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Anti-proliferative activity of hop-derived prenylflavonoids against human cancer cell lines

Antiproliferative Aktivität gegenüber humanen Krebszellen von Prenylflavonoiden aus dem Hopfen

Summary

Flavonoids form a substantial group of secondary plant metabolites that display several health-promoting effects. Therefore, prenylflavonoids, a subclass of flavonoids, have attracted increasing attention. Here, we investigated the possible anti-cancer potential of 6-prenylnaringenin (6-PN) and 8-prenylnaringenin (8-PN), two prenylflavonoids present in hops and beer and demonstrate an unexpectedly pronounced, dose-dependent reduction of cellular proliferation of human PC-3 prostate cancer and UO.31 renal carcinoma cells upon treatment. Based on these findings 6-PN and 8-PN are currently further clinically evaluated in detail.

Zusammenfassung

Flavonoide bilden eine wichtige Gruppe von sekundären Pflanzenstoffen, welche gesundheitsfördernde Effekte aufweisen. Daher liegen ebenfalls Prenylflavonoide, eine Subgruppe der Flavonoide, im Fokus der molekularen medizinischen Forschung. Die Untersuchung der anti-tumoralen Eigenschaften der beiden natürlichen Hopfen- und Bierinhaltsstoffe 6-Prenylnarignenin (6-PN) und 8-Prenylnaringenin (8-PN) zeigte eine unerwartet ausgeprägte, dosisabhängige Wachstumshemmung von humanen PC-3 Prostata- und UO.31 Nierenkarzinomzellen. Diese Ergebnisse verdeutlichen das therapeutische Potential von Nahrungsmittelinhaltsstoffen, weswegen aktuell 6-PN und 8-PN im Detail für den potentiellen klinisch-therapeutischen bzw. präventiven Einsatz evaluiert werden.

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References

  1. Harborne JB, Williams CA. Advances in flavonoid research since 1992. Phytochemistry. 2000;55:481–504.

    CAS  PubMed  Article  Google Scholar 

  2. Yazaki K, Sasaki K, Tsurumaru Y. Prenylation of aromatic compounds, a key diversification of plant secondary metabolites. Phytochemistry. 2009;70:1739–45.

    CAS  PubMed  Article  Google Scholar 

  3. Stevens JF, Page JE. Xanthohumol and related prenylflavonoids from hops and beer: to your good health! Phytochemistry. 2004;65:1317–30.

    CAS  PubMed  Article  Google Scholar 

  4. Possemiers S, Bolca S, Grootaert C, et al. The prenylflavonoid isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine. J Nutr. 2006;136:1862–7.

    CAS  PubMed  Google Scholar 

  5. Miranda CL, Stevens JF, Helmrich A, et al. Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines. Food Chem Toxicol. 1999;37:271–85.

    CAS  PubMed  Article  Google Scholar 

  6. Miranda CL, Aponso GL, Stevens JF, et al. Prenylated chalcones and flavanones as inducers of quinone reductase in mouse Hepa 1c1c7 cells. Cancer Lett. 2000;149:21–9.

    CAS  PubMed  Article  Google Scholar 

  7. Milligan SR, Kalita JC, Heyerick A, et al. Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer. J Clin Endocrinol Metab. 1999;84:2249–52.

    CAS  PubMed  Article  Google Scholar 

  8. Kitaoka M, Kadokawa H, Sugano M, et al. Prenylflavonoids: a new class of non-steroidal phytoestrogen (Part 1). Isolation of 8-isopentenylnaringenin and an initial study on its structure-activity relationship. Planta Med. 1998;64:511–5.

    CAS  PubMed  Article  Google Scholar 

  9. Stevens JF, Taylor AW, Deinzer ML. Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography–tandem mass spectrometry. J Chromatogr A. 1999;832:97–107.

    CAS  PubMed  Article  Google Scholar 

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Acknowledgements

We are grateful to E. Holtorf for excellent technical assistance. This work was supported by grants from the Wissenschaftsfoerderung der Deutschen Brauwirtschaft e.V. (project B103), Pascoe pharmazeutische Praeparate GmbH, the Else Uebelmesser Foundation and by the German Childhood Cancer Foundation (DKS). SV was supported by the Innovation Grant of the University of Tuebingen.

Conflict of interest

The authors declare that there are no actual or potential conflicts of interest in relation to this article. The sponsors had no involvement in the study design, in the collection, analysis and interpretation of data, in the writing of the manuscript and in the decision to submit the manuscript for publication.

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Busch, C., Noor, S., Leischner, C. et al. Anti-proliferative activity of hop-derived prenylflavonoids against human cancer cell lines. Wien Med Wochenschr 165, 258–261 (2015). https://doi.org/10.1007/s10354-015-0355-8

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  • DOI: https://doi.org/10.1007/s10354-015-0355-8

Keywords

  • Prenylflavonoids
  • 6-Prenylnaringenin
  • 8-Prenylnaringenin
  • Nutrition
  • Cancer

Schlüsselwörter

  • Prenylflavonoide
  • 6-Prenylnaringenin
  • 8-Prenylnaringenin
  • Ernährung
  • Krebs