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Chemical Compound Review

hyperforin     (1S,5S,7S,8R)-4-hydroxy-8- methyl-3,5,7...

Synonyms: SureCN98723, CHEMBL501711, CHEBI:5834, HSDB 7646, PDSP2_001346, ...
 
 
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Disease relevance of C07608

 

Psychiatry related information on C07608

  • Behavioral testing revealed a reduction of locomotor activity in mice treated with high-dose (10 mg/kg) hyperforin [6].
  • These results suggest that the effects of H. perforatum extracts on alcohol drinking behaviour are due to the hyperforin content of the herb rather than to other, more polar constituents [7].
  • In a passive avoidance response test on the mouse, a single oral dose (1.25 mg/kg) of hyperforin not only improved memory acquisition and consolidation, but also almost completely reversed scopolamine-induced amnesia [8].
  • In pairwise comparisons, WS 5572 (5% hyperforin) was superior to placebo in alleviating depressive symptoms according to HAMD reduction (Mann-Whitney U-test: p = 0.004), whereas the clinical effects of WS 5573 (0.5% hyperforin) and placebo were descriptively comparable [9].
  • In the forced swimming test, triple administration of hyperforin (5-20 mg/kg) significantly reduced the immobility time of rats, while in the learned helplessness test a daily treatment of 10 mg/kg for seven consecutive days was necessary to elicit an antidepressant effect [10].
 

High impact information on C07608

 

Chemical compound and disease context of C07608

 

Biological context of C07608

 

Anatomical context of C07608

 

Associations of C07608 with other chemical compounds

 

Gene context of C07608

  • In primary cultures of human hepatocytes, CYP2B6 was highly inducible by a number of compounds known to be human PXR ligands, including rifampicin and hyperforin [23].
  • Some herbal constituents (e.g., hyperforin and kava) were shown to activate pregnane X receptor, an orphan nuclear receptor acting as a key regulator of MDR1 and many other genes [24].
  • Hyperforin was a potent noncompetitive inhibitor of CYP2D6 activity (K(i) = 1.5 microM) and competitive inhibitor of CYP2C9 and CYP3A4 activities (K(i) = 1.8 and 0.48 microM, respectively) [25].
  • In thrombin- or ionophore-stimulated human platelets, hyperforin suppressed COX-1 product (12(S)-hydroxyheptadecatrienoic acid) formation with an IC(50) of 0.3 and 3 microM, respectively, being about 3- to 18-fold more potent than aspirin [26].
  • Further study revealed that extracellular signal-regulated kinase 1 and 2 (ERK1/2) were required for the hyperforin-induced expression of IL-8 [27].
 

