Gastrointestinal absorption and urinary excretion of trans-cinnamic and p-coumaric acids in rats

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 8, 2006, Pages 2944-2950

  Garrait, Ghislain ^a   Jarrige, Jean François ^a   Blanquet, Stéphanie ^a   Beyssac, Erick ^a   Cardot, Jean Michel ^a   Alric, Monique ^a,b  

^a CRNH AUVERGNE   (France)

^b UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

Gastrointestinal absorption; p coumaric acid; Rats; trans Cinnamic acid; Urinary excretion

Indexed keywords

4-COUMARIC ACID; CINNAMIC ACID DERIVATIVE; COUMARIC ACID; PARA COUMARIC ACID;

ANIMAL; ARTICLE; INTESTINE ABSORPTION; MALE; RAT; URINE; WISTAR RAT;

ANIMALS; CINNAMATES; COUMARIC ACIDS; INTESTINAL ABSORPTION; MALE; RATS; RATS, WISTAR;

EID: 33646513478     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf053169a     Document Type: Article

References (40)

1. Manach, C.; Scalbert, A.; Morand, C.; Remesy, C.; Jimenez, L. Polyphenols: Food sources and bioavailability. Am. J. Clin. Nutr. 2004, 79, 727-747.
2. Garcia-Conesa, M. T.; Plumb, G. W.; Waldron, K. W.; Ralph, J.; Williamson, G. Ferulic acid dehydrodimers from wheat bran: Isolation, purification and antioxidant properties of 8-O-4-diferulic acid. Redox Rep. 1997, 3, 319-323.
3. Andreasen, M. F.; Kroon, P.; Williamson, G.; Garcia-Conesa, M. T. Esterase activity able to hydrolyse dietary antioxidant hydroxycinnamates is distributed along the intestine of mammals. J. Agric. Food Chem. 2001, 49, 5679-5684.
4. Clifford, M. N.; Copeland, E. L.; Blosidge, J. P.; Mitchell, L. A. Hippuric acid as a major excretion product associated with black tea consumption. Xenobiotica 2000, 30, 317-326.
5. Salunkhe, D. K.; Chaven, J. K.; Kadam, S. S. Plant phenolics: Structure, classification, and biosynthesis. In Dietary Tannins: Consequences and Remedies; CRC Press: Boca Raton, FL, 1990; pp 5-28.
6. Radtke, J.; Linseisen, J.; Wolfram, G. Phenolic acid intake of adults in a Bavarian subgroup of the national food consumption survey. Z. Ernaehrungswiss. 1998, 37, 190-197.
7. Mattila, P.; Kumpulainen, J. Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection. J. Agric. Food Chem. 2002, 50, 3660-3667.
8. Ramanan, P. N.; Rao, M. N. Antimicrobial activity of cinnamic acid derivatives. Indian J. Exp. Biol. 1987, 25, 42-43.
9. Olasupo, N. A.; Fitzgerald, D. J.; Gasson, M. J.; Narbad, A. Activity of natural antimicrobial compounds against Escherichia coli and Salmonella enterica serovar Typhimurium. Lett. Appl. Microbiol. 2003, 37, 448-451.
10. Tawata, S.; Taira, S.; Kobamoto, N.; Zhu, J.; Ishihara, M.; Toyama, S. Synthesis and antifungal activity of cinnamic acid esters. Biosci., Biotechnol., Biochem. 1996, 60, 909-910.
11. Liu, L.; Hudgins, W. R.; Shack, S.; Yin, M. Q.; Samid, D. Cinnamic acid: A natural product with potential use in cancer intervention. Int. J. Cancer 1995, 62, 345-350.
12. Castelluccio, C.; Paganga, G.; Melikian, N.; Bolwell, G. P.; Pridham, J.; Sampson, J.; Rice-Evans, C. Antioxidant potential of intermediates in phenylpropanoid metabolism in higher plants. FEBS Lett. 1995, 368, 188-192.
13. Meyer, A. S.; Donovan, J. L.; Pearson, D. A.; Waterhouse, A. L.; Frankel, E. N. Fruit hydroxycinnamic acids inhibit human low-density lipoprotein oxidation in vitro. J. Agric. Food Chem. 1998, 46, 1783-1787.
14. Lee, J. S.; Jeon, S. M.; Park, E. M.; Huh, T. L.; Kwon, O. S.; Lee, M. K.; Choi, M. S. Cinnamate supplementation enhances hepatic lipid metabolism and antioxidant defense systems in high cholesterol-fed rats. J. Med. Food 2003, 6, 183-191.
15. Zang, L. Y.; Cosma, G.; Gardner, H.; Shi, X.; Castranova, V.; Vallyathan, V. Effect of antioxidant protection by p-coumaric on low-density lipoprotein cholesterol oxidation. Am. J. Physiol. 2000, 279, 954-960.
16. Fahelbum, I. M. S.; James, S. P. The absorption and metabolism of methyl cinnamate. Toxicology 1977, 7, 123-132.
17. Nutley, B. P.; Farmer, P.; Caldwell, J. Metabolism of transcinnamic acid in the rat and the mouse and its variation with dose. Fd Chem. Toxic. 1994, 32, 877-886.
