Bergamottin is a competitive inhibitor of CYP1A1 and is antimutagenic in the Ames test

Food and Chemical Toxicology

Volumn 50, Issue 9, 2012, Pages 3094-3099

  Olguin Reyes S ^a   Camacho Carranza, R ^a   Hernandez Ojeda S ^a   Elinos Baez, M ^a   Espinosa Aguirre, J J ^a  

^a INSTITUTO DE INVESTIGACIONES BIOMÉDICAS   (Mexico)

Author keywords

Antimutagenesis; Bergamottin; Competitive inhibitor; Grape fruit juice; Salmonella typhimurium

Indexed keywords

3 METHYLCHOLANTHRENE; AURANTIIN; BENZO[A]PYRENE; BERGAMOTTIN; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 2A; CYTOCHROME P450 2B1; CYTOCHROME P450 2B2; DIHYDROXYBERGAMOTTIN; ETHOXYRESORUFIN; PLANT MEDICINAL PRODUCT; UNCLASSIFIED DRUG;

AMES TEST; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BIOCHEMISTRY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFICACY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME KINETICS; LIVER MICROSOME; MALE; MICHAELIS MENTEN KINETICS; MUTAGENIC ACTIVITY; MUTAGENICITY; NONHUMAN; RAT;

ANIMALS; ANTIMUTAGENIC AGENTS; CYTOCHROME P-450 CYP1A1; ENZYME INHIBITORS; MALE; MUTAGENICITY TESTS; PSORALENS; RATS; RATS, WISTAR; SALMONELLA TYPHIMURIUM;

ANIMALIA; CITRUS X PARADISI; SALMONELLA TYPHIMURIUM; VITACEAE;

EID: 84864125766     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2012.05.058     Document Type: Article

References (47)

