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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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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 * Oenothein B from ...
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Rosaceae
Rosaceae (), the rose family, is a medium-sized family of flowering plants that includes 4,828 known species in 91 genera. The name is derived from the type genus ''Rosa''. Among the most species-rich genera are ''Alchemilla'' (270), ''Sorbus'' (260), '' Crataegus'' (260), ''Cotoneaster'' (260), ''Rubus'' (250), and ''Prunus'' (200), which contains the plums, cherries, peaches, apricots, and almonds. However, all of these numbers should be seen as estimates—much taxonomic work remains. The family Rosaceae includes herbs, shrubs, and trees. Most species are deciduous, but some are evergreen. They have a worldwide range but are most diverse in the Northern Hemisphere. Many economically important products come from the Rosaceae, including various edible fruits, such as apples, pears, quinces, apricots, plums, cherries, peaches, raspberries, blackberries, loquats, strawberries, rose hips, hawthorns, and almonds. The family also includes popular ornamental trees and shrubs ...
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Sanguisorba Officinalis
''Sanguisorba officinalis'', commonly known as great burnet, is a plant in the family Rosaceae, subfamily Rosoideae. It is native throughout the cooler regions of the Northern Hemisphere in Europe, northern Asia, and northern North America. It is a herbaceous perennial plant growing to 1 m tall, which occurs in grasslands, growing well on grassy banks. It flowers June or July. ''Sanguisorba officinalis'' is an important food plant for the European large blue butterflies '' Phengaris nausithous'' and '' P. teleius''.World Conservation Monitoring Centre 1996. . Downloaded on 6 October 2010 Commercial uses Use is made of its extensive root system for erosion control, as well as a bioremediator, used to reclaim derelict sites such as landfills. Ornamental ''Sanguisorba officinalis'' is one of several ''Sanguisorba'' species cultivated as ornamental plants. The cultivar 'Tanna' is widely available, and has won the Royal Horticultural Society's Award of Garden Merit. The synonym ' ...
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Fragaria × Ananassa
The garden strawberry (or simply strawberry; ''Fragaria × ananassa'') is a widely grown hybrid species of the genus '' Fragaria'', collectively known as the strawberries, which are cultivated worldwide for their fruit. The fruit is widely appreciated for its characteristic aroma, bright red color, juicy texture, and sweetness. It is consumed in large quantities, either fresh or in such prepared foods as jam, juice, pies, ice cream, milkshakes, and chocolates. Artificial strawberry flavorings and aromas are also widely used in products such as candy, soap, lip gloss, perfume, and many others. The garden strawberry was first bred in Brittany, France, in the 1750s via a cross of ''Fragaria virginiana'' from eastern North America and ''Fragaria chiloensis'', which was brought from Chile by Amédée-François Frézier in 1714. Cultivars of ''Fragaria'' × ''ananassa'' have replaced, in commercial production, the woodland strawberry ('' Fragaria vesca''), which was the first stra ...
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Rubus
''Rubus'' is a large and diverse genus of flowering plants in the rose family, Rosaceae, subfamily Rosoideae, with over 1,350 species. Raspberries, blackberries, and dewberries are common, widely distributed members of the genus. Most of these plants have woody stems with prickles like roses; spines, bristles, and gland-tipped hairs are also common in the genus. The ''Rubus'' fruit, sometimes called a bramble fruit, is an aggregate of drupelets. The term "cane fruit" or "cane berry" applies to any ''Rubus'' species or hybrid which is commonly grown with supports such as wires or canes, including raspberries, blackberries, and hybrids such as loganberry, boysenberry, marionberry and tayberry. The stems of such plants are also referred to as canes. Description Most species in the genus are hermaphrodites, ''Rubus chamaemorus'' being an exception. ''Rubus'' species have a basic chromosome number of seven. Polyploidy from the diploid (14 chromosomes) to the tetradecaploid (98 ...
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Rubus Idaeus
''Rubus idaeus'' (raspberry, also called red raspberry or occasionally European red raspberry to distinguish it from other raspberry species) is a red-fruited species of ''Rubus'' native to Europe and northern Asia and commonly cultivated in other temperate regions. Taxonomy A closely related plant in North America, sometimes regarded as the variety ''Rubus idaeus'' var. ''strigosus'', is more commonly treated as a distinct species, ''Rubus strigosus'' (American red raspberry), as is done here. Red-fruited cultivated raspberries, even in North America, are generally ''Rubus idaeus'' or horticultural derivatives of hybrids of ''R. idaeus'' and ''R. strigosus;'' these plants are all addressed in the present article. Description Plants of ''Rubus idaeus'' are generally perennials, which bear biennial stems ("canes") from a perennial root system. In its first year, a new, unbranched stem (" primocane") grows vigorously to its full height of 1.5–2.5 m (5.0–8.3 feet), bearing large ...
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Rubus Chamaemorus
''Rubus chamaemorus'' is a species of flowering plant in the rose family Rosaceae, native to cool temperate regions, alpine and arctic tundra and boreal forest. This herbaceous perennial produces amber-colored edible fruit similar to the blackberry. English common names include cloudberry, nordic berry, bakeapple (in Newfoundland and Labrador), knotberry and knoutberry (in England), aqpik or low-bush salmonberry (in Alaska – not to be confused with salmonberry, ''Rubus spectabilis''), and averin or evron (in Scotland). Description Unlike most ''Rubus'' species, the cloudberry is dioecious, and fruit production by a female plant requires pollination from a male plant. The cloudberry grows to high. The leaves alternate between having 5 and 7 soft, handlike lobes on straight, branchless stalks. After pollination, the white (sometimes reddish-tipped) flowers form raspberry-sized aggregate fruits which are more plentiful in wooded rather than sun-exposed habitats. Consisting of ...
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Dimer (chemistry)
A dimer () ('' di-'', "two" + ''-mer'', "parts") is an oligomer consisting of two monomers joined by bonds that can be either strong or weak, covalent or intermolecular. Dimers also have significant implications in polymer chemistry, inorganic chemistry, and biochemistry. The term ''homodimer'' is used when the two molecules are identical (e.g. A–A) and ''heterodimer'' when they are not (e.g. A–B). The reverse of dimerization is often called dissociation. When two oppositely charged ions associate into dimers, they are referred to as ''Bjerrum pairs'', after 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. Under special conditions, most OH-containing molecules form dimers, e.g. the water dimer. Excimers and exciplexes are excited structures with a short lifetime. ...
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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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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 gallic a ...
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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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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 ...
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