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Phenolic content in wine

Phenolic compounds—natural phenol and polyphenols—occur naturally in wine. These include a large group of several hundred chemical compounds that affect the taste, aroma, bouquet, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins (enocyanin), flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

Origin of the phenolic compounds
The natural phenols are not evenly distributed within the grape. Phenolic acids are largely present in the pulp, anthocyanins and stilbenoids in the skin, and other phenols (catechins, proanthocyanidins and flavonols) in the skin and the seeds. During the growth cycle of the grapevine, sunlight will increase the concentration of phenolics in the grape berries, their development being an important component of canopy management. The proportion of the different phenols in any one wine will therefore vary according to the type of vinification. Red wine will be richer in phenols abundant in the skin and seeds, such as enocyanin, proanthocyanidins and flavonols, whereas the phenols in white wine will essentially originate from the pulp, and these will be the phenolic acids together with lower amounts of catechins and stilbenes. Red wines will also have the phenols found in white wines. Wine simple phenols are further transformed during wine aging into complex molecules formed notably by the condensation of proanthocyanidins and anthocyanins, which explains the modification in the color. Anthocyanins react with catechins, proanthocyanidins and other wine components during wine aging to form new polymeric pigments resulting in a modification of the wine color and a lower astringency. Average total polyphenol content measured by the Folin method is 216 mg/100 ml for red wine and 32 mg/100 ml for white wine. The content of phenols in rosé wine (82 mg/100 ml) is intermediate between that in red and white wines. In winemaking, the process of maceration or "skin contact" is used to increase the concentration of phenols in wine. Phenolic acids are found in the pulp or juice of the wine and can be commonly found in white wines which usually do not go through a maceration period. The process of oak aging can also introduce phenolic compounds into wine, most notably vanillin which adds vanilla aroma to wines. Most wine phenols are classified as secondary metabolites and were not thought to be active in the primary metabolism and function of the grapevine. However, there is evidence that in some plants flavonoids play a role as endogenous regulators of auxin transport. They are water-soluble and are usually secreted into the vacuole of the grapevine as glycosides. == Grape polyphenols ==
Grape polyphenols
Vitis vinifera, the common grape vine, from which European style wines are made the world over, produces many phenolic compounds. There is a varietal effect on the relative composition. Flavonoids or extended skin contact allows the extraction of phenolic compounds from the skins of the grape into the wine In red wine, up to 90% of the wine's phenolic content falls under the classification of flavonoids. These phenols, mainly derived from the stems, seeds and skins are often leached out of the grape during the maceration period of winemaking. The amount of phenols leached is known as extraction. These compounds contribute to the astringency, color and mouthfeel of the wine. In white wines the number of flavonoids is reduced due to the lesser contact with the skins that they receive during winemaking. There is on-going study into the health benefits of wine derived from the antioxidant and chemopreventive properties of flavonoids. Flavonols Within the flavonoid category is a subcategory known as flavonols, which includes the yellow pigment - quercetin. Like other flavonoids, the concentration of flavonols in the grape berries increases as they are exposed to sunlight. Wine grapes facing too much sun exposure can see an accelerated ripening period, leading to a lessened ability for the synthesis of flavonols. Some viticulturalists will use measurement of flavonols such as quercetin as an indication of a vineyard's sun exposure and the effectiveness of canopy management techniques. Anthocyanins Anthocyanins are phenolic compounds found throughout the plantkingdom, being frequently responsible for the blue to red colors found in flowers, fruits and leaves. In wine grapes, they develop during the stage of veraison, when the skin of red wine grapes changes color from green to red to black. As the sugars in the grape increase during ripening so does the concentration of anthocyanins. An issue associated with climate change has been the accumulation of sugars within the grape accelerating rapidly and outpacing the accumulation of anthocyanins, in particular of enocyanin, There are several types of anthocyanins (as the glycoside) found in wine grapes which are responsible for the vast range of coloring from ruby red through to dark black found in wine grapes. Ampelographers can use this observation to assist in the identification of different grape varieties. The European vine family Vitis vinifera is characterized by anthocyanins that are composed of only one molecule of glucose while non-vinifera vines such as hybrids and the American Vitis labrusca will have anthocyanins with two molecules. This phenomenon is due to a double mutation in the anthocyanin 5-O-glucosyltransferase gene of V. vinifera. In the mid-20th century, French ampelographers used this knowledge to test the various vine varieties throughout France to identify which vineyards still contained non-vinifera plantings. wine has a high pH level which means that there is a higher concentration of blue and colorless anthocyanin pigments in the wine. The resulting wine's coloring will have more blue hues than bright