Research of hop polyphenols impact on malt hopped wort aroma formation model experiments
Keywords:hop polyphenol compounds, hop, polyphenol, essential oils, polyphenol stabilizers, terpene hydrocarbon
Currently, a lot of research is being done on the flavoring compounds of hops. However, much less attention has been paid to the aroma formation considering the hop polyphenol different groups by various methods at the wort hopping stage. Therefore, the main goal of the research is an impact of hopping conditions on the polyphenolic compounds, when the hop is extracted variously into both wort and water to better understand extraction conditions, mechanisms, and factors as well as aroma formation considering various groups of polyphenols. As shown the hop variety, boiling time, and treatment type affect the hop polyphenols amount extracted into the wort. Aromatics varied upon a hop variety and wort boiling time accompanying a positive softening effect regarding aroma formated from malt wort compounds comparing to hopped aqueous extracts. The research proved the most noticeable pH (7 and above) impact on aroma formation caused by the polyphenol conversion. As also shown the first time, a temperature and acidic pH doubled the rutin amount, as well as the best extraction of the prenylflavanoid isoxanthohumol, was achieved by boiling at an alkaline medium pH. The results obtained indicate that various hydrophilic amino acids containing in the wort can stabilize polyphenols affecting the quality indicators of beer produced from different grain raw materials.
Almaguer, C., Schönberger, C., Gastl, M., Arendt, E. K., Becker, T. 2014. Humulus lupulus – a story that begs to be told. A review. Journal of the Institute of Brewing, vol. 120. no. 4. p. 289-314. https://doi.org/10.100 2/jib.160
Andrade, N., Araújo, J. R., Correia-Branco, A., Carletti, J. V., Martel, F. 2017. Effect of dietary polyphenols on fructose uptake by human intestinal epithelial (CaСО2) cells. Journal of Functional Foods, vol. 36, p. 429-439. https://doi.org/10.1016/j.jff.2017.07.032
Basílio, N., Pina, F. 2016. Chemistry and Photochemistry of Anthocyanins and Related Compounds: A Thermodynamic and Kinetic Approach. Molecules, vol. 21, no. 11, 25 p. https://doi.org/10.3390/molecules21111502
Baxter, N. J., Lilley, T. H., Haslam, E., Williamson, M. P. 1997. Multiple Interactions Between Polyphenols and a Salivary Proline-Rich Protein Repeat Result in Complexation and Precipitation. Biochemistry, vol. 36, no. 18, p. 5566-5577. https://doi.org/10.1021/bi9700328
Bejblová, M., Žilková, N., Čejka, J. 2008. Transformations of aromatic hydrocarbons over zeolites. Research on Chemical Intermediates, vol. 34, no. 5, p. 439-454. https://doi.org/10.1163/156856708784795572
Biendl, M., Pinzl, C. 2009. Hops and Health. Master Brewers Association of the Americas, vol. 46, p. 1-7. https://doi.org/10.1094/TQ-46-2-0416-01
Bordenave, N., Hamaker, B. R., Ferruzzi, M. G. 2014. Nature and consequences of non-covalent interactions between flavonoids and macronutrients in foods. Food and Function, vol. 5, no. 1, p. 18-34. https://doi.org/10.1039/C3FO60263J
Boussetta, N., Vorobiev, E., Deloison, V., Pochez, F., Falcimaigne-Cordin, A., Lanoisellé, J. L. 2011.Valorization of grape pomace by extraction of phenolic antioxidants: Application of high voltage electrical discharges. Food Chemistry, vol. 128, no. 2, p. 364-370. https://doi.org/10.1016/j.foodchem.2011.03.035
Callemien, D., Collin, S. 2009. Structure, Organoleptic Properties, Quantification Methods, and Stability of Phenolic Compounds in Beer - A Review. Foods Reviews International, vol. 26, no. 1, p. 1-84. https://doi.org/10.1080/87559120903157954
