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Phenolic content in wine

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, 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.[1] The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

The phenolic compounds in Syrah grapes contribute to the taste, color and mouthfeel of the wine.

Origin of the phenolic compounds edit

The natural phenols are not evenly distributed within the fruit. 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.[2] 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 anthocyanin, 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.[3][4] 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.[5]

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.[6] They are water-soluble and are usually secreted into the vacuole of the grapevine as glycosides.

Grape polyphenols edit

Vitis vinifera produces many phenolic compounds. There is a varietal effect on the relative composition.

Flavonoids edit

 
The process of maceration or extended skin contact allows the extraction of phenolic compounds (including those that form a wine's color) 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.[7]

Flavonols edit

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.[8] 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 edit

Anthocyanins are phenolic compounds found throughout the plant kingdom, 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.[8] This leaves viticulturists with the choice of harvesting grapes with too high sugar content or with too low anthocyanin content. In most grapes anthocyanins are found only in the outer cell layers of the skin, leaving the grape juice inside virtually colorless. Therefore, to get color pigmentation in the wine, the fermenting must needs to be in contact with the grape skins in order for the anthocyanins to be extracted. Hence, white wine can be made from red wine grapes in the same way that many white sparkling wines are made from the red wine grapes of Pinot noir and Pinot Meunier. The exception to this is the small class of grapes known as teinturiers, such as Alicante Bouschet, which have a small amount of anthocyanins in the pulp that produces pigmented juice.[9]

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.[10] 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.[9]

Red-berried Pinot grape varieties are also known to not synthesize para-coumaroylated or acetylated anthocyanins as other varieties do.[11]

 
Tempranillo 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.[9] Pyranoanthocyanins are chemical compounds formed in red wines by yeast during fermentation processes[12] or during controlled oxygenation processes[13] during the aging of wine.[14]

Tannins edit

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 drying sensation 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.[15] 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. The management of tannins in the winemaking process is a key component in the resulting quality.[16]

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 < 8). Grape seed extracts contain three monomers (catechin, epicatechin and epicatechin gallate) and procyanidin oligomers. Grape skin extracts contain four monomers (catechin, epicatechin, gallocatechin and epigallocatechin), as well as procyanidins and prodelphinidins oligomers.[17] The tannins are formed by enzymes during metabolic processes of the grapevine. The amount of tannins found naturally in grapes varies depending on the variety with Cabernet Sauvignon, Nebbiolo, Syrah and Tannat being 4 of the most tannic grape varieties. The reaction of tannins and anthocyanins with the phenolic compound catechins creates another class of tannins known as pigmented tannins which influence the color of red wine.[18] Commercial preparations of tannins, known as enological tannins, made from oak wood, grape seed and skin, plant gall, chestnut, quebracho, gambier[19] and myrobalan fruits,[20] can be added at different stages of the wine production to improve color durability. The tannins derived from oak influence are known as "hydrolysable tannins" being created from the ellagic and gallic acid found in the wood.[16]

 
Fermenting with the stem, seeds and skin will increase the tannin content of the wine.

In the vineyards, there is also a growing distinction being made between "ripe" and "unripe" tannins present in the grape. This "physiological ripeness", which is roughly determined by tasting the grapes off the vines, is being used along with sugar levels as a determination of when to harvest. The idea is that "riper" tannins will taste softer but still impart some of the texture components found favorable in wine. In winemaking, the amount of the time that the must spends in contact with the grape skins, stems and seeds will influence the amount of tannins that are present in the wine with wines subjected to longer maceration period having more tannin extract. Following harvest, stems are normally picked out and discarded prior to fermentation but some winemakers may intentionally leave in a few stems for varieties low in tannins (like Pinot noir) in order to increase the tannic extract in the wine. If there is an excess in the amount of tannins in the wine, winemakers can use various fining agents like albumin, casein and gelatin that can bind to tannins molecule and precipitate them out as sediments. As a wine ages, tannins will form long polymerized chains which come across to a taster as "softer" and less tannic. This process can be accelerated by exposing the wine to oxygen, which oxidize tannins to quinone-like compounds that are polymerization-prone. The winemaking technique of micro-oxygenation and decanting wine use oxygen to partially mimic the effect of aging on tannins.[16]

