Research

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12 pages, 1665 KiB

Open AccessArticle

Caftaric Acid Isolation from Unripe Grape: A “Green” Alternative for Hydroxycinnamic Acids Recovery

by Veronica Vendramin, Alessia Viel and Simone Vincenzi

Molecules 2021, 26(4), 1148; https://doi.org/10.3390/molecules26041148 - 21 Feb 2021

Cited by 8 | Viewed by 2339

Phenolic acids represent about one-third of the dietary phenols and are widespread in vegetable and fruits. Several plants belonging to both vegetables and medical herbs have been studied for their hydroxycinnamic acid content. Among them, Echinacea purpurea is preferentially used for caffeic acid-derivatives [...] Read more.

Phenolic acids represent about one-third of the dietary phenols and are widespread in vegetable and fruits. Several plants belonging to both vegetables and medical herbs have been studied for their hydroxycinnamic acid content. Among them, Echinacea purpurea is preferentially used for caffeic acid-derivatives extraction. The wine industry is a source of by-products that are rich in phenolic compounds. This work demonstrates that unripe grape juice (verjuice) presents a simple high-pressure liquid chromatography (HPLC) profile for hydroxycinnamic acids (HCAs), with a great separation of the caffeic-derived acids and a low content of other phenolic compounds when compared to E. purpurea and other grape by-products. Here it is shown how this allows the recovery of pure hydroxycinnamic acids by a simple and fast method, fast protein liquid chromatography (FPLC). In addition, verjuice can be easily obtained by pressing grape berries and filtering, thus avoiding any extraction step as required for other vegetable sources. Overall, the proposed protocol could strongly reduce the engagement of solvent in industrial phenolic extraction. Full article

(This article belongs to the Special Issue Polyphenolic Compounds in Wine and Beer)

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17 pages, 2716 KiB

Open AccessArticle

Color Stabilization of Apulian Red Wines through the Sequential Inoculation of Starmerella bacillaris and Saccharomyces cerevisiae

by Matteo Velenosi, Pasquale Crupi, Rocco Perniola, Antonio Domenico Marsico, Antonella Salerno, Hervè Alexandre, Nicoletta Archidiacono, Mario Ventura and Maria Francesca Cardone

Molecules 2021, 26(4), 907; https://doi.org/10.3390/molecules26040907 - 09 Feb 2021

Cited by 7 | Viewed by 2266

Abstract

Mixed fermentation using Starmerella bacillaris and Saccharomyces cerevisiae has gained attention in recent years due to their ability to modulate the qualitative parameters of enological interest, such as the color intensity and stability of wine. In this study, three of the most important [...] Read more.

Mixed fermentation using Starmerella bacillaris and Saccharomyces cerevisiae has gained attention in recent years due to their ability to modulate the qualitative parameters of enological interest, such as the color intensity and stability of wine. In this study, three of the most important red Apulian varieties were fermented through two pure inoculations of Saccharomyces cerevisiae strains or the sequential inoculation of Saccharomyces cerevisiae after 48 h from Starmerella bacillaris. The evolution of anthocyanin profiles and chromatic characteristics were determined in the produced wines at draining off and after 18 months of bottle aging in order to assess the impact of the different fermentation protocols on the potential color stabilization and shelf-life. The chemical composition analysis showed titratable acidity and ethanol content exhibiting marked differences among wines after fermentation and aging. The 48 h inoculation delay produced wines with higher values of color intensity and color stability. This was ascribed to the increased presence of compounds, such as stable A-type vitisins and reddish/violet ethylidene-bridge flavonol-anthocyanin adducts, in the mixed fermentation. Our results proved that the sequential fermentation of Starmerella bacillaris and Saccharomyces cerevisiae could enhance the chromatic profile as well as the stability of the red wines, thus improving their organoleptic quality. Full article

(This article belongs to the Special Issue Polyphenolic Compounds in Wine and Beer)

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25 pages, 6942 KiB

Open AccessArticle

Terroir Effect on the Phenolic Composition and Chromatic Characteristics of Mencía/Jaen Monovarietal Wines: Bierzo D.O. (Spain) and Dão D.O. (Portugal)

by Fernanda Cosme, Alice Vilela, Luís Moreira, Carla Moura, José A. P. Enríquez, Luís Filipe-Ribeiro and Fernando M. Nunes

Molecules 2020, 25(24), 6008; https://doi.org/10.3390/molecules25246008 - 18 Dec 2020

Cited by 5 | Viewed by 2353

Abstract

‘Mencía’/‘Jaen’ it’s an important red grape variety, exclusive of the Iberian Peninsula, used in wine production namely in Bierzo D.O. and Dão D.O., respectively. This work evaluates the effect of the two different “terroirs” on the phenolic composition and chromatic characteristics of ‘Mencía’/‘Jaen’ [...] Read more.

