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Sparteine
Sparteine is a class 1a antiarrhythmic agent; a sodium channel blocker. It is an alkaloid and can be extracted from scotch broom. It is the predominant alkaloid in ''Lupinus mutabilis'', and is thought to chelate the bivalent cations calcium and magnesium. It is not FDA approved for human use as an antiarrhythmic agent, and it is not included in the Vaughan Williams classification of antiarrhythmic drugs. It is also used as a chiral ligand in organic chemistry, especially in syntheses involving organolithium reagents. Biosynthesis Sparteine is a lupin alkaloid containing a tetracyclic bis-quinolizidine ring system derived from three C5 chains of lysine, or more specifically, L-lysine. The first intermediate in the biosynthesis is cadaverine, the decarboxylation product of lysine catalyzed by the enzyme lysine decarboxylase (LDC). Three units of cadaverine are used to form the quinolizidine skeleton. The mechanism of formation has been studied enzymatically, as well as with ...
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Organolithium Reagent
In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers. They have also been applied in asymmetric synthesis in the pharmaceutical industry. Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C−Li bond is highly ionic. Owing to the polar nature of the C−Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes pyrophoric. History and dev ...
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Scotch Broom
''Cytisus scoparius'' ( syn. ''Sarothamnus scoparius''), the common broom or Scotch broom, is a deciduous leguminous shrub native to western and central Europe. In Britain and Ireland, the standard name is broom; this name is also used for other members of the Genisteae tribe, such as French broom or Spanish broom; and the term ''common broom'' is sometimes used for clarification. In other English-speaking countries, the most common name is "Scotch broom" (or Scots broom); however, it is known as English broom in Australia. Classification The two subspecies of ''Cytisus scoparius'' are: * ''Cytisus scoparius'' subsp. ''scoparius'' - throughout the species' range * ''Cytisus scoparius'' subsp. ''maritimus'' (Rouy) Heywood - Western Europe, on maritime cliffs, differs in prostrate growth, not over 0.4 m tall, and downy young shoots Cultivation ''Cytisus scoparius'' is widely cultivated as an ornamental plant, with several cultivars selected for variation in flower colour, inclu ...
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Quinolizidine Alkaloids
Quinolizidine alkaloids are natural products that have a quinolizidine structure; this includes the lupine alkaloids. Occurrence Quinolizidine alkaloids can be found in the plant family of legumes, especially in papilionaceous plants. While the lupine alkaloids (following their name) can be found in lupines, tinctorin, for example, was isolated from the dyer's broom. Examples More than 200 quinolizidine alkaloids are known which can be classified into 6 structural types: * the lupinine type with 34 known structures, including lupinine and its derivatives * the camoensine type with 6 known structures, including camoensin * the spartein type with 66 structures, including sparteine, lupanine, angustifoline * the α-pyridone type with 25 structures, including anagyrine and cytisine * the matrine type with 31 structures, including matrine * and the ormosanin type with 19 structures, including ormosanine. (–)-Lupinine Structural Formula V2.svg, (–)-lupinine (6R,7S,9S,1 ...
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Lupinus Mutabilis
''Lupinus mutabilis'' is a species of lupin grown in the Andes, mainly for its edible bean. Vernacular names include tarwi (in Quechua II, pronounced ''tarhui''), chocho, altramuz, Andean lupin, South American lupin, Peruvian field lupin, and pearl lupin. Its nutrient-rich seeds are high in protein, as well as a good source for cooking oil. However, their bitter taste has made ''L. mutabilis'' relatively unknown outside the Andes, though modern technology makes it easier to remove the bitter alkaloids. Like other species of lupin beans, it is expanding in use as a plant-based protein source. Origin and Dissemination The origin of ''L. mutabilis'' has been identified in the Andean region of Ecuador, Peru and Bolivia.Neglected crops: 1492 from a different perspective' (1994). Ed.: J.E. Hernándo Bermejo and J. León; publ. in collab. with the Botanical Garden of Córdoba (Spain) In this area, the greatest genetic variability in the world was found. The plant has been domestica ...
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Lupinus
''Lupinus'', commonly known as lupin, lupine, or regionally bluebonnet etc., is a genus of plants in the legume family Fabaceae. The genus includes over 199 species, with centers of diversity in North and South America. Smaller centers occur in North Africa and the Mediterranean. They are widely cultivated, both as a food source and as ornamental plants, but are invasive to some areas. Description The species are mostly herbaceous perennial plants tall, but some are annual plants and a few are shrubs up to tall. An exception is the ''chamis de monte'' (''Lupinus jaimehintoniana'') of Oaxaca in Mexico, which is a tree up to tall. Lupins have soft green to grey-green leaves which may be coated in silvery hairs, often densely so. The leaf blades are usually palmately divided into five to 28 leaflets, or reduced to a single leaflet in a few species of the southeastern United States and eastern South America. The flowers are produced in dense or open whorls on an erect spik ...