A study in wine production and consumption has shown that tannins, in the form of proanthocyanidins, have a beneficial effect on vascular health. The study showed that tannins suppressed production of the peptide responsible for hardening arteries. To support their findings, the study also points out that wines from the regions of southwest France and Sardinia are particularly rich in proanthocyanidins, and that these regions also produce populations with longer life spans.[21]

Reactions of tannins with the phenolic compound anthocyanidins creates another class of tannins known as pigmented tannins which influences the color of red wine.[18]

Addition of enological tannins edit

Commercial preparations of tannins, known as enological tannins, made from oak wood, grape seed and skin, plant gall, chestnut, quebracho, gambier[19] and myrobalan fruits,[20] can be added at different stages of the wine production to improve color durability.

Effects of tannins on the drinkability and aging potential of wine edit

Tannins are a natural preservative in wine. Un-aged wines with high tannin content can be less palatable than wines with a lower level of tannins. Tannins can be described as leaving a dry and puckered feeling with a "furriness" in the mouth that can be compared to a stewed tea, which is also very tannic. This effect is particularly profound when drinking tannic wines without the benefit of food.

Many wine lovers see natural tannins (found particularly in varietals such as Cabernet Sauvignon and often accentuated by heavy oak barrel aging) as a sign of potential longevity and ageability. Tannins impart a mouth-puckering astringency when the wine is young but "resolve" (through a chemical process called polymerization) into delicious and complex elements of "bottle bouquet" when the wine is cellared under appropriate temperature conditions, preferably in the range of a constant 55 to 60 °F (13 to 16 °C).[22] Such wines mellow and improve with age with the tannic "backbone" helping the wine survive for as long as 40 years or more.[23] In many regions (such as in Bordeaux), tannic grapes such as Cabernet Sauvignon are blended with lower-tannin grapes such as Merlot or Cabernet Franc, diluting the tannic characteristics. White wines and wines that are vinified to be drunk young (for examples, see nouveau wines) typically have lower tannin levels.

Other flavonoids edit

Flavan-3-ols (catechins) are flavonoids that contribute to the construction of various tannins and contribute to the perception of bitterness in wine. They are found in highest concentrations in grape seeds but are also in the skin and stems. Catechins play a role in the microbial defense of the grape berry, being produced in higher concentrations by the grape vines when it is being attacked by grape diseases such as downy mildew. Because of that grape vines in cool, damp climates produce catechins at high levels than vines in dry, hot climates. Together with anthocyanins and tannins they increase the stability of a wines color-meaning that a wine will be able to maintain its coloring for a longer period of time. The amount of catechins present varies among grape varieties with varietals like Pinot noir having high concentrations while Merlot and especially Syrah have very low levels.[17] As an antioxidant, there are some studies into the health benefits of moderate consumption of wines high in catechins.[24]

In red grapes, the main flavonol is on average quercetin, followed by myricetin, kaempferol, laricitrin, isorhamnetin, and syringetin.[25] In white grapes, the main flavonol is quercetin, followed by kaempferol and isorhamnetin. The delphinidin-like flavonols myricetin, laricitrin, and syringetin are missing in all white varieties, indicating that the enzyme flavonoid 3',5'-hydroxylase is not expressed in white grape varieties.[25]

Myricetin, laricitrin[26] and syringetin,[27] flavonols which are present in red grape varieties only, can be found in red wine.[28]

Non-flavonoids edit

Hydroxycinnamic acids edit

Hydroxycinnamic acids are the most important group of nonflavonoid phenols in wine. The four most abundant ones are the tartaric acid esters trans-caftaric, cis- and trans-coutaric, and trans-fertaric acids. In wine they are present also in the free form (trans-caffeic, trans-p-coumaric, and trans-ferulic acids).[29]

Stilbenoids edit

V. vinifera also produces stilbenoids.

Resveratrol is found in highest concentration in the skins of wine grapes. The accumulation in ripe berries of different concentrations of both bound and free resveratrols depends on the maturity level and is highly variable according to the genotype.[30] Both red and white wine grape varieties contain resveratrol, but more frequent skin contact and maceration leads to red wines normally having ten times more resveratrol than white wines.[31] Resveratrol produced by grape vines provides defense against microbes, and production can be further artificially stimulated by ultraviolet radiation. Grapevines in cool, damp regions with higher risk of grape diseases, such as Bordeaux and Burgundy, tend to produce grapes with higher levels of resveratrol than warmer, drier wine regions such as California and Australia. Different grape varieties tend to have differing levels, with Muscadines and the Pinot family having high levels while the Cabernet family has lower levels of resveratrol. In the late 20th century interest in the possible health benefits of resveratrol in wine was spurred by discussion of the French paradox involving the health of wine drinkers in France.[32]

