Review: Stability of phenolic compounds during beer processing and alternatives to increase their biovailability
DOI:
https://doi.org/10.34117/bjdv11n10-025Keywords:
beer, phenolic compounds, antioxidant, bioavailabilityAbstract
Studies on antioxidants, especially phenolic compounds from beer and beer raw materials, have been increasingly explored, as phenolic compounds play an important role in human nutrition and health. This review provides an overview of the influence of malting and fermentation on the overall phenolic content from the barley malting process to the final beverage. Beer phenolics are mainly sourced from barley malt because of its proportion used in brewing beer, and can be found in both free and agglomerated forms, in concentrations up to 50% lower compared to sweet wort. Bound phenolics are released during malting, leading to an increase in free phenolics in the sweet wort. The phenolic content of the wort increases during the mash and hop stages. The wort boiling and fermentation stages are responsible for significant phenolic losses, as is the clarification and stabilization of beer made with polyvinylpolypyrrolidone (PVPP). Special yeasts, manipulation of enzymatic activity, dry-hopping, enrichment with xanthohumol and use of dark malts are alternatives to increase bioavailability in beer, benefits both for its stability and for the health of the consumer.
References
ALARA, O. R.; ABDURAHMAN, N. H.; UKAEGBU, C. I. Extraction of phenolic compounds: A review. Current Research in Food Science, [s. l.], v. 4, p. 200-214, 2021.
ALMAGUER, C. et al. Humulus Lupulus - a story that begs to be told: A review. Journal of the Institute of Brewing, [s. l.], v. 120, n. 4, p. 289-314, 2014.
BALASUNDRAM, N.; SUNDRAM, K.; SAMMAN, S. Phenolic compounds in plants and agri-industrial by products: Antioxidant activity, occurrence, and potential uses. Food Chemistry, [s. l.], v. 99, n. 1, p. 191-203, 2006.
BAMFORTH, C. W. The Science of beer haze. Journal of the American Society of Brewing Chemists, [s. l.], v. 57, n. 3, p. 51-90, 1999.
BRAVO, A. et al. Formation of α-dicarbonyl compounds in beer during storage of pilsner. Journal of Agricultural and Food Chemistry, [s. l.], v. 56, n. 11, p. 4134-4144, 2008.
BRAVO, L. Polyphenols: Chemistry, dietary sources, metabolismo, and nutritional significance. Nutritional Reviews, [s. l.], v. 56, n. 11, p. 317-333, 1998.
CASTRO, M. C. et al. Lignin derived phenolic compounds in cachaça aged in new barrels made from two oak species. Helyion, [s. l.], v. 6, n. 11, p. 01-06, 2020.
CHEYNIER, V. Phenolic compounds: From plants to foods. Phytochemistry Reviews, [s. l.], v. 11, n. 2, p. 153-177, 2012.
CHIVA-BLANCH, G. et al. Effects of wine, alcohol and polyphenols on cardiovascular disease risk factors: Evidences from human studies. Alcohol and Alcoholism, [s. l.], v. 48, n. 3, p. 270-277, 2013.
DELCOUR, J. A. et al. The reactions between polyphenols and aldehydes and the influence of acetaldehyde on haze formation in beer. Journal of the Institute of Brewing, [s. l.], v. 88, n. 4, p. 234-243, 1982.
DRESEL, M.; DUNKEL, A.; HOFMANN, T. Sensomics Analysis of Key Bitter Compounds in the Hard Resin of Hops (Humulus Lupulus L.) and Their Contribution to the Bitter Profile Of Pilsner Type Beer. Journal of Agricultural and Food Chemistry, [s. l.], v. 63, n. 13, p. 3402-3418, 2015.
DUCRUET, J. et al. Amber Ale beer enriched with goji berries: The effect on bioactive compound content and sensorial properties. Food Chemistry, [s. l.], v. 226, p. 109-118, 2017.
