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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 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 .... There were no toxic effects in rats on a 6% diet of punicalagins for 37 days. In laboratory research, punicalagins had carbonic anhydrase inhibitor activity. References {{pomegranate ellagitannin Pomegranate ellagitannins Carbonic anhydrase inhibitors ...
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Pomegranate Ellagitannins
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 ...
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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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Gallagyl
Gallagic acid is a polyphenolic chemical compound that can be found in the ellagitannins, a type of tannin, found in ''Punica granatum'' (pomegranate).Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins and phenolic acids from Punica granatum L. Reddy Muntha K., Gupta Sashi K., Jacob Melissa R., Khan Shabana I. and Ferreira Daneel, Planta medica, 2007, vol. 73, no5, pp. 461-467, It is a building block of the corresponding tannin punicalagin, 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 bein ..., punicacortein C and 2-O-galloyl-punicalin. See also * Gallagic acid dilactone (a.k.a. gallagyldilactone or terminalin) References Ellagitannins Pomegranate ellagitannins {{aromatic-stub ...
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Phenolic Compound
In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (— O H) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, . Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule. Phenols are both synthesized industrially and produced by plants and microorganisms. Properties Acidity Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12). Deprotonation of a phenol forms a corresponding negative phenolate ion or phenoxide ion, and the corresponding salts are called phenolates or phenoxides (aryloxides according to the IUPAC Gold Book). Condensation with aldehydes and ketones Phenols are susceptible to Electrophilic aromatic substitutions. Condensation with fo ...
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Pomegranate
The pomegranate (''Punica granatum'') is a fruit-bearing deciduous shrub in the family Lythraceae, subfamily Punicoideae, that grows between tall. The pomegranate was originally described throughout the Mediterranean Basin, Mediterranean region. It was introduced into Spanish America in the late 16th century and into California by New Spain, Spanish settlers in 1769. The fruit is typically in season in the Southern Hemisphere from March to May, and in the Northern Hemisphere from September to February. As intact sarcotestas or juice, pomegranates are used in baking, cooking, juice blends, meal garnish (food), garnishes, smoothies, and alcoholic beverages, such as cocktails and wine. Pomegranates are widely cultivated throughout the Middle East and Caucasus region, North Africa, north and tropical Africa, Iran, Armenia, the Indian subcontinent, Central Asia, the drier parts of Southeast Asia, and the Mediterranean Basin. Etymology The name pomegranate derives from medie ...
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Terminalia Catappa
''Terminalia catappa'' is a large tropical tree in the leadwood tree family, Combretaceae, native to Asia, Australia, the Pacific, Madagascar and Seychelles. Common names in English include country almond, Indian almond, Malabar almond, sea almond, tropical almond, beach almond and false kamani. Description The tree grows to tall, with an upright, symmetrical crown and horizontal branches. The fruit are corky and light, and dispersed by water. As the tree gets older, its crown becomes more flattened to form a spreading, vase shape. Its branches are distinctively arranged in tiers. The leaves are large, long and broad, ovoid, glossy dark green, and leathery. They are dry-season deciduous; before falling, they turn pinkish-reddish or yellow-brown, due to pigments such as violaxanthin, lutein, and zeaxanthin. The trees are monoecious, with distinct male and female flowers on the same tree. Both are in diameter, white to greenish, inconspicuous with no petals; they are produced ...
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Terminalia Myriocarpa
''Terminalia myriocarpa'', the East Indian almond, is a tree species in the genus '' Terminalia'' found in Southeast Asia. Ecology The larvae of the moth '' Acrocercops terminaliae'' feed on ''T. myriocarpa''. Chemistry The phenolic compounds methyl (S)-flavogallonate, gallic acid, methyl gallate, ethyl gallate, 2,3-di-O- S)-4,5,6,4′,5′,6′-hexahydroxybiphenyl-2,2′-diyldicarbonyl(α/β)-D-glucopyranose, vitexin, isovitexin, orientin, iso-orientin, kaempferol 3-O-β-D-rutinoside, rutin, neosaponarin, ellagic acid, flavogallonic acid and (α/β)-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 ... can be isolated from the leaves of ''T. myriocarpa''.Pharmacologically Active Ellagitannins from Terminalia myriocarpa. Mohamed S.A. Marzouk, Sayed A.A. El-Toumy, Fat ...
