Jump to main content
Jump to site search

Issue 22, 2010
Previous Article Next Article

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

Author affiliations

Abstract

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

Graphical abstract: 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

Back to tab navigation

Supplementary files

Publication details

The article was received on 17 May 2010, accepted on 01 Jul 2010 and first published on 14 Sep 2010


Article type: Paper
DOI: 10.1039/C0OB00137F
Org. Biomol. Chem., 2010,8, 5199-5211

  •   Request permissions

    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

    R. Fumeaux, C. Menozzi-Smarrito, A. Stalmach, C. Munari, K. Kraehenbuehl, H. Steiling, A. Crozier, G. Williamson and D. Barron, Org. Biomol. Chem., 2010, 8, 5199
    DOI: 10.1039/C0OB00137F

Search articles by author

Spotlight

Advertisements