DVORAKOVA, M. et al. Characterization of monomeric and oligomeric flavan-3-ols from barley and malt by liquid chromatography – ultraviolet detection – electrospray ionization mass spectrometry. Journal of Chromathography A, [s. l.], v. 1189, p. 398-405, 2008.
ENOMOTO, H. Unique distribution of ellagitannins in ripe strawberry fruit revealed by mass spectrometry imaging. Current Research in Food Science, [s. l.], v. 4, n. June, p. 821-828, 2021.
FORSTER, A.; GAHR, A. On the Fate of Certain Hop Substances during Dry Hopping. Brewing Science, [s. l.], v. 66, n. 7-8, p. 93-103, 2013.
GERHAUSER, C. et al. Cancer Chemopreventive Activity of Xanthohumol, a Natural Product Derived from Hop. Molecular Cancer Therapeutics, [s. l.], v. 1, p. 959-969, 2002.
GOUPY, P. et al. Antioxidant composition and activity of barley (Hordeum vulgare) and malt extracts and of isolated phenolic compounds. Journal of the Science of Food and Agriculture, [s. l.], v. 79, p. 1625-1634, 1999.
GUPTA M., ABU-GHANNAM M., GALLAGHAR E. Barley for Brewing: Characteristic Changes during Malting, Brewing and Applications of its By-Products. Comprehensive Reviews in Food Science and Food Safety, [s. l.], v. 9, p. 318-328, 2010.
HA, K. S. et al. Stimulation of Phenolics, Antioxidant and α-Glucosidase Inhibitory Activities During Barley (Hordeum vulgare L.) Seed Germination. Plant Foods for Human Nutrition, [s. l.], v. 71, n. 2, p. 211-217, 2016.
HARBORNE, J. B. General Procedures and Measurement of Total Phenolics. In: DEY, P. M.; HARBONE, J. B. (ed.). Methods in Plant Biochemistry. London: Academic Press, 1989. p. 1-28.
HELENO, S. A. et al. Bioactivity of phenolic acids: Metabolites versus parent compounds: A review. Food Chemistry, [s. l.], v. 173, p. 501-513, 2015.
HEUBERGER, A. L. et al. Metabolomic profiling of beer reveals effect of temperature on non-volatile small molecules during short-term storage. Food Chemistry, [s. l.], v. 135, n. 3, p. 1284-1289, 2012.
HRABIA, O. et al. Effect of dry hopping on the oxidative stability of beer. Food Chemistry, [s. l.], v. 394, n. 5, p. 1939-1953, 2022.
INTELMANN, D. et al. Comprehensive sensomics analysis of hop-derived bitter compounds during storage of beer. Journal of Agricultural and Food Chemistry, [s. l.], v. 59, n. 5, p. 1939-1953, 2011.
JERKOVIC, V.; CALLEMIEN, D.; COLLIN, S.; Determination of Stilbenes in Hop Pellets from Different Cultivars. Journal of Agricultural and Food Chemistry, [s. l.], v. 53, p. 4202-4206, 2005.
JUNG, K. et al. Influence of Peach (Prunus persica L. Batsch) Fruit Addition on Quality Characteristics and Antioxidant Activities of Beer. International Journal of Sciences, [s. l.], v. 3, n. 8, p. 186-191, 2017.
KEUKELEIRE, D. Fundamentals of Beer and Hop Chemistry. Química nova, Campinas, v. 23, n. 1, p. 108-112, 2000.
KHANBABAEE, K.; VAN REE, T. Tannins: Classification and definition. Natural Product Reports, [s. l.], n. 18, n. 6, p. 641-649, 2001.
KŰHBECK, F. et al. Influence of lauter turbidity and hot trub on wort composition, fermentation, and beer quality. Journal of the American Society of Brewing Chemists, [s. l.], v. 64, n. 1, p. 16-28, 2006.
KUMAR, S.; PANDEY, A. K Chemistry and Biological Activities of Flavonoids: An Overview. The Scientific World Journal, [s. l.], v. 2013, 2013.
