Transepithelial transport of microbial metabolites of quercetin in intestinal Caco-2 cell monolayers

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 3, 2005, Pages 601-607

  Konishi, Yutaka ^a  

^a KIRIN BREWERY CO LTD   (Japan)

Author keywords

Caco 2; Hydroxylated phenylacetic acids; Microbial metabolite; Monocarboxylic acid transporter; Quercetin

Indexed keywords

3,4 DIHYDROXYPHENYLACETIC ACID; 4 HYDROXYPHENYLACETIC ACID; ANTIOXIDANT; CATECHIN; FLAVONOL DERIVATIVE; HOMOVANILLIC ACID; MONOCARBOXYLATE TRANSPORTER; QUERCETIN;

ANTIOXIDANT ACTIVITY; APICAL MEMBRANE; ARTICLE; BASOLATERAL MEMBRANE; CELL MEMBRANE PERMEABILITY; CELL STRAIN CACO 2; COLON FLORA; CONTROLLED STUDY; COULOMETRY; DIETARY INTAKE; DIFFUSION; ELECTROCHEMICAL DETECTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; INTESTINE ABSORPTION; INTESTINE EPITHELIUM; METABOLITE; MICROBIAL METABOLISM; MONOLAYER CULTURE; TIGHT JUNCTION; TRANSEPITHELIAL TRANSPORT;

3,4-DIHYDROXYPHENYLACETIC ACID; BIOLOGICAL TRANSPORT; CACO-2 CELLS; DIFFUSION; EPITHELIUM; HOMOVANILLIC ACID; HUMANS; INTESTINES; MONOCARBOXYLIC ACID TRANSPORTERS; QUERCETIN;

EID: 13244258342     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf048662l     Document Type: Article

References (49)

