Absorption and metabolism of chlorogenic acids in cultured gastric epithelial monolayers

Drug Metabolism and Disposition

Volumn 39, Issue 12, 2011, Pages 2338-2346

  Farrell, Tracy L ^a   Dew, Tristan P ^a   Poquet, Laure ^b   Hanson, Peter ^c   Williamson, Gary ^a,b  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b NESTLÉ RESEARCH CENTER   (Switzerland)

^c ASTON UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 O CAFFEOYLQUINIC ACID LACTONE; 3 O FERULOYLQUINIC ACID; 3,4 DI O CAFFEOYLQUINIC ACID; 3,5 DI O CAFFEOYLQUINIC ACID; 4 FERULOYLQUINIC ACID; 4 O CAFFEOYLQUINIC ACID; 4 O CAFFEOYLQUINIC ACID LACTONE; 4,5 DI O CAFFEOYLQUINIC ACID; 5 FERULOYLQUINIC ACID; 5 O CAFFEOYLQUINIC ACID; CAFFEIC ACID; CHLOROGENIC ACID; COUMARIC ACID; DIHYDROCAFFEIC ACID; DIHYDROFERULIC ACID; DIMETHOXYCINNAMIC ACID; DRUG METABOLITE; FERULIC ACID; ISOFERULIC ACID; PARA COUMARIC ACID; UNCLASSIFIED DRUG;

ACIDITY; ANIMAL CELL; ARTICLE; CELL STRAIN CACO 2; COFFEE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ABSORPTION; DRUG METABOLISM; DRUG PENETRATION; DRUG STRUCTURE; DRUG TRANSFORMATION; DRUG TRANSPORT; DRUG UPTAKE; FLUID INTAKE; HUMAN; HUMAN CELL; INCUBATION TIME; INTESTINE EPITHELIUM CELL; KINETICS; METHYLATION; MONOLAYER CULTURE; NONHUMAN; PRIORITY JOURNAL; STOMACH EPITHELIUM; STOMACH MUCOSA; STOMACH PH;

CELLS, CULTURED; CHLOROGENIC ACID; GASTRIC MUCOSA; HUMANS; HYDROGEN-ION CONCENTRATION;

EID: 81855183900     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.111.040147     Document Type: Article

References (39)

