Table of Contents

    Topic review

    Polyphenolic Compounds in Wine/Beer

    Subjects: Food Chemistry
    View times: 45
    Submitted by: Sanja Radonjić

    Definition

    Phenolic compounds present in beer and wine have shown high antioxidant and anti-inflammatory features, and in the last decades beneficial effects on human health due to moderate beer and wine consumption have been indicated by many research studies. Due to the different used raw material and technological processes, there are differences between wine and beer in the presence, as well in the concentrations, of phenolic substances. It was shown that some polyphenol classes can only be found in beer (chalcones and flavanones) and other are mainly found in wine (stilbenes, proanthocyanidins), while flavanols and flavan-3-ols are found in similar concentrations in both beverages. Both beverages represent natural fermented products, and minor changes within the growth of raw material and clime conditions, as well as within the used technology, will impact the final chemical composition of these products. The brewing industry and winemakers put a lot of effort in obtaining a final product that will be unique, with more potent antioxidant activity, and with satisfying sensory characteristics, to attract consumers, who are now more aware of alcoholic beverages influence on human health. From the winemaker's point of view, the aim is to produce wine that will satisfy all required safety conditions, and with this added value, and at the same time attempting not to increase the costs. In the brewing industry, besides changing hopping regimes and influencing other technology phases, craft breweries that have expanded rapidly all over the world, are doing their best to produce authentic beer, in terms of flavor and in same time improving the antioxidant capacity. Both industries should consider changes in clime conditions, and research on new modified technologies is always an open issue, like the use of some by-products and additives within the production.

    1. Introduction 

    Wine has existed on Earth for more than 6000 years [1], while beer has existed for over 5000 years [2]. Throughout history, both drinks were produced in Ancient Egypt and regions of Mesopotamia. Wine was used in various therapies and treatments, while beer was an essential part of diet, first to appear when people began agriculture. The brewing industry is more linked to northern Europe, where due to cold conditions viticulture development was inhibited. Both of these beverages are very complex in terms of their ingredients, and besides their long traditions, there are so many characteristics and parameters that determine their final quality, from the quality of raw material (malt and hop for beer and grape for wine), yeast, regimes of alcoholic fermentation, conditions of aging etc. However, the parameters of all the phases of production and composition of these two beverages have been very well studied by many researchers, since the early 20th century. Besides their flavor, which determines their use, wine and beer are known as rich with bioactive compounds, i.e., antioxidants that increase the interest in their nutritional profile. A great number of studies and comprehensive reviews have dealt with the bioactive compounds responsible for the possible health benefits due to moderate wine and beer consumption, and with the different methods of improvement of the antioxidant compounds in these two beverages [3][4][5][6][7][8][9][10][11][12][13][14]. Much of this research supports the thesis that moderate consumption of alcoholic beverages, such are red wine and beer, positively influences the decrease of cardiovascular disease [3]. Key roles as antioxidants in wine and beer belong to the phenolic compounds, and many of them, such as flavonoids, have an effect on cardiovascular and chronic degenerative diseases [15][16], non-flavonoids (stilbenes, hydroxycinnamic, and hydroxybenzoic acids) also positively affect the cardiovascular system [17]. In addition, it has been recently shown that there is a relation between beer consumption and higher protection against coronary diseases, compared to other spirits, and beer is also associated with bone density increase, and with immunological and cardiovascular benefits [18][19][20]. However, there are huge differences between the phenolic profile and content among red wine and beer, primarily due to the different raw material used in their production. The importance of phenolic compounds for wine and beer is very significant, as their presence influences the final quality of these products. Some polyphenol classes can only be found in beer (chalcones and flavanones) and others are mainly found in wine (stilbenes, proanthocyanidins), while flavanols and flavan-3-ols are found in similar concentrations in both beverages. In beer quality they play a key role, as they influence the time of transport and storage, flavor stability, clarity, and color of beer. Additionally, phenolic compounds are essential in wine, because they determine the sensorial wine characteristics (taste and fragrance), color, microbiological and oxidative stability, and chemical properties of wine, as they interact with other compounds including other polyphenols, proteins, and polysaccharides.

    Production of wine and beer consists of many technological phases, which are influenced by many parameters, and the huge numbers of occurring variables; the changes in biochemistry are very complex. In both beverages, the composition of phenolic compounds is very diverse and depends on many similar parameters, first of all on the genetic factors of the raw material and the environmental conditions during their growth, as well as technological and aging factors [21]. In regards to beer, malt and hops represent the two main ingredients on which antioxidant compounds depend; actually 70–80% are derived from malt, and the remaining from hops [22][23], and this ratio also depends on the type of the beer [24]. Furthermore, during beer making, important technological phases, in which the change of polyphenolic compounds occurs, begins with the malting process (steeping and germination), kilning, mashing, wort separation and boiling, whirlpool rest, through to the fermentation, maturation, and at the end, to the stabilization/filtration and bottling. Primarily classification of beer is made based on the fermentation process [25], and in these terms there are lagers, ales, and lambic types of beer. The most consumed are lagers, produced by low fermentation at lower temperatures (6–15 °C), while in contrast ale-type beer is made by high fermentation at higher temperatures between 16–24 °C, and as a result of spontaneous fermentation there is lambic beer. Exclusively, grape is used as the raw material for wine production, and based on the color of the used grape varieties, wine is classified into red and white. The main difference, and at the same time the most important, between the making of red and white is that during the making of red, along with alcoholic fermentation, maceration i.e., extraction of color and other substances from grape skin and seed occurs, while within the process of the alcoholic fermentation of whites only colorless and clarified grape juice is used in the process of alcoholic fermentation. As for making rose wine, winemakers use limited skin contact in order to extract color and some compounds, depending on the desired degree of complexity. Due to this maceration, occurring along with alcoholic fermentation during red winemaking, in which the phenolic compounds are extracted from grapes, this step represents the key one in determining the content of polyphenolic compounds in red wine. Furthermore, because of this step, it is commonly known that red wine contains more antioxidant compounds, and has been more studied and reviewed by researchers in the last decades [14][26][27][28][29][30][31][32][33][34]. Another important step during winemaking in which it is possible to increase polyphenolic compounds is ageing in wood barrels, or with addition of oak alternatives.

