(2R,3S,4S)-3,4,5,7,3',4'-hexahydroxyflavan
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(2R,3S,4S)-3,4,5,7,3',4'-hexahydroxyflavan
Leucocyanidin is a colorless chemical compound that is a member of the class of Natural product, natural products known as leucoanthocyanidins. Chemistry (+)-Leucocyanidin can be synthesized from (+)-dihydroquercetin by reduction with sodium borohydride. Molar equivalents of synthetic (2R,3S,4R or S)-leucocyanidin and (+)-catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all-''trans''-[4,8]- and [4,6]-bi-[(+)-catechins] (procyanidin B3, procyanidins B3, procyanidin B6, B6) the all-''trans''-[4,8:4,8]- and [4,8:4,6]-tri-[(+)-catechins] (procyanidin C2 and isomer). Metabolism Leucocyanidin oxygenase uses leucocyanidin, 2-oxoglutarate, and O2 to produce ''cis''-dihydroquercetin, ''trans''-dihydroquercetin (taxifolin), succinate, CO2, and H2O. Leucoanthocyanidin reductase (LAR or leucocyanidin reductase LCR) uses (2''R'',3''S'')-catechin, Nicotinamide adenine dinucleotide phosphate, NADP+, and H2O to produce 2,3-''trans''-3,4-cis-leucocy ...
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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 ring Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atom ...s (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 configura ...
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Natural Product
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis (both semisynthesis and total synthesis) and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients. Within the field of organic chemistry, the definition of natural products is usually restricted to organic compounds isolated from natural sources that are produced by the pathways of primary or secondary metabolism. Within the field of medicinal chemistry, the definition is often further restricted to secondary metabolites. Secondary metabolites (or specialized metabolites ...
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Aesculus Hippocastanum
''Aesculus hippocastanum'', the horse chestnut, is a species of flowering plant in the maple, soapberry and lychee family Sapindaceae. It is a large, deciduous, synoecious (hermaphroditic-flowered) tree. It is also called horse-chestnut, European horsechestnut, buckeye, and conker tree. It is not to be confused with the Spanish chestnut, ''Castanea sativa'', which is a tree in another family, Fagaceae. Description ''Aesculus hippocastanum'' is a large tree, growing to about tall with a domed crown of stout branches. On old trees, the outer branches are often pendulous with curled-up tips. The leaves are opposite and palmately compound, with 5–7 leaflets long, making the whole leaf up to across, with a petiole. The leaf scars left on twigs after the leaves have fallen have a distinctive horseshoe shape, complete with seven "nails". The flowers are usually white with a yellow to pink blotch at the base of the petals; they are produced in spring in erect panicles tall w ...
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Hypericum Perforatum
''Hypericum perforatum'', known as St. John's wort, is a flowering plant in the family Hypericaceae and the type species of the genus ''Hypericum''. Possibly a hybrid between '' H. maculatum'' and '' H. attenuatum'', the species can be found across temperate areas of Eurasia and has been introduced as an invasive weed to much of North and South America, as well as South Africa and Australia. While the species is harmful to livestock and can interfere with prescription drugs, it has been used in folk medicine over centuries, and remains commercially cultivated in the 21st century. Hyperforin, a phytochemical constituent of the species, is under basic research for possible therapeutic properties. Description ''Hypericum perforatum'' is an herbaceous perennial plant with extensive, creeping rhizomes. Its reddish stems are erect and branched in the upper section, and can grow up to high. The stems are woody near their base and may appear jointed from leaf scars. The branche ...
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Humulus Lupulus
''Humulus lupulus'', the common hop or hops, is a species of flowering plant in the hemp family Cannabinaceae, native to Europe, western Asia and North America. It is a perennial, herbaceous climbing plant which sends up new shoots in early spring and dies back to a cold-hardy rhizome in autumn. It is dioecious (having separate male and female plants). As the female cone-shaped flowers (hops) are used to preserve and flavor beer, the species is widely cultivated by the brewing industry. Description ''Humulus lupulus'' is a perennial herbaceous plant up to tall, living up to 20 years. It has simple leaves with 3–5 deep lobes that can be opposite or alternate. The species is triggered by the longer summer days to flower, usually around July or August. The plant is dioecious, with male and female flowers on separate plants. The fragrant flowers are wind-pollinated. The staminate (male) flowers do not have petals, while the pistillate (female) flowers have petals enveloping th ...
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Hordeum Vulgare
Barley (''Hordeum vulgare''), a member of the grass family, is a major cereal grain grown in temperate climates globally. It was one of the first cultivated grains, particularly in Eurasia as early as 10,000 years ago. Globally 70% of barley production is used as animal fodder, while 30% as a source of fermentable material for beer and certain distilled beverages, and as a component of various foods. It is used in soups and stews, and in barley bread of various cultures. Barley grains are commonly made into malt in a traditional and ancient method of preparation. In 2017, barley was ranked fourth among grains in quantity produced () behind maize, rice and wheat. Etymology The Old English word for barley was ', which traces back to Proto-Indo-European and is cognate to the Latin word ' "flour" (''see corresponding entries''). The direct ancestor of modern English ''barley'' in Old English was the derived adjective ''bærlic'', meaning "of barley". The first citation of th ...
