Casuarictin
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Casuarictin
Casuarictin is an ellagitannin, a type of hydrolysable tannin. It can be found in ''Casuarina'' and ''Stachyurus'' species.Tannins of Casuarina and Stachyurus species. I: Structures of pendunculagin, casuarictin, strictinin, casuarinin, casuariin, and stachyurin. Okuda T., Yoshida T., Ashida M. and Yazaki K., Journal of the Chemical Society, 1983, number 8, pages 1765-1772, It is formed from two hexahydroxydiphenic acid units and one gallic acid unit linked to a glucose molecule. The molecule is formed from tellimagrandin II, itself formed from pentagalloyl glucose via oxidation. Casuarictin is transformed into pedunculagin via loss of a gallate group, and further into 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 glycosidi ... via glucose pyranose ring opening. Oligomers Sa ...
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Casuarina
''Casuarina'' is a genus of 17 tree species in the family Casuarinaceae, native to Australia, the Indian subcontinent, southeast Asia, islands of the western Pacific Ocean, and eastern Africa. It was once treated as the sole genus in the family, but has since been split into four genera (see: Casuarinaceae).Flora of Australia''Casuarina''/ref> They are evergreen shrubs and trees growing to tall. The slender, green to grey-green twigs bearing minute scale-leaves in whorls of 5–20. The apetalous flowers are produced in small catkin-like inflorescences. Most species are dioecious, but a few are monoecious. The fruit is a woody, oval structure superficially resembling a conifer cone, made up of numerous carpels, each containing a single seed with a small wing. The generic name is derived from the Malay word for the cassowary, ''kasuari'', alluding to the similarities between the bird's feathers and the plant's foliage, though the tree is called ''ru'' in Modern Malay. ...
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Stachyurus
''Stachyurus'' is the only genus in the flowering plant family Stachyuraceae, native to the Himalayas and eastern Asia. They are deciduous shrubs or small trees with pendent racemes of 4-petalled flowers which appear on the bare branches before the leaves. The plants have leaves with serrate margins. Pendunculagin, casuarictin, strictinin, casuarinin and casuariin are ellagitannins found in species in this genus. ''Stachyurus praecox'' from Japan, and the slightly later-flowering ''S. chinensis'' from China, are both cultivated as ornamental plants, valued for their exceptionally early flowering periods. Species list * ''Stachyurus chinensis'' * ''Stachyurus coaetaneus'' * ''Stachyurus cordatulus'' * ''Stachyurus himalaicus'' * ''Stachyurus obovatus'' * ''Stachyurus praecox'' * ''Stachyurus retusus'' * ''Stachyurus salicifolius'' * ''Stachyurus yunnanensis ''Stachyurus'' is the only genus in the flowering plant family Stachyuraceae, native to the Himalayas and ...
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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 galloy ...
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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 7 ...
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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 ...
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Pedunculagin
Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group. Natural occurrence Pedunculagin is found in plants in orders in the clade Rosidae. It can be found the pericarp of pomegranates (''Punica granatum''), in the family Lythraceae, in the order Myrtales. It is also found in plants in the order Fagales such as walnuts (''Juglans regia'') in the family Juglandaceae, in '' Alnus sieboldiana'' and in the Manchurian alder ('' Alnus hirsuta var. microphylla''), both species in the family Betulaceae and it is one of the main oak wood ellagitannins along with castalagin, vescalagin, grandinin and roburins A-E (genus ''Quercus'', in the family Fagaceae). It is also found in the Indian gooseberry (''Phyllanthus emblica''), a plant in the family Phyllanthaceae, in the order Malpighiales. Galloyl pedunculagin can be found in '' Platycarya strobilacea''. Research Pedunculagin is a highly active carbonic anhydrase inhibitor ''in vitro''. Chem ...
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Sanguiin H-6
Sanguiin H-6 is an ellagitannin. Natural occurrence Sanguiin H-6 can be found in Rosaceae such as the great burnet (''Sanguisorba officinalis''), in strawberries (''Fragaria × ananassa'') and in ''Rubus'' species such as red raspberries (''Rubus idaeus'') or cloudberries ('' Rubus chamaemorus''). Chemistry Sanguiin H-6 is dimer of casuarictin linked by a bond between the gallic acid residue and one of the 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 ... units. It has sanguisorbic acid ester groups as linking units between glucopyranose moieties. Sanguiin H-6 contributes to the antioxidant capacity of raspberries. It is an isomer of agrimoniin. References External links Sanguiin H-6 on www.phenol-explorer.eu {{Ellagitannin Ellagitannins ...
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Lambertianin C
Lambertianin C is an ellagitannin. Natural occurrence Lambertianin C can be found in ''Rubus'' species such as '' Rubus lambertianus'', in cloudberries (''Rubus chamaemorus'') and in red raspberries (''Rubus idaeus''). Chemistry Lambertianin C is trimer of casuarictin linked by 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 hydr ... ester groups between glucopyranose moieties. It contributes to the antioxidant capacity of raspberries. References External links Lambertianin C at www.phenol-explorer.eu {{Ellagitannin Ellagitannins Natural phenol trimers Rubus ...
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Lambertianin D
Lambertianin D is an ellagitannin found in ''Rubus lambertianus''. It is tetramer of casuarictin linked by 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 hydr ... ester groups between glucopyranose moieties. References Ellagitannins Natural phenol tetramers {{aromatic-stub ...
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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 ...
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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. It is a white solid, although samples are typically brown owing to partial oxidation. Salts and esters of gallic acid are termed "gallates". Isolation and derivatives Gallic acid is easily freed from gallotannins by acidic or alkaline hydrolysis. When heated with concentrated sulfuric acid, gallic acid converts to rufigallol. Hydrolyzable tannins break down on hydrolysis to give gallic acid and glucose or ellagic acid and glucose, known as gallotannins and ellagitannins, respectively. Biosynthesis Gallic acid is formed from 3-dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3,5-didehydroshikimate. This latter compound aromatizes. Reactions Oxidation and oxidative coupling Alkaline solutions of ...
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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 energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world. In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as starch and amylopectin, and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar. The naturally occurring form of glucose is -glucose, while -glucose is produced synthetically in comparatively small amounts and is less biologically active. Glucose is a monosaccharide containing six carbon atoms and an aldehyde group, and is therefore an aldohexose. The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) fo ...
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