    2. Bioactive Compounds in Beer and Wine

    The largest group within natural antioxidant compounds is the group of polyphenols, consisting of very diverse chemical compounds that can be classified in many ways, but that generally are divided into two main classes: flavonoids and non-flavonoids. Within the class of non-flavonoids, natural polyphenolic compounds can be present in chemical structures, such as: phenolic acids, stilbenes, lignans, chalcones, and tannins (hydrolysable and condensed) [34][35][36], Figure 1. Phenolic acids in wine act as copigments, and they do not impact odor and flavor. Stilbenes are the most well known as antioxidants, and within the chalcones group there is xanthohumol; present in beer, and of huge importance, as this compound possess high biological activity. Flavan-3-ols influence bitterness, astringency, and wine structure, and participate in the stabilization of color during aging. Tannins also contribute to the sensory characteristics, particularly of red wine, as they are related to the astringency, they also interact with other macromolecules (proteins and polysaccharides) influencing the colloidal behavior of wine. Condensed tannins (proanthocyanidins) in the brewing industry are interesting as they influence haze formation in beer. Anthocyanins are responsible for the color of red grapes and wines.

    Figure 1. Natural phenolic compound classification [8].

    As is expected, due to different used raw material and technological processes, there are differences between wine and beer, in the presence, as well in the concentrations, of phenolic substances. Moreover, the antioxidant compounds in beer belong to different groups of chemical substances such are: thiols [37], SO2 [38] (product of the Maillard reaction [39][40]), α-acids derived from hops [41][42][43], and phenolic compounds [44][45][46]. Thiols have been suggested to correlate with sulfites in the antioxidative mechanism, and are important for beer's oxidative stability. Sulfites were found to be the only compound that was able to delay the formation of radicals [38], and actually give antioxidant and antimicrobe properties in wine too. The main product of the Maillard reaction is melanoidin, which affects the color, flavor, and body of beer. Hop α-acids (also called humulones) represent the main bittering compound in beer, and have shown a high ability to quench radicals, while iso-α-acids possess this activity to a lower extent. In addition, iso-α-acids can influence beer staling, but not to a high degree. 

    The polyphenol complexes of beer and red wine, additionally, represent a source of dietary antioxidants. As both beverages are very popular and widely consumed, benefits of the light-moderate consumption of wine and beer are supported by scientific literature data. Polyphenols from red wine and beer could act as antioxidants, and also as anti-inflammatory agents contributing to the defense against atherosclerotic pathologies [19][47]. The beneficial moderate consumption of beer is also based on antioxidant compounds present in beer, i.e., on their redox properties [48]. Antioxidants present in beer improve several diseases, and are associated with benefits to the cardiovascular and immunological system [19][20]. It was shown that after consumption of non-alcoholic beer, the decrease of several inflammation biomarkers, homocysteine, and systolic blood pressure occurred. These influences were mainly attributed to the polyphenolic compounds in beer. Furthermore, several studies have shown that the light-moderate intake of alcohol is associated with lower incidence of diabetes type-2, a higher level of high-density lipoprotein cholesterol, as well as with lipid oxidative stress reduction [49][50][51][52]. Torres et al. [53] reported that moderate wine intake, compared to other alcoholic beverages like vodka, rum, and brandy increased total antioxidant capacity, and decreased pro-inflammatory factors along with a fat-enriched diet that was consumed by young healthy volunteers. This is also supported by the phenomenon known as the "French paradox", which indicates that moderate daily drinking of red wine contributes to lower coronary heart diseases incidence, despite their diets possessing a higher amount of saturated fatty acids and total fat [54]. However, excessive intake of alcohol beverages is associated with chronic disease development and other very serious problems, representing the leading risk factor for mortality [55]. Roercke et al. [3] reported there is an important influence of drinking patterns, such are episodic heavy drinking within average moderate drinkers, and some other important influencing parameters in term of health issues like smoking status, age, body mass index, and physical activity, and all of them have to be considered in order to estimate dose of alcohol as well the risks. After all, chronic heavy and episodic drinking should be avoided. In the Dietary Guidelines for Americans (2015–2020), moderate intake of alcohol proposes up to one unit of alcohol per day for women and two for men [56].

    However, the positive influence of single polyphenols on human health occurs at higher concentrations than those found in beer and wine, indicating the synergistic action of different polyphenolic mixtures [57]. Ranges of some of the most important phenolic compounds, found in red wine and beer are presented in Table 1. Phenolic acids also possess antioxidant and anti-inflammatory properties [58]. Based on literature data, beer has shown higher upper values for content of p-coumaric acid, and all hydroxybenzoic acids, while for other polyphenolic compounds it was mainly the opposite, and higher concentrations dominated in red wine. Flavonols are considered very important bioactive compounds, and have shown positive effects against certain cancers and cardiovascular diseases in some epidemiological studies [59][60]. Concentrations of all three presented flavonols (quercetin, myricetin, and kaempferol) were much higher in red wine than in beer. Stilbenes, particularly resveratrol, are the most associated with wine's beneficial properties. Resveratrol is recognized as an antioxidant, anticancer, cardioprotective, and anti-inflammatory agent. Due to its bioactivity, trans-resveratrol was proposed for many diseases as a therapeutic agent [61]. The content of stilbenes is not comparable for wine and beer, as based on literature data these compounds are rarely, or never, found in beer. It was also indicated that flavan-3-ols may show cardioprotective activity, and their antioxidant activity was shown in some studies [59]. Flavones are also recognized as molecules with important biological activity (anti-tumor, antioxidant, and anti-inflammatory), and were used as treatment for some neurodegenerative disorders and coronary heart diseases [62]. Flavanones also belong to antioxidant agents and the found concentrations in wine and beer were very low, while a lower content of naringerin was found in red wine compared to beer. Tannins also showed potent radical scavenging, anti-inflammatory, and antioxidant activity [63], and much higher levels of condensed tannins were found in red wine. Besides the presented polyphenolic compounds there are also some compounds found in wine and not in beer and the opposite. Within the compounds found in beer, two very important ones are xanthohumol and melanoidin. Both, xanthohumol and melanoidin have shown antimicrobial properties, melanoidin also possess antihypertensive, prebiotic, and antiallergenic properties [64], while xanthohumol showed anti-cancer, anti-inflammatory, anti-obesity, etc. properties [65][66]. Depending on the raw material and brewing process, the content of melanoidin ranges from 0.58 mg/L in alcohol free beer to 1.49 mg/L for dark beer, while in blond beer 0.61 mg/L was determined [67][68]. In wine, among the phenolic compounds with biological activity, there are also anthocyanins. The most common anthocyanins found in red wine, malvidin-3-glucoside and malvidin-3-galactoside, have shown anti-inflammatory effects, and their synergistic activity was observed [69].