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Hippophae Rhamnoides
''Hippophae rhamnoides'', also known as sea-buckthorn, is a species of flowering plant in the family Elaeagnaceae, native to the cold-temperate regions of Europe and Asia. It is a spiny deciduous shrub. The plant is used in the food and cosmetics industries, in traditional medicine, as animal fodder, in horticulture, and for ecological purposes. Description and biology ''Hippophae rhamnoides'' is a hardy, deciduous shrub that can grow between 2 and 4 m high (between 7 and 13 ft). It has a rough, brown or black bark and a thick, grayish-green crown. The leaves are alternate, narrow and lanceolate, with silvery-green upper faces. It is dioecious, meaning that the male and female flowers grow on different shrubs. The sex of seedlings can only be determined at the first flowering, which mostly occurs after three years. The male inflorescence is built up of four to six apetalous flowers, while the female inflorescence normally consists of only one apetalous flower and co ...
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Hamamelis Virginiana
''Hamamelis virginiana'', known as witch-hazel, common witch-hazel, and American witch-hazel, is a species of flowering shrub native to eastern North America, from Nova Scotia west to Minnesota, and south to central Florida to eastern Texas. Description It is a small, deciduous tree or shrub growing up to 6 m (rarely to 10 m) tall, often with a dense cluster of stems from its base. The bark is light brown, smooth, scaly, inner bark reddish purple. The branchlets are pubescent at first, later smooth, light orange brown, marked with occasional white dots, finally dark or reddish brown. The foliage buds are acute, slightly falcate, downy, light brown. The leaves are oval, long and broad, oblique at the base, acute or rounded at the apex, with a wavy-toothed or shallowly lobed margin, and a short, stout petiole long; the midrib is more or less hairy, stout, with six to seven pairs of primary veins. The young leaves open involute, covered with stellate rusty down; when full grown, ...
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Gleditsia Triacanthos
The honey locust (''Gleditsia triacanthos''), also known as the thorny locust or thorny honeylocust, is a deciduous tree in the family Fabaceae, native to central North America where it is mostly found in the moist soil of river valleys. Honey locust is highly adaptable to different environments, has been introduced worldwide, and can be an aggressive, invasive species outside of its native range. Description The honey locust, ''Gleditsia triacanthos'', can reach a height of . They exhibit fast growth, but live a medium life span of about 120 years. The leaves are pinnately compound on older trees but bipinnately compound on vigorous young trees. The leaflets are (smaller on bipinnate leaves) and bright green. They turn yellow in the autumn. Honey locusts leaf out relatively late in spring, but generally slightly earlier than the black locust (''Robinia pseudoacacia''). The strongly scented, cream-colored flowers appear in late spring, in clusters emerging from the base o ...
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Erythroxylon Coca
Coca is any of the four cultivated plants in the family Erythroxylaceae, native to western South America. Coca is known worldwide for its psychoactive alkaloid, cocaine. The plant is grown as a cash crop in the Argentine Northwest, Bolivia, Alto Rio Negro Territory in Brazil, Colombia, Venezuela, Ecuador, and Peru, even in areas where its cultivation is unlawful. There are some reports that the plant is being cultivated in the south of Mexico, by using seeds imported from South America, as an alternative to smuggling its recreational product cocaine. It also plays a role in many traditional Amazonian and Andean cultures as well as the Sierra Nevada de Santa Marta in northern Colombia. The cocaine alkaloid content of dry ''Erythroxylum coca'' var. ''coca'' leaves was measured ranging from 0.23% to 0.96%. Coca-Cola used coca leaf extract in its products from 1885 until about 1903, when it began using decocainized leaf extract. Extraction of cocaine from coca requires severa ...
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Cinnamomum Camphora
''Camphora officinarum'' is a species of evergreen tree that is commonly known under the names camphor tree, camphorwood or camphor laurel. Description ''Camphora officinarum'' is native to China south of the Yangtze River, Taiwan, southern Japan, Korea, India and Vietnam, and has been introduced to many other countries. It grows up to tall. In Japan, where the tree is called ''kusunoki'', five camphor trees are known with a trunk circumference above , with the largest individual, , reaching 24.22 m. The leaves have a glossy, waxy appearance and smell of camphor when crushed. In spring, it produces bright green foliage with masses of small white flowers. It produces clusters of black, berry-like fruit around in diameter. Its pale bark is very rough and fissured vertically. Certain trees in Japan are considered sacred. An example of the importance of a sacred tree is the 700-year old camphor growing in the middle of Kayashima Station. Locals protested against moving the ...
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Cerasus Vulgaris
''Prunus cerasus'' (sour cherry, tart cherry, or dwarf cherry) is a species of ''Prunus'' in the subgenus '' Cerasus'' (cherries), native to much of Europe and southwest Asia. It is closely related to the sweet cherry (''Prunus avium''), but has a fruit that is more acidic. Its sour pulp is edible. The tree is smaller than the sweet cherry (growing to a height of 4–10 m), has twiggy branches, and its crimson-to-near-black cherries are borne upon shorter stalks. There are two main varieties (groups of cultivars) of the sour cherry: the dark-red Morello cherry and the lighter-red Amarelle cherry. Origins and cultivation ''Prunus cerasus'', a tetraploid with 2n=32 chromosomes, is thought to have originated as a natural hybrid between ''Prunus avium'' and ''Prunus fruticosa'' in the Iranian Plateau or Eastern Europe where the two species come into contact. ''Prunus fruticosa'' is believed to have provided its smaller size and sour tasting fruit. The hybrids then stabilized and ...
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