High gastrointestinal permeability and local metabolism of naringenin: Influence of antibiotic treatment on absorption and metabolism

British Journal of Nutrition

Volumn 114, Issue 2, 2015, Pages 169-180

  Orrego Lagarón, Naiara ^a   Martínez Huélamo, Miriam ^a,b   Vallverdú Queralt, Anna ^a,b   Lamuela Raventos, Rosa M ^a,b   Escribano Ferrer, Elvira ^a,b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b Instituto de Salud Carlos III   (Spain)

Author keywords

Gastrointestinal tract; In situ single pass perfusion; Metabolism; Naringenin; Rifaximin

Indexed keywords

ANTIBIOTIC AGENT; HIPPURIC ACID; NAPROXEN; NARINGENIN; POLYPHENOL; RIFAXIMIN; 4-HYDROXYHIPPURIC ACID; ANTIINFECTIVE AGENT; FLAVANONE DERIVATIVE; HIPPURIC ACID DERIVATIVE; RIFAMYCIN;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BILE; BIOAVAILABILITY; COLON; CONTROLLED STUDY; FIRST PASS EFFECT; GASTROINTESTINAL ABSORPTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTESTINE FLORA; INTESTINE MUCOSA PERMEABILITY; INTESTINE PERFUSION; MALE; METABOLISM; MOUSE; NONHUMAN; PLASMA; SMALL INTESTINE; SOLID PHASE EXTRACTION; STOMACH; TANDEM MASS SPECTROMETRY; ANIMAL; BLOOD; DRUG EFFECTS; GASTROINTESTINAL TRACT; INTESTINE ABSORPTION; PERFUSION; PH;

ANIMALIA; MUS;

ANIMALS; ANTI-BACTERIAL AGENTS; BILE; BIOLOGICAL AVAILABILITY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLAVANONES; GASTROINTESTINAL TRACT; HIPPURATES; HYDROGEN-ION CONCENTRATION; INTESTINAL ABSORPTION; MALE; MICE; PERFUSION; POLYPHENOLS; RIFAMYCINS; TANDEM MASS SPECTROMETRY;

EID: 84938557394     PISSN: 00071145     EISSN: 14752662     Source Type: Journal    
DOI: 10.1017/S0007114515001671     Document Type: Article

References (48)

