Preparation and characterization of catechin sulfates, glucuronides, and methylethers with metabolic interest.
Catechins are major polyphenols in many plant foods that have been related to health promotion. In the human organism they are largely metabolized to different conjugates (sulfates, glucuronides, and methylethers), which are further found in plasma and would contribute to the biological effects associated with the intake of the parent compounds. Circulating metabolites are likely to possess biological properties different from those of the original compounds, and therefore, it is important to evaluate their activity, for which sufficient amounts of them are required that cannot be obtained by isolation from biological fluids. This paper describes the preparation of the methyl, sulfate, and glucuronide derivatives of catechins using different chemical syntheses and their characterization by HPLC-DAD-ESI/MS. MS2 fragmentation of the compounds was also described that allowed the determination of the location of the different substituents on the catechin aglycones. The procedures optimized allowed the preparation of (epi)catechin sulfates, glucuronides, and methylethers conjugated at positions 3' and 4', as well as the sulfates at positions 5 and 7 with satisfactory yields for their further isolation by semipreparative-HPLC in view of their use in in vitro/ex vivo assays.
González-Manzano
Susana
S
Unidad de Nutrición y Bromatología, Facultad de Farmacia, Universidad de Salamanca, Campus Miguel de Unamuno, E-37007, Salamanca, Spain.
González-Paramás
Ana
A
Santos-Buelga
Celestino
C
Dueñas
Montserrat
M
D002392:Catechin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004987:Ethers / Q000138:chemical synthesis*; D020719:Glucuronides / Q000138:chemical synthesis*; D008745:Methylation; D021241:Spectrometry, Mass, Electrospray Ionization; D013463:Sulfuric Acid Esters / Q000138:chemical synthesis*
D004987:Ethers; D020719:Glucuronides; D013463:Sulfuric Acid Esters; C466639:catechin sulfate; D002392:Catechin