Mesquitol
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Mesquitol
Mesquitol is a flavan-3-ol, a type of flavonoid. ''Prosopis juliflora'', an invasive New World mesquite now found in Kenya, has unusually high levels of (-)-mesquitol in its heartwood. Mesquitol, with its pyrogallol-type A-ring, is more susceptible to quinone formation at this ring, leading to aryl–aryl bond formation at carbon 5. The structural moieties constitute the proteracacinidin class of proanthocyanidins. Mesquitol-(5→8)-catechin atropisomers can be isolated from ''Prosopis glandulosa ''Prosopis glandulosa'', commonly known as honey mesquite, is a species of small to medium-sized, thorny shrub or tree in the legume family (Fabaceae). Distribution The plant is primarily native to the Southwestern United States and Northern M ...''.Synthesis of condensed tannins. Part 17. Oligomeric (2R,3S)-3,3′,4′,7,8-pentahydroxyflavans: atropisomerism and conformation of biphenyl and m-terphenyl analogues from Prosopis glandulosa(‘mesquite’). Esmé Young, Edward V. Br ...
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Flavan-3-ol
Flavan-3-ols (sometimes referred to as flavanols) are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2''H''-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They are found in most plants and have a role in plant defense. Chemical structure The single-molecule (monomer) catechin, or isomer epicatechin (see diagram), adds four hydroxyls to flavan-3-ol, making building blocks for concatenated polymers (proanthocyanidins) and higher order polymers (anthocyanidins). Flavan-3-ols possess two chiral carbons, meaning four diastereoisomers occur for each of them. They are distinguished from the yellow, ketone-containing flavonoids such as quercitin and rutin, which are called flavonols. Early use of the term bioflavonoid was imprecisely applied to include the flava ...
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Flavanols
Flavan-3-ols (sometimes referred to as flavanols) are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2''H''-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They are found in most plants and have a role in plant defense. Chemical structure The single-molecule (monomer) catechin, or isomer epicatechin (see diagram), adds four hydroxyls to flavan-3-ol, making building blocks for concatenated polymers (proanthocyanidins) and higher order polymers (anthocyanidins). Flavan-3-ols possess two chiral carbons, meaning four diastereoisomers occur for each of them. They are distinguished from the yellow, ketone-containing flavonoids such as quercitin and rutin, which are called flavonol, flavonols. Early use of the term bioflavonoid was imprecisely applied to include ...
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Prosopis Juliflora
''Prosopis juliflora'' ( es, bayahonda blanca, Cuji Venezuela, Trupillo Colombia, Aippia Wayuunaiki and long-thorn kiawe in Hawaii) is a shrub or small tree in the family Fabaceae, a kind of mesquite. It is native to Mexico, South America and the Caribbean. It has become established as an invasive weed in Africa, Asia, Australia and elsewhere. It is a contributing factor to continuing transmission of malaria, especially during dry periods when sugar sources from native plants are largely unavailable to mosquitoes. Description Growing to a height of up to , ''P. juliflora'' has a trunk diameter of up to . Its leaves are deciduous, geminate-pinnate, light green, with 12 to 20 leaflets. Flowers appear shortly after leaf development. The flowers are in long green-yellow cylindrical spikes, which occur in clusters of 2 to 5 at the ends of branches. Pods are long and contain between 10 and 30 seeds per pod. A mature plant can produce hundreds of thousands of seeds. See ...
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New World
The term ''New World'' is often used to mean the majority of Earth's Western Hemisphere, specifically the Americas."America." ''The Oxford Companion to the English Language'' (). McArthur, Tom, ed., 1992. New York: Oxford University Press, p. 33: "[16c: from the feminine of ''Americus'', the Latinized first name of the explorer Amerigo Vespucci (1454–1512). The name ''America'' first appeared on a map in 1507 by the German cartographer Martin Waldseemüller, referring to the area now called Brazil]. Since the 16c, a name of the western hemisphere, often in the plural ''Americas'' and more or less synonymous with ''the New World''. Since the 18c, a name of the United States of America. The second sense is now primary in English: ... However, the term is open to uncertainties: ..." The term gained prominence in the early 16th century, during Europe's Age of Discovery, shortly after the Italian explorer Amerigo Vespucci concluded that America (now often called ''the Am ...
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Mesquite
Mesquite is a common name for several plants in the genus ''Prosopis'', which contains over 40 species of small leguminous trees. They are native to dry areas in the Americas. They have extremely long roots to seek water from very far under ground. As a legume, mesquites are one of the few sources of fixed nitrogen in the desert habitat. These trees bloom from spring to summer. They often produce fruits known as "pods". ''Prosopis'' spp. are able to grow up to tall, depending on site and climate. They are deciduous and depending on location and rainfall have either deep or shallow roots. ''Prosopis'' is considered long-lived because of the low mortality rate after the dicotyledonous stage and juveniles are also able to survive in conditions with low light and drought. The Cahuilla indigenous people of western North America were known to eat the seeds of mesquite. History ''Prosopis'' spp. have been in North America since the Pliocene era and their wood has been dated to 3300 ...