    Table 1. Ranges of some phenolic compounds in red wine and beer.

     

    Red Wine

    References

    Beer

    References

    Cinnamic Acids (mg/L)

    ferulic acid

    0.05–10.43

    [30][70][71][72]

    0.01–5.04

    [12][45][46][73][74][75][76][77][78][79][80][81][82]

    p-coumaric acid

    0.02–8.00

    [27][30][70][71][72]

    0.003–55.80

    [9][12][45][73][78][79]

    caffeic acid

    0.02–644.50

    [27][30][70][71][83]

    0.00–23.50

    [9][45][46][73][74][75][76][77][78][79][81][82][84]

    Hydroxybenzoic Acids (mg/L)

    gallic acid

    27.10–66.10

    [28][71]

    0.00–142.20

    [9][46][73][74][75][76][77][78][80][81][82]

    protocatechuic acid

    0.91–1.78

    [28][30]

    0.01–5.10

    [12][75][76][77][78][80][81][82][84]

    p-hydroxybenzoic acid

    2.75–6.20

    [28]

    0.00–16.84

    [12][45][73][75][76][78]

    Stilbenes (mg/L)

    resveratrol

    0,51–11.70

    [28][85]

    0.002–0.081

    [86]

    trans-resveratrol

    0.21–23.00

    [27][70][71][87][88][89]

    -

    -

    cis-resveratrol

    0.01–7.00

    [71][87][88]

    -

    -

    total stilbenes

    1.00–5.50

    [71]

    -

    -

    Tannins (mg/L)

    hydrolysable tannins

    0.4–50.0

    [90][91][92][93][94]

    1.5

    [81]

    Flavan-3-ols (mg/L)

    catechin

    6.98–91.99

    [27][30][36]

    0.03–6.54

    [12][73][74][75][77][80][81][82]

    epicatechin

    8.07–52.85

    [27][30][36]

    0–4.55

    [9][74][75][80][81][82]

    Flavones (mg/L)

    luteolin

    0.20–1.00

    [95][96][97][98]

    0.10–0.19

    [82]

    apigenin

    0.00–4.70

    [99]

    0.80–0.81

    [82]

    Flavonols (mg/L)

    myricetin

    0.70–30.40

    [27][30]

    0.15–0.16

    [82]

    quercetin

    1.27–65.90

    [27][30][36]

    0.06–1.79

    [74][80][82]

    kaempferol

    0.61–26.80

    [27]

    0.10–1.64

    [80][100]

    Flavanones (mg/L)

    naringenin

    0.90 to 4.20

    [89]

    0.06–2.34

    [80]

    3. Impact of Technologies in Order to Increase Phenolics in Wine and Beer

    The only material for wine production is grape, while for beer production there is malt (sometimes along with some adjuncts such as rice, sugar, corn, and wheat), water, and hop. The process within both the production of beer and wine is alcoholic fermentation and, for that purpose, usually commercial dry yeasts are used. Basic brewing and winemaking technology are presented at Scheme 1 and Scheme 2, respectively.

    Scheme 1. Basic steps in brewing technology.

    Scheme 2. Basic steps in winemaking technology.

    4. Conclusions

    Phenolic compounds present in beer and wine have shown high antioxidant and anti-inflammatory features, and in the last decades beneficial effects on human health due to moderate beer and wine consumption have been indicated by many research studies. In this survey, a comparative overview of qualitative and quantitative phenolic compound profiles in wine and beer was evaluated. As was expected, due to the different used raw material and technological processes, there are differences between wine and beer in the presence, as well in the concentrations, of phenolic substances. It was shown that some polyphenol classes can only be found in beer (chalcones and flavanones) and other are mainly found in wine (stilbenes, proanthocyanidins), while flavanols and flavan-3-ols are found in similar concentrations in both beverages. Both beverages represent natural fermented products, and minor changes within the growth of raw material and clime conditions, as well as within the used technology, will impact the final chemical composition of these products. Considering the literature data, the obtained results favor wine as the beverage with a higher content of bioactive compounds, particularly phenolic compounds, and as was expected, with higher antioxidant activity. Overall, in order to decide which of these two alcoholic beverages represents the better choice as a functional drink, a lot of parameters should be considered (social occasion, quantity, individual tolerance, etc.). As it was mentioned, drinking pattern is very important, only light-moderate drinking is recommended, and it should not be forgotten that the choice firstly depends on individual preference.

    Nowadays, the brewing industry and winemakers put a lot of effort in obtaining a final product that will be unique, with more potent antioxidant activity, and with satisfying sensory characteristics, to attract consumers, who are now more aware of alcoholic beverages influence on human health. Winemakers began even from the vineyard, applying new additives that would improve phenolic composition in the grape, and afterwards, taking care through every step to the final product. After all, from the winemaker's point of view, the aim is to produce wine that will satisfy all required safety conditions, and with this added value, and at the same time attempting not to increase the costs. A good solution to this, is the use of all by-products, which occur during grape processing and winemaking. In the brewing industry, besides changing hopping regimes and influencing other technology phases, craft breweries that have expanded rapidly all over the world, are doing their best to produce authentic beer, in terms of flavor. Research on using different kinds of fruit in order to obtain special beer with added value, with a focus on sensory improvement and differentiation, has been performed. Both industries should consider changes in clime conditions, and research on new modified technologies is always an open issue, like the use of some by-products and additives within the production.