1. Alvarez-Gonzalez I., Madrigal-Bujaidar E., Dorado V., Espinosa-Aguirre J.J. Inhibitory effect of naringin on the micronuclei induced by ifosfamide in mouse, and evaluation of its modulatory effect on the Cyp3a subfamily. Mutat. Res. 2001, 480-481:171-178.
2. Bailey D.G., Arnold J.M., Munoz C., Spence J.D. Grapefruit juice-felodipine interaction: mechanism, predictability, and effect of naringin. Clin. Pharmacol. Ther. 1993, 53:637-642.
3. Bailey D.G., Dresser G.K., Kreeft J.H., Munoz C., Freeman D.J., Bend J.R. Grapefruit-felodipine interaction: effect of unprocessed fruit and probable active ingredients. Clin. Pharmacol. Ther. 2000, 68:468-477.
4. Baumgart A., Schmidt M., Schmitz H.J., Schrenk D. Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes. Biochem. Pharmacol. 2005, 69:657-667.
5. Burke D., Thompson S., Weaver R., Wolf Mayers. Cytochrome P450 especificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochem. Pharmacol. 1994, 48:923-936.
6. Cai Y., Baer-Dubowska W., Ashwood-Smith M., DiGiovanni J. Inhibitory effects of naturally occurring coumarins on the metabolic activation of benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene in cultured mouse keratinocytes. Carcinogenesis 1997, 18:215-222.
7. Cai Y., Baer-Dubowska W., Ashwood-Smith M.J., Ceska O., Tachibana S., DiGiovanni J. Mechanism-based inactivation of hepatic ethoxyresorufin O-dealkylation activity by naturally occurring coumarins. Chem. Res. Toxicol. 1996, 9:729-736.
8. Cai Y., Bennett D., Nair R.V., Ceska O., Ashwood-Smith M.J., DiGiovanni J. Inhibition and inactivation of murine hepatic ethoxy- and pentoxyresorufin O-dealkylase by naturally occurring coumarins. Chem. Res. Toxicol. 1993, 6:872-879.
9. De Castro W.V., Mertens-Talcott S., Rubner A., Butterweck V., Derendorf H. Variation of flavonoids and furanocoumarins in grapefruit juices: a potential source of variability in grapefruit juice-drug interaction studies. J. Agric. Food Chem. 2006, 54:249-255.
10. De Flora S., Camoirano A., D'Agostini F., Balansky R. Modulation of the mutagenic response in prokaryotes. Mutat. Res. 1992, 267:183-192.
11. Dresser G.K., Bailey D.G., Leake B.F., Schwarz U.I., Dawson P.A., Freeman D.J., Kim R.B. Fruit juices inhibit organic anion transporting polypeptide-mediated drug uptake to decrease the oral availability of fexofenadine. Clin. Pharmacol. Ther. 2002, 71:11-20.
12. Edwards D.J., Bernier S.M. Naringin and naringenin are not the primary CYP3A inhibitors in grapefruit juice. Life Sci. 1996, 59:1025-1030.
13. Fuhr U., Klittich K., Staib A.H. Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man. Br. J. Clin. Pharmacol. 1993, 35:431-436.
14. Fuhr U., Maier A., Keller A., Steinijans V.W., Sauter R., Staib A.H. Lacking effect of grapefruit juice on theophylline pharmacokinetics. Int. J. Clin. Pharmacol. Ther. 1995, 33:311-314.
15. Fuhr U., Kummert A.L. The fate of naringin in humans: a key to grapefruit juice-drug interactions?. Clin. Pharmacol. Ther. 1995, 58:365-373.
16. Fujii-Kuriyama Y., Kawajiri K. Molecular mechanisms of the physiological functions of the aryl hydrocarbon (dioxin) receptor, a multifunctional regulator that senses and responds to environmental stimuli. Proc. Jpn. Acad. Ser. B Phys. Biol. Sci. 2010, 86:40-53.
17. Fukuda K., Ohta T., Oshima Y., Ohashi N., Yoshikawa M., Yamazoe Y. Specific CYP3A4 inhibitors in grapefruit juice. Fourocoumarin dimers as components of drug interaction. Pharmacogenetics 1997, 7:391-396.
18. Girennavar B., Jayaprakasha G.K., Patil B.S. Potent inhibition of human cytochrome P450 3A4, 2D6, and 2C9 isoenzymes by grapefruit juice and its furocoumarins. J. Food Sci. 2007, 72:C417-C421.
19. Girennavar B., Poulose S.M., Jayaprakasha G.K., Bhat N.G., Patil B.S. Furocoumarins from grapefruit juice and their effect on human CYP 3A4 and CYP 1B1 isoenzymes. Bioorg. Med. Chem. 2006, 14:2606-2612.
20. Granfors M.T., Backman J.T., Neuvonen M., Neuvonen P.J. Ciprofloxacin greatly increases concentrations and hypotensive effect of tizanidine by inhibiting its cytochrome P450 1A2-mediated presystemic metabolism. Clin. Pharmacol. Ther. 2004, 76:598-606.
21. Guo L.Q., Fukuda K., Ohta T., Yamazoe Y. Role of furanocoumarin derivatives on grapefruit juice-mediated inhibition of human CYP3A activity. Drug Metab. Dispos. 2000, 28:766-771.
22. Gupta M.C., Garg S.K., Badyal D., Malhotra S., Bhargava V.K. Effect of grapefruit juice on the pharmacokinetics of theophylline in healthy male volunteers. Methods Find Exo. Clin. Pharmacol. 1999, 21:679-682.
