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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 ''Terminalia leiocarpa'' 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 (wine), oak barrels. During Aging of wine, 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 : Oak, ''Quercus'' (oak) and ''Chestnut, 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 Wine, wines, ...
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Ellagitannin
image:Castalagin.svg, 130px, Castalagin is a representative ellagitannin, characterized by coupled gallic acid substituents 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 Hexahydroxydiphenic acid, hexahydroxydiphenoyl units, as well as galloyl units and/or Sanguisorbic acid, 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 ...
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Terminalia Avicennoides
''Terminalia avicennioides'' () is a tree species in the genus '' Terminalia'' found in West Africa. Castalagin and flavogallonic acid dilactoneThe use of microfluorometric method for activity-guided isolation of antiplasmodial compound from plant extracts. M. N. Shuaibu, P. A. Wuyep, T. Yanagi, K. Hirayama, T. Tanaka and I. Kouno, Parasitol Res (2008) 102, pp. 1119–1127, are hydrolysable tannins found in ''T. avicennoides''. See also * Bògòlanfini Bògòlanfini or bogolan (; "mud cloth"; sometimes called mud-dyed cloth or mud-painted cloth in English language, English) is a handmade Malian cotton fabric traditionally dyed with fermented mud. It has an important place in traditional Malian ..., a handmade Malian cotton fabric dyed yellow in wool solution, made from the leaves of ''T. avicennoides'' References External links avicennioides Plants described in 1832 {{Myrtales-stub ...
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Terminalia Leiocarpa
''Terminalia leiocarpa'' (African birch; ) is a species of tree in the genus ''Terminalia''. It is a deciduous tree native of tropical Africa from Senegal and Guinea in the west to Eritrea in the east and as far south as the Democratic Republic of the Congo. ''Terminalia leiocarpa'' germinates in the new soils produced by seasonal wetlands. It is a forest fringe plant, growing at the edges of the rainforest, although not deep in the rainforest. It also grows in savanna, and along riverbanks, where it forms gallery forests. The tree flowers in the rainy season, from June to October. The fruit are winged samaras, and are dispersed by ants. Ethnobotany It is one of the plants used to make ''bògòlanfini'', a traditional Malian mudcloth. Small branches with leaves are crushed to make one of the yellow dyes. The inner bark of the tree is used as a human and livestock anthelmintic for treating worms, and for treatment of a few protozoan diseases in animals, '' nagana'' (an anim ...
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Anthocyanins (wine)
Phenolic compounds— natural phenol and polyphenols—occur naturally in wine. These 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. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids. Origin of the phenolic compounds The natural phenols are not evenly distributed within the grape. 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 th ...
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Casuarinin
Casuarinin is an ellagitannin. It is found in the pericarp of pomegranates (''Punica granatum''). It is also found in ''Casuarina'' and '' Stachyurus'' species and in '' Alnus sieboldiana''. It is an isomer of casuarictin. It is a highly active carbonic anhydrase inhibitor. Biosynthesis In some plants including oak and chestnut, the ellagitannins are formed from 1,2,3,4,6-pentagalloyl-glucose and further elaborated via oxidative dehydrogenation (tellimagrandin II and casuarictin formations). After conversion of casuarictin to pedunculagin, the pyranose ring of the glucose opens and the family of compounds including casuariin, casuarinin, castalagin Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of ''Terminalia leiocarpa'' and ''Terminalia avicennoides''. Castalagin is the diastereomer of vescalagin in C-1 of the glycosidic c ..., and castalin, vescalagin and vescalin forms.
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Catechin
Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids. The name of the catechin chemical family derives from ''catechu'', which is the tannic juice or boiled extract of ''Mimosa catechu'' (''Acacia catechu'' L.f.). Chemistry Catechin possesses two benzene rings (called the A and B rings) and a dihydropyran heterocycle (the C ring) with a hydroxyl group on carbon 3. The A ring is similar to a resorcinol moiety while the B ring is similar to a catechol moiety. There are two chirality (chemistry), chiral centers on the molecule on carbons 2 and 3. Therefore, it has four diastereoisomers. Two of the isomers are in trans configuration, ''trans'' configuration and are called ''catechin'' and the other two are in cis configuration, ''cis'' configuration and are called ''epicatechin''. The most common catechin isomer is (+)-catechin. The other stereoisomer is (−)-catechin or ''en ...