    The entry is from 10.3390/molecules25214960

    References

    1. Li, H.; Wang, H.; Li, H.; Goodman, S.; van der Leed, P.; Xu, Z.; Fortunato, A.; Yanga, P. The worlds of wine: Old, new and ancient. Wine Econ. Pol. 2018, 7, 178–182, doi:10.1016/j.wep.2018.10.002.
    2. Wang, J.; Liu, L.; Ball, T.; Yu, L.; Li, Y.; Xing, F. Revealing a 5000-y-old beer recipe in china. Proc. Natl. Acad. Sci. USA 2016, 113, 6444–6448, doi:10.1073/pnas.1601465113.
    3. Roerecke, M.; Rehm, J. Alcohol consumption, drinking patterns, and ischemic heart disease: A narrative review of meta-analyses and a systematic review and meta-analysis of the impact of heavy drinking occasions on risk for moderate drinkers. BMC Med. 2014, 12, 182, doi:10.1186/s12916-014-0182-6.
    4. Gromes, R.; Zeuch, M.; Piendl, A. Further investigations into the dietary fibre content of beers. Brau. Int. 2000, 18, 24–28.
    5. Powell, J.J.; McNaughton, S.A.; Jugdaohsingh, R.; Anderson, S.H.; Dear, J.; Khot, F.; Mowatt, L.; Gleason, K.L.; Sykes, M.; Thompson, R.P.; et al. A provisional database for the silicon content of foods in the United Kingdom. Br. J. Nutr. 2005, 94, 804–812, doi:10.1079/bjn20051542.
    6. Castaldo, L.; Narváez, A.; Izzo, L.; Graziani, G.; Gaspari, A.; Di Minno, G.; Ritieni, A. Red wine consumption and cardiovascular health. Molecules 2019, 24, 3626, doi:10.3390/molecules24193626.
    7. Di Pietro, M.B.; Bamforth, C.W. A comparison of the antioxidant potential of wine and beer. J. Inst. Brew. 2011, 117, 547–555, doi:10.1002/j.2050-0416.2011.tb00503.x.
    8. Martinez-Gomez, A.; Caballero, I.; Blanco, C.A. Phenols and melanoidins as natural antioxidants in beer. structure, reactivity and antioxidant activity. Biomolecules 2020, 10, 400, doi:10.3390/biom10030400.
    9. Habschied, K.; Lončarić, A.; Mastanjević, K. Screening of polyphenols and antioxidative activity in industrial beers. Foods 2020, 9, 238, doi:10.3390/foods9020238.
    10. Horincar, G.; Enachi, E.; Bolea, C.; Râpeanu, G.; Aprodu, I. Value-added lager beer enriched with eggplant (Solanum melongena l.) peel extract. Molecules 2020, 25, 731, doi:10.3390/molecules25030731.
    11. Wannenmacher, J.; Gastl, M.; Becker, T. Phenolic substances in beer: Structural diversity, reactive potential and relevance for brewing process and beer quality. Compr. Rev. Food Sci. 2018, 17, 953–988, doi:10.1111/1541-4337.12352.
    12. Wannenmacher, J.; Cotterchio, C.; Schlumberger, M.; Reuber, V.; Gastl, M.; Becker, T. Technological influence on sensory stability and antioxidant activity of beers measured by ORAC and FRAP. J. Sci. Food Agric. 2019, 99, 6628–6637, doi:10.1002/jsfa.9979.
    13. Martínez-Gil, A.; del Alamo-Sanza, M.; Sánchez-Gómez, R.; Nevares, I. Alternative woods in enology: Characterization of tannin and low molecular weight phenol compounds with respect to traditional oak woods. A Review. Molecules 2020, 25, 1474, doi:10.3390/molecules25061474.
    14. Jeremic, J.; Vongluanngam, I.; Ricci, A.; Parpinello, G.P.; Versari, A. The oxygen consumption kinetics of commercial oenological tannins in model wine solution and chianti red wine. Molecules 2020, 25, 1215, doi:10.3390/molecules25051215.
    15. Afroz, R.; Tanvir, E.; Little, P. Honey-derived flavonoids: Natural products for the prevention of atherosclerosis and cardiovascular diseases. Clin. Exp. Pharmacol. 2016, 6, 1–4, doi:10.4172/2161-1459.1000208.
    16. Mozaffarian, D.; Rosenberg, I.; Uauy, R.; History of modern nutrition science—Implications for current research, dietary guidelines, and food policy. BMJ 2018, 361, 2392, doi:10.1136/bmj.k2392.
    17. Cheng, C.K.; Luo, J.; Lau, C.W.; Chen, Z.; Tian, X.Y.; Huang, Y. Pharmacological basis and new insights of resveratrol action in the cardiovascular system. Br. J. Pharmacol. 2019, 177, 1258–1277, doi:10.1111/bph.14801.
    18. De Gaetano, G.; Cerletti, C.; Alkerwi, A.; Iacoviello, L.; Badimon, L.; Costanzo, S.; Pounis, G.; Trevisan, M.; Panico, S.; Stranges, S.; et al. Effects of moderate beer consumption on health and disease: A consensus document. Nutr. Metab. Cardiovasc. Dis. 2016, 26, 443–467, doi:10.1016/j.numecd.2016.03.007.
    19. Redondo, N.; Nova, E.; Díaz-Prieto, L.E.; Marcos, A. Effects of moderate beer consumption on health. Nutr. Hosp. 2018, 35, 41–44, doi:10.20960/nh.2286.
    20. Chiva-Blanch, G.; Magraner, E.; Condines, X.; Valderas-Martínez, P.; Roth, I.; Arranz, S.; Casas, R.; Navarro, M.; Hervas, A.; Sisó, A.; et al. Effects of alcohol and polyphenols from beer on atherosclerotic biomarkers in high cardiovascular risk men: A randomized feeding trial. Nutr. Metab. Cardiovasc. Dis. 2014, 25, 36–45, doi:10.1016/j.numecd.2014.07.008.
    21. Lugasi, A. Polyphenol content and antioxidant properties of beer. Acta Aliment. 2003, 32, 181–192, doi:10.1556/aalim.32.2003.2.7.
