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Ellagitannin
The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl groups are linked through C-C bonds, whereas the galloyl groups in gallotannins are linked by depside bonds. Ellagitannins contain various numbers of hexahydroxydiphenoyl units, as well as galloyl units and/or sanguisorboyl units bounded to sugar moiety. In order to determine the quantity of every individual unit, the hydrolysis of the extracts with trifluoroacetic acid in methanol/water system is performed. Hexahydroxydiphenic acid, created after hydrolysis, spontaneously lactonized to ellagic acid, and sanguisorbic acid to sanguisorbic acid dilactone, while gallic acid remains intact. Ellagitannins generally form macrocycles, whereas gallotannins do not. Examples * Castalagin * Castalin * Casuarictin * Grandinin * Oeno ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Castalagin
Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of ''Anogeissus leiocarpus'' and '' Terminalia avicennoides''. Castalagin is the diastereomer of vescalagin in C-1 of the glycosidic chain. Castalagin/ vescalagin are the most abundant ellagitannins in white wine stored in oak barrels. During aging of wines, these two compounds were progressively extracted from the wood and were transformed into new derivatives by chemical reactions. Therefore, castalagin/ vescalagin and their derivatives contribute to the color and the taste of wines and spirits stored in oak barrels. Sources Castalagin was first isolated in Fagaceae family woody species : ''Quercus'' (oak) and ''Castanea'' (chestnut) by Walter Mayer and co-workers (1967). In some chestnut species, such as ''Castanea sativa'', heartwood could contain 63 mg of castalagin/ vescalagin per gram of dry wood. In some wines, these two isomers represent about 40 to 70 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Vescalagin
Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of ''Anogeissus leiocarpus'' and '' Terminalia avicennoides''. Castalagin is the diastereomer of vescalagin in C-1 of the glycosidic chain. Castalagin/ vescalagin are the most abundant ellagitannins in white wine stored in oak barrels. During aging of wines, these two compounds were progressively extracted from the wood and were transformed into new derivatives by chemical reactions. Therefore, castalagin/ vescalagin and their derivatives contribute to the color and the taste of wines and spirits stored in oak barrels. Sources Castalagin was first isolated in Fagaceae family woody species : ''Quercus'' (oak) and '' Castanea'' (chestnut) by Walter Mayer and co-workers (1967). In some chestnut species, such as ''Castanea sativa'', heartwood could contain 63 mg of castalagin/ vescalagin per gram of dry wood. In some wines, these two isomers represent about 40 to 70% ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Urolithin A
Urolithin A is a metabolite compound resulting from the transformation of Ellagitannin, ellagitannins by the gut bacteria. It belongs to the class of organic compounds known as benzo-coumarins or dibenzo-α-pyrones. Its precursors – Ellagic acid, ellagic acids and ellagitannins – are ubiquitous in nature, including edible plants, such as Pomegranate, pomegranates, Strawberry, strawberries, Raspberry, raspberries, Walnut, walnuts, and others. Since the 2000s, urolithin A has been the subject of preliminary studies regarding its possible biological effects. Urolithin A is not known to be found in any food source. Its bioavailability mostly depends on individual microbiota composition, as only some bacteria are able to convert ellagitannins into urolithins. Chemistry Urolithin A belongs to the class of Organic compound, organic compounds known as benzo-coumarins or dibenzo-α-pyrones. These are polycyclic compound, polycyclic aromatic compounds containing a 1-benzopyra ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pomegranate Ellagitannin
The pomegranate ellagitannins, which include punicalagin isomers, are ellagitannins found in the sarcotestas, rind (peel), bark or heartwood of pomegranates (''Punica granatum''). Chemistry As the chemistry of punicalagins became known it was found to be not unique to pomegranate. Punicalagins are present in numerous species of the genus '' Terminalia'', species '' chebula'' Retz. (“Fructus Chebulae”), ''myriocarpa'', '' catappa'' and citrina (tropical flowering trees historically used in African traditional medicine for antibiotic and antifungal purposes). They have also been isolated from '' Cistus salvifolius'' (a Mediterranean shrub) and ''Combretum molle'' (an African shrub). Pomegranate fruits natural phenols can be extracted with ethyl acetate and fractionation can afford the ellagitannin punicalagins. Dietary supplementation A few dietary supplements and nutritional ingredients are available that contain extracts of whole pomegranate and/or are standardized to p ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Urolithin
Urolithins are microflora metabolites of dietary ellagic acid derivatives, such as ellagitannins. They are produced in the gut, and found in the urine in the form of urolithin B glucuronide after absorption of ellagitannins-containing foods, such as pomegranate. During intestinal metabolism by bacteria, ellagitannins and punicalagins are converted to urolithins, which have unknown biological activity ''in vivo''. Ellagitannins exhibit low bioavailability and are transformed in the gut to ellagic acid and its microbiota metabolites. Urolithins are found in plasma mostly as glucuronides at low concentrations. Urolithins production is dependent on the gut microbiome enterotype. Individuals producing urolithins show a much higher abundance of the ''Clostridium leptum'' group of Firmicutes phylum than ''Bacteroides'' or ''Prevotella''. Known molecules * Urolithin A (3,8-Dihydroxyurolithin) * Urolithin A glucuronide * Urolithin B (3-Hydroxyurolithin) * urolithin B glucuronide * U ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hexahydroxydiphenic Acid