1. Xu H, Kulkarni KH, Singh R, et al. (2009). Disposition of naringenin via glucuronidation pathway is affected by compensating efflux transporters of hydrophilic glucuronides. Mol Pharm 6, 1703-1715
2. Yoshimura M, Sano A, Kamei J, et al. (2009). Identification and quantification of metabolites of orally administered naringenin chalcone in rats. J Agric Food Chem 57, 6432-6437
3. Felgines C, Texier O, Morand C, et al. (2000). Bioavailability of the flavanone naringenin and its glycosides in rats. Am J Physiol Gastrointest Liver Physiol 279, G1148-G1154
4. Chabane MN, Al Ahmad A, Peluso J, et al. (2009). Quercetin and naringenin transport across human intestinal Caco-2 cells. J Pharm Pharmacol 61, 1473-1483
5. Amidon GL, Lennernäs H, Shah VP, et al. (1995). A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm Res 12, 413-420
6. Azuma K, Ippoushi K, Ito H, et al. (2002). Combination of lipids and emulsifiers enhances the absorption of orally administered quercetin in rats. J Agric Food Chem 50, 1706-1712
7. Jeong EJ, Jia X, & Hu M. (2005). Disposition of formononetin via enteric recycling: metabolism and excretion in mouse intestinal perfusion and Caco-2 cell models. Mol Pharm 2, 319-328
8. Escribano E, García Sala X, Salamanca J, et al. (2012). Singlepass intestinal perfusion to establish the intestinal permeability of model drugs in mouse. Int J Pharm 436, 472-477
9. Lieber CS, Leo MA, Mak KM, et al. (2004). Model of nonalcoholic steatohepatitis. Am J Clin Nutr 79, 502-509
10. Vallverdú-Queralt A, De Alvarenga JF, Estruch R, et al. (2013). Bioactive compounds present in the Mediterranean sofrito. Food Chem 41, 3365-3372
11. Martínez-Huélamo M, Tulipani S, & Torrado X. (2012). Validation of a new LC-MS/MS method for the detection and quantification of phenolic metabolites from tomato sauce in biological samples. J Agric Food Chem 60, 4542-4549
12. Dahan A, West BT, & Amidon GL. (2009). Segmental-dependent membrane permeability along the intestine following oral drug administration: evaluation of a triple single-pass intestinal perfusion (TSPIP) approach in the rat. Eur J Pharm Sci 36, 320-329
13. Eisen EJ. (1976). Results of growth curve analyses in mice and rats. J Anim Sci 42, 1008-1023
14. Miglioli PA, Allerberger F, Calabró GB, et al. (2001). Effects of daily oral administration of rifaximin and neomycin on faecal aerobic flora in rats. Pharmacol Res 44, 373-375
15. Scarpignato C, & Pelosini I. (2005). Rifaximin, a poorly absorbed antibiotic: pharmacology and clinical potential. Chemotherapy 51, Suppl. 1, S36-S66
16. Tulipani S, Martinez-Huelamo M, Rotches Ribalta M, et al. (2012). Oil matrix effects on plasma exposure and urinary excretion of phenolic compounds from tomato sauces: evidence from a human pilot study. Food Chem 130, 581-590
17. Varma MVS, & Panchagnula R. (2005). Prediction of in vivo intestinal absorption enhancement on P-glycoprotein inhibition, from rat in situ permeability. J Pharm Sci 94, 1694-1704
18. Zakeri-Milani P, Valizadeh H, Tajerzadeh H, et al. (2007). Predicting human intestinal permeability using single-pass intestinal perfusion in rat. J Pharm Sci 10, 368-379
19. Sutton SC, Rinaldi MTS, & Vukovinsky KE. (2001). Comparison of the gravimetric, phenol red, and 14C-PEG-3350 methods to determine water absorption in the rat single-pass intestinal perfusion model. AAPS Pharm Sci 3, 1-5
20. Japar D, Wu SP, Hu Y, et al. (2010). Significance and regional dependency of peptide transporter (PEPT) 1 in the intestinal permeability of glycylsarcosine: in situ single-pass perfusion studies in wild-type and Pept1 knockout mice. Drug Metab and Dispos 38, 1740-1746
21. Incecayir T, Tsume Y, & Amidon GL. (2013). Comparison of the permeability of metoprolol and labetalol in rat, mouse, and Caco-2 cells: use as a reference standard for BCS classification. Mol Pharm 10, 958-966
22. Masaoka Y, Tanaka Y, Kataoba M, et al. (2006). Site of absorption after oral administration: assessment of membrane permeability and luminal concentration of drugs in each segment of gastrointestinal tract. Eur J Pharm Sci 29, 240-250
23. McConnell EL, Basit AW, & Murdan S. (2008). Measurements of rat and mouse gastrointestinal pH, fluid and lymphoid tissue, and implications for in vivo experiments. J Pharm Pharm 60, 63-70