    22. Arranz, S.; Valderas-Martínez, P.; Chiva-Blanch, G.; Medina-Remón, A.; Lamuela-Raventós, R.M.; Estruch, R. Wine, beer, alcohol and polyphenols on cardiovascular disease and cancer. Nutrients 2012, 4, 759–781, doi:10.3390/nu4070759.
    23. Quifer, P.; Martínez, M.; Jáuregui, O.; Estruch, R.; Lamuela, R.; Chiva, G.; Vallverdú-Queralt, A. A comprehensive characterisation of beer polyphenols by high resolution mass spectrometry (LC–ESI-LTQ-Orbitrap-MS). Food Chem. 2014, 169, 336–343, doi:10.1016/j.foodchem.2014.07.154.
    24. Čechovská, L.; Konečný, M.; Velíšek, J.; Cejpek, K. Effect of Maillard reaction on reducing power of malts and beers. Czech J. Food Sci. 2012, 30, 548–556, doi:10.17221/288/2012-CJFS.
    25. Capece, A.; Romaniello, R.; Pietrafesa, A.; Siesto, G.; Pietrafesa, R.; Zambuto, M.; Romano, P. Use of Saccharomyces cerevisiae var. boulardii in co-fermentations with S. cerevisiae for the production of craft beers with potential healthy value-added. Int. J. Food Microbiol. 2018, 284, 22–30, doi:10.1016/j.ijfoodmicro.2018.06.028.
    26. Lingua, M.S.; Neme Tauil, R.M.; Batthyány, C.; Wunderlin, D.A.; Baroni, M.V. Proteomic analysis of Saccharomyces cerevisiae to study the effects of red wine polyphenols on oxidative stress. J. Food Sci. Technol. 2019, 56, 4129–4138, doi:10.1007/s13197-019-03883-7.
    27. Grieco, F.; Carluccio, M.A.; Giovinazzo, G. Autochthonous Saccharomyces cerevisiae starter cultures enhance polyphenols content, antioxidant activity, and anti-inflammatory response of Apulian red wines. Foods 2019, 8, 453, doi:10.3390/foods8100453.
    28. Generalić Mekinić, I.; Skračić, Ž.; Kokeza, A.; Soldo, B.; Ljubenkov, I.; Banović, M.; Skroza, D. Effect of winemaking on phenolic profile, colour components and antioxidants in Crljenak kaštelanski (sin. Zinfandel, Primitivo, Tribidrag) wine. J. Food Sci. Technol. 2019, 56, 1841–1853, doi:10.1007/s13197-019-03638-4.
    29. Mitić, M.; Kostić, D.; Pavlović, A. The phenolic composition and the antioxidant capacity of Serbian red wines. Adv. Technol. 2014, 3, 16–22, doi:10.5937/savteh1401016M.
    30. Mitić, M.; Kostić, D.; Pavlović, A.; Micić, R.; Stojanović, B.; Paunović, D.; Dimitrijević, D. Antioxidant activity and polyphenol profile of Vranac red wines from Balkan region. Hem. Ind. 2016, 70, 265–275, doi:10.2298/HEMIND150130032M.
    31. Kondrashov, A.; Ševčík, R.; Benákova, H.; Koštířová, M.; Štípek, S. The key role of grape variety for antioxidant capacity of red wines. e-SPEN Eur. e-J. Clin. Nutr. Metab. 2009, 4, 41–46, doi:10.1016/j.eclnm.2008.10.004.
    32. Di Majo, D.; La Guardia, M.; Giammanco, S.; La Neve, L.; Giammanco, M. The antioxidant capacity of red wine in relationship with its polyphenolic constituents. Food Chem. 2008, 111, 45–49, doi:10.1016/j.foodchem.2008.03.037.
    33. Raičević, D.; Božinović, Z.; Petkov, M.; Ivanova-Petropulos, V.; Kodžulović, V.; Mugoša, M.; Šućur, S.; Maraš, V. Polyphenolic content and sensory profile of Montenegrin Vranac wines produced with different oenological products and maceration. Maced. J. Chem. Chem. Eng. 2017, 36, 229–238, doi:10.20450/mjcce.2017.1145.
    34. Callemien, D.; Collin, S. Structure, organoleptic properties, quantification methods, and stability of phenolic compounds in beer-a review. Food Rev. Int. 2010, 26, 1–84, doi:10.1080/87559120903157954.
    35. Gerhäuser, C. Beer constituents as potential cancer chemopreventive agents. Eur. J. Cancer 2005, 41, 1941–1954, doi:10.1016/j.ejca.2005.04.012.
    36. Shahidi, F.; Nazk, M. Phenolics in Food and Nutraceuticals, 2nd ed.; CRC Press LLC: Boca Raton, FL, USA, 2004; doi:10.1201/9780203508732.
    37. Andersen, M.L.; Gundermann, M.; Danielsen, B.P.; Lund, M.N. Kinetic models for the role of protein thiols during oxidation in beer. J. Agric. Food Chem. 2017, 65, 10820–10828, doi:10.1021/acs.jafc.7b05012.
    38. Andersen, M.L.; Outtrup, H.; Skibsted, L.H. Potential antioxidants in beer assessed by ESR spin trapping. J. Agric. Food Chem. 2000, 48, 3106–3111, doi:10.1021/jf000354+.
    39. Lindenmeier, M.; Faist, V.; Hofmann, T. Structural and functional characterization of pronyl-lysine, a novel protein modification in bread crust melanoidins showing in vitro antioxidative and phase I/II enzyme modulating activity. J. Agric. Food Chem. 2002, 50, 6997–7006, doi:10.1021/jf020618n.
    40. Maillard, M.N.; Billaud, C.; Chow, Y.N.; Ordonaud, C.; Nicolas, J. Free radical scavenging, inhibition of polyphenoloxidase activity and copper chelating properties of model Maillard systems. LWT Food Sci. Technol. 2007, 40, 1434–1444, doi:10.1016/j.lwt.2006.09.007.
    41. Kunz, T.; Frenzel, J.; Wietstock, P.C.; Methner, F.J. Possibilities to improve the antioxidative capacity of beer by optimized hopping regimes. J. Inst. Brew. 2014, 120, 415–425, doi:10.1002/jib.162.
