PAMPA permeability, plasma protein binding, blood partition, pharmacokinetics and metabolism of formononetin, a methoxylated isoflavone

Food and Chemical Toxicology

Volumn 49, Issue 5, 2011, Pages 1056-1062

  Singh, Sheelendra Pratap ^a   Wahajuddin, ^a   Tewari, Divyesh ^a   Pradhan, Tejaswini ^a   Jain, Girish Kumar ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Formononetin; Isoflavone; Permeability; Pharmacokinetics; Protein binding; RBC uptake

Indexed keywords

DAIDZEIN; FORMONONETIN;

ANIMAL EXPERIMENT; ARTICLE; ARTIFICIAL MEMBRANE; BLOOD SAMPLING; CONTROLLED STUDY; DISTRIBUTION VOLUME; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG METABOLISM; DRUG PENETRATION; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG UPTAKE; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; LIQUID CHROMATOGRAPHY; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; PH; PLASMA CONCENTRATION-TIME CURVE; PLASMA PROTEIN BINDING; QUANTITATIVE ANALYSIS; RAT; TANDEM MASS SPECTROMETRY; TIME TO MAXIMUM PLASMA CONCENTRATION;

ANIMALS; BIOLOGICAL AVAILABILITY; BLOOD PROTEINS; CELL MEMBRANE PERMEABILITY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, LIQUID; ERYTHROCYTES; FEMALE; GLUCURONIDES; HYDROLYSIS; ISOFLAVONES; PLANT EXTRACTS; PLASMA; PROTEIN BINDING; RATS; RATS, SPRAGUE-DAWLEY; TRIFOLIUM;

RATTUS; TRIFOLIUM PRATENSE;

EID: 79953058035     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fct.2011.01.012     Document Type: Article

References (27)