1. Andrade-Cetto A and Vázquez RC (2010) Gluconeogenesis inhibition and phytochemical composition of two Cecropia species. J Ethnopharmacol 130:93-97.
2. Andreasen MF, Kroon PA, Williamson G, and Garcia-Conesa MT (2001) Esterase activity able to hydrolyze dietary antioxidant hydroxycinnamates is distributed along the intestine of mammals. J Agric Food Chem 49:5679-5684. (Pubitemid 33089725)
3. Ashton M and Hanson PJ (2002) Disparate effects of non-steroidal anti-inflammatory drugs on apoptosis in guinea-pig gastric mucous cells: inhibition of basal apoptosis by diclofenac. Br J Pharmacol 135:407-416. (Pubitemid 34151173)
4. Battram DS, Arthur R, Weekes A, and Graham TE (2006) The glucose intolerance induced by caffeinated coffee ingestion is less pronounced than that due to alkaloid caffeine in men. J Nutr 136:1276-1280.
5. Chan LM, Lowes S, and Hirst BH (2004) The ABCs of drug transport in intestine and liver: efflux proteins limiting drug absorption and bioavailability. Eur J Pharm Sci 21:25-51. (Pubitemid 38050202)
6. Chu YF, Chen YM, Black RM, Brown PH, Lyle BJ, Liu RH, and Ou BX (2011) Type 2 diabetes-related bioactivities of coffee: assessment of antioxidant activity, NF-kappa B inhibition, and stimulation of glucose uptake. Food Chem 124:914-920.
7. Clifford MN (2000) Chlorogenic acids and other cinnamates - nature, occurrence, dietary burden, absorption and metabolism. J Sci Food Agric 80:1033-1043.
8. n of four new classes of chlorogenic acids in green coffee beans: dimethoxycinnamoylquinic acids, diferuloylquinic acids, caffeoyl-dimethoxycinnamoylquinic acids, and feruloyl-dimethoxycin-namoylquinic acids. J Agric Food Chem 54:1957-1969.
9. Clifford MN, Wu W, Kirkpatrick J, Jaiswal R, and Kuhnert N (2010) Profiling and characterisation by liquid chromatography/multi-stage mass spectrometry of the chlorogenic acids in Gardeniae Fructus. Rapid Commun Mass Spectrom 24:3109-3120.
10. Farah A, Monteiro M, Donangelo CM, and Lafay S (2008) Chlorogenic acids from green coffee extract are highly bioavailable in humans. J Nutr 138:2309-2315.
11. Farrell T, Poquet L, Dionisi F, Barron D, and Williamson G (2011) Characterization of hydroxycinnamic acid glucuronide and sulfate conjugates by HPLC-DAD-MS(2): enhancing chromatographic quantification and application in Caco-2 cell metabolism. J Pharm Biomed Anal 55:1245-1254.
12. Faulds CB, Aliwan FO, de Vries RP, Pickersgill RW, Visser J, and Williamson G (1998) Chemical and thermal stability of ferulic acid (feruloyl) esterases from Aspergillus: stability and stabilization of biocatalysts, in Progress in Biotechnology (Ballesteros A, Plou FJ, Iborra JL, and Halling PJ eds) vol 15, pp 41-46, Elsevier Science BV, Amsterdam.
13. Fricker G, Drewe J, Huwyler J, Gutmann H, and Beglinger C (1996) Relevance of p-glycoprotein for the enteral absorption of cyclosporin A: in vitro-in vivo correlation. Br J Pharmacol 118:1841-1847. (Pubitemid 26252682)
14. Fumeaux R, Menozzi-Smarrito C, Stalmach A, Munari C, Kraehenbuehl K, Steiling H, Crozier A, Williamson G, and 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. Org Biomol Chem 8:5199-5211.
15. Guy PA, Renouf M, Barron D, Cavin C, Dionisi F, Kochhar S, Rezzi S, Williamson G, and Steiling H (2009) Quantitative analysis of plasma caffeic and ferulic acid equivalents by liquid chromatography tandem mass spectrometry. J Chromatogr B 877:3965-3974.
16. Hall LR, Dial EJ, Smith GS, and Lichtenberger LM (1995) Expression of P-glycoprotein (P-Gly) in the rodent gastric-mucosa - possible role in phospholipid secretion (Abstract). Gastroenterology 108:A106.
17. Henry-Vitrac C, Ibarra A, Roller M, Mérillon JM, and Vitrac X (2010) Contribution of chlorogenic acids to the inhibition of human hepatic glucose-6-phosphatase activity in vitro by Svetol, a standardized decaffeinated green coffee extract. J Agric Food Chem 58:4141-4144.
18. Hubatsch I, Ragnarsson EG, and Artursson P (2007) Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers. Nat Protoc 2:2111-2119. (Pubitemid 351565848)
19. Huntley JF, Newlands GF, Gibson S, Ferguson A, and Miller HR (1985) Histochemical demonstration of chymotrypsin like serine esterases in mucosal mast cells in four species including man. J Clin Pathol 38:375-384. (Pubitemid 15106596)
