Skip to main content

Advertisement

Log in

Use of High Hydrostatic Pressure to Increase the Content of Xanthohumol in Beer Wort

  • Original Paper
  • Published:
Food and Bioprocess Technology Aims and scope Submit manuscript

Abstract

During beer production, xanthohumol (XN) extracted from hop through wort boiling is largely converted into its isomeric flavanone, isoxanthohumol (IXN), due to the thermal treatment. XN has a great biological interest as a functional compound (being anti-carciogenic, antioxidant, anti-inflammatory, and anti-infective) and its loss leads to beers with very small amounts of XN and reduced functional properties. In this work, we studied the use of high-pressure treatments (HP; 100, 200, 250, 300, 400 and 500 MPa for 5 min and 250 and 400 MPa for 15 min), applied to previously boiled worts with a second hop dosage, as an extractive procedure, to produce XN-enriched beer worts. The results indicated that beer worts processed by HP showed higher levels of XN. The best results were obtained for 250 MPa, 5 min, resulting in an increase of 4-fold in XN, compared with beer worts produced only by boiling, and 2-fold compared with a method mimicking a recently proposed methodology also intended to improve XN in wort (called XAN method). Combinations of lower pressures with short pressurisation periods proved to be more efficient to increase the amount of XN in the wort. Moreover, HP-processed worts showed lower levels of IXN compared with samples produced by the mimicked XAN method. Physical–chemical characteristics of worts (pH, colour, bitterness and original extract) produced by HP, were similar to those produced only by boiling. These results clearly indicate the potential of using HP treatments to increase the XN content in beer wort, together with less isomerisation to IXN, and open promising possibilities to produce beers with higher amounts of XN, with potentially enhanced functional properties and health promoting properties.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  • Analytica-EBC. (1998). European Brewery Convention. Nurnberg: Verlag Hans Carl Getranke-Fachverlag.

    Google Scholar 

  • Back, W., Zuercher, A., & Wunderlich, S. (2004) Production of beer and other drinks with a high xanthohumol content is effected by addition to a malt or fruit wort of hops with a high xanthohumol content. Patent No DE10256166-A1; DE10256166-B4.

  • Bhattacharya, S., Virani, S., Zavro, M., & Haas, G. J. (2003). Inhibition of Streptococcus mutans and other oral streptococci by hop (Humulus lupulus L.) constituents. Economic Botany, 57(1), 118–125.

    Article  Google Scholar 

  • Biendl, M., Methner, F., Stettner, G., & Walker, C. (2004). Brewing trials with a xanthohumol-enriched hop product. Brauwelt International, 22, 182–184.

    Google Scholar 

  • Buckwold, V. E., Wilson, R. J. H., Nalca, A., Beer, B. B., Voss, T. G., Turpin, J. A., et al. (2004). Antiviral activity of hop constituents against a series of DNA and RNA viruses. Antiviral Research, 61(1), 57–62.

    Article  CAS  Google Scholar 

  • Cho, Y. C., Kim, H. J., Kim, Y. J., Lee, K. Y., Choi, H. J., Lee, I. S., et al. (2008). Differential anti-inflammatory pathway by xanthohumol in IFN-gamma and LPS-activated macrophages. International Immunopharmacology, 8(4), 567–573.

    Article  CAS  Google Scholar 

  • Corrales, M., Garcia, A. F., Butz, P., & Tauscher, B. (2009). Extraction of anthocyanins from grape skins assisted by high hydrostatic pressure. Journal of Food Engineering, 90(4), 415–421.

    Article  CAS  Google Scholar 

  • Correia, I., Nunes, A., Saraiva, J. A., Barros, A. S., & Delgadillo, I. (2011). High pressure treatments largely avoid/revert decrease of cooked sorghum protein digestibility when applied before/after cooking. LWT-Food Science and Technology, 44(4), 1245–1249.

