Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Quantitation of 8-prenylnaringenin, a novel phytoestrogen in hops (Humulus lupulus L.), hop products, and beers, by benchtop HPLC-MS using electrospray ionization


8-Prenylnaringenin (8-PN), a potent phytoestrogen, present in hops (Humulus lupulus L.), hop products, and most beers, exhibits an estrogenic activity greater than that of any of the known phytoestrogens. A sensitive, selective, and robust analytical method, based on HPLC-MS (High Performance Liquid Chromatography—Mass Spectrometry) using atmospheric pressure electrospray ionization, has been developed for systematic investigation of the development and the localization of this estrogenic trait in the hop plant, as well as for quantitative determination of 8-PN in hop varieties, hop products, and beers. Excellent linearity was obtained in the range of 3.7–2,200 μg L−1 (γ=0.9999, n=7) and the limit of detection wasca 1 μg L−1. Recoveries were between 93.8% (110 μg L−1) and 96.5% (370 μg L−1) for hop products, and between 63.4% (18.5 μgL−1) and 72.8% (37 μg L−1) for beers. Good precision was achieved with relative standard deviations of less than 5% within-day (n=6) and less than 10% from-day-to-day (n=18).

This is a preview of subscription content, log in to check access.


  1. [1]

    H. Adlercrentz, Scand. J. Clin. Lab. Invest.50 (Suppl 201), 3 (1990).

  2. [2]

    R. G. Ziegler, R. N. Hoover, M. C. Pike, J. Natl. Cancer Inst.85, 1819 (1993).

  3. [3]

    D. Ingram, K. Sanders, M. Kolybaba, D. Lopez, Lancet,350, 990 (1997).

  4. [4]

    H. Adlercreutz, B. R. Goldin, S. L. Gorbach, K. A. V. Höckerstedt, S. Watanabe, E. K. Hämäläinen, M. H. Markkanen, T. H. Mäkela, K. T. Wähälä, T. A. Hase, T. Fotsis, J. Nutr.125 (Suppl), 757S (1995).

  5. [5]

    D. C. Knight, J. A. Eden, Obstet. Gynecol.87, 897 (1996).

  6. [6]

    H. Adlercreutz, W. Mazur, Ann. Med.29, 95 (1997).

  7. [7]

    D. De Keukeleire, S. R. Milligan, L. De Cooman, A. Heyerick, Pharm. Pharmacol. Lett.7, 83 (1997).

  8. [8]

    S. R. Milligan, J. C. Kalita, A. Heyerick, H. Rong, L. De Cooman, D. De Keukeleire, J. Clin. Endocrinol. Metab.83, 2249 (1999).

  9. [9]

    S. R. Milligan, J. C. Kalita, King's College London, unpublished results (1999).

  10. [10]

    E. R. Rosenblum, I. M. Campbell, D. H. Vanthiel, J. S. Gavaler, Alcohol. Clin. Exp. Res.16, 843 (1992).

  11. [11]

    O. Lapcik, M. Hill, R. Hampl, K. Wähälä, H. Adlercreutz, Steroids63, 14 (1998).

  12. [12]

    J. F. Stevens, A. W. Taylor, M. L. Deinzer, J. Chromatogr. A832, 97 (1999).

  13. [13]

    L. Zhao, X. Bu, Y. Li, Bull. Soc. Chim. Belges104, 119 (1995).

  14. [14]

    H. Rong, J. F. Stevens, M. L. Deinzer, L. De Cooman, D. De Keukeleire, Planta Med.64, 620 (1998).

  15. [15]

    K. Lazou, Y. Zhao, P. Sandra, Ghent University, unpublished results (1999).

  16. [16]

    J. F. Stevens, M. Ivancic, V. L. Hsu, M. L. Deinzer, Phytochemistry44, 1575 (1997).

  17. [17]

    G. Charalambous, in J. R. A. Pollock, Ed., Brewing Science Vol. 2, Academic Press, London, 1991, p. 167.

  18. [18]

    K. W. M. Zuurbier, S. Y. Fung, J. J. C. Scheffer, R. Verpoorte, Phytochemistry38, 77 (1995).

  19. [19]

    R.P. Combes, The Brewer, January, 29 (1998).

Download references

Author information

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Rong, H., Zhao, Y., Lazou, K. et al. Quantitation of 8-prenylnaringenin, a novel phytoestrogen in hops (Humulus lupulus L.), hop products, and beers, by benchtop HPLC-MS using electrospray ionization. Chromatographia 51, 545–552 (2000). https://doi.org/10.1007/BF02490811

Download citation

Key Words

  • Column liquid chromatography
  • Electrospray MS detection
  • 8-Prenylnaringenin
  • Hops