Piceatannol is also present in grape [33] from where it can be extracted and found in red wine.[28]

Phenolic acids edit

Vanillin is a phenolic aldehyde most commonly associated with the vanilla notes in wines that have been aged in oak. Trace amounts of vanillin are found naturally in grapes, but they are most prominent in the lignin structure of oak barrels. Newer barrels will impart more vanillin, with the concentration present decreasing with each subsequent usage.[34]

Phenols from oak ageing edit

 
Phenolic compounds like tannins and vanillin 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.[35]

4-Ethylphenol and 4-ethylguaiacol are produced during ageing of red wine in oak barrels that are infected by brettanomyces .[36]

Natural phenols and polyphenols from cork stoppers edit

 
Extracted cork closure inscribed with "Bottled at origin" in Spanish

Low molecular weight polyphenols, as well as ellagitannins, are susceptible to be extracted from cork stoppers into the wine.[37] 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.[38]

Guaiacol is one of the molecules responsible for the cork taint wine fault.[39]

Phenolic content in relation with wine making techniques edit

Extraction levels in relation with grape pressing techniques edit

Flash release is a technique used in wine pressing.[40] The technique allows for a better extraction of phenolic compounds.[41]

Microoxygeneation edit

The exposure of wine to oxygen in limited quantities affects phenolic content.[42]

Phenolic compounds found in wine edit

 
LC chromatograms at 280 nm of a pinot 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.

Effects edit

Polyphenol compounds may interact with volatiles and contribute to the aromas in wine.[49] Although wine polyphenols are speculated to provide antioxidant or other benefits, there is little evidence that wine polyphenols actually have any effect in humans.[50][51][52][53] 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.[50]

See also edit

References edit

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  2. ^ Costa de Camargo, Adriano; Bismara Regitano-d'Arce, Marisa Aparecida; Camarão Telles Biasoto, Aline; Shahidi, Fereidoon (2014). "Low Molecular Weight Phenolics of Grape Juice and Winemaking Byproducts: Antioxidant Activities and Inhibition of Oxidation of Human Low-Density Lipoprotein Cholesterol and DNA Strand Breakage". Journal of Agricultural and Food Chemistry. 62 (50): 12159–12171. doi:10.1021/jf504185s. PMID 25417599.
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External links edit

  • Wine polyphenols vary with age and variety (Polyphenols on www.guideduvin.com) (in French)
  • Polyphenol concentrations in red, white and rosé wines at www.phenol-explorer.eu