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Alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.Chemical Encyclopedia: alkaloids
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Alkaloids are produced by a large variety of organisms including , , Medicinal plant, plants, an ...
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Antiarrhythmic Agents
Antiarrhythmic agents, also known as cardiac dysrhythmia medications, are a group of pharmaceuticals that are used to suppress abnormally fast rhythms ( tachycardias), such as atrial fibrillation, supraventricular tachycardia and ventricular tachycardia. Many attempts have been made to classify antiarrhythmic agents. Many of the antiarrhythmic agents have multiple modes of action, which makes any classification imprecise. Vaughan Williams classification The Vaughan Williams classification was introduced in 1970 by Miles Vaughan Williams.Vaughan Williams, EM (1970) "Classification of antiarrhythmic drugs". In ''Symposium on Cardiac Arrhythmias'' (Eds. Sandoe E; Flensted-Jensen E; Olsen KH). Astra, Elsinore. Denmark (1970) Vaughan Williams was a pharmacology tutor at Hertford College, Oxford. One of his students, Bramah N. Singh, contributed to the development of the classification system. The system is therefore sometimes known as the Singh-Vaughan Williams classification. The ...
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Lupin Poisoning
Lupin or lupini beans are the yellow legume seeds of the genus ''Lupinus''. They are traditionally eaten as a pickled snack food, primarily in the Mediterranean basin ('' L. albus''), Latin America ('' L. mutabilis'') and North Africa ('' L. angustifolius''). The most ancient evidence of lupin is from ancient Egypt, dating back to the 22nd century BCE. The bitter variety of the beans are high in alkaloids and are extremely bitter unless rinsed methodically. Low alkaloid cultivars called ''sweet lupins'' have been bred, and are increasingly planted. History and distribution The earliest archaeological reports on lupins are referred to the Twelfth Dynasty of Egyptian Pharaohs. In their tombs, seeds of ''Lupinus digitatus'' Forsk., already domesticated in those times, were discovered. Seven seeds of this species were also retrieved in the tombs of this dynasty dated back to the 22nd century BCE. They are the most ancient evidence of lupin in the Mediterranean. Lupin is commonly us ...
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Cadaverine
Cadaverine is an organic compound with the formula (CH2)5(NH2)2. Classified as diamine, it is a colorless liquid with an unpleasant odor. It is present in small quantities in living organisms but is often associated with the putrefaction of animal tissue. Production Cadaverine is produced by decarboxylation of lysine.Wolfgang Legrum: ''Riechstoffe, zwischen Gestank und Duft'', Vieweg + Teubner Verlag (2011) S. 65, It can be synthesized by many methods including the hydrogenation of glutaronitrile and the reactions of 1,5-dichloropentane. History Putrescine and cadaverine were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919). Receptors In zebrafish, the trace amine-associated receptor 13c (or TAAR13c) has been identified as a high-affinity receptor for cadaverine. In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the human TAAR6 and TAAR8. Clinical significance Elevated levels of ...
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Lysine
Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. It contains an α-amino group (which is in the protonated form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain lysyl ((CH2)4NH2), classifying it as a basic, charged (at physiological pH), aliphatic amino acid. It is encoded by the codons AAA and AAG. Like almost all other amino acids, the α-carbon is chiral and lysine may refer to either enantiomer or a racemic mixture of both. For the purpose of this article, lysine will refer to the biologically active enantiomer L-lysine, where the α-carbon is in the ''S'' configuration. The human body cannot synthesize lysine. It is essential in humans and must therefore be obtained from the diet. In organisms that synthesise lysine, two main biosynthetic pathways exist, the diaminopimelate and α-aminoadipate pathways, which employ distinct e ...
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Antiarrhythmic Agent
Antiarrhythmic agents, also known as cardiac dysrhythmia medications, are a group of pharmaceuticals that are used to suppress abnormally fast rhythms ( tachycardias), such as atrial fibrillation, supraventricular tachycardia and ventricular tachycardia. Many attempts have been made to classify antiarrhythmic agents. Many of the antiarrhythmic agents have multiple modes of action, which makes any classification imprecise. Vaughan Williams classification The Vaughan Williams classification was introduced in 1970 by Miles Vaughan Williams.Vaughan Williams, EM (1970) "Classification of antiarrhythmic drugs". In ''Symposium on Cardiac Arrhythmias'' (Eds. Sandoe E; Flensted-Jensen E; Olsen KH). Astra, Elsinore. Denmark (1970) Vaughan Williams was a pharmacology tutor at Hertford College, Oxford. One of his students, Bramah N. Singh, contributed to the development of the classification system. The system is therefore sometimes known as the Singh-Vaughan Williams classification. The ...
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