title: First chemical synthesis and in vitro characterization of the potential human metabolites 5-o-feruloylquinic acid 4'-sulfate and 4'-O-glucuronide.
abstract: Feruloylquinic acids are a major class of biologically active phenolic antioxidants in coffee beans, but their metabolic fate is poorly understood. The present study investigated the phase II metabolism of feruloylquinic acids with selected human sulfotransferases (SULT1A1 and SULT1E1) and uridine 5'-diphosphoglucuronosyltransferases (UGT1A1 and UGT1A9). For unequivocal metabolite identification, the chemical synthesis of two potential human metabolites of 5-O-feruloylquinic acid, the 4'-sulfated and 4'-O-glucuronidated conjugates, has been performed for the first time. Following incubation with human SULT1A1 or SULT1E1, formation of 5-O-feruloylquinic acid 4'-O-sulfate was confirmed by matching its HPLC and MS data with those of the authentic standard. On the other hand, no glucuronide conjugates were detected after incubation with human uridine 5'-diphosphoglucuronosyltransferases. These results suggest that sulfation can take place on the ferulic acid moiety of feruloylquinic acids and may be a major metabolic pathway for feruloylquinic acids in humans.
authors.affiliation: Nestlé Research Center, Lausanne, Switzerland.
authors.forename: Candice
authors.initials: C
authors.lastname: Menozzi-Smarrito
authors.forename: Chi Chun
authors.initials: CC
authors.lastname: Wong
authors.forename: Walter
authors.initials: W
authors.lastname: Meinl
authors.forename: Hansruedi
authors.initials: H
authors.lastname: Glatt
authors.forename: René
authors.initials: R
authors.lastname: Fumeaux
authors.forename: Caroline
authors.initials: C
authors.lastname: Munari
authors.forename: Fabien
authors.initials: F
authors.lastname: Robert
authors.forename: Gary
authors.initials: G
authors.lastname: Williamson
authors.forename: Denis
authors.initials: D
authors.lastname: Barron
mesh_terms: D015239:Arylsulfotransferase / Q000378:metabolism*; D003373:Coumaric Acids / Q000378:metabolism; D020719:Glucuronides / Q000138:chemical synthesis* / Q000378:metabolism; D014453:Glucuronosyltransferase / Q000378:metabolism*; D006801:Humans; D011801:Quinic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D011994:Recombinant Proteins / Q000378:metabolism; D015238:Sulfotransferases / Q000378:metabolism*; D000090264:UDP-Glucuronosyltransferase 1A9; D000099148:UGT1A1 Enzyme
chemical_list: D015239:Arylsulfotransferase; D003373:Coumaric Acids; D020719:Glucuronides; D014453:Glucuronosyltransferase; D011801:Quinic Acid; D011994:Recombinant Proteins; D015238:Sulfotransferases; D000090264:UDP-Glucuronosyltransferase 1A9; D000099148:UGT1A1 Enzyme; C561252:5-O-feruloylquinic acid 4'-O-glucuronide; C561253:5-O-feruloylquinic acid 4'-sulfate; C000715591:UGT1A9 protein, human; C004999:ferulic acid; C117544:SULT1A1 protein, human; C020122:estrone sulfotransferase