Analytical method development for synthesized conjugated metabolites of trans-resveratrol, and application to pharmacokinetic studies

Journal of Pharmaceutical and Biomedical Analysis

Volumn 63, Issue , 2012, Pages 1-8

  Iwuchukwu, Otito F ^a   Sharan, Satish ^a   Canney, Daniel J ^a   Nagar, Swati ^a  

^a TEMPLE UNIVERSITY   (United States)

Author keywords

Glucuronides; LC MS MS; Metabolites; Pharmacokinetics; Resveratrol; Sulfates

Indexed keywords

RESVERATROL; RESVERATROL 3 MONOGLUCURONIDE; RESVERATROL 3 MONOSULFATE; RESVERATROL 4' MONOGLUCURONIDE; RESVERATROL 4' MONOSULFATE; UNCLASSIFIED DRUG;

ACCURACY; ANALYTIC METHOD; ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; DRUG BIOAVAILABILITY; DRUG CONJUGATION; DRUG PURIFICATION; DRUG SYNTHESIS; LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY MASS SPECTROMETRY; MALE; MASS SPECTROMETRY; MOUSE; NONHUMAN; PLASMA CONCENTRATION-TIME CURVE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS;

ANIMALS; BIOLOGICAL AVAILABILITY; BIOTRANSFORMATION; CHROMATOGRAPHY, LIQUID; GLUCURONIDES; INJECTIONS, INTRA-ARTERIAL; MALE; MICE; MICE, INBRED C57BL; MODELS, ANIMAL; REFERENCE STANDARDS; REPRODUCIBILITY OF RESULTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STILBENES; SULFATES; TANDEM MASS SPECTROMETRY;

EID: 84858080543     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2011.12.006     Document Type: Article

References (32)