1. Hollman, P. C.; Feskens, E. J.; Katan, M. B. Tea flavonols in cardiovascular diseases and cancer epidemiology. Proc. Soc. Exp. Biol. Med. 1999, 220, 198-202.
2. Mukamal, K. J.; Maclure, M.; Muller, J. E.; Sherwood, J. B.; Mittleman, M. A. Tea consumption and mortality after acute myocardial infarction. Circulation 2002, 105, 2476-2481.
3. Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Structure-antioxidant activity relationship of flavonoids and phenolic acids. Free Radical Biol. Med. 1990, 20, 933-956.
4. Okuda, T.; Mori, K.; Hayatsu, H. Inhibitory effect of tannins on direct-acting mutagens. Chem. Pharm. Bull. 1984, 32, 3755-3758.
5. Henry, J. P.; Stephan-Larson, P. Reduction chronic psychosocial hypertension in mice by decaffeinated tea. Hypertension 1984, 6, 437-444.
6. Formica, J. V.; Regelson, W. Whole grain intake and cancer: an expanded review and meta-analysis. Food Chem. Toxicol. 1995, 33, 1061-1080.
7. Chen, L.; Lee, M. J.; Li, H.; Yang, C. S. Absorption, distribution, and elimination of tea polyphenols in rats. Drug Metab. Dispos. 1997, 25, 1045-1050.
8. Chow, H. H.; Cai, Y.; Alberts, D. S.; Hakim, I.; Dorr, R.; Shahi, F.; Crowell, J. A.; Yang, C. S.; Hara, Y. Phase I pharmacokinetics study of tea polyphenols following single-dose administration of epigallocatechin gallate and polyphenone E. Cancer Epidemiol., Biomarkers Prev. 2001, 10, 53-58.
9. Scalbert, A.; Williamson, G. Dietary intake and bioavailability of polyphenols. J. Nutr. 2000, 130, 2073S-2085S.
10. Scalbert, A.; Morand, C.; Manach, C.; Remesy, C. Absorption and metabolism of polyphenols in the gut and impact on health. Biomed. Pharmacother. 2002, 56, 276-282.
11. Lee, M. J.; Wang, Z. Y.; Li, H.; Chen, L.; Sun, Y.; Gobbo, S.; Balentine, D. A.; Yang, C. S. Analysis of plasma and urinary tea polyphenols in human subjects. Cancer Epidemiol., Biomarkers Prev. 1995, 4, 393-399.
12. Nakagawa, K.; Okuda, S.; Miyazawa, T. Dose-dependent incorporation of tea catechins, (-)-epigallocatechin-3-gallate and (-)-epigallocatechin, into human plasma. Biosci., Biotechnol., Biochem. 1997, 61, 1981-1985.
13. Piskula, M. K.; Terao, J. Accumulation of (-)-epicatechin metabolites in rat plasma after oral administration and distribution of conjugation enzymes in rats tissues. J. Nutr. 1998, 128, 1172-1178.
14. Hollman, P. C. H.; van Trijp, J. M. P.; Buysman, M. N. C. P.; van der Gaag, M. S.; Mengelers, M. J. B.; de Vries, J. H. M.; Katan, M. B. Relative bioavailability of the antioxidant flavonoid quercetin from various food in man. FEBS Lett. 1997, 418, 152-156.
15. Shimoi, K.; Yoshizumi, K.; Kido, T.; Usui, Y.; Yumoto, T. Absorption and urinary excretion of quercetin, rutin, and αGrutin, a water soluble flavonoid, in rats. J. Agric. Food Chem. 2003, 51, 2785-2789.
16. Clifford, M. N. Chlorogenic acids and other cinnamates: nature, occurrence, and dietary burden. J. Sci. Food Agric. 1999, 79, 362-372.
17. Giovannucci, E. Meta-analysis of coffee consumption and risk of colorectal cancer. Am. J. Epidemiol. 1998, 147, 1043-1052.
18. Favero, A.; Franceschi, S.; La Vecchia, C.; Negri, E.; Conti, E.; Montella, M. Meal frequency and coffee intake in colon cancer. Nutr. Cancer 1998, 30, 182-185.
19. Tavani, A.; Pregnolato, A.; La Vecchia, C.; Negri, E.; Talamini, R.; Franceschi, S. Coffee and tea intake and risk of cancers of the colon and rectum: a study of 3,530 cases and 7,057 controls. Int. J. Cancer 1997, 73, 193-197.
20. Gonthier, M. P.; Verny, M. A.; Besson, C.; Remesy, C.; Scalbert, A. Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. J. Nutr. 2003, 133, 1853-1859.
21. Rechner, A. R.; Kuhnle, G.; Bremner, P.; Hubbard, G. P.; Moore, K. P.; Rice-Evans, C. A. The metabolic fate of dietary polyphenols in humans. Free Radical Biol. Med. 2002, 33, 220-235.
22. Gonthier, M. P.; Cheynier, V.; Donovan, J. L.; Manach, C.; Morand, C.; Mila, I.; Lapierre, C.; Remesy, C.; Scalbert, A. Microbial aromatic acid metabolites formed in the gut account for a major fraction of the polyphenols excreted in urine of rats fed red wine polyphenols. J. Nutr. 2003, 133, 461-467.
23. Rechner, A. R.; Smith, M. A.; Kuhnle, G.; Gibson, G. R.; Debnam, E. S.; Srai, S. K. S.; Moore, K. P.; Rice-Evans, C. A. Colonic metabolism of dietary polyphenols: Influence of structure on microbial fermentation products. Free Radical Biol. Med. 2004, 36, 212-225.
24. Olthof, M. R.; Hollman, P. C.; Buijsman, M. N.; van Amelsvoort, J. M.; Katan, M. B. Chlorogenic acid, quercetin-3-rutinoside and black tea polyphenols are extensively metabolized in humans. J. Nutr. 2003, 133, 1806-1814.
25. Konishi, Y.; Kobayashi, S. Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter. J. Agric. Food Chem. 2004, 52, 6418-6424.
