Deconjugation kinetics of glucuronidated phase II flavonoid metabolites by β-glucuronidase from neutrophils

Drug Metabolism and Pharmacokinetics

Volumn 25, Issue 4, 2010, Pages 379-387

  Bartholomé, Roger ^a   Haenen, Guido ^a   Hollman, Peter C H ^b   Bast, Aalt ^a   Dagnelie, Pieter C ^a   Roos, Dirk ^c   Keijer, Jaap ^b   Kroon, Paul A ^d   Needs, Paul W ^d   Arts, Ilja C W ^a  

^a MAASTRICHT UNIVERSITY   (Netherlands)

^b WAGENINGEN UNIVERSITY   (Netherlands)

^c UNIVERSITY OF AMSTERDAM   (Netherlands)

^d INSTITUTE OF FOOD RESEARCH   (United Kingdom)

Author keywords

Deconjugation; Enzyme kinetics; Flavonoids; Inflammation; Metabolismreferences; Neutrophils; Quercetin; glucuronidase

Indexed keywords

3' METHYLQUERCETIN 3 GLUCURONIDE; 4 METHYLUMBELLIFERYL BETA DEXTRO GLUCURONIDE; 4 NITROPHENOL GLUCURONIDE; BETA GLUCURONIDASE; GLUCURONIDE; QUERCETIN 3 GLUCURONIDE; QUERCETIN 3' GLUCURONIDE; QUERCETIN 4' GLUCURONIDE; QUERCETIN 7 GLUCURONIDE; UNCLASSIFIED DRUG;

ADULT; BONE MARROW CELL; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME SPECIFICITY; ENZYME SUBSTRATE COMPLEX; FEMALE; HELIX POMATIA; HUMAN; HYDROLYSIS; IN VIVO STUDY; MALE; NEUTROPHIL; NOTE; PH MEASUREMENT;

EID: 77956955600     PISSN: 13474367     EISSN: 18800920     Source Type: Journal    
DOI: 10.2133/dmpk.DMPK-10-RG-002     Document Type: Note

References (42)