    42. Wietstock, P.; Kunz, T.; Shelhammer, T.; Schon, T.; Methner, F.J. Behaviour of antioxidants derived from hops during wort boiling. J. Inst. Brew. 2010, 116, 157–166, doi:10.1002/j.2050-0416.2010.tb00412.x.
    43. Ting, P.L.; Lusk, L.; Refling, J.; Kay, S.; Ryder, D. Identification of antiradical hop compounds. J. Am. Soc. Brew. Chem. 2008, 66, 116–126, doi:10.1094/ASBCJ-2008-0310-01.
    44. Leopoldini, M.; Russo, N.; Toscano, M. The molecular basis of working mechanism of natural polyphenolic antioxidants. Food Chem. 2011, 125, 288–306, doi:10.1016/j.foodchem.2010.08.012.
    45. Szwajgier, D. Content of individual phenolic acids in worts and beers and their possible contribution to the antiradical activity of beer. J. Inst. Brew. 2009, 115, 243–252, doi:10.1002/j.2050-0416.2009.tb00376.x.
    46. Piazzon, A.; Forte, M.; Nardini, M. Characterization of phenolics content and antioxidant activity of different beer types. J. Agric. Food Chem. 2010, 58, 10677–10683, doi:10.1021/jf101975q.
    47. Snopek, L.; Mlcek, J.; Sochorova, L.; Baron, M.; Hlavacova, I.; Jurikova, T.; Kizek, R.; Sedlackova, E.; Sochor, J. Contribution of red wine consumption to human health protection. Molecules 2018, 23, 1684, doi:10.3390/molecules2307168.
    48. Osorio-Paz, I.; Brunauer, R.; Alavez, S. Beer and its non-alcoholic compounds in health and disease. Crit. Rev. Food Sci. Nutr. 2019, 1, 1–14, doi:10.1080/10408398.2019.1696278.
    49. Di Renzo, L.; Marsella, L.T.; Carraro, A.; Valente, R.; Gualtieri, P.; Gratteri, S.; Tomasi, D.; Gaiotti, F.; De Lorenzo, A. Changes in LDL oxidative status and oxidative and inflammatory gene expression after red wine intake in healthy people: A randomized trial. Mediat. Inflamm. 2015, 2015, 317348:1–317348:13, doi:10.1155/2015/317348.
    50. Annunziata, G.; Maisto, M.; Schisano, C.; Ciampaglia, R.; Narciso, V.; Hassan, S.T.; Tenore, G.C.; Novellino, E. Effect of grape pomace polyphenols with or without pectin on TMAO serum levels assessed by LC/MS-based assay: A preliminary clinical study on overweight/obese subjects. Front. Pharmacol. 2019, 10, 575:1–575:11, doi:10.3389/fphar.2019.00575.
    51. Nova, E.; San Mauro-Martín, I.; Díaz-Prieto, L.E.; Marcos, A. Wine and beer within a moderate alcohol intake is associated with higher levels of HDL-c and adiponectin. Nutr. Res. 2019, 63, 42–50, doi:10.1016/j.nutres.2018.12.007.
    52. Golan, R.; Gepner, Y.; Shai, I. Wine and health–new evidence. Eur. J. Clin. Clin. Nutr. 2018, 72, 55–59, doi:10.1038/s41430-018-0309-5.
    53. Torres, A.; Cachofeiro, V.; Millán, J.; Lahera, V.; Nieto, M.; Martin, R.; Bello, E.; Alvarez-Sala, L.; Nieto, M. Red wine intake but not other alcoholic beverages increases total antioxidant capacity and improves pro-inflammatory profile after an oral fat diet in healthy volunteers. Rev. Clín. Esp. 2015, 215, 486–494, doi:10.1016/j.rce.2015.07.002.
    54. Lippi, G.; Franchini, M.; Favaloro, E.J.; Targher, G. Moderate red wine consumption and cardiovascular disease risk: Beyond the “French paradox”. In Proceedings of Seminars in Thrombosis and Hemostasis; Favaloro, E.J., Levi, M., Lisman, T., Kwaan, H.C., Schulman, S., Eds.; Thieme Medical Publishers: Stuttgart, Germany, 2010; pp. 59–70.
    55. Lim, S.S.; Vos, T.; Flaxman, A.D.; Danaei, G.; Shibuya, K.; Adair-Rohani, H.; Amann, M.; Anderson, H.R.; Andrews, K.G.; Aryee, M.; et al. A comparative risk assessment of burden of disease and injury attributable to 67 risk factors and risk factor clusters in 21 regions, 1990–2010: A systematic analysis for the global burden of disease study 2010. Lancet 2012, 380, 2224–2260, doi:10.1016/S0140-6736(12)61766-8.
    56. De Salvo, K.B.; Olson, R.; Casavale, K.O. Dietary guidelines for Americans. JAMA 2016, 315, 457–458, doi:10.1001/jama.2015.18396.
    57. Giovinazzo, G.; Ingrosso, I.; Paradiso, A.; De Gara, L.; Santino, A. Resveratrol biosynthesis: Plant metabolic engineering for nutritional improvement of food. Plant Foods Hum. Nutr. 2012, 67, 191–199, doi:10.1007/s11130-012-0299-8.
    58. Calabriso, N.; Scoditti, E.; Massaro, M.; Pellegrino, M.; Storelli, C.; Ingrosso, I.; Giovinazzo, G.; Carluccio, M.A. Multiple anti-inflammatory and anti-atherosclerotic properties of red wine polyphenolic extracts: Differential role of hydroxycinnamic acids, flavonols and stilbenes on endothelial inflammatory gene expression. Eur. J. Nutr. 2016, 55, 477–489, doi:10.1007/s00394-015-0865-6.
    59. Giovinazzo, G.; Grieco, F. Functional properties of grape and wine polyphenols. Plant Foods Hum. Nutr. 2015, 70, 454–462, doi:10.1007/s11130-015-0518-1.
    60. Lesjak, M.; Beara, I.; Simin, N.; Pintać, D.; Majkić, T.; Bekvalac, K.; Orčić, D.; Mimica-Duk, N. Antioxidant and anti-inflammatory activities of quercetin and its derivatives. J. Funct. Foods 2018, 40, 68–75, doi:10.1016/j.jff.2017.10.047.
