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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.
Org Biomol Chem. 2010 Nov 21; 8(22):5199-211.OB

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.

Authors+Show Affiliations

Nestlé Research Center, PO Box 44, CH-1000, Lausanne 26, Switzerland.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Clinical Trial
Journal Article

Language

eng

PubMed ID

20842300

Citation

Fumeaux, René, et al. "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." Organic & Biomolecular Chemistry, vol. 8, no. 22, 2010, pp. 5199-211.
Fumeaux R, Menozzi-Smarrito C, Stalmach A, et al. 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. Org Biomol Chem. 2010;8(22):5199-211.
Fumeaux, R., Menozzi-Smarrito, C., Stalmach, A., Munari, C., Kraehenbuehl, K., Steiling, H., Crozier, A., Williamson, G., & Barron, D. (2010). 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. Organic & Biomolecular Chemistry, 8(22), 5199-211. https://doi.org/10.1039/c0ob00137f
Fumeaux R, et al. 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. Org Biomol Chem. 2010 Nov 21;8(22):5199-211. PubMed PMID: 20842300.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 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. AU - Fumeaux,René, AU - Menozzi-Smarrito,Candice, AU - Stalmach,Angelique, AU - Munari,Caroline, AU - Kraehenbuehl,Karin, AU - Steiling,Heike, AU - Crozier,Alan, AU - Williamson,Gary, AU - Barron,Denis, Y1 - 2010/09/14/ PY - 2010/9/16/entrez PY - 2010/9/16/pubmed PY - 2011/2/8/medline SP - 5199 EP - 211 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 8 IS - 22 N2 - 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. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/20842300/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_ L2 - https://doi.org/10.1039/c0ob00137f DB - PRIME DP - Unbound Medicine ER -