    Article  CAS  Google Scholar 

  • Delmulle, L., Bellahcene, A., Dhooge, W., Comhaire, F., Roelens, F., Huvaere, K., et al. (2006). Anti-proliferative properties of prenylated flavonoids from hops (Humulus lupulus L.) in human prostate cancer cell lines. Phytomedicine, 13(9–10), 732–734.

    Article  CAS  Google Scholar 

  • Figueiredo, A., Evtuguin, D., & Saraiva, J. (2010). Effect of high pressure treatment on structure and properties of cellulose in eucalypt pulps. Cellulose, 17(6), 1193–1202.

    Article  CAS  Google Scholar 

  • Fischer, S., Schoberl, H., Russ, W., & Meyer-Pittroff, R. (1998). The effects of hydrostatic high pressure on the brewing process and beer. In Ludwig, H. International Conference on Advances in High Pressure Bioscience and Biotechnology, pp. 419–422.

  • Gerhauser, C. (2005). Beer constituents as potential cancer chemopreventive agents. European Journal of Cancer, 41(13), 1941–1954.

    Article  Google Scholar 

  • Gerhauser, C., Alt, A., Heiss, E., Gamal-Eldeen, A., Klimo, K., Knauft, J., et al. (2002). Cancer chemopreventive activity of xanthohumol, a natural product derived from hop. Molecular Cancer Therapeutics, 1(11), 959–969.

    CAS  Google Scholar 

  • Goldammer, T. (2008). The Brewer’s handbook—the complete book to brewing beer. Virginia: Apex Publishers.

    Google Scholar 

  • Gómez-Guillén, M. C., Giménez, B., & Montero, P. (2005). Extraction of gelatin from fish skins by high pressure treatment. Food Hydrocolloids, 19, 923–928.

    Article  Google Scholar 

  • He, X., Kim, S. S., Park, S. J., Seong, D. H., Yoon, W. B., Lee, H. Y., et al. (2010). Combined effects of probiotic fermentation and high-pressure extraction on the antioxidant, antimicrobial, and antimutagenic activities of Deodeok (Codonopsis lanceolata). Journal of Agricultural and Food Chemistry, 58(3), 1719–1725.

    Article  CAS  Google Scholar 

  • He, X., Yoon, W. B., Park, S. J., Park, D. S., & Ahn, J. (2011). Effects of pressure level and processing time on the extraction of total phenols, flavonoids, and phenolic acids from Deodeok (Codonopsis lanceolata). Food Science and Biotechnology, 20(2), 499–505.

    Article  CAS  Google Scholar 

  • Herath, W., Ferreira, D., Khan, S. I., & Khan, I. A. (2003). Identification and biological activity of microbial metabolites of xanthohumol. Chemical and Pharmaceutical Bulletin, 51(11), 1237–1240.

    Article  CAS  Google Scholar 

  • Jun, X. (2009). Caffeine extraction from green tea leaves assisted by high pressure processing. Journal of Food Engineering, 94(1), 105–109.

    Article  CAS  Google Scholar 

  • Koo, J. H., Kim, H. T., Yoon, H. Y., Kwon, K. B., Choi, I. W., Jung, S. H., et al. (2008). Effect of xanthohumol on melanogenesis in B16 melanoma cells. Experimental & Molecular Medicine, 40(3), 313–319.

    Article  CAS  Google Scholar 

  • Magalhães, P. J., Guido, L. F., Cruz, J. M., & Barros, A. A. (2007). Analysis of xanthohumol and isoxanthohumol in different hop products by liquid chromatography-diode array detection-electrospray ionization tandem mass spectrometry. Journal of Chromatography. A, 1150, 295–301.

    Article  Google Scholar 

  • Magalhães, P. J., Dostalek, P., Cruz, J. M., Guido, L. F., & Barros, A. A. (2008). The impact of a xanthohumol-enriched hop product on the behavior of xanthohumol and isoxanthohumol in pale and dark beers: a pilot scale approach. Journal of the Institute of Brewing, 114(3), 246–256.