phenolic, content, wine, phenolic, content, wine, refers, phenolic, compounds, natural, phenol, polyphenols, wine, which, include, large, group, several, hundred, chemical, compounds, that, affect, taste, color, mouthfeel, wine, these, compounds, include, phen. The phenolic content in wine refers to the phenolic compounds natural phenol and polyphenols in wine which include a large group of several hundred chemical compounds that affect the taste color and mouthfeel of wine These compounds include phenolic acids stilbenoids flavonols dihydroflavonols anthocyanins 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 1 The non flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic caffeic and cinnamic acids The phenolic compounds in Syrah grapes contribute to the taste color and mouthfeel of the wine Contents 1 Origin of the phenolic compounds 2 Grape polyphenols 2 1 Flavonoids 2 1 1 Flavonols 2 1 2 Anthocyanins 2 1 3 Tannins 2 1 3 1 Addition of enological tannins 2 1 3 2 Effects of tannins on the drinkability and aging potential of wine 2 2 Other flavonoids 2 3 Non flavonoids 2 3 1 Hydroxycinnamic acids 2 3 2 Stilbenoids 2 3 3 Phenolic acids 3 Phenols from oak ageing 4 Natural phenols and polyphenols from cork stoppers 5 Phenolic content in relation with wine making techniques 5 1 Extraction levels in relation with grape pressing techniques 5 2 Microoxygeneation 6 Phenolic compounds found in wine 7 Effects 8 See also 9 References 10 External linksOrigin of the phenolic compounds editThe natural phenols are not evenly distributed within the fruit 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 2 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 anthocyanin 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 3 4 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 rose 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 5 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 6 They are water soluble and are usually secreted into the vacuole of the grapevine as glycosides Grape polyphenols editVitis vinifera produces many phenolic compounds There is a varietal effect on the relative composition Flavonoids edit Main article Flavonoids nbsp The process of maceration or extended skin contact allows the extraction of phenolic compounds including those that form a wine s color 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 7 Flavonols edit Main article 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 8 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 edit Main article Anthocyanin Anthocyanins are phenolic compounds found throughout the plant kingdom 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 8 This leaves viticulturists with the choice of harvesting grapes with too high sugar content or with too low anthocyanin content In most grapes anthocyanins are found only in the outer cell layers of the skin leaving the grape juice inside virtually colorless Therefore to get color pigmentation in the wine the fermenting must needs to be in contact with the grape skins in order for the anthocyanins to be extracted Hence white wine can be made from red wine grapes in the same way that many white sparkling wines are made from the red wine grapes of Pinot noir and Pinot Meunier The exception to this is the small class of grapes known as teinturiers such as Alicante Bouschet which have a small amount of anthocyanins in the pulp that produces pigmented juice 9 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 10 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 9 Red berried Pinot grape varieties are also known to not synthesize para coumaroylated or acetylated anthocyanins as other varieties do 11 nbsp Tempranillo 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 9 Pyranoanthocyanins are chemical compounds formed in red wines by yeast during fermentation processes 12 or during controlled oxygenation processes 13 during the aging of wine 14 Tannins edit Main article Tannin 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 drying sensation 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 15 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 The management of tannins in the winemaking process is a key component in the resulting quality 16 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 lt 8 Grape seed extracts contain three monomers catechin epicatechin and epicatechin gallate and procyanidin oligomers Grape skin extracts contain four monomers catechin epicatechin gallocatechin and epigallocatechin as well as procyanidins and prodelphinidins oligomers 17 The tannins are formed by enzymes during metabolic processes