‘Mencía’/‘Jaen’ it’s an important red grape variety, exclusive of the Iberian Peninsula, used in wine production namely in Bierzo D.O. and Dão D.O., respectively. This work evaluates the effect of the two different “terroirs” on the phenolic composition and chromatic characteristics of ‘Mencía’/‘Jaen’ monovarietal wines produced at an industrial scale in the same vintage. Using Principal Component Analysis (PCA), Partial Least Squares-Discrimination Analysis (PLS-DA), and Orthogonal PLS-DA (OPLS-DA) it was found that peonidin-3-coumaroylglucoside, petunidin-3-glucoside, malvidin-3-coumaroylglucoside, peonidin-3-glucoside, malvidin-3-acetylglucoside, malvidin-3-glucoside, and ferulic acid were the phenolic compounds with the highest differences between the two regions. PLS regression allowed to correlate the differences in lightness (L*) and redness (a*) of wines from ‘Jaen’ and ‘Mencía’ to differences in colored anthocyanins, polymeric pigments, total pigments, total anthocyanins, cyanidin-3-acetylglucoside, delphinidin-3-acetylglucoside, delphinidin-3-glucoside, peonidin-3-coumaroylglucoside, petunidin-3-glucoside and malvidin-3-glucoside in wines, and the colorless ferulic, caffeic, and coutaric acids, and ethyl caffeate. The wines a* values were more affected by colored anthocyanins, ferulic acid, total anthocyanins, delphinidin-3-acetylglucoside, delphinidin-3-glucoside and petunidin-3-acetylglucoside, and catechin. The positive influence of ferulic acid in the a* values and ferulic, caffeic, coutaric acids, and ethyl caffeate on the L* values can be due to the co-pigmentation phenomena. The higher dryness and lower temperatures during the September nights in this vintage might explain the differences observed in the anthocyanin content and chromatic characteristics of the wines. Full article

(This article belongs to the Special Issue Polyphenolic Compounds in Wine and Beer)

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18 pages, 2150 KiB

Open AccessArticle

Unraveling the Antioxidant, Binding and Health-Protecting Properties of Phenolic Compounds of Beers with Main Human Serum Proteins: In Vitro and In Silico Approaches

by Raja Mohamed Beema Shafreen, Selvaraj Alagu Lakshmi, Shunmugiah Karutha Pandian, Yong Seo Park, Young Mo Kim, Paweł Paśko, Joseph Deutsch, Elena Katrich and Shela Gorinstein

Molecules 2020, 25(21), 4962; https://doi.org/10.3390/molecules25214962 - 27 Oct 2020

Cited by 10 | Viewed by 2159

Abstract

Our recently published in vivo studies and growing evidence suggest that moderate consumption of beer possesses several health benefits, including antioxidant and cardiovascular effects. Although beer contains phenolic acids and flavonoids as the major composition, and upon consumption, the levels of major components [...] Read more.

Our recently published in vivo studies and growing evidence suggest that moderate consumption of beer possesses several health benefits, including antioxidant and cardiovascular effects. Although beer contains phenolic acids and flavonoids as the major composition, and upon consumption, the levels of major components increase in the blood, there is no report on how these beer components interact with main human serum proteins. Thus, to address the interaction potential between beer components and human serum proteins, the present study primarily aims to investigate the components of beer from different industrial sources as well as their mode of interaction through in silico analysis. The contents of the bioactive compounds, antioxidant capacities and their influence on binding properties of the main serum proteins in human metabolism (human serum albumin (HSA), plasma circulation fibrinogen (PCF), C-reactive protein (CRP) and glutathione peroxidase 3 (GPX3)) were studied. In vitro and in silico studies indicated that phenolic substances presented in beer interact with the key regions of the proteins to enhance their antioxidant and health properties. We hypothesize that moderate consumption of beer could be beneficial for patients suffering from coronary artery disease (CAD) and other health advantages by regulating the serum proteins. Full article

(This article belongs to the Special Issue Polyphenolic Compounds in Wine and Beer)

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16 pages, 1259 KiB

Open AccessArticle

Association of Moderate Beer Consumption with the Gut Microbiota and SCFA of Healthy Adults

by Natalia González-Zancada, Noemí Redondo-Useros, Ligia E. Díaz, Sonia Gómez-Martínez, Ascensión Marcos and Esther Nova

Molecules 2020, 25(20), 4772; https://doi.org/10.3390/molecules25204772 - 17 Oct 2020

Cited by 15 | Viewed by 3672

Abstract

Fermented alcoholic drinks’ contribution to the gut microbiota composition is mostly unknown. However, intestinal microorganisms can use compounds present in beer. This work explored the associations between moderate consumption of beer, microbiota composition, and short chain fatty acid (SCFA) profile. Seventy eight subjects [...] Read more.

