 (link)] and used as standards. The Iso-Disc P-34, 3 mm diameter PTFE membrane (0.45 μm pore size) was from Supelco (Bellefonte, PA, USA). All the other reagents and chemicals employed in this study were of analytical grade and were purchased from Sigma (St. Louis, MO, USA).

All the solvents used for plant extraction and quantitative HPLC analysis were of analytical grade and supplied by Merck Millipore, S.A. Acetonitrile and acetic acid were supplied by Sigma-Aldrich (South Africa). Protocatechuic acid, p-coumaric acid, 3-β-D-glucopyranosyliriflophenone (IMG), hesperidin, mangiferin, and scolymoside were purchased from Sigma-Aldrich (South Africa). Eriocitrin was purchased from Extrasynthese (France) and vicenin-2 was purchased from Phytolab (Germany). Isomangiferin was purchased from Chemos GmbH (Germany). 3′,5′-Di-β-D-glucopyranosylphloretin (PDG) and 3-β-D-glucospyranosyl-4-β-D-glucopyranosyloxyiriflophenone (IDG) were isolated from Cyclopia subternata (unpublished results) and Cyclopia genistoides (Beelders et al., 2014 (link)), respectively. Castor oil, 17β-estradiol, and SOC endocrine drugs were purchased from Sigma-Aldrich. All reagents for the estimation of biochemical parameters were purchased from Horiba ABX Pentra (Montpellier, France).