of the grapevine The amount of tannins found naturally in grapes varies depending on the variety with Cabernet Sauvignon Nebbiolo Syrah and Tannat being 4 of the most tannic grape varieties The reaction of tannins and anthocyanins with the phenolic compound catechins creates another class of tannins known as pigmented tannins which influence the color of red wine 18 Commercial preparations of tannins known as enological tannins made from oak wood grape seed and skin plant gall chestnut quebracho gambier 19 and myrobalan fruits 20 can be added at different stages of the wine production to improve color durability The tannins derived from oak influence are known as hydrolysable tannins being created from the ellagic and gallic acid found in the wood 16 nbsp Fermenting with the stem seeds and skin will increase the tannin content of the wine In the vineyards there is also a growing distinction being made between ripe and unripe tannins present in the grape This physiological ripeness which is roughly determined by tasting the grapes off the vines is being used along with sugar levels as a determination of when to harvest The idea is that riper tannins will taste softer but still impart some of the texture components found favorable in wine In winemaking the amount of the time that the must spends in contact with the grape skins stems and seeds will influence the amount of tannins that are present in the wine with wines subjected to longer maceration period having more tannin extract Following harvest stems are normally picked out and discarded prior to fermentation but some winemakers may intentionally leave in a few stems for varieties low in tannins like Pinot noir in order to increase the tannic extract in the wine If there is an excess in the amount of tannins in the wine winemakers can use various fining agents like albumin casein and gelatin that can bind to tannins molecule and precipitate them out as sediments As a wine ages tannins will form long polymerized chains which come across to a taster as softer and less tannic This process can be accelerated by exposing the wine to oxygen which oxidize tannins to quinone like compounds that are polymerization prone The winemaking technique of micro oxygenation and decanting wine use oxygen to partially mimic the effect of aging on tannins 16 A study in wine production and consumption has shown that tannins in the form of proanthocyanidins have a beneficial effect on vascular health The study showed that tannins suppressed production of the peptide responsible for hardening arteries To support their findings the study also points out that wines from the regions of southwest France and Sardinia are particularly rich in proanthocyanidins and that these regions also produce populations with longer life spans 21 Reactions of tannins with the phenolic compound anthocyanidins creates another class of tannins known as pigmented tannins which influences the color of red wine 18 Addition of enological tannins edit Commercial preparations of tannins known as enological tannins made from oak wood grape seed and skin plant gall chestnut quebracho gambier 19 and myrobalan fruits 20 can be added at different stages of the wine production to improve color durability Effects of tannins on the drinkability and aging potential of wine edit Tannins are a natural preservative in wine Un aged wines with high tannin content can be less palatable than wines with a lower level of tannins Tannins can be described as leaving a dry and puckered feeling with a furriness in the mouth that can be compared to a stewed tea which is also very tannic This effect is particularly profound when drinking tannic wines without the benefit of food Many wine lovers see natural tannins found particularly in varietals such as Cabernet Sauvignon and often accentuated by heavy oak barrel aging as a sign of potential longevity and ageability Tannins impart a mouth puckering astringency when the wine is young but resolve through a chemical process called polymerization into delicious and complex elements of bottle bouquet when the wine is cellared under appropriate temperature conditions preferably in the range of a constant 55 to 60 F 13 to 16 C 22 Such wines mellow and improve with age with the tannic backbone helping the wine survive for as long as 40 years or more 23 In many regions such as in Bordeaux tannic grapes such as Cabernet Sauvignon are blended with lower tannin grapes such as Merlot or Cabernet Franc diluting the tannic characteristics White wines and wines that are vinified to be drunk young for examples see nouveau wines typically have lower tannin