24. Komiya I, Park JY, Kamani A, et al. (1980). Quantitative mechanistic studies in simultaneous fluid flow and intestinal absorption using steroids as model solutes. Int J Pharm 4, 249-262
25. Vallverdú-Queralt A, Regueiro J, Martinez-Huelamo, et al. (2014). A comprehensive study on the phenolic profile of widely used culinary herbs and spices: rosemary, thyme, oregano, cinnamon, cumin and bay. Food Chem 154, 299-307
26. DrugBank. (2014). DrugBank database (open data drug and drug target data base). http://www.drugbank.ca/drugs/DB03467 (accessed May 2014
27. Fagerholm U, Johansson M, & Lennernäs H. (1996). Comparison between permeability coefficients in rat and human jejunum. Pharm Res 13, 1336-1342
28. Takanaga H, Ohnishi A, Matsuo H, et al. (1998). Inhibition of vinblastine efflux mediated by P-glycoprotein by grapefruit juice components in Caco-2 cells. Biol Pharm Bull 21, 1062-1066
29. Bailey DG, Malcolm J, Arnold O, et al. (1998). Grapefruit juice-drug interactions. Br J Clin Pharmacol 46, 101-110
30. Le Goff N, Koffel JC, Vandenschrieck S, et al. (2002). Comparison of in vitro hepatic models for the prediction of metabolic interaction between simvastatin and naringenin. Eur J Drug Metab Pharmacokinet 27, 233-241
31. Le Goff-Klein N, Koffel JC, Jung L, et al. (2005). In vitro inhibition of simvastatin metabolism, a HMG-CoA reductase inhibitor in human and rat liver by bergamottin, a component of grapefruit juice. Eur J Pharm Sci 18, 31-35
32. Hsiu SL, Huang TY, Hou YC, et al. (2002). Comparison of metabolic pharmacokinetics of naringin and naringenin in rabbits. Life Sci 70, 1481-1489
33. Chen G, Zhang D, Jing N, et al. (2003). Human gastrointestinal sulfotransferases: identification and distribution. Toxicol Appl Pharmacol 187, 186-197
34. Gregory P, Lewinsky R, Gardner-Stephen D, et al. (2004). Regulation of UDP glucuronosyltransferases in the gastrointestinal tract. Toxicol Appl Pharmacol 199, 354-356
35. Fang T, Wang Y, Ma Y, et al. (2006). A rapid LC/MS/MS quantitation assay for naringin and its two metabolites in rats plasma. J Pharm Biomed Anal 40, 454-459
36. Manach C, Scalbert A, Morand C, et al. (2004). Polyphenols: food sources and bioavailability. Am J Clin Nutr 79, 727-747
37. Rechner AR, Smith MA, Kuhnle G, et al. (2004). Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products. Free Radic Biol Med 36, 212-225
38. Possimiers S, Bolca S, Verstraete W, et al. (2011). The intestinal microbiome: a separate organ inside the body with the metabolic potential to influence the bioactivity of botanicals. Fitoterapia 82, 53-66
39. Boto-Ordóñez M, Rothwell JA, Andres-Lacueva C, et al. (2014). Prediction of the wine polyphenol metabolic space: an application of the Phenol-Explorer database. Mol Nutr Food Res 58, 466-477
40. Cong D, Fong AK, Lee R, et al. (2001). Absorption of benzoic acid in segmental regions of the vascularly perfused rat small intestine preparation. Drug Metab Dispos 29, 1539-1547
41. Gao K, Xu A, Krul C, et al. (2006). Of the major phenolic acids formed during human microbial fermentation of tea, citrus, and soy flavonoid supplements, only 3, 4-dihydroxyphenylacetic acid has antiproliferative activity. J Nutr 136, 52-57
42. Aura AM. (2008). Microbial metabolism of dietary phenolic compounds in the colon. Phytochem Rev 7, 407-429
43. Serra A, Macià A, Romero MP, et al. (2012). Metabolic pathway of the colonic metabolism of flavonoids (flavonols, flavones and flavonones) and phenolic acids. Food Chem 130, 383-393
44. Konishi Y, & Kobayashi S. (2004). Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers. J Agric Food Chem 52, 6418-6424
45. Spoelstra SF. (1978). Degradation of tyrosine in anaerobically stored piggery wastes and in pig feces. Appl Environ Microbiol 36, 631-638
46. Lord RS, & Bradley JA. (2008). Clinical applications of urinary organic acids. Part 2. Dysbiosis markers. Altern Med Rev 13, 292-306
47. Gao J, Gillilland MIII, & Owyang C. (2014). Rifaximin, gut microbes and mucosal inflammation: unravelling a complex relationship. Gut Microbes 5, 571-575
48. Miene C, Weise A, & Glei M. (2011). Impact of polyphenol metabolites produced by colonic microbiota on expression of COX-2 and GSTT2 in human colon cells (LT97). Nutr Cancer 63, 653-662