    61. Wang, P.; Sang, S. Metabolism and pharmacokinetics of resveratrol and pterostilbene. BioFactors 2018, 44, 16–25, doi:10.1002/biof.1410.
    62. Singh, M.; Kaur, M.; Silakari, O. Flavones: An important scaffold for medicinal chemistry. Eur. J. Med. Chem. 2014, 84, 206–239, doi:10.1016/j.ejmech.2014.07.013.
    63. Ghosh, D. Tannins from foods to combat diseases. Int. J. Pharma Res. Rev. 2015, 4, 40–44.
    64. Rufián Henares, J.; Morales, F. Functional properties of melanoidins: In vitro antioxidant, antimicrobial and antihypertensive activities. Food Res. Int. 2013, 40, 995–1002, doi:10.1016/j.foodres.2007.05.002.
    65. Samuels, J.; Shashidharamurthy, R.; Rayalam, S. Novel anti-obesity effects of beer hops compound xanthohumol: Role of AMPK signalling pathway. Nutr. Metab. 2018, 15, 42:1–42:11, doi:10.1186/s12986-018-0277-8.
    66. Liu, M.; Hansen, P.E.; Wang, G.; Qiu, L.; Dong, J.; Yin, H.; Qian, Z.; Yang, M.; Miao, J. Pharmacological profile of xanthohumol, a prenylated flavonoid from hops (Humulus lupulus). Molecules 2015, 20, 754–779, doi:10.3390/molecules20010754.
    67. Rivero, D.; Pérez, S.; González, M.L.; Valls, V.; Codoñer, P.; Muñiz, P. Inhibition of induced DNA oxidative damage by beers: Correlation with the content of polyphenols and melanoidins. J. Agric. Food Chem. 2005, 53, 3637–3642, doi:10.1021/jf048146v.
    68. Zhao, H.; Li, H.; Sun, G.; Yang, B.; Zhao, M. Assessment of endogenous antioxidative compounds and antioxidant activities of lager beers. J. Sci. Food Agric. 2013, 93, 910–917, doi:10.1002/jsfa.5824.
    69. Huang, W.Y.; Liu, Y.M.; Wang, J.; Wang, X.N.; Li, C.Y. Anti-inflammatory effect of the blueberry anthocyanins malvidin-3-glucoside and malvidin-3-galactoside in endothelial cells. Molecules 2014, 19, 12827–12841, doi:10.3390/molecules190812827.
    70. Radonjić, S.; Košmerl, T.; Ota, A.; Prosen, H.; Maraš, V.; Demšar, L.; Polak, T. Technological and microbiological factors affecting polyphenolic profile of Montenegrin red wines. Chem. Ind. Chem. Eng. Q. 2019, 25, 309–319, doi:10.2298/CICEQ180814009R.
    71. Pajović-Šćepanović, R.; Wendelin, S.; Eder, R. Phenolic composition and varietal discrimination of Montenegrin red wines (Vitis vinifera var. Vranac, Kratošija, and Cabernet Sauvignon) Eur. Food Res. Technol. 2018, 244, 2243–2254, doi:10.1007/s00217-018-3133-1.
    72. Lima, A.; Oliveira, C.; Santos, C.; Campos, F.M.; Couto, J.A. Phenolic composition of monovarietal red wines regarding volatile phenols and its precursors. Eur. Food Res. Technol. 2018, 244, 1985–1994, doi:10.1007/s00217-018-3110-8.
    73. Bartolomé, B.; Peña-Neira, A.; Gómez-Cordovés, C. Phenolics and related substances in alcohol-free beers. Eur. Food Res. Technol. 2000, 210, 419–423, doi:10.1007/s002170050574.
    74. Dvořáková, M.; Hulín, P.; Karabín, M.; Dostálek, P. Determination of polyphenols in beer by an effective method based on solid-phase extraction and high performance liquid chromatography with diode-array detection. Czech J. Food Sci. 2007, 25, 182–188, doi:10.17221/690-CJFS.
    75. Jandera, P.; Škeříková, V.; Řehová, L.; Hájek, T.; Baldriánová, L.; Škopová, G.; Kellner, V.; Horna, A. RP-HPLC analysis of phenolic compounds and flavonoids in beverages and plant extracts using a CoulArray detector. J. Sep. Sci. 2005, 28, 1005–1022, doi:10.1002/jssc.200500003.
    76. McMurrough, I.; Roche, G.P.; Cleary, K.G. Phenolic acids in beers and worts. J. Inst. Brew. 1984, 90, 181–187, doi:10.1002/j.2050-0416.1984.tb04260.x.
    77. Zhao, H.; Chen, W.; Lu, J.; Zhao, M. Phenolic profiles and antioxidant activities of commercial beers. Food Chem. 2010, 119, 1150–1158, doi:10.1016/j.foodchem.2009.08.028.
    78. Floridi, S.; Montanari, L.; Marconi, O.; Fantozzi, P. Determination of free phenolic acids in wort and beer by coulometric array detection. J. Agric. Food Chem. 2003, 51, 1548–1554, doi:10.1021/jf0260040.
    79. Marques, D.; Cassis, M.; Quelhas, J.; Bertozzi, J.; Visentainer, J.; Oliveira, C.; Monteiro, A. Characterization of craft beers and their bioactive compounds. Chem. Eng. Trans. 2017, 57, 1747–1752.
    80. Marova, I.; Parilova, K.; Friedl, Z.; Obruca, S.; Duronova, K. Analysis of phenolic compounds in lager beers of different origin: A contribution to potential determination of the authenticity of Czech beer. Chromatographia 2011, 73, 83–95, doi:10.1007/s10337-011-1916-7.
    81. Alonso Garcıa, A.; Cancho Grande, B.; Simal Gandara, J. Development of a rapid method based on solid-phase extraction and liquid chromatography with ultraviolet absorbance detection for the determination of polyphenols in alcohol-free beers. J. Chromatogr. A 2004, 1054, 175–180, doi:10.1016/j.chroma.2004.07.092.
    82. Kellner, V.; Jurková, M.; Čulík, J.; Horák, T.; Čejka, P. Some phenolic compounds in Czech hops and beer of pilsner type. Brew. Sci. 2007, 60, 31–37.