Fermented alcoholic drinks’ contribution to the gut microbiota composition is mostly unknown. However, intestinal microorganisms can use compounds present in beer. This work explored the associations between moderate consumption of beer, microbiota composition, and short chain fatty acid (SCFA) profile. Seventy eight subjects were selected from a 261 healthy adult cohort on the basis of their alcohol consumption pattern. Two groups were compared: (1) abstainers or occasional consumption (ABS) (n = 44; <1.5 alcohol g/day), and (2) beer consumption ≥70% of total alcohol (BEER) (n = 34; 200 to 600 mL 5% vol. beer/day; <15 mL 13% vol. wine/day; <15 mL 40% vol. spirits/day). Gut microbiota composition (16S rRNA gene sequencing) and SCFA concentration were analyzed in fecal samples. No differences were found in α and β diversity between groups. The relative abundance of gut bacteria showed that Clostridiaceae was lower (p = 0.009), while Blautia and Pseudobutyrivibrio were higher (p = 0.044 and p = 0.037, respectively) in BEER versus ABS. In addition, Alkaliphilus, in men, showed lower abundance in BEER than in ABS (p = 0.025). Butyric acid was higher in BEER than in ABS (p = 0.032), and correlated with Pseudobutyrivibrio abundance. In conclusion, the changes observed in a few taxa, and the higher butyric acid concentration in consumers versus non-consumers of beer, suggest a potentially beneficial effect of moderate beer consumption on intestinal health. Full article

(This article belongs to the Special Issue Polyphenolic Compounds in Wine and Beer)

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9 pages, 1111 KiB

Open AccessArticle

Ethylchloroformate Derivatization for GC–MS Analysis of Resveratrol Isomers in Red Wine

by Elisa Di Fabio, Alessio Incocciati, Federica Palombarini, Alberto Boffi, Alessandra Bonamore and Alberto Macone

Molecules 2020, 25(20), 4603; https://doi.org/10.3390/molecules25204603 - 09 Oct 2020

Cited by 6 | Viewed by 2442

Abstract

Resveratrol (3,5,4′-trihydroxystilbene) is a natural compound that can be found in high concentrations in red wine and in many typical foods found in human diet. Over the past decades, resveratrol has been widely investigated for its potential beneficial effects on human health. At [...] Read more.

Resveratrol (3,5,4′-trihydroxystilbene) is a natural compound that can be found in high concentrations in red wine and in many typical foods found in human diet. Over the past decades, resveratrol has been widely investigated for its potential beneficial effects on human health. At the same time, numerous analytical methods have been developed for the quantitative determination of resveratrol isomers in oenological and food matrices. In the present work, we developed a very fast and sensitive GC–MS method for the determination of resveratrol in red wine based on ethylchloroformate derivatization. Since this reaction occurs directly in the water phase during the extraction process itself, it has the advantage of significantly reducing the overall processing time for the sample. This method presents low limits of quantification (LOQ) (25 ng/mL and 50 ng/mL for cis- and trans-resveratrol, respectively) and excellent accuracy and precision. Ethylchloroformate derivatization was successfully applied to the analysis of resveratrol isomers in a selection of 15 commercial Italian red wines, providing concentration values comparable to those reported in other studies. As this method can be easily extended to other classes of molecules present in red wine, it allows further development of new GC–MS methods for the molecular profiling of oenological matrices. Full article

(This article belongs to the Special Issue Polyphenolic Compounds in Wine and Beer)

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11 pages, 936 KiB

Open AccessArticle

Beer Phenolic Composition of Simple Phenols, Prenylated Flavonoids and Alkylresorcinols

by Anna Boronat, Natalia Soldevila-Domenech, Jose Rodríguez-Morató, Miriam Martínez-Huélamo, Rosa M. Lamuela-Raventós and Rafael de la Torre

Molecules 2020, 25(11), 2582; https://doi.org/10.3390/molecules25112582 - 02 Jun 2020

Cited by 32 | Viewed by 3720

Abstract

Beer is a fermented beverage with beneficial phenolic compounds and is widely consumed worldwide. The current study aimed to describe the content of three families of phenolic compounds with relevant biological activities: prenylated flavonoids (from hops), simple phenolic alcohols (from fermentation) and alkylresorcinols [...] Read more.

