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Ellagitannins
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 * Oenothein B from ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Urolithin A
Urolithin A is a metabolite compound resulting from the transformation of ellagitannins by the gut bacteria. It belongs to the class of organic compounds known as benzo-coumarins or dibenzo-α-pyrones. Its precursors – ellagic acids and ellagitannins – are ubiquitous in nature, including edible plants, such as pomegranates, strawberries, raspberries, 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 compounds known as benzo-coumarins or dibenzo-α-pyrones. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Biochemistry and metabolism Pome ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Urolithin A
Urolithin A is a metabolite compound resulting from the transformation of ellagitannins by the gut bacteria. It belongs to the class of organic compounds known as benzo-coumarins or dibenzo-α-pyrones. Its precursors – ellagic acids and ellagitannins – are ubiquitous in nature, including edible plants, such as pomegranates, strawberries, raspberries, 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 compounds known as benzo-coumarins or dibenzo-α-pyrones. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Biochemistry and metabolism Pome ... [...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 pu ... [...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] |
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] |
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] |
Sanguisorbic Acid
Sanguisorbic acid is a constituent of some ellagitannins. It is constituted by a hexahydroxydiphenic acid unit linked by an O-C bond to a gallic acid. The differences with its isomers, valoneic acid and nonahydroxytriphenic acid, are that the hydroxyl that links the hexahydroxydiphenoyl (HHDP) group to the galloyl group belongs to the galloyl group in valoneic acid, while in nonahydroxytriphenic acid, the hexahydroxydiphenic acid unit is linked by a C-C bond to gallic acid. It is found in 2,3-O-hexahydroxydiphenoyl-4,6-O-sanguisorboyl-(α/β)-glucose, an ellagitannin found in '' Rubus sanctus''. It is also found in lambertianin A, B, C and D, all ellagitannins found in '' Rubus lambertianus''. See also * Valoneic acid Valoneic acid is a hydrolysable tannin. It is a component of some hydrolysable tannins such as mallojaponin. The difference with its isomer sanguisorbic acid is that the hydroxyl that links the hexahydroxydiphenoyl (HHDP) group to the galloyl ... Re ... [...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 by ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Punicalin
Punicalin is an ellagitannin. It can be found in ''Punica granatum'' (pomegranate) or in the leaves of ''Terminalia catappa'', a plant used to treat dermatitis and hepatitis. It is also reported in ''Combretum glutinosum'', all three species being Myrtales, the two last being Combretaceae. It is a highly active carbonic anhydrase inhibitor. Chemistry The molecule contains a gallagic acid component linked to a glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using .... References Pomegranate ellagitannins Carbonic anhydrase inhibitors {{aromatic-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sanguisorbic Acid
Sanguisorbic acid is a constituent of some ellagitannins. It is constituted by a hexahydroxydiphenic acid unit linked by an O-C bond to a gallic acid. The differences with its isomers, valoneic acid and nonahydroxytriphenic acid, are that the hydroxyl that links the hexahydroxydiphenoyl (HHDP) group to the galloyl group belongs to the galloyl group in valoneic acid, while in nonahydroxytriphenic acid, the hexahydroxydiphenic acid unit is linked by a C-C bond to gallic acid. It is found in 2,3-O-hexahydroxydiphenoyl-4,6-O-sanguisorboyl-(α/β)-glucose, an ellagitannin found in '' Rubus sanctus''. It is also found in lambertianin A, B, C and D, all ellagitannins found in '' Rubus lambertianus''. See also * Valoneic acid Valoneic acid is a hydrolysable tannin. It is a component of some hydrolysable tannins such as mallojaponin. The difference with its isomer sanguisorbic acid is that the hydroxyl that links the hexahydroxydiphenoyl (HHDP) group to the galloyl ... Re ... [...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 Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of '' Anogeissus leioca ...) of the other one. References Ellagitannins Tannin dimers {{aromatic-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Punicalagin
Punicalagin is an ellagitannin, a type of phenolic compound. It is found as alpha and beta isomers in pomegranates (''Punica granatum''), ''Terminalia catappa'', ''Terminalia myriocarpa'', and in ''Combretum molle'', the velvet bushwillow, a plant species found in South Africa. These three genera are all Myrtales and the last two are both Combretaceae. Research Punicalagins are water-soluble and hydrolyze into smaller phenolic compounds, such as ellagic acid. There were no toxic effects in rats on a 6% diet of punicalagins for 37 days. In laboratory research, punicalagins had carbonic anhydrase inhibitor Carbonic anhydrase inhibitors are a class of pharmaceuticals that suppress the activity of carbonic anhydrase. Their clinical use has been established as anti-glaucoma agents, diuretics, antiepileptics, in the management of mountain sickness, ... activity. References {{pomegranate ellagitannin Pomegranate ellagitannins Carbonic anhydrase inhibitors ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