1. B B. Aggarwal, S Shishodia (Eds), Resveratrol in Health and Disease, CRC Press, Taylor and Francis Group, Boca Raton FL, 2006.
2. Baur J.A., Sinclair D.A. Therapeutic potential of resveratrol: the in vivo evidence. Nat. Rev. Drug Discov. 2006, 5:493-506.
3. Walle T., Hsieh F., DeLegge M.H., Oatis J.E., Walle U.K. High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab. Dispos. 2004, 32:1377-1382.
4. Bertelli A.A.E. Pharmacokinetics and metabolism of resveratrol. Resveratrol in Health and Disease 2006, CRC Press, Boca Raton, FL. B.B. Aggarwal, S. Shishodia (Eds.).
5. Almeida L., Vaz-da-Silva M., Falcao A., Soares E., Costa R., Loureiro A.I., Fernandes-Lopes C., Rocha J.F., Nunes T., Wright L., Soares-da-Silva P. Pharmacokinetic and safety profile of trans-resveratrol in a rising multiple-dose study in healthy volunteers. Mol. Nutr. Food Res. 2009, 53:S7-S15.
6. Boocock D.J., Faust G.E., Patel K.R., Schinas A.M., Brown V.A., Ducharme M.P., Booth T.D., Crowell J.A., Perloff M., Gescher A.J., Steward W.P., Brenner D.E. Phase I dose escalation pharmacokinetic study in healthy volunteers of resveratrol, a potential cancer chemopreventive agent. Cancer Epidemiol. Biomarkers Prev. 2007, 16:1246-1252.
7. Calamini B., Ratia K., Malkowski M.G., Cuendet M., Pezzuto J.M., Santarsiero B.D., Mesecar A.D. Pleiotropic mechanisms facilitated by resveratrol and its metabolites. Biochem. J. 2010, 429:273-282.
8. Marier J.F., Vachon P., Gritsas A., Zhang J., Moreau J.P., Ducharme M.P. Metabolism and disposition of resveratrol in rats: extent of absorption, glucuronidation, and enterohepatic recirculation evidenced by a linked-rat model. J. Pharmacol. Exp. Ther. 2002, 302:369-373.
9. Juan M.E., Maijo M., Planas J.M. Quantification of trans-resveratrol and its metabolites in rat plasma and tissues by HPLC. J. Pharm. Biomed. Anal. 2010, 51:391-398.
10. Wang L.X., Heredia A., Song H., Zhang Z., Yu B., Davis C., Redfield R. Resveratrol glucuronides as the metabolites of resveratrol in humans: characterization, synthesis, and anti-HIV activity. J. Pharm. Sci. 2004, 93:2448-2457.
11. Kawai N., Fujibayashi Y., Kuwabara S., K.-i.Takao, Ijuin Y., Kobayashi S. Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC. Tetrahedron 2000, 56:6467-6478.
12. Kawai N., K.-i.Takao, Kobayashi S. Synthetic study of akaterpin: determination of the relative stereochemistry of the upper decalin moiety with disulfated hydroquinone. Tetrahedron Lett. 1999, 40:4193-4196.
13. Fairley B., Botting N.P., Cassidy A. The synthesis of daidzein sulfates. Tetrahedron 2003, 59:5407-5410.
14. Murias M., Miksits M., Aust S., Spatzenegger M., Thalhammer T., Szekeres T., Jaeger W. Metabolism of resveratrol in breast cancer cell lines: impact of sulfotransferase 1A1 expression on cell growth inhibition. Cancer Lett. 2008, 261:172-182.
15. Vitaglione P., Sforza S., Galaverna G., Ghidini C., Caporaso N., Vescovi P.P., Fogliano V., Marchelli R. Bioavailability of trans-resveratrol from red wine in humans. Mol. Nutr. Food Res. 2005, 49:495-504.
16. Wenzel E., Soldo T., Erbersdobler H., Somoza V. Bioactivity and metabolism of trans-resveratrol orally administered to Wistar rats. Mol. Nutr. Food Res. 2005, 49:482-494.
17. Yu C., Shin Y.G., Chow A., Li Y., Kosmeder J.W., Lee Y.S., Hirschelman W.H., Pezzuto J.M., Mehta R.G., van Breemen R.B. Human, rat, and mouse metabolism of resveratrol. Pharm. Res. 2002, 19:1907-1914.
18. Shah V.P., Midha K.K., Findlay J.W., Hill H.M., Hulse J.D., McGilveray I.J., McKay G., Miller K.J., Patnaik R.N., Powell M.L., Tonelli A., Viswanathan C.T., Yacobi A. Bioanalytical method validation - a revisit with a decade of progress. Pharm. Res. 2000, 17:1551-1557.
19. Soidinsalo O., Wähälä K. Synthesis of phytoestrogenic isoflavonoid disulfates. Steroids 2004, 69:613-616.
20. Wang D., Hang T., Wu C., Liu W. Identification of the major metabolites of resveratrol in rat urine by HPLC-MS/MS. J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. 2005, 829:97-106.
21. Boxenbaum H. Interspecies variation in liver weight, hepatic blood flow, and antipyrine intrinsic clearance: extrapolation of data to benzodiazepines and phenytoin. J. Pharmacokinet. Biopharm. 1980, 8:165-176.
22. Davies B., Morris T. Physiological parameters in laboratory animals and humans. Pharm. Res. 1993, 10:1093-1095.
23. Kenealey J.D., Subramanian L., van Ginkel P., Darjatmoko S., Lindstrom M., Somoza V., Ghosh S., Song Z., Hsung R., Kwon G.S., Eliceiri K., Albert D., Polans A. Resveratrol metabolites do not elicit early pro-apoptotic mechanisms in neuroblastoma cells. J. Agric. Food Chem. 2011, 59:4979-4986.
24. Miksits M., Wlcek K., Svoboda M., Kunert O., Haslinger E., Thalhammer T., Szekeres T., Jager W. Antitumor activity of resveratrol and its sulfated metabolites against human breast cancer cells. Planta Med. 2009, 75:1227-1230.
25. Wenzel E., Somoza V. Metabolism and bioavailability of trans-resveratrol. Mol. Nutr. Food Res. 2005, 49:472-481.
26. Hoshino J., Park E.J., Kondratyuk T.P., Marler L., Pezzuto J.M., van Breemen R.B., Mo S., Li Y., Cushman M. Selective synthesis and biological evaluation of sulfate-conjugated resveratrol metabolites. J. Med. Chem. 2010, 53:5033-5043.
27. Kapetanovic I.M., Muzzio M., Huang Z., Thompson T.N., McCormick D.L. Pharmacokinetics, oral bioavailability, and metabolic profile of resveratrol and its dimethylether analog, pterostilbene, in rats. Cancer Chemother. Pharmacol. 2010, 68:593-601.
28. Brown V.A., Patel K.R., Viskaduraki M., Crowell J.A., Perloff M., Booth T.D., Vasilinin G., Sen A., Schinas A.M., Piccirilli G., Brown K., Steward W.P., Gescher A.J., Brenner D.E. Repeat dose study of the cancer chemopreventive agent resveratrol in healthy volunteers: safety, pharmacokinetics, and effect on the insulin-like growth factor axis. Cancer Res. 2010, 70:9003-9011.
29. Nunes T., Almeida L., Rocha J.F., Falcao A., Fernandes-Lopes C., Loureiro A.I., Wright L., Vaz-da-Silva M., Soares-da-Silva P. Pharmacokinetics of trans-resveratrol following repeated administration in healthy elderly and young subjects. J. Clin. Pharmacol. 2009, 49:1477-1482.
30. Azorin-Ortuno M., Yanez-Gascon M.J., Pallares F.J., Vallejo F., Larrosa M., Garcia-Conesa M.T., Tomas-Barberan F., Espin J.C. Pharmacokinetic study of trans-resveratrol in adult pigs. J. Agric. Food Chem. 2010.
31. Vitrac X., Desmouliere A., Brouillaud B., Krisa S., Deffieux G., Barthe N., Rosenbaum J., Merillon J.M. Distribution of [14C]-trans-resveratrol, a cancer chemopreventive polyphenol, in mouse tissues after oral administration. Life Sci. 2003, 72:2219-2233.
32. Alfaras I., Perez M., Juan M.E., Merino G., Prieto J.G., Planas J.M., Alvarez A.I. Involvement of breast cancer resistance protein (BCRP1/ABCG2) in the bioavailability and tissue distribution of trans-resveratrol in knockout mice. J. Agric. Food Chem. 2010, 58:4523-4528.