levels Other flavonoids edit Flavan 3 ols catechins are flavonoids that contribute to the construction of various tannins and contribute to the perception of bitterness in wine They are found in highest concentrations in grape seeds but are also in the skin and stems Catechins play a role in the microbial defense of the grape berry being produced in higher concentrations by the grape vines when it is being attacked by grape diseases such as downy mildew Because of that grape vines in cool damp climates produce catechins at high levels than vines in dry hot climates Together with anthocyanins and tannins they increase the stability of a wines color meaning that a wine will be able to maintain its coloring for a longer period of time The amount of catechins present varies among grape varieties with varietals like Pinot noir having high concentrations while Merlot and especially Syrah have very low levels 17 As an antioxidant there are some studies into the health benefits of moderate consumption of wines high in catechins 24 In red grapes the main flavonol is on average quercetin followed by myricetin kaempferol laricitrin isorhamnetin and syringetin 25 In white grapes the main flavonol is quercetin followed by kaempferol and isorhamnetin The delphinidin like flavonols myricetin laricitrin and syringetin are missing in all white varieties indicating that the enzyme flavonoid 3 5 hydroxylase is not expressed in white grape varieties 25 Myricetin laricitrin 26 and syringetin 27 flavonols which are present in red grape varieties only can be found in red wine 28 Non flavonoids edit See also Wine and health Hydroxycinnamic acids edit Hydroxycinnamic acids are the most important group of nonflavonoid phenols in wine The four most abundant ones are the tartaric acid esters trans caftaric cis and trans coutaric and trans fertaric acids In wine they are present also in the free form trans caffeic trans p coumaric and trans ferulic acids 29 Stilbenoids edit V vinifera also produces stilbenoids Resveratrol is found in highest concentration in the skins of wine grapes The accumulation in ripe berries of different concentrations of both bound and free resveratrols depends on the maturity level and is highly variable according to the genotype 30 Both red and white wine grape varieties contain resveratrol but more frequent skin contact and maceration leads to red wines normally having ten times more resveratrol than white wines 31 Resveratrol produced by grape vines provides defense against microbes and production can be further artificially stimulated by ultraviolet radiation Grapevines in cool damp regions with higher risk of grape diseases such as Bordeaux and Burgundy tend to produce grapes with higher levels of resveratrol than warmer drier wine regions such as California and Australia Different grape varieties tend to have differing levels with Muscadines and the Pinot family having high levels while the Cabernet family has lower levels of resveratrol In the late 20th century interest in the possible health benefits of resveratrol in wine was spurred by discussion of the French paradox involving the health of wine drinkers in France 32 Piceatannol is also present in grape 33 from where it can be extracted and found in red wine 28 Phenolic acids edit Vanillin is a phenolic aldehyde most commonly associated with the vanilla notes in wines that have been aged in oak Trace amounts of vanillin are found naturally in grapes but they are most prominent in the lignin structure of oak barrels Newer barrels will impart more vanillin with the concentration present decreasing with each subsequent usage 34 Phenols from oak ageing edit nbsp Phenolic compounds like tannins and vanillin 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 35 4 Ethylphenol and 4 ethylguaiacol are produced during ageing of red wine in oak barrels that are infected by brettanomyces 36 Natural phenols and polyphenols from cork stoppers edit nbsp Extracted cork closure inscribed with Bottled at origin in SpanishLow molecular weight polyphenols as well as ellagitannins are susceptible to be extracted from cork stoppers into the wine 37 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 38 Guaiacol is one of the molecules responsible for the cork taint wine fault 39 Phenolic content in relation with wine making techniques editExtraction levels in relation with grape pressing techniques edit Flash release is a technique used in wine pressing 40 The technique allows for a better extraction of phenolic compounds 41 Microoxygeneation edit The exposure of wine to oxygen in limited quantities affects phenolic