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Tannin
From Wikipedia, the free encyclopedia
Tannins are astringent, bitter plant polyphenols that either bind and precipitate or shrink proteins. The term tannin refers to the use of tannins in tanning animal hides into leather; however, the term is widely applied to any large polyphenolic compound containing sufficient hydroxyls and other suitable groups (such as carboxyls) to form strong complexes with proteins and other macromolecules. Tannins have molecular weights ranging from 500 to over 3,000.[1] Tannins are incompatible with alkalies, gelatin, heavy metals, iron, lime water, metallic salts, strong oxidizing agents and zinc sulfate.
| Base Unit: |  |
 |
|---|---|---|
| Class/Polymer: | Hydrolyzable Tannins | Condensed Tannins |
Tannins are usually divided into hydrolyzable tannins and condensed tannins (proanthocyanidins).
Contents |
At the center of a hydrolyzable tannin molecule, there is a polyol carbohydrate (usually D-glucose). The hydroxyl groups of the carbohydrate are partially or totally esterified with phenolic groups such as gallic acid (in gallotannins) or ellagic acid (in ellagitannins). Hydrolyzable tannins are hydrolyzed by weak acids or weak bases to produce carbohydrate and phenolic acids.
Examples of gallotannins are the gallic acid esters of glucose in tannic acid (C76H52O46), found in the leaves and bark of many plant species.
Condensed tannins, also known as proanthocyanidins, are polymers of 2 to 50 (or more) flavonoid units that are joined by carbon-carbon bonds, which are not susceptible to being cleaved by hydrolysis. While hydrolyzable tannins and most condensed tannins are water soluble, some very large condensed tannins are insoluble.
The tea plant (Camellia sinensis) is an example of a plant said to have a naturally high tannin content. When any type of tea leaf is steeped in hot water it brews a "tart" (astringent) flavour that is characteristic of tannins. This is due to the catechins and other flavonoids. Tea "tannins" are chemically distinct from other types of plant tannins such as tannic acid[2] and tea extracts have been reported to contain no tannic acid[3].
Tannins (mainly condensed tannins) are also found in wine, particularly red wine. Tannins in wine can come from many sources and the tactile properties differ depending on the source. Tannins in grape skins and seeds (the latter being especially harsh) tend to be more noticeable in red wines, which are fermented while in contact with the skins and seeds. Tannins extracted from grapes are condensed tannins, which are polymers of procyanidin monomers. Hydrolysable tannins are extracted from the oak wood the wine is aged in. Hydrolysable tannins are more easily oxidised than condensed tannins.
Modern winemakers take great care to minimize undesirable tannins from seeds by crushing grapes gently to extract their juice. Pressing the grapes results in press wine which is more tannic and might be kept separately. Wines can also take on tannins if matured in oak or wood casks with a high tannin content. Tannins play an important role in preventing oxidation in aging wine and appear to polymerize and make up a major portion of the sediment in wine.
Recently, a study in wine production and consumption has shown that tannins in the form of procyanidins, 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 procyanidins, and that these regions also produce populations with longer life spans.[4]
Effects of tannins on the drinkability of wine.
Tannins in wine have been described as having the effect of making wine difficult to drink compared to a wine with a lower level of tannins. The tannins can be described as leaving a dry and puckerd feeling with a "furriness" in the mouth that can be compared to a stewed tea, which is also very tannic.
Pomegranates contain a diverse array of tannins, particularly hydrolysable tannins. The most abundant of pomegranate tannins are called punicalagins. Punicalagins have a molecular weight of 1038 and are the largest molecule found intact in rat plasma after oral ingestion[5] and were found to show no toxic effects in rats who were given a 6% diet of punicalagins for 37 days.[6]. Punicalagins are also found to be the major component responsible for pomegranate juice's antioxidant and health benefits [7]
Several dietary supplements and nutritional ingredients are available that contain extracts of whole pomegranate and/or are standardized to punicalagins, the marker compound of pomegranate. Extracts of pomegranate are also Generally Recognized as Safe (GRAS) by the United States Food and Drug Administration. It has been recommended to look for pomegranate ingredients that mimic the polyphenol ratio of the fruit, as potent synergistic effects have been observed in 'natural spectrum' extracts, especially pomegranate concentrate normalized to punicalagins.[8]
Some persimmons are highly astringent and therefore inedible when they are not extremely ripe (specifically the Korean, American, and Hachiya or Japanese). This is due to the high level of tannins, and if eaten by humans (and many other animals), the mouth will become completely dry, yet the saliva glands will continue to secrete saliva which cannot affect the tannin-laced food. Areca Catechu also contains tannin which contributes to its antibacterial properties
Most berries, such as cranberries[9] strawberries and blueberries,[10] contain both hydrolyzable and condensed tannins.