Beer is a fermented beverage with beneficial phenolic compounds and is widely consumed worldwide. The current study aimed to describe the content of three families of phenolic compounds with relevant biological activities: prenylated flavonoids (from hops), simple phenolic alcohols (from fermentation) and alkylresorcinols (from cereals) in a large sample of beers (n = 45). The prenylated flavonoids analyzed were xanthohumol, isoxanthohumol, 6- and 8-prenylnaringenin. The total prenylated flavonoids present in beer ranged from 0.0 to 9.5 mg/L. The simple phenolic alcohols analyzed were tyrosol and hydroxytyrosol, ranging from 0.2 to 44.4 and 0.0 to 0.1 mg/L, respectively. Our study describes, for the first time, the presence of low amounts of alkylresorcinols in beer, in concentrations ranging from 0.02 to 11.0 µg/L. The results in non-alcoholic beer and the differences observed in the phenolic composition among different beer types and styles highlight the importance of the starting materials and the brewing process (especially fermentation) on the final phenolic composition of beer. In conclusion, beer represents a source of phenolic compounds in the diet that could act synergistically, triggering beneficial health effects in the context of its moderate consumption. Full article

(This article belongs to the Special Issue Polyphenolic Compounds in Wine and Beer)

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15 pages, 823 KiB

Open AccessArticle

Phenolics Profile and Antioxidant Activity of Special Beers

by Mirella Nardini and Maria Stella Foddai

Molecules 2020, 25(11), 2466; https://doi.org/10.3390/molecules25112466 - 26 May 2020

Cited by 28 | Viewed by 3638

Abstract

The antioxidant activity and polyphenols content of beer associated with its low alcohol content are relevant factors for an evaluation of the nutritional quality of beer. To investigate the effect of adding foods on the nutritional quality of beer, seven special beers that [...] Read more.

The antioxidant activity and polyphenols content of beer associated with its low alcohol content are relevant factors for an evaluation of the nutritional quality of beer. To investigate the effect of adding foods on the nutritional quality of beer, seven special beers that were commercially available and produced adding natural foods (walnut, chestnut, cocoa, honey, green tea, coffee, and licorice) during the fermentation process were analyzed for their polyphenols and flavonoids contents, phenolics profile, and antioxidant activity. The results obtained showed that most of the special beers under study possessed antioxidant activity, as well as total polyphenols and flavonoids contents notably higher as compared with the five conventional beers analyzed. The highest polyphenols and flavonoids contents were exhibited in cocoa, walnut, chestnut, and licorice beers, followed by coffee, honey, and green tea beers. Antioxidant activity decreased in the order walnut, cocoa, chestnut, licorice, coffee, honey, and green tea. Most special beers were enriched in catechin, epicatechin, rutin, myricetin, quercetin, and resveratrol. The content of phenolic acids, especially ferulic, p-coumaric, syringic, and sinapic acids was generally higher in special beers as compared with conventional beers. Our findings showed that the addition of natural foods during the fermentation process remarkably increased antioxidant activity of beer and qualitatively and quantitatively improved its phenolics profile. Full article

(This article belongs to the Special Issue Polyphenolic Compounds in Wine and Beer)

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Review

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26 pages, 901 KiB

Open AccessFeature PaperReview

The Role of Bioactive Phenolic Compounds on the Impact of Beer on Health

by Roberto Ambra, Gianni Pastore and Sabrina Lucchetti

Molecules 2021, 26(2), 486; https://doi.org/10.3390/molecules26020486 - 18 Jan 2021

Cited by 30 | Viewed by 5347

Abstract

This review reports recent knowledge on the role of ingredients (barley, hop and yeasts), including genetic factors, on the final yield of phenolic compounds in beer, and how these molecules generally affect resulting beer attributes, focusing mainly on new attempts at the enrichment [...] Read more.