18. Ader, P.; Grenacher, B.; Langguth, P.; Scharrer, E.; Wolffram, S. Cinnamate uptake by rat small intestine: Transport kinetics and transepithelial transfer. Exp. Physiol. 1996, 81, 943-955.
19. +-dependent mucosal uptake of cinnamic acid across the jejunul brush border in rats. J. Nutr. 1995, 125, 1300-1308.
20. Konishi, Y.; Hagiwara, K.; Shimizu, M. Transepithelial transport of fluorescein in Caco-2 cell monolayers and use of such transport in in vitro evaluation of phenolic acid availability. Biosci., Biotechnol., Biochem. 2002, 66, 2449-2457.
21. Konishi, Y.; Kobayashi, S.; Shimizu, M. Transepithelial transport of p-coumaric acid and gallic acid in Caco-2 cell monolayers. Biosci., Biotechnol., Biochem. 2003, 67, 2317-2324.
22. Blanquet, S.; Meunier, J. P.; Minekus, M.; Marol-Bonnin, S.; Alric, M. Recombinant Saccharomyces cerevisiae expressing P450 in artificial digestive system: A model for biodetoxication in the human digestive environment. Appl. Environ. Microbiol. 2003, 69, 2884-2892.
23. Kern, S. M.; Bennett, R. N.; Needs, P. W.; Mellon, F. A.; Kroon, P. A.; Garcia-Conesa, M. T. Characterization of metabolites of hydroxycinnamates in the in vitro model of human small intestinal epithelium Caco-2 cells. J. Agric. Food Chem. 2003, 51, 7884-7891.
24. Barthe, L.; Bessouet, M.; Woodley, J. F.; Houin, G. The improved everted gut sac: A simple method to study intestinal P-glycoprotein. Int. J. Pharm. 1998, 173, 255-258.
25. Chan, K.; Liu, Z. Q.; Jiang, Z. H.; Zhou, H.; Wong, Y. F.; Xu, H. X.; Liu, L. The effects of sinomenine on intestinal absorption of paeoniflorin by the everted rat gut sac model. J. Ethnopharmacol. 2005, in press.
26. +/glucose cotranporter. Re-evaluation of function and distribution of expression. J. Biol. Chem. 1994, 269, 12032-12039.
27. Tomei, S.; Torimoto, M.; Hayashi, Y.; Inoue, K.; Yuasa, H.; Watanabe, J. Kinetic characterization of carrier-mediated transport systems for D-glucose and taurocholate in the everted sacs of the rat colon. Biol. Pharm. Bull. 2003, 26, 899-901.
28. Crespy, V.; Morand, C.; Besson, C.; Manach, C.; Demigne, C.; Remesy, C. Quercetin, but not its glycosides, is absorbed from the rat stomach. J. Agric. Food Chem. 2002, 50, 618-621.
29. Zhao, Z.; Egahira, Y.; Sanada, H. Ferulic acid is quickly absorbed from rat stomach as the free form and then conjugated mainly in liver. J. Nutr. 2004, 134, 3083-3088.
30. Utoguchi, N.; Audus, K. L. Carrier-mediated transport of valproic acid in BeWo cells, a human trophoblast cell line. Int. J. Pharm. 2000, 195, 115-124.
31. Koehler-Stec, E. M.; Simpson, I. A.; Vannucci, S. J.; Landschulz, K. T.; Landschulz, W. H. Monocarboxylate transporter expression in mouse brain. Am. J. Physiol. 1998, 275, 516-524.
32. Tamai, I.; Sai, Y.; Ono, A.; Kido, Y.; Yabuuchi, H.; Takanaga, H.; Satoh, E.; Ogihara, T.; Amano, O.; Izeki, S.; Tsuji, A. Immunohistochemical and functional characterization of pH-dependent intestinal absorption of weak organic acids by the monocarboxylic acid transporter MCT1. J. Pharm. Pharmacol. 1999, 51, 1113-1121.
33. Konishi, Y.; Hitomi, Y.; Yoshioka, E. Intestinal absorption of p-coumaric and gallic acids in rats after oral administration. J. Agric. Food Chem. 2004, 52, 2527-2532.
34. Sangster, J. Octanol-water partition coefficients: Fundamentals and physical chemistry; Foog, P. G. T., Ed.; Wiley and Sons: Chichester, U.K., 1997.
35. Hansch, C.; Leo, A.; Hoekman, D. Exploring QSAR: Hydrophobic, Electronic, and Steric Constants; American Chemical Society: Washington, DC, 1995.
36. 14C]-ferulic acid in the rat. Arch. Int. Physiol. Biochim. 1971, 79, 589-618.
37. Raper, H. S.; Wayne, E. J. A quantitative study of oxidation of phenyl-fatty acids in the animal organism. Biochem. J. 1928, 22, 188-192.
38. Hoskins, J. A.; Holliday, S. B.; Greenway, A. M. The metabolism of cinnamic acid by healthy and phenylketonuric adults: A kinetic study. Biomed. Mass Spectrom. 1984, 11, 296-300.
39. Olthof, M. R.; Hollman, P. C.; Buijsman, M. N. C. P.; Van Amelsvoort, J. M. M.; Katan, M. B. Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. J. Nutr. 2003, 133, 1806-1814.
40. Scalbert, A.; Williamson, G. Dietary intake and bioavailability of polyphenols. J. Nutr. 2000, 130, 2073S-2085S.