1. Arts, I. C. W., Hollman, P. C. H., Feskens, E. J. M., Bueno de Mesquita, H. B. and Kromhout, D.: Catechin intake and associated dietary and lifestyle factors in a representative sample of Dutch men and women. Eur. J. Clin. Nutr., 55: 76-81 (2001).
2. Hollman, P. C. H. and Arts, I. C. W.: Flavonols, flavones and flavanols-nature, occurrence and dietary burden. J. Sci. Food Agric., 80: 1081-1093 (2000).
3. Arts, I. C. W. and Hollman, P. C. H.: Polyphenols and disease risk in epidemiologic studies. Am. J. Clin. Nutr., 81: 317S-325S (2005).
4. Yang, C. S., Landau, J. M., Huang, M.T. and Newmark, H.L.: Inhibition of carcinogenesis by dietary polyphenolic compounds. Annu. Rev. Nutr., 21: 381-406 (2001).
5. Nijveldt, R. J., van Nood, E., van Hoorn, D. E. C., Boelens, P. G., van Norren, K. and van Leeuwen, P. A. M.: Flavonoids: a review of probable mechanisms of action and potential applications. Am. J. Clin. Nutr., 74: 418-425 (2001).
6. Sesink, A. L. A., O'Leary, K. A. and Hollman, P. C. H.: Querce-tin glucuronides but not glucosides are present in human plasma after consumption of quercetin-3-glucoside or quercetin-4?-glucoside. J. Nutr., 131: 1938-1941. (2001).
7. Day, A. J., Bao, Y. P., Morgan, M. R. A. and Williamson, G.: Conjugation position of quercetin glucuronides and effect on biological activity. Free Radic. Biol. Med., 29: 1234-1243 (2000).
8. de Boer, V. C. J., de Goffau, M. C., Arts, I. C. W., Hollman, P. C. H. and Keijer, J.: SIRT1 stimulation by polyphenols is affected by their stability and metabolism. Mech. Ageing Dev., 127: 618-627 (2006).
9. Paigen, K.: Mammalian beta-glucuronidase: genetics, molecular biology, and cell biology. Prog. Nucleic Acid Res. Mol. Biol., 37: 155-205 (1989).
10. O'Leary, K. A., Day, A. J., Needs, P. W., Mellon, F. A., O'Brien, N. M. and Williamson, G.: Metabolism of quercetin-7- and quer-cetin-3-glucuronides by an in vitro hepatic model: the role of human [beta]-glucuronidase, sulfotransferase, catechol-O-methyltransferase and multi-resistant protein 2 (MRP2) in flavo-noid metabolism. Biochem. Pharmacol., 65: 479-491 (2003).
11. Shimoi, K., Saka, N., Kaji, K., Nozawa, R. and Kinae, N.: Metabolic fate of luteolin and its functional activity at focal site. Biofactors, 12: 181-186 (2000).
12. Marshall, T., Shult, P. and Busse, W. W.: Release of lysosomal enzyme beta-glucuronidase from isolated human eosinophils. J. Allergy Clin. Immunol., 82: 550-555 (1988).
13. Shimoi, K., Saka, N., Nozawa, R., Sato, M., Amano, I., Nakaya-ma, T. and Kinae, N.: Deglucuronidation of a flavonoid, luteolin monoglucuronide, during Inflammation. Drug Metab. Dispos., 29: 1521-1524 (2001).
14. Bosslet, K., Straub, R., Blumrich, M., Czech, J., Gerken, M., Sperker, B., Kroemer, H. K., Gesson, J. P., Koch, M. and Mon-neret, C.: Elucidation of the mechanism enabling tumor selective prodrug monotherapy. Cancer Res., 58: 1195-1201 (1998).
15. Sperker, B., Werner, U., Murdter, T. E., Tekkaya, C., Fritz, P., Wacke, R., Adam, U., Gerken, M., Drewelow, B. and Kroemer, H. K.: Expression and function of beta-glucuronidase in pancreatic cancer: potential role in drug targeting. Naunyn. Schmiedebergs Arch. Pharmacol., 362: 110-115 (2000).
16. Wu, C. H., Balasubramanian, W. R., Ko, Y. P., Hsu, G., Chang, S. E., Prijovich, Z. M., Chen, K. C. and Roffler, S. R.: A simple method for the production of recombinant proteins from mammalian cells. Biotechnol. Appl. Biochem., 40: 167-172 (2004).
17. Pedruzzi, E., Fay, M., Elbim, C., Gaudry, M. and Gougerot-Pocidalo, M. A.: Differentiation of PLB-985 myeloid cells into mature neutrophils, shown by degranulation of terminally differentiated compartments in response to N-formyl peptide and priming of superoxide anion production by granulocyte-macrophage colony-stimulating factor. Br. J. Haematol., 117: 719-726 (2002).
18. Gungor, N., Godschalk, R. W. L., Pachen, D. M., Van Schooten, F. J. and Knaapen, A. M.: Activated neutrophils inhibit nucleo-tide excision repair in human pulmonary epithelial cells: role of myeloperoxidase. FASEB J., 21: 2359-2367 (2007).
19. Needs, P. W. and Kroon, P. A.: Convenient syntheses of meta-bolically important quercetin glucuronides and sulfates. Tetrahedron, 62: 6862-6868 (2006).
20. Lineweaver, H. and Burk, D.: The Determination of Enzyme Dissociation Constants. J. Am. Chem. Soc., 56: 658-666 (1934).
21. Mandell, B. F., Ohliger, D. and Rella, J.: Rapid simultaneous assessment of neutrophil superoxide generation and lysosomal enzyme release. J. Immunol. Methods, 100: 211-214 (1987).
