First synthesis, characterization, and evidence for the presence of hydroxycinnamic acid sulfate and glucuronide conjugates in human biological fluids as a result of coffee consumption

• DOI: 10.1039/c0ob00137f
• Publication Date: 2010-09-14T13:01:58Z
• Authors: René Fumeaux; Candice Menozzi-S...; Angelique Stalmach; Caroline Munari; Karin Kraehenbuehl; Heike Steiling; Alan Crozier; Gary Williamson; Denis Barron
• Keywords: Hydroxycinnamic acid; Glucuronide; Conjugate; Coumaric acid

A systematic investigation of the human metabolism hydroxycinnamic acid conjugates was carried out. set 24 potential metabolites coffee polyphenols has been chemically prepared, and used as analytical standards for unequivocal identifications. These included glucuronide sulfate esters caffeic, ferulic, isoferulic, m-coumaric p-coumaric acids well their dihydro derivatives. particular focus made on caffeic 3,4-dihydroxyphenylpropionic derivatives, especially conjugates, which regioselective preparation particularly challenging, have so far never identified metabolites. Ten out synthesized in plasma and/or urine after consumption. number these were synthesized, characterized detected first time. This case dihydroisoferulic 3′-O-glucuronide, 3′-sulfate, derivatives acid.