    Article  Google Scholar 

  • Magalhães, P. J., Carvalho, D. O., Cruz, J. M., Guido, L. F., & Barros, A. A. (2009). Fundamentals and health benefits of xanthohumol, a natural product derived from Hops and Beer. Natural Product Communications, 4(5), 591–610.

    Google Scholar 

  • Miranda, C. L., Stevens, J. F., Helmrich, A., Henderson, M. C., Rodriguez, R. J., Yang, Y. H., et al. (1999). Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines. Food and Chemical Toxicology, 37(4), 271–285.

    Article  CAS  Google Scholar 

  • Monteiro, R., Calhau, C., Silva, A. O. E., Pinheiro-Silva, S., Cuerreiro, S., Gartner, F., et al. (2008). Xanthohumol inhibits inflammatory factor production and angiogenesis in breast cancer xenografts. Journal of Cellular Biochemistry, 104(5), 1699–1707.

    Article  CAS  Google Scholar 

  • Mujica-Paz, H., Valdez-Fragoso, A., Samson, C. T., Welti-Chanes, J., & Torres, J. A. (2011). High-pressure processing technologies for the pasteurization and sterilization of foods. Food and Bioprocess Technology, 4(6), 969–985.

    Article  Google Scholar 

  • Natarajan, P., Katta, S., Andrei, I., Ambati, V. B. R., Leonida, M., & Haas, G. J. (2008). Positive antibacterial co-action between hop (Humulus lupulus) constituents and selected antibiotics. Phytomedicine, 15(13), 194–201.

    Article  CAS  Google Scholar 

  • Nowakowska, Z. (2007). A review of anti-infective and anti-inflammatory chalcones. European Journal of Medicinal Chemistry, 42(2), 125–137.

    Article  CAS  Google Scholar 

  • Perez-Lamela, C., Ledward, D. A., Reed, R. J. R., & Simal-Gandara, J. (2002). Application of high-pressure treatment in the mashing of white malt in the elaboration process of beer. Journal of the Science of Food and Agriculture, 82(3), 258–262.

    Article  CAS  Google Scholar 

  • Perez-Lamela, C., Reed, R. J. R., & Simal-Gandara, J. (2004). High pressure application to wort and beer. Deutsche Lebensmittel-Rundschau, 100(2), 53–56.

    CAS  Google Scholar 

  • Prasad, K. N., Yang, B., Zhao, M. M., Ruenroengklin, N., & Jiang, Y. M. (2009). Application of ultrasonication or high-pressure extraction of flavonoides from litchi fruit pericarp. Journal of Food Process Engineering, 32(6), 828–843.

    Article  Google Scholar 

  • Prasad, N. K., Yang, B., Zhao, M. M., Wang, B. S., Chen, F., & Jiang, Y. M. (2009). Effects of high-pressure treatment on the extraction yield, phenolic content and antioxidant activity of litchi (Litchi chinensis Sonn.) fruit pericarp. International Journal of Food Science and Technology, 44(5), 960–966.

    Article  CAS  Google Scholar 

  • Ramirez, R., Saraiva, J., Lamela, C. P., & Torres, J. A. (2009). Reaction kinetics analysis of chemical changes in pressure-assisted thermal processing. Food Engineering Reviews, 1(1), 16–30.

    Article  CAS  Google Scholar 

  • Salvador, A. C., Santos, M. D., & Saraiva, J. A. (2010). Effect of the ionic liquid bmim Cl and high pressure on the activity of cellulase. Green Chemistry, 12(4), 632–635.

    Article  CAS  Google Scholar 

  • Saraiva, J. A., & Rodrigues, I. M. (2011). Inhibition of potato tuber sprouting by pressure treatments. International Journal of Food Science and Technology, 46(1), 61–66.