22. Contractor, S. F. and Shane, B.: Purification and characterization of lysosomal -glucuronidase from human placenta. Biochem. J., 128: 11-18 (1972).
23. Shimoi, K. and Nakayama, T.: Glucuronidase deconjugation in inflammation. Methods Enzymol., 400: 263-272 (2005).
24. O'Leary, K. A., Day, A. J., Needs, P. W., Sly, W. S., O'Brien, N. M. and Williamson, G.: Flavonoid glucuronides are substrates for human liver beta-glucuronidase. FEBS Lett., 503: 103-106 (2001).
25. Wiener, S. L., Wiener, R., Janov, C., Darmstadt, R., Upmanis, S., Urivetzky, M. and Meilman, E.: Kinetic study of neutrophil and inflammatory fluid beta glucuronidase. Res. Commun. Chem. Pathol. Pharmacol., 10: 491-499 (1975).
26. Zenser, T. V., Lakshmi, V. M. and Davis, B. B.: Human and Es-cherichia coli beta-glucuronidase hydrolysis of glucuronide conjugates of benzidine and 4-aminobiphenyl, and their hydroxy metabolites. Drug Metab. Dispos., 27: 1064-1067 (1999).
27. Murdter, T. E., Friedel, G., Backman, J. T., McClellan, M., Schick, M., Gerken, M., Bosslet, K., Fritz, P., Toomes, H., Kroemer, H. K. and Sperker, B.: Dose optimization of a dox-orubicin prodrug (HMR 1826) in isolated perfused human lungs: low tumor pH promotes prodrug activation by beta-glucuronidase. J. Pharmacol. Exp. Ther., 301: 223-228 (2002).
28. Moro, L., de Bernard, B. and Gonano, F.: Properties of beta-glucuronidase activity in human synovial fluid. Clin. Chim. Acta, 65: 371-377 (1975).
29. Peters, W. H., Jansen, P. L., Cuypers, H. T., de Abreu, R. A. and Nauta, H.: Deconjugation of glucuronides catalysed by UD-Pglucuronyltransferase. Biochim. Biophys. Acta, 873: 252-259 (1986).
30. Lin, C. W., Orcutt, M. L. and Fishman, W. H.: Purification and characterization of mouse kidney beta-glucuronidase. J. Biol. Chem., 250: 4737-4743 (1975).
31. Faurschou, M. and Borregaard, N.: Neutrophil granules and secretory vesicles in inflammation. Microbes Infect., 5: 1317-1327 (2003).
32. Punnia-Moorthy, A.: Evaluation of pH changes in inflammation of the subcutaneous air pouch lining in the rat, induced by car-rageenan, dextran and Staphylococcus aureus. J. Oral Pathol., 16: 36-44 (1987).
33. Clapp, W. D., Becker, S., Quay, J., Watt, J. L., Thorne, P. S., Frees, K. L., Zhang, X., Koren, H. S., Lux, C. R. and Schwartz, D. A.: Grain dust-induced airflow obstruction and inflammation of the lower respiratory tract. Am. J. Respir. Crit. Care Med., 150: 611-617 (1994).
34. Jagielo, P. J., Thorne, P. S., Watt, J. L., Frees, K. L., Quinn, T. J. and Schwartz, D. A.: Grain dust and endotoxin inhalation challenges produce similar inflammatory responses in normal subjects. Chest, 110: 263-270 (1996).
35. Cullen, M. R. and Merrill, W. W.: Association between neu-trophil concentration in bronchoalveolar lavage fluid and recent losses in diffusing capacity in men formerly exposed to asbestos. Chest, 102: 682-687 (1992).
36. Hollman, P. C. and Katan, M. B.: Absorption, metabolism and health effects of dietary flavonoids in man. Biomed. Phar-macother., 51: 305-310 (1997).
37. Wilms, L. C., Boots, A. W., de Boer, V. C., Maas, L. M., Pachen, D. M., Gottschalk, R. W., Ketelslegers, H. B., Godschalk, R. W., Haenen, G. R., van Schooten, F. J. and Kleinjans, J. C.: Impact of multiple genetic polymorphisms on effects of a 4-week blueberry juice intervention on ex vivo induced lymphocytic DNA damage in human volunteers. Carcinogenesis, 28: 1800-1806 (2007).
38. de Boer, V. C. J., Dihal, A. A., van der Woude, H., Arts, I. C. W., Wolffram, S., Alink, G. M., Rietjens, I. M. C. M., Keijer, J. and Hollman, P. C. H.: Tissue distribution of quercetin in rats and pigs. J. Nutr., 135: 1718-1725 (2005).
39. Arts, I. C. W., Sesink, A. L. A., Faassen-Peters, M. and Hollman, P. C. H.: The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides. Br. J. Nutr., 91: 841-847 (2004).
40. Khan, T., Soller, B., Naghavi, M. and Casscells, W.: Tissue pH determination for the detection of metabolically active, inflamed vulnerable plaques using near-infrared spectroscopy: an in-vitro feasibility study. Cardiology, 103: 10-16 (2005).
41. Andersson, S. E., Lexmuller, K., Johansson, A. and Ekstrom, G. M.: Tissue and intracellular pH in normal periarticular soft tissue and during different phases of antigen induced arthritis in the rat. J. Rheumatol., 26: 2018-2024 (1999).
42. Olthof, M. R., Hollman, P. C. H., Vree, T. B. and Katan, M. B.: Bioavailabilities of quercetin-3-glucoside and quercetin-4?-gluc-oside do not differ in humans. J. Nutr., 130: 1200-1203 (2000).