Codorniu‐Hernández, E., Mesa‐Ibirico, A., Hernández‐Santiesteban, R., Montero‐Cabrera, L. A., Martínez‐Luzardo F., Santana‐Romero, J. L., Borrmannm, T., Stohrer, W. D. 2005. Essential amino acids interacting with flavonoids: A theoretical approach. International Journal of Quantum Chemistry, vol. 103, no. 1, p. 82-104. https://doi.org/10.1002/qua.20391
Condelli, N., Dinnella, C., Cerone, A., Monteleone, E., Bertuccioli, M. 2006. Prediction of Perceived Astringency Induced by Phenolic Compounds II: Criteria for Panel Selection and Preliminary Application on Wine Samples. Food Quality and Preferences, vol. 17, no. 1-2, p. 96-107. https://doi.org/10.1016/j.foodqual.2005.04.009
Dadic, М., Belleau, G. 1973. Polyphenolʹs and Beer Aroma. Proceedings. Annual meeting – American Society of Brewing Chemists, vol. 31, no. 1, p. 107-114. https://doi.org/10.1080/00960845.1973.12006011
Dangles, O., IFenger, J. A. 2018. The Chemical Reactivity of Anthocyanins and Its Consequences in Food Science and Nutrition. Molecules, vol. 23, no. 8, 23 p. https://doi.org/10.3390/molecules23081970
De Keukeleire, J., Ooms, G., Heyerick, A., Roldan-Ruiz, I., Van Bockstaele, E., De Keukeleire, D. 2003. Formation and Accumulation of α-Acids, β-Acids, Desmethylxanthohumol, and Xanthohumol during Flowering of Hops (Humulus Lupulus L.). Journal of Agricultural and Food Chemistry, vol. 51, no. 15, p. 4436-4441. https://doi.org/10.1021/jf034263z
Dostálek, P., Karabín, M., Jelínek, L. 2017. Hop Phytochemicals and Their Potential Role in Metabolic Syndrome Prevention and Therapy. Molecules, vol. 22, no. 10, 11 p. https://doi.org/10.3390/molecules22101761
Dresel, M., Dunkel, A., Hoffman, T. 2015. Sensomics Analysis of Key Bitter Compounds in the Hard Resin of Hops (Humulus lupulus L.) and Their Contribution to the Bitter Profile of Pilsener-Type Beer. Journal of Agricultural and Food Chemistry, vol. 63, no. 13, p. 3402-3418. https://doi.org/10.1021/acs.jafc.5b00239
EBC. 2010. European Brewery Convention (EBC). Nuremberg, Fachverlag Hans Carl.
El Gharras, H. 2009. Polyphenols: Food Sources, Properties, and Applications - A Review. International Journal of Food Science & Technology, vol. 44, no. 12, p. 2512-2518. https://doi.org/10.1111/j.1365-2621.2009.02077.x
Floridi, S., Miniati, E., Montanari, L., Fantozzi, P. 2001. Carbohydrate determination in wort and beer by HPLC-ELSD. Monatsschrift fuer Brauwissenschaft, vol. 54, p. 209-215.
Forster, A., Gar, F., Gar, A. 2013. About the influence of hops on the quality of beer. Brawvelt, no. 1, p. 14-18.
Fox, G. 2018. Starch in Brewing Applications. In Sjöö, M., Nilsson, L. Starch in Food. Structure, Function and Applications. 2nd edition, Cambridge, UK : Woodhead Publishing, p. 633-659. https://doi.org/10.1016/B978-0-08-100868-3.00016-0
Gauche, C., da Silva Malagoli, E., Bordignon Luiz, M. T. 2010. Effect of pH on the copigmentation of anthocyanins from Cabernet Sauvignon grape extracts with organic acids. Scientia Agricola, vol. 67, no. 1, p. 41-46. https://doi.org/10.1590/S0103-90162010000100006
Guerra, P. V., Yaylyan, V. A. 2014. Interaction of Flavanols with Amino Acids: Postoxidative Reactivity of the β-Ring of Catechin with Glycine. Journal of Agriculture and Food Chemistry, vol. 62, no. 17, p. 3831-3836. https://doi.org/10.1021/jf5005989
He, Y., Dong, J., Yin, H., Zhao, Y., Chen, R., Wan, X., Chen, P., Hou, X., Liu, J., Chen, L. 2014. Wort composition and its impact on the flavour active higher alcohol and ester formation of beer – a review. Journal of the Institute of Brewing, vol. 120, no. 3, p. 157-163. https://doi.org/10.1002/jib.145
Higgs, T., Stantic, B., Hoque, M. T., Sattar, A. 2008. Hydrophobic-Hydrophilic Forces and their Effects on Protein Structural Similarity. Supplementary Conference Proceedings, p. 1-12.