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Pyrogallol
Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a water-soluble, white solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomers of benzenetriols. Production and reactions It is produced in the manner first reported by Scheele in 1786: heating gallic acid to induce decarboxylation. Gallic acid is also obtained from tannin. Many alternative routes have been devised. One preparation involves treating ''para''-chlorophenoldisulfonic acid with potassium hydroxide, a variant on the time-honored route to phenols from sulfonic acids. When in alkaline solution, pyrogallol undergoes deprotonation of one or more phenolic groups. Such solutions absorb oxygen from the air, turning brown. This conversion can be used to determine the amount of oxygen in a gas sample, notably by the use of the Orsat apparatus. Polyhydroxybenzenes are relatively electron-rich. One manifestation is the easy C-acetylation of pyrog ...
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Quinone
The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds, resulting in "a fully Conjugated system, conjugated cyclic diketone, dione structure". The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone" (thus the name of the class). Other important examples are 1,2-benzoquinone (''ortho''-quinone), 1,4-naphthoquinone and anthraquinone, 9,10-anthraquinone. The name is derived from that of quinic acid (with the suffix "-one" indicating a ketone), since it is one of the compounds obtained upon oxidation of quinic acid. Quinic acid, like quinine is obtained from cinchona bark, called wikt:quinaquina, quinaquina in the indigenous languages of Peruvian tribes. Properties Quinones are oxidized derivatives of aromatic compounds and are often re ...
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Proteracacinidin
Proteracacinidins are polymeric condensed tannins composed of mesquitol. This type of tannin can be found in ''Acacia caffra'' ('' Senegalia caffra'').A novel doubly-linked proteracacinidin analogue from Acacia caffra. E Malan, A Sireeparsad, JFW Burger and D Ferreira, Tetrahedron letters, 1994 The oxydative depolymerisation of proteracacinidins yields the anthocyanidin Anthocyanidins are common plant pigments, the sugar-free counterparts of anthocyanins. They are based on the flavylium cation, an oxonium ion, with various groups substituted for its hydrogen atoms. They generally change color from red through ... teracacinidin. References Condensed tannins Senegalia {{phenol-stub ...
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Proanthocyanidin
Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins. Proanthocyanidins were discovered in 1947 by Jacques Masquelier, who developed and patented techniques for the extraction of oligomeric proanthocyanidins from pine bark and grape seeds. Often associated with prevention of urinary tract infections (UTIs) by consuming cranberries, grape seeds or red wine, proanthocyanidins have not been conclusively shown as effective for preventing or treating UTIs. Distribution in plants Proanthocyanidins, including the lesser bioactive and bioavailable polymers (four or more catechins), represent a group of condensed flavan-3-ols, such as procyanidins, prodelphinidins and propelargonidins. They can be found in many plant ...
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Atropisomer
Atropisomers are stereoisomers arising because of hindered rotation about a single bond, where energy differences due to steric strain or other contributors create a barrier to rotation that is high enough to allow for isolation of individual conformers. They occur naturally and are important in pharmaceutical design. When the substituents are achiral, these conformers are enantiomers (''atropoenantiomers''), showing axial chirality; otherwise they are diastereomers (''atropodiastereomers''). Etymology and history The word ''atropisomer'' ( el, άτροπος, , meaning "without turn") was coined in application to a theoretical concept by German biochemist Richard Kuhn for Karl Freudenberg's seminal ''Stereochemie'' volume in 1933. Atropisomerism was first experimentally detected in a tetra substituted biphenyl, a diacid, by George Christie and James Kenner in 1922. Michinori Ōki further refined the definition of atropisomers taking into account the temperature-dependence asso ...
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Prosopis Glandulosa
''Prosopis glandulosa'', commonly known as honey mesquite, is a species of small to medium-sized, thorny shrub or tree in the legume family (Fabaceae). Distribution The plant is primarily native to the Southwestern United States and Northern Mexico. Its range extends on the northeast through Texas and into southwestern Kansas and Oklahoma and northwestern Louisiana, and west to southern California. It can be part of the Mesquite Bosque plant association community in the Sonoran Desert ecoregion of California and Arizona (U.S.), and Sonora state (México), and in the Chihuahuan Desert of New Mexico and Texas in the US, and Chihuahua in Mexico. Description ''Prosopis glandulosa'' has rounded big and floppy, drooping branches with feathery foliage and straight, paired spines on twigs. This tree normally reaches , but can grow as tall as . It is considered to have a medium growth rate. It flowers from March to November, with pale, yellow, elongated spikes and bears straight ...
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