content 42 Phenolic compounds found in wine edit nbsp LC chromatograms at 280 nm of a pinot red wine top a Beaujolais rose 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 A aesculetin Anthocyanidin caftaric acid adducts 43 44 Astilbin Astringin B type proanthocyanidin dimers B type proanthocyanidin trimers Caffeic acid Caftaric acid Castalagin Castavinol C1 Castavinol C2 Castavinol C3 Castavinol C4 Catechin 45 Catechin 4 8 malvidin 3 O glucoside 46 Compound NJ2 Coniferyl aldehyde Coumaric acid 45 Coutaric acid Cyanidin Cyanin Cyanidin 3 5 O diglucoside Cyanidin 3O glucoside Cyanidin acetyl 3O glucoside Cyanidin coumaroyl 3O glucoside Cyanidin 3 O glucoside pyruvic acid Cyanidin 3 O acetylglucoside pyruvic acid Cyanidin coumaroylglucoside pyruvic acid Delphinidin Delphinidin 3O glucoside Delphinidin acetyl 3O glucoside Delphinidin coumaroyl 3O glucoside Delphinidin 3 O glucoside pyruvic acid Delphinidin 3 O acetylglucoside pyruvic acid Delphinidin 3 O coumaroylglucoside pyruvic acid Delphinidin 3 O glucoside 4 vinylcatechol Delphinidin 3 O acetylglucoside 4 vinylcatechol Delphinidin 3 O coumaroylglucoside 4 vinylcatechol Delphinidin 3 O glucoside 4 vinylphenol Delphinidin 3 O acetylglucoside 4 vinylphenol Delphinidin 3 O coumaroylglucoside 4 vinylphenol Delphinidin 3 O glucoside 4 vinylguaiacol Delphinidin 3 O glucoside 4 vinyl epi catechin Delphinidin 3 O acetylglucoside 4 vinyl epi catechin Delta viniferin Dihydro resveratrol 47 Ellagic acid Engeletin Epicatechin gallate Epigallocatechin Epsilon viniferin Ethyl caffeate Ethyl gallate Ethyl protocatechuate 4 Ethylguaiacol 4 Ethylphenol Fertaric acid Ferulic acid Gallic acid 45 Gentisic acid Grandinin Grape reaction product GRP Guaiacol Hopeaphenol p Hydroxybenzoic acid Isorhamnetol 3 glucoside Kaempferol Kaempferol glucoside astragalin Kaempferol glucuronide Malvidin Malvidin 3O glucoside oenin Malvidin acetyl 3O glucoside Malvidin cafeoyl 3O glucoside Malvidin coumaroyl 3Oglucoside Malvidin glucoside ethyl catechin Malvidin 3 O glucoside pyruvic acid Malvidin 3 O acetylglucoside pyruvic acid Malvidin 3 O coumaroylglucoside pyruvic acid Malvidin 3 O glucoside acetaldehyde Malvidin 3 O acetylglucoside acetaldehyde Malvidin 3 O coumaroylglucoside acetaldehyde Malvidin 3 O glucoside 4 vinylcatechol Malvidin 3 O acetylglucoside 4 vinylcatechol Malvidin 3 O coumaroylglucoside 4 vinylcatechol Malvidin 3 O glucoside 4 vinylphenol Malvidin 3 O acetylglucoside 4 vinylphenol Malvidin 3 O coumaroylglucoside 4 vinylphenol Malvidin 3 O caffeoylglucoside 4 vinylphenol Malvidin 3 O glucoside 4 vinylguaiacol Malvidin 3 O acetylglucoside 4 vinylguaiacol Malvidin 3 O coumaroylglucoside vinylguaiacol Malvidin 3 O glucoside 4 vinyl epi catechin Malvidin 3 O acetylglucoside 4 vinyl epi catechin Malvidin 3 O coumaroylglucoside 4 vinyl epi catechin Methyl gallate Myricetol Myricetol 3 glucoside Myricetol 3 glucuronide Oxovitisin A Pallidol Pelargonin Pelargonidin 3 5 O diglucoside Peonidin 3O glucoside Peonidin acetyl 3O glucoside Peonidin 3 6 p caffeoyl glucoside Peonidin coumaroyl 3O glucoside Peonidin 3 O glucoside pyruvic acid Peonidin 3 O acetylglucoside pyruvic acid Peonidin 3 O coumaroylglucoside pyruvic acid Peonidin 3 O glucoside 4 vinylcatechol Peonidin 3 O acetylglucoside 4 vinylcatechol Peonidin 3 O coumaroylglucoside 4 vinylcatechol Peonidin 3 O glucoside 4 vinylphenol Peonidin 3 O acetylglucoside 4 vinylphenol Peonidin 3 O coumaroylglucoside 4 vinylphenol Peonidin 3 O glucoside 4 vinylguaiacol Peonidin 3 O glucoside 4 vinyl epi catechin Peonidin 3 O acetylglucoside 4 vinyl epi catechin Petunidin Petunidin 3O glucoside Petunidin acetyl 3O glucoside Petunidin coumaroyl 3O glucoside Petunidin 3 O glucoside pyruvic acid Petunidin 3 O acetylglucoside pyruvic acid Petunidin 3 O coumaroylglucoside pyruvic acid Petunidin 3 O glucoside 4 vinylcatechol Petunidin 3 O acetylglucoside 4 vinylcatechol Petunidin 3 O coumaroylglucoside 4 vinylcatechol Petunidin 3 O glucoside 4 vinylphenol Petunidin 3 O acetylglucoside 4 vinylphenol Petunidin 3 O coumaroylglucoside 4 vinylphenol Petunidin 3 O glucoside 4 vinylguaiacol Petunidin 3 O glucoside 4 vinyl epi catechin Petunidin 3 O acetylglucoside 4 vinyl epi catechin Phloroglucinol carboxylic acid Piceatannol Piceids Pinotin A Oligomeric procyanidins Procyanidin B1 Procyanidin B2 Procyanidin B3 Procyanidin B4 B1 3 O gallate B2 3 O gallate B2 3 O gallate procyanidin C1 epicatechin 4b 8 epicatechin 4b 8 epicatechin Procyanidin C2 catechin 4a 8 catechin 4a 8 catechin procyanidin T2 trimer 48 Protocatechuic acid protocatechuic aldehyde Quercetin Quercetol glucoside Quercetol glucuronide Resveratrol