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Combretum Molle
''Combretum molle'', the velvet bushwillow, is a medium to large tree species in the genus ''Combretum'' found in western, eastern and southern Africa. The larvae of '' Parosmodes morantii'' and '' Acalyptris molleivora'' feed on ''C. molle''. It is recorded to contain antioxidants such as punicalagin, which is also found in the other Myrtale pomegranates (''Punica granatum''), a somewhat related plant. It also contains the 1alpha-hydroxycycloartenoid saponins mollic acid glucoside and mollic acid 3β-D- xyloside. Extracts from the bark of ''C. molle'' show antibacterial and antifungal as well as ''in vitro'' antiprotozoal activities. Mollic acid glucoside shows cardiovascular effects. Combretum molle, nuwe loof, b, Faerie Glen NR.jpg, Combretum molle, loof en bloeisels, Jan Celliers Park, naby.jpg, Combretum molle00.jpg, See also * List of Southern African indigenous trees and woody lianes References External links * molle MOLLE (pronounced ,, ho ...
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Myrtales
The Myrtales are an order of flowering plants placed as a sister to the eurosids II clade as of the publishing of the ''Eucalyptus grandis'' genome in June 2014. The APG III system of classification for angiosperms still places it within the eurosids. This finding is corroborated by the placement of the Myrtales in the Malvid clade by the One Thousand Plant Transcriptomes Initiative. The following families are included as of APGIII: * Alzateaceae S. A. Graham * Combretaceae R. Br. ( leadwood family) * Crypteroniaceae A. DC. * Lythraceae J. St.-Hil. (loosestrife and pomegranate family) * Melastomataceae Juss. (including Memecylaceae DC.) * Myrtaceae Juss. (myrtle family; including Heteropyxidaceae Engl. & Gilg, Psiloxylaceae Croizat) * Onagraceae Juss. (evening primrose and Fuchsia family) * Penaeaceae Sweet ex Guill. (including Oliniaceae Arn., Rhynchocalycaceae L. A. S. Johnson & B. G. Briggs) * Vochysiaceae A. St.-Hil. The Cronquist system gives essentially the same co ...
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Combretaceae
The Combretaceae, often called the white mangrove family, are a family of flowering plants in the order Myrtales. The family includes about 530 species of trees, shrubs, and lianas in ca 10 genera. The family includes the leadwood tree, ''Combretum imberbe''. Three genera, '' Conocarpus'', '' Laguncularia'', and '' Lumnitzera'', grow in mangrove habitats (mangals). The Combretaceae are widespread in the subtropics and tropics. Some members of this family produce useful construction timber, such as idigbo from '' Terminalia ivorensis''. The commonly cultivated ''Quisqualis indica'' is now placed in the genus ''Combretum''. Many plants in the Quisqualis species contain the Non-proteinogenic amino acid excitotoxin Quisqualic acid, a potent AMPA agonist.Excitotoxic cell death and delayed rescue in human neurons derived from NT2 cells, M Munir, L Lu and P Mcgonigl, Journal of Neuroscience, Vol 15, 7847–7860 White mangroves The family name comes from the type genus ''Combretum''; it ...
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Hydrolyze
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis is the cleavage of biomolecules where a water molecule is consumed to effect the separation of a larger molecule into component parts. When a carbohydrate is broken into its component sugar molecules by hydrolysis (e.g., sucrose being broken down into glucose and fructose), this is recognized as saccharification. Hydrolysis reactions can be the reverse of a condensation reaction in which two molecules join into a larger one and eject a water molecule. Thus hydrolysis adds water to break down, whereas condensation builds up by removing water. Types Usually hydrolysis is a chemical process in which a molecule of water is added to a substance. Sometimes this addition causes both the substance and water molecule to split into two parts. In su ...
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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 ...
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