Iacobucci, G. A., Sweeny, J. G. 1983. The chemistry of anthocyanins, anthocyanidins and related flavylium salts. Tetrahedron, vol. 39, no. 19, p. 3005-3038. https://doi.org/10.1016/S0040-4020(01)91542-X
Ioannou, I., Hafsa, I., Hamdi, S., Charbonnel, C., Ghoul, M. 2012. Review of the effects of food processing and formulation flavonol and anthocyanin behaviour. Journal of Food Engineering, vol. 111, no. 2, p. 208-217. https://doi.org/10.1016/j.jfoodeng.2012.02.006
Jurić, A., Ćorić, N., Odak, A., Herceg, Z., Tišma, M. 2015. Analysis of total polyphenols, bitterness and haze in pale and dark lager beers produced under different mashing and boiling conditions. Journal of the Institute of Brewing, vol. 121, no. 4, p. 541-547. https://doi.org/10.1002/jib.254
Kishimoto, T. 2008. Hop-Derived Odorants Contributing to the Aroma Characteristics of Beer : dissertation thesis. Kyoto, Japan : Kyoto University, 93 p.
Langstaff, S. A., Lewis, M. J. 1993. The mouthfeel of beer - a review. Journal of the Institute of Brewing, vol. 99, no. 1, p. 31-37. https://doi.org/10.1002/j.2050-0416.1993.tb01143.x
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, vol. 114, no. 3, p. 246-256. https://doi.org/10.1002/j.2050-0416.2008.tb00335.x
McLaughlin, I. R., Lederer, C., Shellhammer, T. H. 2008. Bitterness-Modifying Properties of Hop Polyphenols Extracted from Spent Hop Material. Journal of the American Society of Brewing Chemists, vol. 66, no. 3, p. 174-183. https://doi.org/10.1094/ASBCJ-2008-0619-01
McMurrough, I., Madigan, D., Donnelly, D., Hurley, J., Doyle, A. M., Hennigan, G., McNulty, N., Smyth, M. R. 1996. Control of ferulic acid and 4-vinyl guaiacol in brewing. Journal of the Institute of Brewing, vol. 102, no. 5, p. 327-332. https://doi.org/10.1002/j.2050-0416.1996.tb00918.x
МEBAK. 2011. Collection of Brewing Analysis Methods of the Mitteleuropäische Brautechnische Analysenkommission, Freising-Weihenstephan.
Meilgaard, M. 2001. Effects on Flavor of Innovations in Brewery Equipment and Processing: A Review. Journal of the Institute of Brewing, vol. 107, no. 5, p. 271-286. https://doi.org/10.1002/j.2050-0416.2001.tb00098.x
Meilgaard, M. C. 1975. Flavor chemistry of beer: Part II: Flavour and threshold of 239 aroma volatiles. Master Brewers Association of the Americas, vol. 12, no. 3, p. 151-168.
Mikyška, A., Dušek, M., Slabý, M. 2019. How does fermentation, filtration and stabilization of beer affect polyphenols with health benefits. Kvasný průmysl, vol. 65, no. 4, p. 120-126. https://doi.org/10.18832/kp2019.65.120
Mikyška, А., Hrabák, М., Hašková, D., Šrogl, J. 2002. The Role of Malt and Hop P in Beer Quality, Flavour and Haze Stability. Journal of the Institute of Brewing, vol. 108, no. 1, p. 78-85. https://doi.org/10.1002/j.2050-0416.2002.tb00128.x
Moens, E., Bolca, S., Van de Wiele, T.,Van Landschoot, A., Goeman, J. L., Possemiers, S., Vestraete, W. 2020. Exploration of isoxanthohumol bioconversion from spent hops into 8-prenylnaringenin using resting cells of Eubacterium limosum. AMB Express, vol. 10, 11 p. https://doi.org/10.1186/s13568-020-01015-5
Mori, M., Kondo, T., Yoshida, K. 2009. Anthocyanin Components and Mechanism for Color Development in Blue Veronica flowers. Bioscience, Biotechnology, and Biochemistry, vol. 73, no. 10, p. 2329-2331. https://doi.org/10.1271/bbb.90349
Otter, G. E., Taylor, L. 1976. The determination of amino acids in wort, beer and brewing materials using gas chromatography. Journal of the Institute of Brewing, vol. 82, no. 5, p. 264-269. https://doi.org/10.1002/j.2050-0416.1976.tb03767.x
Praet, T. 2016. Chemical-analytical and sensory characterisation of kettle hoppy aroma of beer : dissertation thesis. Leuven, Belgium, 274 p.