ruby red hues. The color variation in the finished red wine is partly derived from the ionization of anthocyanin pigments caused by the acidity of the wine. In this case, the three types of anthocyanin pigments are red, blue and colorless with the concentration of those various pigments dictating the color of the wine. A wine with low pH (and such greater acidity) will have a higher occurrence of ionized anthocyanins which will increase the amount of bright red pigments. Wines with a higher pH will have a higher concentration of blue and colorless pigments. As the wine ages, anthocyanins will react with other acids and compounds in wines such as tannins, pyruvic acid and acetaldehyde which will change the color of the wine, causing it to develop more "brick red" hues. These molecules will link up to create polymers that eventually exceed their solubility and become sediment at the bottom of wine bottles. or during controlled oxygenation processes during the aging of wine. Tannins Tannins refer to the diverse group of chemical compounds in wine that can affect the color, aging ability and texture of the wine. While tannins cannot be smelled or tasted, they can be perceived during wine tasting by the tactile sensation of astringency and sense of bitterness that they can leave in the mouth. This is due to the tendency of tannins to react with proteins, such as the ones found in saliva. The management of tannins in the winemaking process is a key component in the resulting quality. In food and wine pairing, foods that are high in proteins (such as red meat) are often paired with tannic wines to minimize the astringency of tannins. However, many wine drinkers find the perception of tannins to be a positive trait, especially as it relates to mouthfeel. Tannins are found in the skin, stems, and seeds of wine grapes but can also be introduced to the wine through the use of oak barrels and chips or with the addition of tannin powder. The natural tannins found in grapes are known as proanthocyanidins due to their ability to release red anthocyanin pigments when they are heated in an acidic solution. Grape extracts are mainly rich in monomers and small oligomers (mean degree of polymerization Phenols from oak ageing ==
Phenols from oak ageing
can be extracted from aging in oak wine barrels Oak barrel will add compounds such as vanillin and hydrolysable tannins (ellagitannins). The hydrolyzable tannins present in oak are derived from lignin structures in the wood. They help protect the wine from oxidation and reduction. 4-Ethylphenol and 4-ethylguaiacol are produced during ageing of red wine in oak barrels that are infected by brettanomyces. == Natural phenols and polyphenols from cork stoppers ==
Natural phenols and polyphenols from cork stoppers
Low molecular weight polyphenols, as well as ellagitannins, are susceptible to be extracted from cork stoppers into the wine. The identified polyphenols are gallic, protocatechuic, vanillic, caffeic, ferulic, and ellagic acids; protocatechuic, vanillic, coniferyl, and sinapic aldehydes; the coumarins aesculetin and scopoletin; the ellagitannins are roburins A and E, grandinin, vescalagin and castalagin. Guaiacol is one of the molecules responsible for the cork taint wine fault. == Phenolic content in relation with wine making techniques ==
Phenolic content in relation with wine making techniques
Extraction levels in relation with grape pressing techniques Flash release is a technique used in wine pressing. The technique allows for a better extraction of phenolic compounds. Microoxygeneation The exposure of wine to oxygen in limited quantities affects phenolic content. == Phenolic compounds found in wine ==
Phenolic compounds found in wine
red wine (top), a Beaujolais rosé (middle) and a white wine (bottom). The picture shows peaks corresponding to the different phenolic compounds. The hump between 9 and 15 minutes corresponds to the presence of tannins, mostly present in the red wine. Depending on the methods of production, wine type, grape varieties, ageing processes, the following phenolics can be found in wine. The list, sorted in alphabetical order of common names, is not exhaustive. • Acutissimin AaesculetinAnthocyanidin-caftaric acid adducts • AstilbinAstringinB type proanthocyanidin dimers • B type proanthocyanidin trimers • Caffeic acidCaftaric acidCastalaginCastavinol C1Castavinol C2Castavinol C3Castavinol C4CatechinCatechin-(4,8)-malvidin-3-O-glucosideCompound NJ2Coniferyl aldehydeCoumaric acidEllagic acidEngeletinEpicatechin gallateEpigallocatechinEpsilon-viniferinEthyl caffeateEthyl gallateEthyl protocatechuate4-Ethylguaiacol4-EthylphenolFertaric acidFerulic acidGallic acidProtocatechuic acidprotocatechuic aldehydeQuercetinQuercetol glucosideQuercetol glucuronideResveratrolRoburin ARoburin EScopoletinSinapic aldehydeSinapinic acidSyringic acidTyrosolVanillic acidvanillinVescalagin4-VinylphenolVitisin AVitisin BVinylpyranomalvidin-3O-glucoside-procyanidin dimerVinylpyranoMv-3-coumaroylglucoside-procyanidin dimerVinylpyranomalvidin-3O-glucoside-catechinVinylpyranomalvidin-3O-coumaroylglucoside-catechinVinylpyranomalvidin-3O-phenolVinylpyranopetunidin-3O-glucoside-catechinVinylpyranopeonidin-3O-glucoside-catechinVinylpyranomalvidin-3O-acetylglucoside-catechin == Effects ==
Effects
Polyphenol compounds may interact with volatiles and contribute to the aromas in wine. Although wine polyphenols are speculated to provide antioxidant or other benefits, there is little evidence that wine polyphenols actually have any effect in humans. Limited preliminary research indicates that wine polyphenols may decrease platelet aggregation, enhance fibrinolysis, and increase HDL cholesterol, but high-quality clinical trials have not confirmed such effects, as of 2017. == See also ==
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