1. Barve A., Chen C., Hebbar V., Desiderio J., Saw C.L., Kong A.N. Metabolism, oral bioavailability and pharmacokinetics of chemopreventive kaempferol in rats. Biopharm. Drug Dispos. 2009, 30:356-365.
2. Breinholt V., Hossaini A., Svendsen G.W., Brouwer C., Nielsen E. Estrogenic activity of flavonoids in mice. The importance of estrogen receptor distribution, metabolism and bioavailability. Food Chem. Toxicol. 2000, 38:555-564.
3. Chen J., Wang S., Jia X., Bajimaya S., Lin H., Tam V.H., Hu M. Disposition of flavonoids via recycling: comparison of intestinal versus hepatic disposition. Drug Metab. Dispos. 2005, 33:1777-1784.
4. Coldham N.G., Zhang A.Q., Key P., Sauer M.J. Absolute bioavailability of [14C] genistein in the rat; plasma pharmacokinetics of parent compound, genistein glucuronide and total radioactivity. Eur. J Drug. Metab. Pharmacokinet. 2002, 27:249-258.
5. Davies B., Morris T. Physiological parameters in laboratory animals and humans. Pharm. Res. 1993, 10:1093-1095.
6. Dressman J.B., Berardi R.R., Dermentzoglou L.C., Russell T.L., Schmaltz S.P., Barnett J.L., Jarvenpaa K.M. Upper gastrointestinal (GI) pH in young, healthy men and women. Pharm. Res. 1990, 7:756-761.
7. Huh J.E., Kwon N.H., Baek Y.H., Lee J.D., Choi D.Y., Jingushi S., Kim K.I., Park D.S. Formononetin promotes early fracture healing through stimulating angiogenesis by up-regulating VEGFR-2/Flk-1 in a rat fracture model. Int. Immunopharmacol. 2009, 9:1357-1365.
8. Jia X., Chen J., Lin H., Hu M. Disposition of flavonoids via enteric recycling: enzyme-transporter coupling affects metabolism of biochanin A and formononetin and excretion of their phase II conjugates. J. Pharmacol. Exp. Ther. 2004, 310:1103-1113.
9. Matsumoto H., Ikoma Y., Sugiura M., Yano M., Hasegawa Y. Identification and quantification of the conjugated metabolites derived from orally administered hesperidin in rat plasma. J. Agric. Food Chem. 2004, 52:6653-6659.
10. Mehrotra N., Lal J., Puri S.K., Madhusudanan K.P., Gupta R.C. In vitro and in vivo pharmacokinetic studies of bulaquine (analogue of primaquine), a novel antirelapse antimalarial, in rat, rabbit and monkey-highlighting species similarities and differences. Biopharm. Drug Dispos. 2007, 28:209-227.
11. Moon Y.J., Sagawa K., Frederick K., Zhang S., Morris M.E. Pharmacokinetics and bioavailability of the isoflavone biochanin A in rats. AAPS J. 2006, 8:E433-E442.
12. Peterson T.G., Ji G.P., Kirk M., Coward L., Falany C.N., Barnes S. Metabolism of the isoflavones genistein and biochanin A in human breast cancer cell lines. Am. J. Clin. Nutr. 1998, 68:1505S-1511S.
13. Rudy A.C., Poynor W.J. Binding of pyrimethamine to human plasma proteins and erythrocytes. Pharm. Res. 1990, 7:1055-1060.
14. Russell T.L., Berardi R.R., Barnett J.L., Dermentzoglou L.C., Jarvenpaa K.M., Schmaltz S.P., Dressman J.B. Upper gastrointestinal pH in seventy-nine healthy, elderly, North American men and women. Pharm. Res. 1993, 10:187-196.
15. Setchell K.D., Brown N.M., Desai P., Zimmer-Nechemias L., Wolfe B.E., Brashear W.T., Kirschner A.S., Cassidy A., Heubi J.E. Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements. J. Nutr. 2001, 131:1362S-1375S.
16. Sfakianos J., Coward L., Kirk M., Barnes S. Intestinal uptake and biliary excretion of the isoflavone genistein in rats. J. Nutr. 1997, 127:1260-1268.
17. Singh, S.P., Wahajuddin, Yadav, D.K., Rawat, P., Maurya, R., Jain, G.K., Quantitative determination of formononetin and its metabolite in rat plasma after intravenous bolus administration by HPLC coupled with tandem mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 878, 391-397.
18. Taylor J.I., Grace P.B., Bingham S.A. Optimization of conditions for the enzymatic hydrolysis of phytoestrogen conjugates in urine and plasma. Anal. Biochem. 2005, 341:220-229.
19. Tham D.M., Gardner C.D., Haskell W.L. Clinical review 97: potential health benefits of dietary phytoestrogens: a review of the clinical, epidemiological, and mechanistic evidence. J. Clin. Endocrinol. Metab. 1998, 83:2223-2235.
20. Tolleson W.H., Doerge D.R., Churchwell M.I., Marques M.M., Roberts D.W. Metabolism of biochanin A and formononetin by human liver microsomes in vitro. J. Agric. Food Chem. 2002, 50:4783-4790.
21. Wallace S.M., Reigelman S. Uptake of acetazolamide by human erythrocytes in vitro. J. Pharm. Sci. 1977, 66:729-731.
22. Wang Q.Y., Meng Q.H., Zhang Z.T., Tian Z.J., Liu H. Synthesis, solubility, lipids-lowering and liver-protection activities of sulfonated formononetin. Yao. Xue. Xue. Bao. 2009, 44:386-389.
23. Wong C.K., Keung W.M. Daidzein sulfoconjugates are potent inhibitors of sterol sulfatase (EC 3.1.6.2). Biochem. Biophys. Res. Commun. 1997, 233:579-583.
24. Wu J.H., Li Q., Wu M.Y., Guo D.J., Chen H.L., Chen S.L., Seto S.W., Au A.L., Poon C.C., Leung G.P., Lee S.M., Kwan Y.W., Chan S.W. Formononetin, an isoflavone, relaxes rat isolated aorta through endothelium-dependent and endothelium-independent pathways. J. Nutr. Biochem. 2010, 21:613-620.
25. Yu S., Li S., Yang H., Lee F., Wu J.T., Qian M.G. A novel liquid chromatography/tandem mass spectrometry based depletion method for measuring red blood cell partitioning of pharmaceutical compounds in drug discovery. Rapid Commun. Mass Spectrom. 2005, 19:250-254.
26. Zhang Y., Song T.T., Cunnick J.E., Murphy P.A., Hendrich S. Daidzein and genistein glucuronides in vitro are weakly estrogenic and activate human natural killer cells at nutritionally relevant concentrations. J. Nutr. 1999, 129:399-405.
27. Zhang L., Zuo Z., Lin G. Intestinal and hepatic glucuronidation of flavonoids. Mol. Pharm. 2007, 4:833-845.