LEONARD, W. et al. Fermentation transforms the phenolic profiles and bioactivities of plant-based foods. Biotechnology Advances, [s. l.], v. 49, 107763, 2021.
LI, H. et al. Antioxidant activity and typical ageing compounds: their evolutions and relationships during the storage of lager beers. International Journal of Food Science and Technology, [s. l.], v. 51, n. 9, p. 2026-2033, 2016.
MAGALHÃES, P. et al. Isolation of phenolic compounds from hop extracts using polyvinylpolypyrrolidone: Characterization by high-performance liquid chromatography-diode array detection-electrospray tandem mass spectrometry. Journal of Chromatography A, [s. l.], v. 1217, n. 19, p. 3258-3268, 2010.
MALFLIET, S. et al. Flavour instability of pale lager beers: Determination of analytical markers in relation to sensory ageing. Journal of the Institute of Brewing, [s. l.], v. 114, n. 2, p. 180-192, 2008.
MALLET, J. Malt: A Practical Guide from Field to Brewhouse, 1964. Boulder: Brewers Publications, 2014.
MARCHIONI, E. et al. Effects of Processing Steps on the Phenolic Content and Antioxidant Activity of Beer. Journal of Agricultural and Food Chemistry, [s. l.], v. 59, p. 1249-1255, 2011.
MARTINEZ, A. et al. Physicochemical characterization of special persimmon fruit beers using bohemian pilsner malt as a base. Journal of the Institute of Brewing, [s. l.], v. 123, n. 3, p. 319-327, 2017.
MIEDL, M.; BAMFORTH, C. W. The relative importance of temperature and time in the cold conditioning of beer. Journal of the American Society of Brewing Chemists, [s. l.], v. 62, n. 2, p. 75-78, 2004.
MIKYŠHA, A. et al. The role of malt and hop polyphenols in beer quality, flavour and haze stability. Journal of the Institute of Brewing, [s. l.], v. 108, n. 1, p. 78-85, 2002.
MIKYŠHA, A.; KROFTA, K. Assessment of changes in hop resins and polyphenols during long-term storage. Journal of the Institute of Brewing, [s. l.], v. 118, n. 3, p. 269-279, 2012.
MITIĆ, S. S. et al. Phenolic Profiles and Total Antioxidant Capacity of Marketed Beers in Serbia. International Journal of Food Properties, [s. l.], v. 17, n. 4, p. 908-922, 2014.
MOREIRA, M. M. et al. Brewer's spent grain from different types of malt: Evaluation of the antioxidant activity and identification of the major phenolic compounds. Food Research International, [s. l.], v. 54, n. 1, p. 382-388, 2013.
NACZK, M.; SHAHIDI, F. Extraction and analysis of phenolics in food. Journal of Chromatography A, [s. l.], v. 1054, p. 95-111, 2004.
NARDINI, M.; FODDAI, M. S. Phenolics Profile and Antioxidant Activity of Special Beers. Molecules, [s. l.], v. 25, n. 11, p. 1-15, 2020.
NARDINI, M.; GARAGUSO, I. Characterization of bioactive compounds and antioxidant activity of fruit beers. Food Chemistry, [s. l.], v. 305, 2020.
NNS, E. et al. Effect of Heat Treatment on the Antioxidant Activity, Color, and Free Phenolic Acid Profile of Malt. Journal of Agricultural and Food Chemistry, [s. l.], v. 55, p. 6539-6546, 2007.
OLANIRAN, A. O. et al. Flavour-active volatile compounds in beer: production, regulation and control. Journal of the Institute of Brewing, [s. l.], v. 123, n. 1, p. 13-23, 2017.
OLIVOTO, T. et al. Plant secondary metabolites and its dynamical systems of induction in response to environmental factors: A review. African Journal of Agricultural Research, [s. l.], v. 12, n. 2, p. 71-84, 2017.
