Secoisolariciresinol

The phytoestrogen standards used in the analytical method were purchased from ExtraSynthese (Lyon, France), except for puerarin, equol and calycosin, which were obtained from TCI (Tokyo Chemical Industry; Tokyo, Japan), and calycosin-7-O-β-D-glucoside, lariciresinol, matairesinol and secoisolariciresinol, which were obtained from Biosynth Carbosynth (Compton, UK). The molecule of 2-(4-chlorophenyl) malonaldehyde, used as the internal standard (I.S.), was purchased from Sigma-Aldrich (St. Louis, MO, USA). Acetonitrile (ACN) and water (LC-MS grade) were purchased from J.T. Baker (Phillipsburg, NJ, USA), while the formic acid (LC-MS grade), dimethyl sulfoxide (DMSO) and analytical-grade solvents used for the sample extractions (acetonitrile, methanol and acetic acid) were obtained from Fischer Chemicals (Hampton, NH, USA). Magnesium sulphate anhydrous (MgSO₄) and sodium chloride (analytical grade) were obtained from Chem-Lab (Zedelgem, Belgium), while LiChroprep RP-C18 (40–63 µm) was provided by Merck (Rahway, NJ, USA).

The analytical grade solvents hexane, dichloromethane, and methanol were obtained from Fisher Chemicals (Hampton, NH, USA) and used for the extractions. The LC–MS/MS determinations were performed using water and acetonitrile purchased from J.T. Baker (Phillipsburg, NJ, USA) and formic acid provided by Fisher Chemicals, all of LC–MS grade quality. Potassium hydroxide (KOH) and boron trifluoride (BF₃) (14% in methanol) were obtained from Sigma-Aldrich (Burlington, MA, USA), and hydrochloric acid (HCl) was provided by Fluka (Long Island, NY, USA).
All polyphenol standards used for the analyses were purchased from ExtraSythese, except equol and puerarin which were obtained from TCI (Tokyo Chemical Industry, Tokyo, Japan), and calycosin, calycosin-7-O-β-d-glucoside, matairesinol, lariciresinol, and secoisolariciresinol, which were purchased from Biosynth Carbosynth (Gardner, MA, USA). The purity of all standards was >95%, expect 3′,4′,7-trihydroxyflavone, the purity of which was >90%. The 2-(4-chlorophenyl) malonaldehyde was provided by Sigma-Aldrich and used as an internal standard. All standards used for the fatty acids’ quantification analysis were included in the Supelco 37 Component FAME Mix from Sigma-Aldrich (St. Louis, MO, USA).

Analytical grade hexane, dichloromethane and methanol were obtained from Fisher Chemicals (Hampton, NH, USA) and used as extraction solvents. LC-MS grade solvents, water and acetonitrile were purchased from J.T. Baker (Phillipsburg, NJ, USA), while formic acid (LC-MS grade) was obtained from Fisher Chemicals. For the LC–MS/MS determinations (Hampton, NH, USA).
All standards used for the phytoestrogens’ quantification analysis were provided by ExtraSynthese (Genay, France), except equol and puerarin, which were obtained from TCI (Tocyo Chemical Industry, Zwijindrecht, Belgium), and calycosin, calycosin-7-O-β-D-glucoside, matairesinol, lariciresinol and secoisolariciresinol, which were purchased from Biosynth Carbosynth (Compton, United Kingdom). The purity of al standards was >95%, except 3′,4′,7-trihydroxyflavone (purity > 90%). The 2-(4-chlorophenyl) malonaldehyde molecules used as internal standard were obtained from Sigma-Aldrich (Burlington, MA, USA)). The standard used for the fatty acids’ quantification analysis was the Supelco 37 Component FAME Mix from Sigma-Aldrich.
Potassium hydroxide (KOH) and boron trifluoride (BF₃) (14% in methanol) were obtained from Sigma-Aldrich, and hydrochloric acid (HCl) was from Fluka (Buchs, Switzerland).