Radzicka, A., Wolfenden, R. 1988. Comparing the polarities of the amino acids: side-chain distribution coefficients between the vapor phase, cyclohexane, 1-octanol, and neutral aqueous solution. Biochemistry, vol. 27, no. 5, p. 1664-1670. https://doi.org/10.1021/bi00405a042
Renard, M. G. C., Watrelot, A. A., Le Bourvellec, C. 2017. Interactions between polyphenols and polysaccharides: Mechanisms and consequences in food processing and digestion. Trends in Food Science and Technology, vol. 60, p. 43-51. https://doi.org/10.1016/j.tifs.2016.10.022
Roland, W. S. U., van Buren, L., Gruppen, H., Driesse, M., Gouka, R. J., Smit, G., Vincken, J. P. 2013. Bitter Taste Receptor Activation by Flavonoids and Isoflavonoids: Modeled Structural Requirements for Activation of hTAS2R14 and hTAS2R39. Journal of Agricultural and Food Chemistry, vol. 61, no. 44, p. 10454-10466. https://doi.org/10.1021/jf403387p
Shoji, T. 2007. Polyphenols as Natural Food Pigments: Changes During Food Processing. American Journal of Food Technology, vol. 2, no. 7, p. 570-581. https://doi.org/10.3923/ajft.2007.570.581
Soares, S., Kohl, S., Thalmann, S., Mateus, N., Meyerhof, W., De Freitas, V. 2013. Different Phenolic Compounds Activate Distinct Human Bitter Taste Receptors. Journal of Agricultural and Food Chemistry, vol. 61, no. 7, p. 1525-1533. https://doi.org/10.1021/jf304198k
Stevens, J. F., Ivancic, M., Hsu, V. L., Deinzer, M. L. 1997. Prenylflavonoids from Humulus lupulus. Phytochemistry, vol. 44, no. 8, p. 1575-1585. https://doi.org/10.1016/S0031-9422(00)00005-4
Teleszko, M., Nowicka, P., Wojdyło, A. 2016. Effect of cultivar and storage temperature on identification and stability of polyphenols in strawberry cloudy juices. Journal of Food Compositions and Analysis, vol. 54, p. 10-19. https://doi.org/10.1016/j.jfca.2016.09.009
Тsao, R. 2010. Chemistry and Biochemistry of Dietary Polyphenols. Nutrients, vol. 2, no. 12, p. 1231-1246. https://doi.org/10.3390/nu2121231
Van Opstaele, F., De Rouck, G., De Clippeleer, J., Aerts, G., De Cooman, L. 2010. Analytical and Sensory Assessment of Hoppy Aroma and Bitterness of Conventionally Hopped and Advanced Hopped Pilsner Beers. Journal of the Institute of Brewing, vol. 116, no. 4, p. 445-458. https://doi.org/10.1002/j.2050-0416.2010.tb00796.x
Wackerbauer, K., Kramer, P., Siepert, J. 1982. Phenolic aromatic substances in beer. Phenolic carboxylic acid and phenols in the raw material and beer preparation. Brauwelt, no. 122, p. 618-620.
Walters, M. T., Heasman, A. P., Hughes, P. S. 1997. Comparcion of (+)-Catechin and Ferulic Acid as Natural Antioxidants and Their Impact on Beer Flavor Stability. Part 2: Extended Storage Trials. Journal of the American Society of Brewing Chemists, vol. 55, p. 91-98. https://doi.org/10.1094/ASBCJ-55-0091
Wannenmacher, J., Gastl, M., Becker, T. 2018. Phenolic Substances in Beer: Structural Diversity, Reactive Potential and Relevance for Brewing Process and Beeer Quality. Comprehensive Reviews in Food Science and Food Safety, vol. 17, no. 4, p. 953-988. https://doi.org/10.1111/1541-4337.12352
Zhuang, S., Shetty, R., Hansen, M., Fromberg, A., Hansen, P. B., Hobley, T. J. 2017. Brewing with 100 % unmalted grains: barley, wheat, oat and rye. European Food Research and Technology, vol. 243, p. 447-454. https://doi.org/10.1007/s00217-016-2758-1
Zorić, Z., Dragović-Uzelac, V., Pedisić, S., Kurtanjek, Ž., Garofulić, I. E. 2014. Kinetics of Degradation of Anthocyanins, Phenolic Acids and Flavonols During Heat Treatment of Freeze-Dried Sour Cherry Marasca Paste. Food Technology and Biotechnology, vol. 52, p. 101-108.
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