Metabolism of hyperforin, the active constituent of St. John's wort, in human liver microsomes

European Journal of Pharmaceutical Sciences

Volumn 42, Issue 3, 2011, Pages 273-284

  Hokkanen, Juho ^a,b   Tolonen, Ari ^a   Mattila, Sampo ^b   Turpeinen, Miia ^a,b  

^a Novamass Ltd   (Finland)

^b UNIVERSITY OF OULU   (Finland)

Author keywords

Cytochrome P450; Human liver microsomes; Hyperforin; LC MS

Indexed keywords

CYTOCHROME P450; CYTOCHROME P450 2C; CYTOCHROME P450 3A; DRUG METABOLITE; HYPERFORIN;

ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; LIVER MICROSOME; PRIORITY JOURNAL; PROTEIN EXPRESSION;

BICYCLO COMPOUNDS; CHROMATOGRAPHY, LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; HYDROXYLATION; HYPERICUM; MICROSOMES, LIVER; PHLOROGLUCINOL; TANDEM MASS SPECTROMETRY; TERPENES;

EID: 79251598311     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2010.12.002     Document Type: Article

References (29)

1. V. Butterweck, V. Christoffel, A. Nahrstedt, F. Petereit, B. Spengler, and H. Winterhoff Step by step removal of hyperforin and hypericin: activity profile of different Hypericum preparations in behavioral models Life Sci. 73 2003 627 639
2. Y. Cui, C.Y.W. Ang, R.D. Beger, T.M. Heinze, L. Hu, and J. Leakey In vitro metabolism of hyperforin in rat liver microsomal systems Drug Metab. Dispos. 32 2003 28 34
3. A.G. Jensen, S.H. Hansen, and E.Ø. Nielsen Adhyperforin as a contributor to the effect of Hypericum perforatum L. in biochemical models of antidepressant activity Life Sci. 68 2001 1593 1605
4. I. Koch, R. Weil, R. Wolbold, J. Brockmöller, E. Hustert, O. Burk, A. Nuessler, P. Neuhaus, M. Eichelbaum, U. Zanger, and L. Wojnowski Interindividual variability and tissue-specificity in the expression of cytochrome P450 3A mRNA Drug Metab. Dispos. 30 2002 1108 1114
5. B.J. Komoroski, S. Zhang, H. Cai, J.M. Hutzler, R. Frye, T.S. Tracy, S.C. Strom, T. Lehmann, C.Y.W. Ang, Y.Y. Cui, and R. Venkataramanan Induction and inhibition of cytochromes P450 by the St. John's wort constituent hyperforin in human hepatocyte cultures Drug Metab. Dispos. 32 2004 512 518
6. G. Laakmann, C. Schüle, T. Baghai, and M. Kieser St. John's wort in mild to moderate depression: the relevance of hyperforin for the clinical efficacy Pharmacopsychiatry 31 S1 1998 54 59
7. J.Y. Lee, R.K. Duke, V.H. Tran, J.M. Hook, and C.C. Duke Hyperforin and its analogues inhibit CYP3A4 enzyme activity Phytochemistry 67 2006 2550 2560
8. K. Linde, M.M. Berner, and L. Kriston St John's wort for major depression Cochrane Database Syst. Rev. 4 2008 CD000448
9. R. Madabushi, B. Frank, B. Drewelow, H. Derendorf, and V. Butterweck Hyperforin in St. John's wort drug interactions Eur. J. Clin. Pharmacol. 62 2006 225 233
10. I. Mai, S. Bauer, E.S. Perloff, A. Johne, B. Uehleke, B. Frank, K. Budde, and I. Roots Hyperforin content determines the magnitude of the St John's wort-cyclosporine drug interaction Clin. Pharmacol. Ther. 76 2004 330 340
11. M.A. Medina, B. Martínez-Poveda, M.I. Amores-Sánchez, and A.R. Quesada Hyperforin: more than an antidepressant bioactive compound? Life Sci. 79 2006 105 111
12. L.B. Moore, B. Goodwin, S.A. Jones, G.B. Wisely, C.J. Serabjit-Singh, T.M. Willson, J.L. Collins, and S.A. Kliewer St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor Proc. Natl. Acad. Sci. U.S.A. 97 2000 7500 7502