20. Johnston KL, Clifford MN, and Morgan LM (2003) Coffee acutely modifies gastrointestinal hormone secretion and glucose tolerance in humans: glycemic effects of chlorogenic acid and caffeine. Am J Clin Nutr 78:728-733. (Pubitemid 39663490)
21. Kavvada KM, Murray JG, Moore VA, Coombes AG, and Hanson PJ (2005) A collagen IV matrix is required for guinea pig gastric epithelial cell monolayers to provide an optimal model of the stomach surface for biopharmaceutical screening. J Biomol Screen 10:495-507. (Pubitemid 41233228)
22. Kavvada KM, Murray JG, Moore VA, Coombes AG, and Hanson PJ (2006) High permeability of the anionic form restricts accumulation of indomethacin by cultured gastric surface epithelial cells exposed to low apical pH. Eur J Pharmacol 549:41-49. (Pubitemid 44468067)
23. Kern SM, Bennett RN, Needs PW, Mellon FA, Kroon PA, and Garcia-Conesa MT (2003) Characterization of metabolites of hydroxycinnamates in the in vitro model of human small intestinal epithelium caco-2 cells. J Agric Food Chem 51:7884-7891.
24. Kirat D, Kondo K, Shimada R, and Kato S (2009) Dietary pectin up-regulates monocaboxylate transporter 1 in the rat gastrointestinal tract. Exp Physiol 94:422-433.
25. Konishi Y and Kobayashi S (2004) Transepithelial transport of chlorogenic acid, caffeic acid, and their colonic metabolites in intestinal caco-2 cell monolayers. J Agric Food Chem 52:2518-2526.
26. Konishi Y, Zhao Z, and Shimizu M (2006) Phenolic acids are absorbed from the rat stomach with different absorption rates. J Agric Food Chem 54:7539-7543. (Pubitemid 44645769)
27. Lafay S, Gil-Izquierdo A, Manach C, Morand C, Besson C, and Scalbert A (2006) Chlorogenic acid is absorbed in its intact form in the stomach of rats. J Nutr 136:1192-1197.
28. Monteiro M, Farah A, Perrone D, Trugo LC, and Donangelo C (2007) Chlorogenic acid compounds from coffee are differentially absorbed and metabolized in humans. J Nutr 137:2196-2201. (Pubitemid 47529576)
29. Muthusamy VS, Saravanababu C, Ramanathan M, Bharathi Raja R, Sudhagar S, Anand S, and Lakshmi BS (2010) Inhibition of protein tyrosine phosphatase 1B and regulation of insulin signalling markers by caffeoyl derivatives of chicory (Cichorium intybus) salad leaves. Br J Nutr 104:813-823.
30. Nagy K, Redeuil K, Williamson G, Rezzi S, Dionisi F, Longet K, Destaillats F, and Renouf M (2011) First identification of dimethoxycinnamic acids in human plasma after coffee intake by liquid chromatography-mass spectrometry. J Chromatogr A 1218:491-497.
31. Passamonti S, Vrhovsek U, and Mattivi F (2002) The interaction of anthocyanins with bilitranslocase. Biochem Biophys Res Commun 296:631-636.
32. Pietraforte D, Castelli M, Metere A, Scorza G, Samoggia P, Menditto A, and Minetti M (2006) Salivary uric acid at the acidic pH of the stomach is the principal defense against nitrite-derived reactive species: sparing effects of chlorogenic acid and serum albumin. Free Radic Biol Med 41:1753-1763. (Pubitemid 44839140)
33. Rocha BS, Gago B, Barbosa RM, and Laranjinha J (2009) Dietary polyphenols generate nitric oxide from nitrite in the stomach and induce smooth muscle relaxation. Toxicology 265:41-48.
34. Stalmach A, Mullen W, Barron D, Uchida K, Yokota T, Cavin C, Steiling H, Williamson G, and Crozier A (2009) Metabolite profiling of hydroxycinnamate derivatives in plasma and urine after the ingestion of coffee by humans: identification of biomarkers of coffee consumption. Drug Metab Dispos 37:1749-1758.
35. Sugano K, Kansy M, Artursson P, Avdeef A, Bendels S, Di L, Ecker GF, Faller B, Fischer H, Gerebtzoff G, et al. (2010) Coexistence of passive and carrier-mediated processes in drug transport. Nat Rev Drug Discov 9:597-614.
36. Tsuchiya S, Tachida Y, Segi-Nishida E, Okuno Y, Tamba S, Tsujimoto G, Tanaka S, and Sugimoto Y (2009) Characterization of gene expression profiles for different types of mast cells pooled from mouse stomach subregions by an RNA amplification method. BMC Genomics 10:35.
37. van Dam RM and Hu FB (2005) Coffee consumption and risk of type 2 diabetes: a systematic review. JAMA 294:97-104.
38. Wang Z, Clifford MN, and Sharp P (2008) Analysis of chlorogenic acids in beverages prepared from Chinese health foods and investigation, in vitro, of effects on glucose absorption in cultured Caco-2 cells. Food Chem 108:369-373.
39. Williamson G, Kroon PA, and Faulds CB (1998) Hairy plant polysaccharides: a close shave with microbial esterases. Microbiology 144:2011-2023. (Pubitemid 28403014)