26. Konishi, Y.; Kobayashi, S.; Shimizu, M. Tea polyphenols inhibit the transport of dietary phenolic acids mediated by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers. J. Agric. Food Chem. 2003, 51, 7296-7302.
27. Konishi, Y.; Kobayashi, S. Transepithelial transport of chlorogenic acid, caffeic acid, and their colonic metabolites in intestinal Caco-2 cell monolayers. J. Agric. Food Chem. 2004, 52, 2518-2526.
28. Aura, A. M.; O'Leary, K. A.; Williamson, G.; Ojala, M.; Bailey, M.; Puupponen-Pimia, R.; Nuutila, A. M.; Oksman-Caldentey, K. M.; Poutanen, K. Quercetin derivatives are deconjugated and converted to hydroxyphenylacetic acids but not methylated by human fecal flora in vitro. J. Agric. Food Chem. 2002, 50, 1725-1730.
29. Kim, D. H.; Jung, E. A.; Sohng, I. S.; Han, J. A.; Kim, T. H.; Han, M. J. Intestinal bacterial metabolism of flavonoids and its relation to some biological activities. Arch. Pharm. Res. 1998, 21, 17-23.
30. Hidalgo, I. J.; Raub, T. J.; Borchardt, R. T. Characterization of the human colon carcinoma cell line (Caco-2) as a model system for intestinal epithelial permeability. Gastroenterology 1989, 96, 736-749.
31. Hilgers, A. R.; Conradi, R. A.; Burton, P. S. Caco-2 cell monolayers as a model for drug transport across the intestinal mucosa. Pharm. Res. 1990, 7, 902-910.
32. Artursson, P.; Karlsson, J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem. Biophys. Res. Commun. 1991, 175, 880-885.
33. Yamaoka, K.; Tanigawara, Y.; Nakagawa, T.; Uno, T. A pharmacokinetics analysis program (MULTI) for microcomputer. J. Pharmacobio-Dyn. 1981, 4, 879-885.
34. Guo, C.; Cao, G.; Sofic, E.; Prior, R. L. High-performance liquid chromatography coupled with coulometric array detection of electroactive components in fruits and vegetables: relationship to oxygen radical absorbance capacity. J. Agric. Food Chem. 1997, 45, 1787-1796.
35. Price, N. T.; Jackson, V. N.; Halestrap, A. P. Cloning and sequencing of four new mammalian monocarboxylate transporter (MCT) homologues confirms the existence of a transporter family with an ancient past. Biochem. J. 1999, 329, 321-329.
36. Konishi, Y.; Shimizu, M. Transepithelial transport of ferulic acid by monocarboxylic acid transporter in Caco-2 cell monolayers. Biosci., Biotechnol, Biochem. 2003, 67, 856-862.
37. Konishi, Y.; Kobayashi, S.; Shimizu, M. Transepithelial transport of p-coumaric acid and gallic acid by monocarboxylic acid transporter in Caco-2 cell monolayers. Biosci., Biotechnol., Biochem. 2003, 67, 2317-2324.
38. Konishi, Y.; Hagiwara, K.; Shimizu, M. Transepithelial transport of fluorescein in Caco-2 cell monolayers and its use in in vitro evaluation of phenolic acids availability. Biosci., Biotechnol., Biochem. 2002, 66, 2449-2457.
39. Rahman, B.; Schneider, H. P.; Broer, A.; Deitmer, J W.; Broer, S. Helix 8 and Helix 10 are involved in substrate recognition in the rat monocarboxylate transporter MCT1. Biochemistry 1999, 38, 11577-11584.
40. Manach, C.; Scalbert, A.; Morand, C.; Remesy, C.; Jimenez, L. Polyphenols: food sources and bioavailability. Am. J. Clin. Nutr. 2004, 79, 727-747.
41. 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.
42. Gonthier, M. P.; Donovan, J. L.; Texier, O.; Felgines, C.; Remesy, C.; Scalbert, A. Metabolism of dietary procyanidins in rats. Free Radical Biol. Med. 2003, 35, 837-844.
43. Price, N. T.; Jackson, V. N.; Halestrap, A. P. Cloning and sequencing of four new mammalian monocarboxylate transporter (MCT) homologues confirms the existence of a transporter family with an ancient past. Biochem. J. 1999, 329, 321-329.
44. Lin, R. Y.; Vera, J. C.; Chaganti, R. S. K.; Golde, D. W. Human monocarboxylate transporter 2 (MCT2) is a high affinity pyruvate transporter. J. Biol. Chem. 1998, 273, 28959-28965.
45. Cummings J. H. The importance of SCFA in man. Scand. J. Gastroenterol. 1984, 19, 89-99.
46. Roediger, W. E. W. Role of anaerobic bacteria in the metaolic welfare of the colonic mucosa in man. Gut 1980, 21, 793-798.
47. Scheppach, W.; Bartram, H. P.; Richter, A.; Richter, F.; Liepold, H.; Dusel, G.; Hofstetter, G.; Ruthlein, J.; Kasper, H. Effect of short-chain fatty acid on the human colonic mucosa in vitro. J. Parenter. Enteral Nutr. 1992, 16, 43-48.
48. Hadjiagapiou, C.; Schmidt, L.; Dudeja, P. K.; Layden, T. J.; Ramaswamy, K. Mechanism of butyrate transport in Caco-2 cells: role of monocarboxylate transporter 1. Am. J. Physiol. Gastrointest. Liver Physiol. 2000, 279, G775-780.
49. Stein, J.; Schroder, O.; Milovic, V.; Caspary, W. F. Mercaptopropionate inhibits butyrate uptake in isolated apical membrane vesicles of the rat distal colon. Gastroenterology 1995, 108, 673-679.