Roburin A Roburin E Scopoletin Sinapic aldehyde Sinapinic acid Syringic acid Tyrosol Vanillic acid vanillin Vescalagin 4 Vinylphenol Vitisin A Vitisin B Vinylpyranomalvidin 3O glucoside procyanidin dimer VinylpyranoMv 3 coumaroylglucoside procyanidin dimer Vinylpyranomalvidin 3O glucoside catechin Vinylpyranomalvidin 3O coumaroylglucoside catechin Vinylpyranomalvidin 3O phenol Vinylpyranopetunidin 3O glucoside catechin Vinylpyranopeonidin 3O glucoside catechin Vinylpyranomalvidin 3O acetylglucoside catechinEffects editPolyphenol compounds may interact with volatiles and contribute to the aromas in wine 49 Although wine polyphenols are speculated to provide antioxidant or other benefits there is little evidence that wine polyphenols actually have any effect in humans 50 51 52 53 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 50 See also editAging of wine Clarification and stabilization of wine Grape seed extract Phenolic content in tea Wine chemistryReferences edit Kennedy JA Matthews MA Waterhouse AL 2002 Effect of Maturity and Vine Water Status on Grape Skin and Wine Flavonoids Am J Enol Vitic 53 4 268 74 doi 10 5344 ajev 2002 53 4 268 S2CID 10545757 Costa de Camargo Adriano Bismara Regitano d Arce Marisa Aparecida Camarao Telles Biasoto Aline Shahidi Fereidoon 2014 Low Molecular Weight Phenolics of Grape Juice and Winemaking Byproducts Antioxidant Activities and Inhibition of Oxidation of Human Low Density Lipoprotein Cholesterol and DNA Strand Breakage Journal of 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Martinez de Toda Fernando January 2021 Current viticultural techniques to mitigate the effects of global warming on grape and wine quality A comprehensive review Food Research International 139 109946 doi 10 1016 j foodres 2020 109946 hdl 10261 229725 ISSN 0963 9969 PMID 33509499 S2CID 230556619 a b c J Robinson ed The Oxford Companion to Wine Third Edition p 24 Oxford University Press 2006 ISBN 0 19 860990 6 JaNvaRy LaSzlo Hoffmann Thomas Pfeiffer Judith Hausmann Ludger ToPfer Reinhard Fischer Thilo C Schwab Wilfried 2009 A Double Mutation in the Anthocyanin 5 O Glucosyltransferase Gene Disrupts Enzymatic Activity in Vitis vinifera L Journal of Agricultural and Food Chemistry 57 9 3512 8 doi 10 1021 jf900146a PMID 19338353 He Fei Mu Lin Yan Guo Liang Liang Na Na Pan Qiu Hong Wang Jun Reeves Malcolm J Duan Chang Qing 2010 Biosynthesis of Anthocyanins and Their Regulation in Colored Grapes Molecules 15 12 9057 91 doi 10 3390 molecules15129057 PMC 6259108 PMID 21150825 He Jingren 2006 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malvidin 3 O glucoside The Journal of Physical Chemistry B 114 42 13487 13496 doi 10 1021 jp104749f PMID 20925351 Gakh Andrei A Anisimova Natalia Yu Kiselevsky Mikhail V Sadovnikov Sergey V Stankov Ivan N Yudin Mikhail V Rufanov Konstantin A Krasavin Mikhail Yu Sosnov Andrey V 2010 Dihydro resveratrol A potent dietary polyphenol Bioorganic amp Medicinal Chemistry Letters 20 20 6149 6151 doi 10 1016 j bmcl 2010 08 002 PMID 20813524 Dallas C Ricardo Da Silva J M Laureano Olga 1995 Degradation of oligomeric procyanidins and anthocyanins in a Tinta Roriz red wine during maturation Vitis 34 1 51 56 doi 10 5073 vitis 1995 34 51 56 Dufour C Bayonove C L 1999 Interactions between wine polyphenols and aroma substances An insight at the molecular level Journal of Agricultural and Food Chemistry 47 2 678 84 doi 10 1021 jf980314u PMID 10563952 a b Haseeb Sohaib Alexander Bryce Baranchuk Adrian 10 October 2017 Wine and cardiovascular health Circulation 136 15 1434 1448 doi 10 1161 circulationaha 117 030387 ISSN 0009 7322 PMID 28993373 S2CID 26520546 Flavonoids Linus Pauling Institute Micronutrient Information Center Oregon State University 2015 Retrieved 11 June 2017 EFSA Panel on Dietetic Products Nutrition and Allergies NDA 2010 Scientific Opinion on the substantiation of health claims related to various food s food constituent s and protection of cells from premature aging antioxidant activity antioxidant content and antioxidant properties and protection of DNA proteins and lipids from oxidative damage pursuant to Article 13 1 of Regulation EC No 1924 20061 EFSA Journal 8 2 1489 doi 10 2903 j efsa 2010 1489 Halliwell B 2007 Dietary polyphenols Good bad or indifferent for your health Cardiovasc Res 73 2 341 347 doi 10 1016 j cardiores 2006 10 004 PMID 17141749 External links editWine polyphenols vary with age and variety Polyphenols on www guideduvin com in French Polyphenol concentrations in red white and rose wines at www phenol explorer eu Retrieved from https en 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