Hexahydroxydiphenic acid is an organic compound with the formula HO)3C6HCO2Hsub>2. It is the oxidatively coupled derivative of gallic acid It is a white solid, although samples are typically brown owing to oxidation. left, 142px, Ellagic acid. Hexahydroxydiphenic acid is a component of some ellagitannins, such as casuarictin. Luteic acid is the monolactone and ellagic acid is the dilactone Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the co ... of hexahydroxydiphenic acid. See also * Diphenic acid References Ellagitannins Pyrogallols Biphenyls Hydroxybenzoic acids {{phenol-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tellimagrandin II
Tellimagrandin II is the first of the ellagitannins formed from 1,2,3,4,6-pentagalloyl-glucose. It can be found in '' Geum japonicum'' and ''Syzygium aromaticum'' (clove).Purification and Characterization of Eugeniin as an Anti-herpesvirus Compound from Geum japonicum and Syzygium aromaticum. Masahiko Kurokawa, Toyoharu Hozumi, Purusotam Basnet, Michio Nakano, Shigetoshi Kadota, Tuneo Namba, Takashi Kawana and Kimiyasu Shiraki, JPET, February 1, 1998 vol. 284 no. 2, pages 728-735article Tellimagrandin II is an isomer of punicafolin or nupharin A, but the hexahydroxydiphenoyl group is not attached to the same hydroxyl groups in the glucose molecule. The compound shows anti-herpesvirus properties. Metabolism It is formed by oxidation of pentagalloyl glucose in '' Tellima grandiflora'' by the enzyme pentagalloylglucose: O(2) oxidoreductase, a laccase-type phenol oxidase. It is further oxidized to casuarictin, a molecule formed via oxidative dehydrogenation of 2 other galloyl gr ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ellagic Acid
Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid. Name The name comes from the French term ''acide ellagique'', from the word ''galle'' spelled backwards because it can be obtained from ''noix de galle'' (galls), and to distinguish it from ''acide gallique'' (gallic acid). The molecule structure resembles to that of two gallic acid molecules being assembled "head to tail" and bound together by a C–C bond (as in biphenyl, or in diphenic acid) and two lactone links (cyclic carboxylic esters). Metabolism Biosynthesis Plants produce ellagic acid from hydrolysis of tannins such as ellagitannin and geraniin. Biodegradation Urolithins are gut flora human metabolites of dietary ellagic acid derivatives. Ellagic acid has low bioavailability, with 90% remaining unabsorbed from the intestines until metabolized by microflora to the more bioavailable urolintins. History Ellagic acid was first discovered b ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Grandinin
Grandinin is an ellagitannin. It can be found in '' Melaleuca quinquenervia'' leavesPolyphenols of Melaleuca quinquenervia leaves - pharmacological studies of grandinin. Moharram F. A., Marzouk M. S., El-Toumy S. A. A., Ahmed A. A. E. and Aboutabl E. A., Phytotherapy Research, Volume 17 Issue 7, Pages 767-773, and in oaks species like the North American white oak (''Quercus alba'') and European red oak (''Quercus robur''). It shows antioxydant activity. It is an astringent compound. It is also found in wine, red or white, aged in oak barrels. It is a castalagin glycoside, by binding of the pentose lyxose. It contains a nonahydroxytriphenic acid moiety. It suppresses the phosphorylation of the epidermal growth factor receptor in human colon carcinoma Colorectal cancer (CRC), also known as bowel cancer, colon cancer, or rectal cancer, is the development of cancer from the colon or rectum (parts of the large intestine). Signs and symptoms may include blood in the sto ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Terflavin B
Terflavin B is an ellagitannin, a type of hydrolysable tannin. It can be found in ''Myrobalanus chebula'' (''Terminalia chebula''), the black chebulic, and in ''Terminalia catappa'', the Indian almond. It is formed from a nonahydroxytriphenic acid dilactone and a gallic acid Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6 H2( OH)3CO2H. It is classified as a phenolic acid. It is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants ... linked to a glucose molecules. References Ellagitannins {{aromatic-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Roburin A
Roburin A is a tannin found in oak wood (''Quercus robur'' and ''Quercus petraea'' or ''Quercus alba'') or oak cork (''Quercus suber''). It is a dimeric compound, composed of two vescalagin subunits probably linked through an ether bond between the diphenoyl group (hexahydroxydiphenic acid or HHDP) of one subunit and the triphenoyl moiety (nonahydroxytriphenic acid Nonahydroxytriphenic acid is a moiety found in some ellagitannins such as roburin A, B,C and D, castalagin or grandinin Grandinin is an ellagitannin. It can be found in ''Melaleuca quinquenervia'' leavesPolyphenols of Melaleuca quinquenervia le ...) of the other one. References Ellagitannins Tannin dimers {{aromatic-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
