Pharmacokinetics of prenylated hop phenols in women following oral administration of a standardized extract of hops

Richard B. van Breemen*, Yang Yuan, Suzanne Banuvar, Lee P. Shulman, Xi Qiu, René F. Ramos Alvarenga, Shao Nong Chen, Birgit M. Dietz, Judy L. Bolton, Guido F. Pauli, Elizabeth Krause, Marlos Viana, Dejan Nikolic

*Corresponding author for this work

Research output: Contribution to journalArticle

49 Scopus citations

Abstract

Scope: Women seeking alternatives to hormone-replacement therapy for menopausal symptoms often try botanical dietary supplements containing extracts of hops (Humulus lupulus L.). Hops contain 8-prenylnaringenin (8-PN), a potent phytoestrogen, the related flavanones 6-prenylnaringenin and isoxanthohumol (IX), and the prenylated chalcone xanthohumol (XN). Methods and results: After chemically and biologically standardizing an extract of spent hops to these marker compounds, an escalating dose study was carried out in menopausal women to evaluate safety and pharmacokinetics. 8-PN, 6-prenylnaringenin, IX, and XN, sex hormones, and prothrombin time were determined in blood samples and/or 24 h urine samples. There was no effect on sex hormones or blood clotting. The maximum serum concentrations of the prenylated phenols were dose-dependent and were reached from 2 to 7 h, indicating slow absorption. The marker compounds formed glucuronides that were found in serum and urine. Secondary peaks at 5 h in the serum concentration-time curves indicated enterohepatic recirculation. The serum concentration-time curves indicated demethylation of IX to form 8-PN and cyclization of XN to IX. Slow absorption and enterohepatic recirculation contributed to half-lives exceeding 20 h. Conclusion: This human study indicated long half-lives of the estrogenic and proestrogenic prenylated phenols in hops but no acute toxicity.

Original languageEnglish (US)
Pages (from-to)1962-1969
Number of pages8
JournalMolecular Nutrition and Food Research
Volume58
Issue number10
DOIs
StatePublished - 2014

Keywords

  • 8-Prenylnaringenin
  • Hops
  • Isoxanthohumol
  • Pharmacokinetics
  • Xanthohumol

ASJC Scopus subject areas

  • Biotechnology
  • Food Science

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    van Breemen, R. B., Yuan, Y., Banuvar, S., Shulman, L. P., Qiu, X., Ramos Alvarenga, R. F., Chen, S. N., Dietz, B. M., Bolton, J. L., Pauli, G. F., Krause, E., Viana, M., & Nikolic, D. (2014). Pharmacokinetics of prenylated hop phenols in women following oral administration of a standardized extract of hops. Molecular Nutrition and Food Research, 58(10), 1962-1969. https://doi.org/10.1002/mnfr.201400245