Coniferyl Alcohol
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Coniferyl Alcohol
Coniferyl alcohol is an organic compound with the formula HO(CH3O)C6H3CH=CHCH2OH. A colourless or white solid, it is one of the monolignols, produced via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. Coniferin is a glucoside of coniferyl alcohol. Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin. Gum benzoin contains significant amount of coniferyl alcohol and its esters. It is found in both gymnosperm and angiosperm plants. Sinapyl alcohol and paracoumaryl alcohol, the other two lignin monomers, are found in angiosperm plants and grasses. Occurrence Coniferyl alcohol is produced from coniferyl aldehyde by the action of dehydrogenase enzymes. It is a queen retinue pheromone (QRP), a type of honey bee pheromone found in the mandibular glands. In ''Forsythia intermedia'' a dirigent protein was found to direct the stereoselective biosynthesis of (+ ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Sinapyl Alcohol
Sinapyl alcohol is an organic compound structurally related to cinnamic acid. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. This phytochemical is one of the monolignols, which are precursor to lignin or lignans. It is also a biosynthetic precursor to various stilbenoids and coumarins. See also *Sinapinic acid *Syringol *Syringaldehyde *Syringic acid *Acetosyringone *Sinapine *Canolol *Phenolic content in wine The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include ... References {{DEFAULTSORT:Sinapyl Alcohol Monolignols Ethers ...
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Monolignols
Monolignols, also called lignols, are the source materials for biosynthesis of both lignans and lignin and consist mainly of paracoumaryl alcohol (H), coniferyl alcohol (G) and sinapyl alcohol (S). These monolignols differ in their degree of methoxilation of the aromatic ring. The monolignols are derived from the amino acid phenylalanine via the phenylpropanoid pathway involving various enzymes. Phenylalanine is first converted to paracoumaryl alcohol (H), which is subsequently elaborated to coniferyl alcohol (G) and sinapyl alcohol (S). This reaction happens in the cytosol, while the polymerization of the monolignols occurs in the apoplast to which the monolignols have to be transported to though the cell membrane. The monolignols have been found as monolignol-4-O-β-d-glucosides, which might be their major way of storage. Another theory for this conversion is that is improving the transportation of the monolignols. The polymerization consists of oxidative coupling reactions, whic ...
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Arabidopsis Thaliana
''Arabidopsis thaliana'', the thale cress, mouse-ear cress or arabidopsis, is a small flowering plant native to Eurasia and Africa. ''A. thaliana'' is considered a weed; it is found along the shoulders of roads and in disturbed land. A winter annual with a relatively short lifecycle, ''A. thaliana'' is a popular model organism in plant biology and genetics. For a complex multicellular eukaryote, ''A. thaliana'' has a relatively small genome around 135 mega base pairs. It was the first plant to have its genome sequenced, and is a popular tool for understanding the molecular biology of many plant traits, including flower development and light sensing. Description ''Arabidopsis thaliana'' is an annual (rarely biennial) plant, usually growing to 20–25 cm tall. The leaves form a rosette at the base of the plant, with a few leaves also on the flowering stem. The basal leaves are green to slightly purplish in color, 1.5–5 cm long, and 2–10 mm broad, with an ...
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Pinoresinol
Pinoresinol is a tetrahydrofuran lignan found in ''Styrax sp.'', ''Forsythia suspensa, and in Forsythia koreana''. It is also found in the caterpillar of the cabbage butterfly, ''Pieris rapae'' where it serves as a defence against ants. In food, it is found in sesame seed, in ''Brassica'' vegetables and in olive oil. Pinoresinol has also been found to be toxic to larvae of the milkweed bug Oncopeltus fasciatus and of the haematophagous insect Rhodnius prolixus, which is a vector of chagas disease. Currently, pinoresinol is isolated from plants with low efficiency and low yield. Biosynthesis A first dirigent protein was discovered in ''Forsythia intermedia''. This protein has been found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol monomers. Recently, a second, enantiocomplementary dirigent protein was identified in ''Arabidopsis thaliana'', which directs enantioselective synthesis of (-)-pinoresinol. Pharmacology Pinoresinol inhibits ...