PASCOE, H. M.; AMES, J. M.; CHANDRA, S. Critical Stages of the Brewing Process for Changes in Antioxidant Activity and Levels of Phenolic Compounds in Ale. Journal of the American Society of Brewing Chemists, [s. l.], v. 61, n. 4, p. 203-209, 2004.
PEŇALVO, J. L. et al. Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry. Journal of Agricultural and Food Chemistry, [s. l.], v. 53, n. 24, p. 9342-9347, 2005.
POZEN, M. A. Enzymes in Brewing. Industrial and Engineering Chemistry, [s. l.], v. 52, n. 3, p. 156-164, 2015.
PRAZERES, E. S. et al. Use of hexamethyldisilazane as a silanizing agent in microwave-assisted derivatization for determining phenolic compounds in wine by gas chromatography. Microchemical Journal, [s. l.], v. 161, 2021.
PRENCIPE, F. P. et al. Development of a new high-performance liquid chromatography method with diode array and electrospray ionization-mass spectrometry detection for the metabolite fingerprinting of bioactive compounds in Humulus lupulus L. Journal of Chromatography A, [s. l.], v. 1349, p. 50-59, 2014.
QINGMING, Y. et al. Antioxidant activities of malt extract from barley (Hordeum vulgare L.) toward various oxidative stress in vitro and in vivo. Food Chemistry, [s. l.], v. 118, p. 84-89, 2010.
RODRIGUES, J. E.; GIL, A. M. NMR methods for beer characterization and quality control. Magnetic Resonance in Chemistry, [s. l.], v. 49, p. 37-45, 2011.
SAMARAS, T. S.; GORDON, M. H.; AMES, J. M. Antioxidant properties of malt model systems. Journal of Agricultural and Food Chemistry, [s. l.], v. 53, n. 12, p. 4938-4945, 2005.
SILVA, C. H. P. M. Microbiologia da Cerveja: Do básico ao Avançado. São Paulo: Editora Livraria da Física, 2019.
SIMIC, G. et al. Evaluation of Total Phenolic Content and Antioxidant Activity of Malting and Hulless Barley Grain and Malt Extracts. Food Technology and Economy, Engineering and Physical Properties, [s. l.], v. 35, n. 1, p. 73-78, 2017.
SOCHA, P. et al. Antioxidant activity and the most abundant phenolics in commercial dark beers. International Journal of Food Properties, [s. l.], v. 20, p. 595-609, 2017.
TAKÓ, M. et al. Plant phenolics and phenolic-enriched extracts as antimicrobial agents against. Antioxidants, [s. l.], v. 9, n. 2, p. 1-21, 2020.
VANBENEDEN, N.; DELVAUX, F.; DELVAUX, F. R. Determination of hydroxycinnamic acids and volatile phenols in wort and beer by isocratic high-performance liquid chromatography using electrochemical detection. Journal of Chromatography A, [s. l.], v. 1136, n. 2, p. 237-242, 2006.
VERBELEN, P. et al. Bioprocess intensification of beer fermentation using immobilised cells. Technologies for Active Food Ingredients and Food Processing. In: ZUIDAM, N.; NEDOVIC, V. (ed.) Encapsulation Technologies for Active Food Ingredients and Food Processing. New York: Springer, 2010. p. 303-325.
WANNENMACHER, J.; GASTL, M.; BECKER, T. Phenolic Substances in Beer: Structural Diversity, Reactive Potential and Relevance for Brewing Process and Beer Quality. Comprehensive Reviews in Food Science and Food Safety, [s. l.], v. 17, n. 4, p. 953-988, 2018.
ZHAO, H. et al. Assessment of endogenous antioxidative compounds and antioxidant activities of lager beers. Journal of the Science of Food and Agriculture, [s. l.], v. 93, n. 4, p. 910-917, 2013.
ZHAO, H.; ZHAO, M. Effects of mashing on total phenolic contents and antioxidant activities of malts and worts. International Journal of Food Science and Technology, [s. l.], v. 47, n. 2, p. 240-247, 2012.

