Polyphenols have been the subject of numerous research over the past years, being referred as the nutraceuticals of modern life. The healthy properties of these compounds have been associated to a natural chemoprevention of 21st century major diseases such as cancer and neurodegenerative diseases (e.g. Parkinson's and Alzheimer's). This association led to an increased consumption of foodstuffs rich in these compounds such as red wine. Related to the ingestion of polyphenols are the herein revised sensorial properties (astringency and bitterness) which are not still pleasant. This review intends to be an outline both at a sensory as a molecular level of the mechanisms underlying astringency and bitterness of polyphenols. Up-to-date knowledge of this matter is discussed in detail.

Sensorial properties of red wine polyphenols: Astringency and bitterness

We review the extraction into wine and evolution of major phenolic classes of sensory relevance. We present a historical background to highlight that previously established aspects of phenolic extraction and retention into red wine are still subjects of much research. We argue that management of the maceration length is one of the most determining factors in defining the proportion and chemical fate of phenolic compounds in wine. The extraction of anthocyanins, flavonols, flavan-3-ols, and oligomeric and polymeric proanthocyanidins (PAs) is discussed in the context of their individual extraction patterns but also with regard to their interaction with other wine components. The same approach is followed to present the sensory implications of phenolic and phenolic-derived compounds in wine. Overall, we conclude that the chemical diversity of phenolic compounds in grapes is further enhanced as soon as vacuolar and pulp components are released upon crushing, adding a variety of new sensory dimensions to the already present chemical diversity. Polymeric pigments formed by the covalent reaction of anthocyanin and PAs are good candidates to explain some of the observed sensory changes in the color, taste, and mouthfeel attributes of red wines during maceration and aging.

Extraction, Evolution, and Sensory Impact of Phenolic Compounds During Red Wine Maceration

Phenolic compounds are important constituents of red wine, contributing to its sensory properties and antioxidant activity. Owing to the diversity and structural complexity, study of these compounds was mainly limited, during the last three decades, on their low-molecular-mass compounds or simple phenolic compounds. Only in recent years, much attention has been paid to highly polymerized polyphenols in grape and red wines. The reason for this is largely due to the development of analytical techniques, especially those of HPLC-ESI-MS, permitting the structural characterization of highly polymerized polyphenols. Furthermore, the knowledge on the biological properties of polymeric polyphenols of red wine is very limited. Grape polyphenols mainly consist of proanthocyanidins (oligomers and polymers) and anthocyanins, and low amount of other phenolics. Red wine polyphenols include both grape polyphenols and new phenolic products formed from them during winemaking process. This leads to a great diversity of new polyphenols and makes wine polyphenol composition more complex. The present paper summarizes the advances in the research of polymeric polyphenols in grape and red wine and their important role in Enology. Scientific results indicate that polymeric polyphenols, as the major polyphenols in grape and red wine, play a major role in red wine sensory properties, color stability and antioxidant activities.

Grape and wine polymeric polyphenols: Their importance in enology.

Astringency, as a kind of puckering, drying, or rough sensation, is widely perceived from natural foods, especially plants rich in phenolic compounds. Although the interaction and precipitation of salivary proteins by phenolic compounds was often believed as the major mechanism of astringency, a definitive theory about astringency is still lacking due to the complex oral sensations. The interaction with oral epithelial cells and the activation of trigeminal chemoreceptors and mechanoreceptors also shed light on some of the phenolic astringency mechanisms, which complement the insufficient mechanism of interaction with salivary proteins. Since phenolic compounds with different types and structures show different astringency thresholds in a certain regularity, there might be some relationships between the phenolic structures and perceived astringency. On the other hand, novel approaches to reducing the unfavorable perception of phenolic astringency have been increasingly emerging; however, the according summary is still sparse. Therefore, this review aims to: (a) illustrate the possible mechanisms of astringency elicited by phenolic compounds, (b) reveal the possible relationships between phenolic structures and perception of astringency, and (c) summarize the emerging mitigation approaches to astringency triggered by phenolic compounds. This comprehensive review would be of great value to both the understanding of phenolic astringency and the finding of appropriate mitigation approaches to phenolic astringency in future research.

https://onlinelibrary.wiley.com/doi/pdf/10.1111/1541-4337.12679

An overview of the perception and mitigation of astringency associated with phenolic compounds.

Microwave assisted extraction of maritime pine (Pinus pinaster) bark: Impact of particle size and characterization

Recent studies have indicated the presence of significant amount of highly polymerized and soluble proanthocyanidins in red wine and such compounds interacted readily with proteins, suggesting that they might be particularly astringent. Thus, the objective of this work was to verify the astringency of polymeric proanthocyanidins and their contribution to red wine astringency. The precipitation reactions of the purified oligomeric procyanidins (degree of polymerization ranging from 2 to 12-15) and polymeric procyanidins (degree of polymerization ranging from 12-15 to 32-34) with human salivary proteins were studied; salivary proteins composition changes before and after the reaction was verified by SDS-PAGE and procyanidins composition changes by spectrometric, direct HPLC and thiolysis-HPLC methods. The astringency intensity of these two procyanidin fractions was evaluated by a sensory analysis panel. For verifying the correlation between polymeric proanthocyanidins and young red wine astringency, the levels of total oligomeric and total polymeric proanthocyanidins and other phenolic composition in various young red wines were quantified and the astringency intensities of these wines were evaluated by a sensory panel. The results showed that polymeric proanthocyanidins had much higher reactivity toward human salivary proteins and higher astringency intensity than the oligomeric ones. Furthermore, young red wine astringency intensities were highly correlated to levels of polymeric proanthocyanidins, particularly at low concentration range (correlation coefficient r = 0.9840) but not significant correlated to total polyphenols (r = 0.2343) or other individual phenolic compounds (generally r < 0.3). These results indicate the important contribution of polymeric proanthocyanidins to red wine astringency and the levels of polymeric polyphenols in red wines may be used as an indicator for its astringency.

Reactivity of polymeric proanthocyanidins toward salivary proteins and their contribution to young red wine astringency.

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Reactivity of polymeric proanthocyanidins toward salivary proteins and their contribution to young red wine astringency.