This review reports recent knowledge on the role of ingredients (barley, hop and yeasts), including genetic factors, on the final yield of phenolic compounds in beer, and how these molecules generally affect resulting beer attributes, focusing mainly on new attempts at the enrichment of beer phenols, with fruits or cereals other than barley. An entire section is dedicated to health-related effects, analyzing the degree up to which studies, investigating phenols-related health effects of beer, have appropriately considered the contribution of alcohol (pure or spirits) intake. For such purpose, we searched Scopus.com for any kind of experimental model (in vitro, animal, human observational or intervention) using beer and considering phenols. Overall, data reported so far support the existence of the somehow additive or synergistic effects of phenols and ethanol present in beer. However, findings are inconclusive and thus deserve further animal and human studies. Full article

(This article belongs to the Special Issue Polyphenolic Compounds in Wine and Beer)

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35 pages, 2646 KiB

Open AccessReview

Wine or Beer? Comparison, Changes and Improvement of Polyphenolic Compounds during Technological Phases

by Sanja Radonjić, Vesna Maraš, Jovana Raičević and Tatjana Košmerl

Molecules 2020, 25(21), 4960; https://doi.org/10.3390/molecules25214960 - 27 Oct 2020

Cited by 31 | Viewed by 5280

Abstract

Wine and beer are nowadays the most popular alcoholic beverages, and the benefits of their moderate consumption have been extensively supported by the scientific community. The main source of wine and beer’s antioxidant behavior are the phenolic substances. Phenolic compounds in wine and [...] Read more.

Wine and beer are nowadays the most popular alcoholic beverages, and the benefits of their moderate consumption have been extensively supported by the scientific community. The main source of wine and beer’s antioxidant behavior are the phenolic substances. Phenolic compounds in wine and beer also influence final product quality, in terms of color, flavor, fragrance, stability, and clarity. Change in the quantity and quality of phenolic compounds in wine and beer depends on many parameters, beginning with the used raw material, its place of origin, environmental growing conditions, and on all the applied technological processes and the storage of the final product. This review represents current knowledge of phenolic compounds, comparing qualitative and quantitative profiles in wine and beer, changes of these compounds through all phases of wine and beer production are discussed, as well as the possibilities for increasing their content. Analytical methods and their importance for phenolic compound determination have also been pointed out. The observed data showed wine as the beverage with a more potent biological activity, due to a higher content of phenolic compounds. However, both of them contain, partly similar and different, phenolic compounds, and recommendations have to consider the drinking pattern, consumed quantity, and individual preferences. Furthermore, novel technologies have been developing rapidly in order to improve the polyphenolic content and antioxidant activity of these two beverages, particularly in the brewing industry. Full article

(This article belongs to the Special Issue Polyphenolic Compounds in Wine and Beer)

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15 pages, 299 KiB

Open AccessReview

Effects of the Non-Alcoholic Fraction of Beer on Abdominal Fat, Osteoporosis, and Body Hydration in Women

by Marta Trius-Soler, Arnau Vilas-Franquesa, Anna Tresserra-Rimbau, Gemma Sasot, Carolina E. Storniolo, Ramon Estruch and Rosa M. Lamuela-Raventós

Molecules 2020, 25(17), 3910; https://doi.org/10.3390/molecules25173910 - 27 Aug 2020

Cited by 13 | Viewed by 5751

Abstract

Several studies have shown that binge drinking of alcoholic beverages leads to non-desirable outcomes, which have become a serious threat to public health. However, the bioactive compounds in some alcohol-containing beverages might mitigate the negative effects of alcohol. In beer, the variety and [...] Read more.

Several studies have shown that binge drinking of alcoholic beverages leads to non-desirable outcomes, which have become a serious threat to public health. However, the bioactive compounds in some alcohol-containing beverages might mitigate the negative effects of alcohol. In beer, the variety and concentration of bioactive compounds in the non-alcoholic fraction suggests that its consumption at moderate levels may not only be harmless but could also positively contribute to an improvement of certain physiological states and be also useful in the prevention of different chronic diseases. The present review focuses on the effects of non-alcoholic components of beer on abdominal fat, osteoporosis, and body hydration in women, conditions selected for their relevance to health and aging. Although beer drinking is commonly believed to cause abdominal fat deposition, the available literature indicates this outcome is inconsistent in women. Additionally, the non-alcoholic beer fraction might improve bone health in postmenopausal women, and the effects of beer on body hydration, although still unconfirmed seem promising. Most of the health benefits of beer are due to its bioactive compounds, mainly polyphenols, which are the most studied. As alcohol-free beer also contains these compounds, it may well offer a healthy alternative to beer consumers. Full article

(This article belongs to the Special Issue Polyphenolic Compounds in Wine and Beer)

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