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Dirigent Protein
Dirigent proteins are members of a class of proteins which dictate the stereochemistry of a compound synthesized by other enzymes. The first dirigent protein was discovered in ''Forsythia intermedia''. This protein has been found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol monomers: Lignan biosynthesis is catalysed by oxidative enzymes. In the test tube the reaction results in a heteregenous mixture of dimeric compounds. When a dirigent protein is present during the reaction, one stereoisomer of one compound is highly enriched. Dirigent proteins appear to possess no oxidative radical forming activity of their own; in the absence of oxidative enzyme, no reaction will occur. Recently, a second, enantiocomplementary dirigent protein was identified in ''Arabidopsis thaliana'', which directs enantioselective synthesis of (-)-pinoresinol. Activity In lignan biosynthesis, oxidative enzymes perform proton coupled electron transfer to remove a ...
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Forsythia Intermedia
''Forsythia'' , is a genus of flowering plants in the olive family Oleaceae. There are about 11 species, mostly native to eastern Asia, but one native to southeastern Europe. ''Forsythia'' – also one of the plant's common names – is named after William Forsyth.Flora of China''Forsythia''/ref>Flora Europaea''Forsythia''/ref>St Andrews Botanic Garden Description ''Forsythia'' are deciduous shrubs typically growing to a height of and, rarely, up to with rough grey-brown bark. The leaves are borne oppositely and are usually simple, though sometimes trifoliate with a basal pair of small leaflets; they range between in length and, rarely, up to , with a margin that is serrated or entire (smooth). Twigs may be hollow or chambered, depending on the species. The flowers are produced in the early spring before the leaves, bright yellow with a deeply four-lobed flower, the petals joined only at the base. These become pendent in rainy weather thus shielding the reproductive ...
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Mandibular Glands
In anatomy, the mandible, lower jaw or jawbone is the largest, strongest and lowest bone in the human facial skeleton. It forms the lower jaw and holds the lower teeth in place. The mandible sits beneath the maxilla. It is the only movable bone of the skull (discounting the ossicles of the middle ear). It is connected to the temporal bones by the temporomandibular joints. The bone is formed in the fetus from a fusion of the left and right mandibular prominences, and the point where these sides join, the mandibular symphysis, is still visible as a faint ridge in the midline. Like other symphyses in the body, this is a midline articulation where the bones are joined by fibrocartilage, but this articulation fuses together in early childhood.Illustrated Anatomy of the Head and Neck, Fehrenbach and Herring, Elsevier, 2012, p. 59 The word "mandible" derives from the Latin word ''mandibula'', "jawbone" (literally "one used for chewing"), from '' mandere'' "to chew" and ''-bula'' (ins ...
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Honey Bee Pheromone
The pheromones of the honey bee are mixtures of chemical substances released by individual bees into the hive or environment that cause changes in the physiology and behaviour of other bees. Introduction Honey bees (''Apis mellifera'') have one of the most complex pheromonal communication systems found in nature, possessing 15 known glands that produce an array of compounds.Free, John B., ''Pheromones of social bees.'' Ithaca, N.Y.: Comstock, 1987.Blum, M.S. 1992. Honey bee pheromones in The Hive and the Honey Bee, revised edition (Dadant and Sons: Hamilton, Illinois), pages 385–389. These chemical messengers secreted by a queen, drone, worker bee or laying worker bee to elicit a response in other bees. The chemical messages are received by the bee's antenna and other body parts. They are produced as a volatile or non-volatile liquid and transmitted by direct contact as a liquid or vapor. Honey bee pheromones can be grouped into releaser pheromones which temporarily affect the ...
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Queen Retinue Pheromone
Queen retinue pheromones (QRP) are a type of honey bee pheromones, so-called because one of their behavioral effects is to attract a circle of bees (a “retinue”) around the queen. In older literature, the queen pheromone is called ''mandibular pheromone'' because some of its components were first identified from the mandibular glands of queens. ''Retinue pheromone'' may be more accurate because the chemical mix in the pheromone comes from several glands. The following compounds have been identified as present in the QRP, of which, only coniferyl alcohol is found in the mandibular glands. The combination of the five QMP compounds and the four compounds below help create the retinue attraction of worker bees around their queen. * Methyl oleate * Coniferyl alcohol * Hexadecan-1-ol * Alpha-linolenic acid ''alpha''-Linolenic acid (ALA), also known as α-Linolenic acid (from Greek ''alpha'' meaning "first" and ''linon'' meaning flax), is an ''n''−3, or omega-3, essential fatt ...
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