    83. Socha, R.; Pająk, P.; Fortuna, T.; Buksa, K. Antioxidant activity and the most abundant phenolics in commercial dark beers. Int. J. Food Prop. 2017, 20, 1–15, doi:10.1080/10942912.2017.1306550.
    84. Nardini, M.; Ghiselli, A. Determination of free and bound phenolic acids in beer. Food Chem. 2004, 84, 137–143, doi:10.1016/S0308-8146(03)00257-7.
    85. Lamuela-Raventos, R.M.; Romero-Perez, A.I.; Waterhouse, A.L.; Carmen de la Torre-Borona, M. Direct HPLC Analysis of cis- and trans-resveratrol and piceid isomers in Spanish red Vitis vinifera wines. J. Agric. Food Chem. 1995, 43, 281–283, doi:10.1021/jf00050a003.
    86. Chiva-Blanch, G.; Urpi-Sarda, M.; Rotchés-Ribalta, M.; Zamora-Ros, R.; Llorach, R.; Lamuela-Raventós, R.M.; Andrés-Lacueva, C. Determination of resveratrol and piceid in beer matrices by solid-phase extraction and liquid chromatography-tandem mass spectrometry. J. Chromatogr. A 2011, 1218, 698–705, doi:10.1016/j.chroma.2010.12.012.
    87. Paulo, L.; Domingues, F.; Queiroz, J.A.; Gallardo, E. Development and validation of an analytical method for the determination of trans- and cis-resveratrol in wine: Analysis of its contents in 186 Portuguese red wines. J. Agric. Food Chem. 2011, 59, 2157–2168, doi:10.1021/jf105004y.
    88. Nour, V.; Trandafir, I.; Muntean, C. Ultraviolet irradiation of trans-resveratrol and HPLC determination of trans-resveratrol and cis-resveratrol in Romanian red wines. J. Chromatogr. Sci. 2012, 50, 920–927, doi:10.1093/chromsci/bms091.
    89. Zoechling, A.; Reiter, E.; Eder, R.; Wendelin, S.; Leiber, F.; Jungbauer, A. The flavonoid kaempferol is responsible for majority of estrogenic activity in red wine. Am. J. Enol. Vitic. 2009, 60, 223–232.
    90. Basalekou, M.; Kyraleou, M.; Pappas, C.; Tarantilis, P.; Kotseridis, Y.; Kallithraka, S. Proanthocyanidin content as an astringency estimation tool and maturation index in red and white winemaking technology. Food Chem. 2019, 299, 125–135, doi:10.1016/j.foodchem.2019.125135.
    91. Stark, T.; Wollmann, N.; Wenker, K.; Lösch, S.; Glabasnia, A.; Hofmann, T. Matrix-calibrated LC-MS/MS quantitation and sensory evaluation of oak ellagitannins and their transformation products in red wines. J. Agric. Food Chem. 2010, 58, 6360–6369, doi:10.1021/jf100884y.
    92. García-Estévez, I.; Escribano-Bailón, M.T.; Rivas-Gonzalo, J.C.; Alcalde-Eon, C. Validation of a mass spectrometry method to quantify oak ellagitannins in wine samples. J. Agric. Food Chem. 2012, 60, 1373–1379, doi:10.1021/jf203836a.
    93. Jourdes, M.; Michel, J.; Saucier, C.; Quideau, S.; Teissedre, P.L. Identification, amounts, and kinetics of extraction of C-glucosidic ellagitannins during wine aging in oak barrels or in stainless steel tanks with oak chips. Anal. Bioanal. Chem. 2011, 401, 1531–1539, doi:10.1007/s00216-011-4949-8.
    94. Ma, W.; Guo, A.; Zhang, Y.; Wang, H.; Liu, Y.; Li, H.J. A review on astringency and bitterness perception of tannins in wine. Trends Food Sci. Technol. 2014, 40, 6–19, doi:10.1016/j.tifs.2014.08.001.
    95. Niculescu, V.C.; Paun, N.; Ionete, R.E. The evolution of polyphenols from grapes to wines. In Grapes and Wines—Advances in Production, Processing, Analysis and Valorization; Jordão, A.M., Cosme, F.; Intech Open: London, UK, 2017; doi:10.5772/intechopen.72800.
    96. Barnaba, C.; Dellacassa, E.; Nicolini, G.; Nardin, T.; Malacarne, M.; Larcher, R. Identification and quantification of 56 targeted phenols in wines, spirits, and vinegars by online solid-phase extraction—Ultrahigh-performance liquid chromatography—Quadrupole-orbitrap mass spectrometry. J. Chromatogr. A 2015, 1423, 124–135, doi:10.1016/j.chroma.2015.10.085.
    97. Cabrera-Banegil, M.; Hurtado-sánchez, M.C.; Galeano-Díaz, T.; Durán-Merás, I. Front-face fluorescence spectroscopy combined with second-order multivariate algorithms for the quantification of polyphenols in red wine samples. Food Chem. 2016, 220, 168–176, doi:10.1016/j.foodchem.2016.09.152.
    98. Kustrin, S.; Hettiarachchi, C.; Morton, D.; Razic, S. Analysis of phenolics in wine by high performance thin-layer chromatography with gradient elution and high resolution plate imaging. J. Pharm. Biomed. Anal. 2014, 102, 93–99, doi:10.1016/j.jpba.2014.08.031.
    99. Justesen, U.; Knuthsen, P.; Leth, T. Quantitative analysis of flavonols, flavones, and flavanones in fruits, vegetables and beverages by high-performance liquid chromatography with photo-diode array and mass spectrometric detection. J. Chromatogr. A 1998, 799, 101–110, doi:10.1016/s0021-9673(97)01061-3.
    100. Achilli, G.; Cellerino, G.P.; Gamache, P.H. Identification and determination of phenolic constituents in natural beverages and plant extracts by means of a coulometric electrode array system. J. Chromatogr. A 1993, 632, 111–117, doi:10.1016/0021-9673(93)80033-5.
    More