    Article  CAS  Google Scholar 

  • Shouqin, Z., Jun, X., & Changzheng, W. (2005). Note: effect of high hydrostatic pressure on extraction of flavonoids in propolis. Food Science and Technology International, 11(3), 213–216.

    Article  CAS  Google Scholar 

  • Stevens, J. F., & Page, J. E. (2004). Xanthohumol and related prenylflavonoids from hops and beer: to your good health! Phytochemistry, 65(10), 1317–1330.

    Article  CAS  Google Scholar 

  • Stevens, J. F., Taylor, A. W., Clawson, J. E., & Deinzer, M. L. (1999). Fate of xanthohumol and related prenylflavonoids from hops to beer. Journal of Agricultural and Food Chemistry, 47(6), 2421–2428.

    Article  CAS  Google Scholar 

  • Stevens, J. F., Taylor, A. W., & Deinzer, M. L. (1999). Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography tandem mass spectrometry. Journal of Chromatography A, 832(1–2), 97–107.

    Article  CAS  Google Scholar 

  • Vincent, A. M., Edwards, J. L., Sadidi, M., & Feldman, E. L. (2008). The antioxidant response as a drug target in diabetic neuropathy. Current Drug Targets, 9(1), 94–100.

    Article  CAS  Google Scholar 

  • Vogel, S., & Heilmann, J. (2008). Synthesis, cytotoxicity, and antioxidative activity of minor prenylated chalcones from Humulus lupulus. Journal of Natural Products, 71(7), 1237–1241.

    Article  CAS  Google Scholar 

  • Wang, Q., Ding, Z. H., Liu, J. K., & Zheng, Y. T. (2004). Xanthohumol, a novel anti-HIV-1 agent purified from hops Humulus lupulus. Antiviral Research, 64(3), 189–194.

    CAS  Google Scholar 

  • Wunderlich, S., Zurcher, A., & Back, W. (2005). Enrichment of xanthohumol in the brewing process. Molecular Nutrition & Food Research, 49(9), 874–881.

    Article  CAS  Google Scholar 

  • Xi, J. (2006). Effect of high pressure processing on the extraction of lycopene in tomato paste waste. Chemical Engineering and Technology, 29(6), 736–739.

    Article  CAS  Google Scholar 

  • Xi, J., Shen, D. J., Zhao, S., Lu, B. B., Li, Y., & Zhang, R. (2009). Characterization of polyphenols from green tea leaves using a high hydrostatic pressure extraction. International Journal of Pharmaceutics, 382(1–2), 139–143.

    Article  CAS  Google Scholar 

  • Zanoli, P., & Zavatti, M. (2008). Pharmacognostic and pharmacological profile of Humulus lupulus L. Journal of Ethnopharmacology, 116(3), 383–396.

    Article  CAS  Google Scholar 

  • Zhang, S. Q., Xi, J., & Wang, C. Z. (2005). High hydrostatic pressure extraction of flavonoids from propolis. Journal of Chemical Technology and Biotechnology, 80(1), 50–54.

    Article  CAS  Google Scholar 

  • Zhang, S., Chen, R., Wu, H., & Wang, C. (2006). Ginsenoside extraction from Panax quinquefolium L. (American ginseng) root by using ultrahigh pressure. Journal of Pharmaceutical and Biomedical Analysis, 41(1), 57–63.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors acknowledge Unicer Bebidas, S.A., for their support, including the supply of hop pellets samples and wort and the financial support from Instituto de Bebidas e Saúde (iBeSa), as part of the Project 11-08 and supply of XN and IXN.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jorge A. Saraiva.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Santos, M.C., Salvador, Â.C., Domingues, F.M. et al. Use of High Hydrostatic Pressure to Increase the Content of Xanthohumol in Beer Wort. Food Bioprocess Technol 6, 2478–2485 (2013). https://doi.org/10.1007/s11947-012-0952-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11947-012-0952-0

Keywords

Navigation