13. S.C. Mueller, J. Majcher-Peszynska, B. Uehleke, S. Klammt, R.G. Mundkowski, W. Miekisch, H. Sievers, S. Bauer, B. Frank, G. Kundt, and B. Drewelow The extent of induction of CYP3A by St. John's wort varies among products and is linked to hyperforin dose Eur. J. Clin. Pharmacol. 62 2006 29 36
14. W.E. Muller Current St. John's wort research from mode of action to clinical efficacy Pharmacol. Res. 47 2003 101 109
15. R.S. Obach Inhibition of human cytochrome P450 enzymes by constituents of St. John's wort, an herbal preparation used in the treatment of depression J. Pharmacol. Exp. 294 2000 88 95
16. D. Pal, and A.K. Mitra MDR- and CYP3A4-mediated drug-herbal interactions Life Sci. 78 2006 2131 2145
17. O. Pelkonen, M. Turpeinen, J. Hakkola, P. Honkakoski, J. Hukkanen, and H. Raunio Inhibition and induction of human cytochrome P450 enzymes: current status Arch. Toxicol. 82 2008 667 715
18. A. Rostami-Hodjegan, and G.T. Tucker Simulation and prediction of in vivo drug metabolism in human populations from in vitro data Nat. Rev. Drug Discov. 6 2007 140 148
19. C.M. Schempp, V. Kirkin, B. Simon-Haarhaus, A. Kersten, J. Kiss, C.C. Termeer, B. Gilb, T. Kaufmann, C. Borner, J.P. Sleeman, and J.C. Simon Inhibition of tumour cell growth by hyperforin, a novel anticancer drug from St. John's wort that acts by induction of apoptosis Oncogene 21 2002 1242 1250
20. C.M. Schempp, K. Pelz, A. Wittmer, E. Schöpf, and J.C. Simon Antibacterial activity of hyperforin from St. John's wort, against multiresistant Staphylococcus aureus and gram-positive bacteria Lancet 353 1999 2129
21. Schwabe, W., 1998. Stable extract of Hypericum perforatum L., a method for producing the same, and corresponding pharmaceutical preparations. International patent, WO 98/44936.
22. L. Sleno, R. Daneshfar, G.P. Eckert, W.E. Müller, and D.A. Volmer Mass spectral characterization of phloroglucinol derivatives hyperforin and adhyperforin Rapid Commun. Mass Spectrom. 20 2006 2641 2648
23. A. Tolonen, A. Petsalo, M. Turpeinen, J. Uusitalo, and O. Pelkonen In vitro interaction cocktail assay for nine major cytochrome P450 enzymes with 13 probe reactions and a single LC/MS/MS run: analytical validation and testing with monoclonal anti-CYP antibodies J. Mass Spectrom. 42 2007 960 966
24. M. Turpeinen, J. Uusitalo, J. Jalonen, and O. Pelkonen Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay Eur. J. Pharm. Sci. 24 2005 123 132
25. M. Turpeinen, L.E. Korhonen, A. Tolonen, J. Uusitalo, R. Juvonen, H. Raunio, and O. Pelkonen Cytochrome P450 (CYP) inhibition screening: comparison of three tests Eur. J. Pharm. Sci. 29 2006 130 138
26. M. Turpeinen, C. Ghiciuc, M. Opritoui, L. Tursas, O. Pelkonen, and M. Pasanen Predictive value of animal models for human cytochrome P450 (CYP)-mediated metabolism: a comparative study in vitro Xenobiotica 37 2007 1367 1377
27. M. Wurglics, and M. Schubert-Zsilavecz Hypericum perforatum: a 'modern' herbal antidepressant: pharmacokinetics of active ingredients Clin. Pharmacokinet. 45 2006 449 468
28. U.M. Zanger, M. Turpeinen, K. Klein, and M. Schwab Functional pharmacogenetics/genomics of human cytochromes P450 involved in drug biotransformation Anal. Bioanal. Chem. 392 2008 1093 1108
29. S.F. Zhou, and X. Lai An update on clinical drug interactions with the herbal antidepressant St. John's wort Curr. Drug Metab. 9 2008 394 409