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Acutissimin A
Acutissimin A is a flavono-ellagitannin, a type of tannin formed from the linking of a flavonoid with an ellagitannin. In 2003, scientists at Institut Européen de Chimie et Biologie in Pessac, France found that when the oak tannin vescalagin interacts with a flavanoid in wine acutissimin A is created. In separate studies this phenolic compound has been shown to be 250 times more effective than the pharmaceutical drug Etoposide in stopping the growth of cancerous tumor A neoplasm () is a type of abnormal and excessive growth of tissue. The process that occurs to form or produce a neoplasm is called neoplasia. The growth of a neoplasm is uncoordinated with that of the normal surrounding tissue, and persists ...s. See also * Phenolic compounds in wine References Flavono-ellagitannins Antineoplastic drugs Pyrogallols {{aromatic-stub ...
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Flavonoid
Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids have the general structure of a 15-carbon skeleton, which consists of two phenyl rings (A and B) and a Heterocyclic compound, heterocyclic ring (C, the ring containing the embedded oxygen). This carbon structure can be abbreviated C6-C3-C6. According to the IUPAC nomenclature, they can be classified into: *flavonoids or bioflavonoids *isoflavonoids, derived from 3-phenylchromone, chromen-4-one (3-phenyl-1,4-benzopyran, benzopyrone) structure *neoflavonoids, derived from 4-phenylcoumarin (4-phenyl-1,2-benzopyran, benzopyrone) structure The three flavonoid classes above are all ketone-containing compounds and as such, anthoxanthins (flavones and flavonols). This class was the first to be termed bioflavonoids. The terms flavonoid and bioflavo ...
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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 Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of ''Terminalia leiocarpa'' and ''Terminalia avicennoides''. Castalagin is the diastereomer of vescalagin in C-1 of the glycosidic c ... subunits probably linked through an ether bond between the diphenoyl group ( hexahydroxydiphenic acid or HHDP) of one subunit and the triphenoyl moiety ( nonahydroxytriphenic acid) of the other one. References Ellagitannins Tannin dimers {{aromatic-stub ...
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Dimer (chemistry)
In chemistry, dimerization is the process of joining two identical or similar Molecular entity, molecular entities by Chemical bond, bonds. The resulting bonds can be either strong or weak. Many symmetrical chemical species are described as dimers, even when the monomer is unknown or highly unstable. The term ''homodimer'' is used when the two subunits are identical (e.g. A–A) and ''heterodimer'' when they are not (e.g. A–B). The reverse of dimerization is often called Dissociation (chemistry), dissociation. When two oppositely-charged ions associate into dimers, they are referred to as ''Bjerrum pairs'', after Danish chemist Niels Bjerrum. Noncovalent dimers Anhydrous carboxylic acids form dimers by hydrogen bonding of the acidic hydrogen and the carbonyl oxygen. For example, acetic acid forms a dimer in the gas phase, where the monomer units are held together by hydrogen bonds. Many OH-containing molecules form dimers, e.g. the water dimer. Dimers that form based on w ...
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Hexahydroxydiphenoyl
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. Occurrence left, 142px, Ellagic acid. Luteic acid and ellagic acid are the mono- and di lactone of hexahydroxydiphenic acid, respectively. Hexahydroxydiphenic acid is a component of some ellagitannin image:Castalagin.svg, 130px, Castalagin is a representative ellagitannin, characterized by coupled gallic acid substituents The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative link ...s, such as casuarictin. See also * Diphenic acid References Ellagitannins Pyrogallols Biphenyls Trihydroxybenzoic acids {{phenol-stub ...
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