If ingested in excessive quantities, tannins inhibit the absorption of minerals such as iron into the body. This is because tannins are metal ion chelators, and tannin-chelated metal ions are not bioavailable. This may not be bad for someone with an infection, as iron is mopped up by the immune system to keep microorganisms from properly multiplying. Tannins have been shown to precipitate proteins,[1] which inhibits in some ruminant animals the absorption of nutrients from high-tannin grains such as sorghum.
In sensitive individuals, large intakes of tannins may cause bowel irritation, kidney irritation, liver damage, irritation of the stomach and gastrointestinal pain. With the exception of tea, long-term and/or excessive use of herbs containing high concentrations of tannins is not recommended. A correlation has been made between esophogeal or nasal cancer in humans and regular consumption of certain herbs with high tannin concentrations.[11]
Tannins are an important ingredient in the process of tanning leather. Oak bark has traditionally been the primary source of tannery tannin, though inorganic tanning agents are also in use today.
Tannins may be employed medicinally in antidiarrheal, hemostatic, and antihemorrhoidal compounds.
Tannins produce different colors with ferric chloride (either blue, blue black, or green to greenish black) according to the type of tannin. Iron gall ink is produced by treating a solution of tannins with iron(II) sulfate.
Tannin is a component in a type of industrial particleboard adhesive developed jointly by the Tanzania Industrial Research and Development Organization and Forintek Labs Canada.
Tannins, including gallo and ellagic acid (epigallitannins), are inhibitors of HIV replication.
- 1,3,4-Tri-O-galloylquinic acid
- 3,5-di-O-galloyl-shikimic acid
- 3,4,5-tri-O-galloylshikimic acid
- punicalin
- punicalagin
inhibited HIV replication in infected H9 lymphocytes with little cytotoxicity. Two compounds, punicalin and punicacortein C, inhibited purified HIV reverse transcriptase.[12]
- ^ a b Bate-Smith and Swain, 1962, Flavonoid compounds. In : Comparative biochemistry. Florkin M. Mason H.S. Eds. Vol III. 75-809. Academic Press, New-York.
- ^ Hamilton-Miller JM. Antimicrobial properties of tea (Camellia sinensis L.). Antimicrob Agents Chemother. 39(11): 2375-2377 (1995) PMID 8585711
- ^ Wheeler, S.R. Tea and Tannins Science 204: 6-8 (1979) [1] as cited in Yam TS, Hamilton-Miller JM, Shah S. The effect of a component of tea (Camellia sinensis) on methicillin resistance, PBP2' synthesis, and beta-lactamase production in Staphylococcus aureus. J Antimicrob Chemother. 42(2):211-216. (1998) PMID 9738838
- ^ R. Corder, W. Mullen, N. Q. Khan, S. C. Marks, E. G. Wood, M. J. Carrier and A. Crozier Nature 444, 566 (30 November 2006)
- ^ Biomed. Pharmacother. 2002, 56, 276-82
- ^ J. Agric. Food Chem. 2003, 51, 3493-3501
- ^ J Agric Food Chem 2000 48 (10) 4581-89
- ^ J Nutr Biochemistry 2005 (16) 360-367
- ^ Vattem, D. A. Ghaedian, R. Shetty, K. Enhancing health benefits of berries through phenolic antioxidant enrichment: focus on cranberry Asia Pacific Journal of Clinical Nutrition (2005) 14(2) 120-130 [2]
- ^ R. Puupponen-Pimiä, L. Nohynek, C. Meier, M. Kähkönen, M. Heinonen, A. Hopia & K.-M. Oksman-Caldentey, Antimicrobial properties of phenolic compounds from berries, Journal of Applied Microbiology 90(4) pp494 (2001) [3]
- ^ Lewis, W.H.; and M.P.F. Elvin-Lewis (1977). "Plants Affecting Man's Health". Medical Botany (John Wiley & Sons).
- ^ [4]
- L. Calvi, G.C.J. Mwalongo, B.A. Mwingira, B. Riedl and J.A. Shields; Characterization of Wattle-Tannin-Based Adhesives for Tanzania (A paper published in Holzforchung Vol 49 No 2, 1995).