Analytical, diagnostic and therapeutic context of C07608

References

  1. Antibacterial activity of hyperforin from St John's wort, against multiresistant Staphylococcus aureus and gram-positive bacteria. Schempp, C.M., Pelz, K., Wittmer, A., Schöpf, E., Simon, J.C. Lancet (1999) [Pubmed]
  2. Hyperforin inhibits cancer invasion and metastasis. Donà, M., Dell'Aica, I., Pezzato, E., Sartor, L., Calabrese, F., Della Barbera, M., Donella-Deana, A., Appendino, G., Borsarini, A., Caniato, R., Garbisa, S. Cancer Res. (2004) [Pubmed]
  3. Inhibition of tumour cell growth by hyperforin, a novel anticancer drug from St. John's wort that acts by induction of apoptosis. Schempp, C.M., Kirkin, V., Simon-Haarhaus, B., Kersten, A., Kiss, J., Termeer, C.C., Gilb, B., Kaufmann, T., Borner, C., Sleeman, J.P., Simon, J.C. Oncogene (2002) [Pubmed]
  4. Pro-apoptotic properties of hyperforin in leukemic cells from patients with B-cell chronic lymphocytic leukemia. Quiney, C., Billard, C., Faussat, A.M., Salanoubat, C., Ensaf, A., Naït-Si, Y., Fourneron, J.D., Kolb, J.P. Leukemia (2006) [Pubmed]
  5. Hyperforin activates nonselective cation channels (NSCCs). Treiber, K., Singer, A., Henke, B., Müller, W.E. Br. J. Pharmacol. (2005) [Pubmed]
  6. Dual modulation of striatal acetylcholine release by hyperforin, a constituent of St. John's wort. Buchholzer, M.L., Dvorak, C., Chatterjee, S.S., Klein, J. J. Pharmacol. Exp. Ther. (2002) [Pubmed]
  7. Correlation of hyperforin content of Hypericum perforatum (St John's Wort) extracts with their effects on alcohol drinking in C57BL/6J mice: a preliminary study. Wright, C.W., Gott, M., Grayson, B., Hanna, M., Smith, A.G., Sunter, A., Neill, J.C. J. Psychopharmacol. (Oxford) (2003) [Pubmed]
  8. Hypericum extract and hyperforin: memory-enhancing properties in rodents. Klusa, V., Germane, S., Nöldner, M., Chatterjee, S.S. Pharmacopsychiatry (2001) [Pubmed]
  9. St. John's wort in mild to moderate depression: the relevance of hyperforin for the clinical efficacy. Laakmann, G., Schüle, C., Baghai, T., Kieser, M. Pharmacopsychiatry (1998) [Pubmed]
  10. Pharmacological activity of hyperforin acetate in rats. Zanoli, P., Rivasi, M., Baraldi, C., Baraldi, M. Behavioural pharmacology. (2002) [Pubmed]
  11. St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor. Moore, L.B., Goodwin, B., Jones, S.A., Wisely, G.B., Serabjit-Singh, C.J., Willson, T.M., Collins, J.L., Kliewer, S.A. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  12. St. John's wort extracts and some of their constituents potently inhibit ultimate carcinogen formation from benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1. Schwarz, D., Kisselev, P., Roots, I. Cancer Res. (2003) [Pubmed]
  13. Vitamin K2 regulation of bone homeostasis is mediated by the steroid and xenobiotic receptor SXR. Tabb, M.M., Sun, A., Zhou, C., Grün, F., Errandi, J., Romero, K., Pham, H., Inoue, S., Mallick, S., Lin, M., Forman, B.M., Blumberg, B. J. Biol. Chem. (2003) [Pubmed]
  14. Hyperforin content determines the magnitude of the St John's wort-cyclosporine drug interaction. Mai, I., Bauer, S., Perloff, E.S., Johne, A., Uehleke, B., Frank, B., Budde, K., Roots, I. Clin. Pharmacol. Ther. (2004) [Pubmed]
  15. Effect of the St. John's wort constituent hyperforin on docetaxel metabolism by human hepatocyte cultures. Komoroski, B.J., Parise, R.A., Egorin, M.J., Strom, S.C., Venkataramanan, R. Clin. Cancer Res. (2005) [Pubmed]
  16. In Vivo Activation of Human Pregnane X Receptor Tightens the Blood-Brain Barrier to Methadone through P-Glycoprotein Up-Regulation. Bauer, B., Yang, X., Hartz, A.M., Olson, E.R., Zhao, R., Kalvass, J.C., Pollack, G.M., Miller, D.S. Mol. Pharmacol. (2006) [Pubmed]
  17. Hyperforin, a bio-active compound of St. John's Wort, is a new inhibitor of angiogenesis targeting several key steps of the process. Martínez-Poveda, B., Quesada, A.R., Medina, M.A. Int. J. Cancer (2005) [Pubmed]
  18. St. John's wort (Hypericum perforatum) and breastfeeding: plasma and breast milk concentrations of hyperforin for 5 mothers and 2 infants. Klier, C.M., Schmid-Siegel, B., Schäfer, M.R., Lenz, G., Saria, A., Lee, A., Zernig, G. The Journal of clinical psychiatry. (2006) [Pubmed]
  19. Effect of St John's wort dose and preparations on the pharmacokinetics of digoxin. Mueller, S.C., Uehleke, B., Woehling, H., Petzsch, M., Majcher-Peszynska, J., Hehl, E.M., Sievers, H., Frank, B., Riethling, A.K., Drewelow, B. Clin. Pharmacol. Ther. (2004) [Pubmed]
  20. Identification of amino acids in rat pregnane X receptor that determine species-specific activation. Tirona, R.G., Leake, B.F., Podust, L.M., Kim, R.B. Mol. Pharmacol. (2004) [Pubmed]
  21. Hyperforin-containing extracts of St John's wort fail to alter gene transcription in brain areas involved in HPA axis control in a long-term treatment regimen in rats. Butterweck, V., Winterhoff, H., Herkenham, M. Neuropsychopharmacology (2003) [Pubmed]
  22. Enhancement of proteolytic processing of the beta-amyloid precursor protein by hyperforin. Froestl, B., Steiner, B., Müller, W.E. Biochem. Pharmacol. (2003) [Pubmed]
  23. Regulation of the human CYP2B6 gene by the nuclear pregnane X receptor. Goodwin, B., Moore, L.B., Stoltz, C.M., McKee, D.D., Kliewer, S.A. Mol. Pharmacol. (2001) [Pubmed]
  24. Herbal modulation of P-glycoprotein. Zhou, S., Lim, L.Y., Chowbay, B. Drug Metab. Rev. (2004) [Pubmed]
  25. Inhibition of human cytochrome P450 enzymes by constituents of St. John's Wort, an herbal preparation used in the treatment of depression. Obach, R.S. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
  26. Hyperforin is a dual inhibitor of cyclooxygenase-1 and 5-lipoxygenase. Albert, D., Zündorf, I., Dingermann, T., Müller, W.E., Steinhilber, D., Werz, O. Biochem. Pharmacol. (2002) [Pubmed]
  27. Hyperforin, the active component of St. John's wort, induces IL-8 expression in human intestinal epithelial cells via a MAPK-dependent, NF-kappaB-independent pathway. Zhou, C., Tabb, M.M., Sadatrafiei, A., Grün, F., Sun, A., Blumberg, B. J. Clin. Immunol. (2004) [Pubmed]
  28. Determination of hyperforin in mouse brain by high-performance liquid chromatography/tandem mass spectrometry. Keller, J.H., Karas, M., Müller, W.E., Volmer, D.A., Eckert, G.P., Tawab, M.A., Blume, H.H., Dingermann, T., Schubert-Zsilavecz, M. Anal. Chem. (2003) [Pubmed]
  29. Hyperforin, a new lead compound against the progression of cancer and leukemia? Quiney, C., Billard, C., Salanoubat, C., Fourneron, J.D., Kolb, J.P. Leukemia (2006) [Pubmed]
  30. Air/light-free hyphenated extraction/analysis system: supercritical fluid extraction on-line coupled with liquid chromatography-UV absorbance/electrospray mass spectrometry for the determination of hyperforin and its degradation products in Hypericum pertoratum. Wang, Z., Ashraf-Khorassani, M., Taylor, L.T. Anal. Chem. (2004) [Pubmed]
 
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