23. He K., Iyer K.R., Hayes R.N., Sinz M.W., Woolf T.F., Hollenberg P.F. Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chem. Res. Toxicol. 1998, 11:252-259.
24. Hollenberg P.F. Mechanisms of cytochrome P450 and peroxidase-catalyzed xenobiotic metabolism. FASEB J. 1992, 6:686-694.
25. Hu Z., Yang X., Ho P.C., Chan S.Y., Heng P.W., Chan E., Duan W., Koh H.L., Zhou S. Herb-drug interactions: a literature review. Drugs 2005, 65:1239-1282.
26. IARC Some naturally occurring and synthetic food components, furocoumarins and ultraviolet radiation. IARC Monograph on the Evaluation of the Carcinogenic Risk of Chemicals for Humans 1986, 40:1-415.
27. Jeffy B.D., Chirnomas R.B., Romagnolo D.F. Epigenetics of breast cancer: polycyclic aromatic hydrocarbons as risk factors. Environ. Mol. Mutagen. 2002, 39:235-244.
28. Kane G.C., Lipsky J.J. Drug-grapefruit juice interactions. Mayo Clin. Proc. 2000, 75:933-942.
29. Kleiner H.E., Reed M.J., DiGiovanni J. Naturally occurring coumarins inhibit human cytochromes P450 and block benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene DNA adduct formation in MCF-7 cells. Chem. Res. Toxicol. 2003, 16:415-422.
30. Kleiner H.E., Vulimiri S.V., Reed M.J., Uberecken A., DiGiovanni J. Role of cytochrome P450 1a1 and 1b1 in the metabolic activation of 7,12-dimethylbenz[a]anthracene and the effects of naturally occurring furanocoumarins on skin tumor initiation. Chem. Res. Toxicol. 2002, 15:226-235.
31. Kleiner H.E., Xia X., Sonoda J., Zhang J., Pontius E., Abey J., Evans R.M., Moore D.D., DiGiovanni J. Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice. Toxicol. Appl. Pharmacol. 2008, 232:337-350.
32. Lin H.L., Kent U.M., Hollenberg P.F. The grapefruit juice effect is not limited to cytochrome P450 (P450) 3A4: evidence for bergamottin-dependent inactivation, heme destruction, and covalent binding to protein in P450s 2B6 and 3A5. J. Pharmacol. Exp. Ther. 2005, 313:154-164.
33. Lohr C., Raquet N., Schrenk D. Application of the concept of relative photomutagenic potencies to selected furocoumarins in V79 cells. Toxicol. In Vitro 2010, 24:558-566.
34. Maron D.M., Ames B.N. Revised methods for the Salmonella mutagenicity test. Mutat. Res. 1983, 113:173-215.
35. Matsushima T., Sawamura M., Hara K., Sigimura T. A safe substitute for polychlorinated biphenyls as an inducer of metabolic activation system. In Vitro Metabolic Activation in Mutagenesis Testing 1976, 85-88. Elsevier, Amsterdam. F.F. de Serres, J.R. Bend, R.M. Philpot (Eds.).
36. Messer A., Raquet N., Lohr C., Schrenk D. Major furocoumarins in grapefruit juice II: phototoxicity, photogenotoxicity, and inhibitory potency vs. cytochrome P45 3A4 activity. Food Chem. Toxicol. 2012, 50:756-760.
37. Nebert D.W. The Ah locus: genetic differences in toxicity, cancer, mutation, and birth defects. Crit. Rev. Toxicol. 1989, 20:153-174.
38. Nelson D.R., Koymans L., Kamataki T., Stegeman J.J., Feyereisen R., Waxman D.J., Waterman M.R., Gotoh O., Coon M.J., Estabrook R.W., Gunsalus I.C., Nebert D.W. P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 1996, 6:1-42.
39. Ohta T., Nagahashi M., Hosoi S., Tsukamoto S. Dihydroxybergamottin caproate as a potent and stable CYP3A4 inhibitor. Bioorg. Med. Chem. 2002, 10:969-973.
40. Pari L., Amudha K. Hepatoprotective role of naringin on nickel-induced toxicity in male Wistar rats. Eur. J. Pharmacol. 2011, 650:364-370.
41. Rendic S. Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab. Rev. 2002, 34:83-448.
42. Seden K., Dickinson L., Khoo S., Back D. Grapefruit-drug interactions. Drugs 2010, 70:2373-2407.
43. Shou M., Krausz K.W., Gonzalez F.J., Gelboin H.V. Metabolic activation of the potent carcinogen dibenzo[a, l]pyrene by human recombinant cytochromes P450, lung and liver microsomes. Carcinogenesis 1996, 17:2429-2433.
44. Stern R.S., Nichols K.T. Therapy with orally administered methoxsalen and ultraviolet A radiation during childhood increases the risk of basal cell carcinoma. The PUVA follow-up study. J. Pediatr. 1996, 129:915-917.
45. Takanaga H., Ohnishi A., Matsuo H., Sawada Y. Inhibition of vinblastine efflux mediated by P-glycoprotein by grapefruit juice components in caco-2 cells. Biol. Pharm. Bull. 1998, 21:1062-1066.
46. Tassaneeyakul W., Guo L.Q., Fukuda K., Ohta T., Yamazoe Y. Inhibition selectivity of grapefruit juice components on human cytochromes P450. Arch. Biochem. Biophys. 2000, 378:356-363.
47. Zhou S.F., Wang B., Yang L.P., Jiu J.P. Structure, function, regulation and polymorphism and the clinical significance of human cytochrome P450 1A2. Drug Metab. Rev. 2010, 42:268-354.