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Characterization of metabolites of hydroxycinnamates in the in vitro model of human small intestinal epithelium caco-2 cells.
J Agric Food Chem. 2003 Dec 31; 51(27):7884-91.JA

Abstract

Hydroxycinnamic acids are antioxidant phenolic compounds which are widespread in plant foods, contribute significantly to total polyphenol intakes, and are absorbed by humans. The extent of their putative health benefit in vivo depends largely on their bioavailability. However, the mechanisms of absorption and metabolism of these phenolic compounds have not been described. In this study, we used the in vitro Caco-2 model of human small intestinal epithelium to investigate the metabolism of the major dietary hydroxycinnamates (ferulate, sinapate, p-coumarate, and caffeate) and of diferulates. The appearance of metabolites in the medium versus time was monitored, and the various conjugates and derivatives produced were identified by HPLC-DAD, LC/MS, and enzyme treatment with beta-glucuronidase or sulfatase. Enterocyte-like differentiated Caco-2 cells have extra- and intracellular esterases able to de-esterify hydroxycinnamate and diferulate esters. In addition, intracellular UDP-glucuronosyltransferases and sulfotransferases existing in Caco-2 cells are able to form the sulfate and the glucuronide conjugates of methyl ferulate, methyl sinapate, methyl caffeate, and methyl p-coumarate. However, only the sulfate conjugates of the free acids, ferulic acid, sinapic acid, and p-coumaric acid, were detected after 24 h. The O-methylated derivatives, ferulic and isoferulic acid, were the only metabolites detected following incubation of Caco-2 cells with caffeic acid. These results show that the in vitro model system differentiated Caco-2 cells have the capacity to metabolize dietary hydroxycinnamates, including various phase I (de-esterification) and phase II (glucuronidation, sulfation, and O-methylation) reactions, and suggests that the human small intestinal epithelium plays a role in the metabolism and bioavailability of these phenolic compounds.

Authors+Show Affiliations

Institute of Food Research, Norwich Research Park, Colney, Norwich NR4 7UA, United Kingdom.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

14690369

Citation

Kern, Sandra M., et al. "Characterization of Metabolites of Hydroxycinnamates in the in Vitro Model of Human Small Intestinal Epithelium Caco-2 Cells." Journal of Agricultural and Food Chemistry, vol. 51, no. 27, 2003, pp. 7884-91.
Kern SM, Bennett RN, Needs PW, et al. Characterization of metabolites of hydroxycinnamates in the in vitro model of human small intestinal epithelium caco-2 cells. J Agric Food Chem. 2003;51(27):7884-91.
Kern, S. M., Bennett, R. N., Needs, P. W., Mellon, F. A., Kroon, P. A., & Garcia-Conesa, M. T. (2003). Characterization of metabolites of hydroxycinnamates in the in vitro model of human small intestinal epithelium caco-2 cells. Journal of Agricultural and Food Chemistry, 51(27), 7884-91.
Kern SM, et al. Characterization of Metabolites of Hydroxycinnamates in the in Vitro Model of Human Small Intestinal Epithelium Caco-2 Cells. J Agric Food Chem. 2003 Dec 31;51(27):7884-91. PubMed PMID: 14690369.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Characterization of metabolites of hydroxycinnamates in the in vitro model of human small intestinal epithelium caco-2 cells. AU - Kern,Sandra M, AU - Bennett,Richard N, AU - Needs,Paul W, AU - Mellon,Fred A, AU - Kroon,Paul A, AU - Garcia-Conesa,Maria-Teresa, PY - 2003/12/24/pubmed PY - 2004/3/6/medline PY - 2003/12/24/entrez SP - 7884 EP - 91 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 51 IS - 27 N2 - Hydroxycinnamic acids are antioxidant phenolic compounds which are widespread in plant foods, contribute significantly to total polyphenol intakes, and are absorbed by humans. The extent of their putative health benefit in vivo depends largely on their bioavailability. However, the mechanisms of absorption and metabolism of these phenolic compounds have not been described. In this study, we used the in vitro Caco-2 model of human small intestinal epithelium to investigate the metabolism of the major dietary hydroxycinnamates (ferulate, sinapate, p-coumarate, and caffeate) and of diferulates. The appearance of metabolites in the medium versus time was monitored, and the various conjugates and derivatives produced were identified by HPLC-DAD, LC/MS, and enzyme treatment with beta-glucuronidase or sulfatase. Enterocyte-like differentiated Caco-2 cells have extra- and intracellular esterases able to de-esterify hydroxycinnamate and diferulate esters. In addition, intracellular UDP-glucuronosyltransferases and sulfotransferases existing in Caco-2 cells are able to form the sulfate and the glucuronide conjugates of methyl ferulate, methyl sinapate, methyl caffeate, and methyl p-coumarate. However, only the sulfate conjugates of the free acids, ferulic acid, sinapic acid, and p-coumaric acid, were detected after 24 h. The O-methylated derivatives, ferulic and isoferulic acid, were the only metabolites detected following incubation of Caco-2 cells with caffeic acid. These results show that the in vitro model system differentiated Caco-2 cells have the capacity to metabolize dietary hydroxycinnamates, including various phase I (de-esterification) and phase II (glucuronidation, sulfation, and O-methylation) reactions, and suggests that the human small intestinal epithelium plays a role in the metabolism and bioavailability of these phenolic compounds. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/14690369/Characterization_of_metabolites_of_hydroxycinnamates_in_the_in_vitro_model_of_human_small_intestinal_epithelium_caco_2_cells_ L2 - https://doi.org/10.1021/jf030470n DB - PRIME DP - Unbound Medicine ER -