Thevetin A
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Thevetin A
Thevetins are a group of poisonous cardiac glycosides. They are obtained especially from the seeds of a West Indian shrub or small tree (''Cascabela thevetia'' syn. ''Thevetia nereifolia'') of the dogbane family (Apocynaceae). Hydrolysis products include glucose, digitalose, and a sterol Sterol is an organic compound with formula , whose molecule is derived from that of gonane by replacement of a hydrogen atom in position 3 by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the go .... File:thevetin A.svg, Thevetin A (C42H64O19) File:thevetin B.svg, Thevetin B (C42H66O18) References Cardiac glycosides {{biochem-stub ...
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Cardiac Glycoside
Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses are as treatments for congestive heart failure and cardiac arrhythmias; however, their relative toxicity prevents them from being widely used. Most commonly found as secondary metabolites in several plants such as foxglove plants, these compounds nevertheless have a diverse range of biochemical effects regarding cardiac cell function and have also been suggested for use in cancer treatment. Classification General structure The general structure of a cardiac glycoside consists of a steroid molecule attached to a sugar (glycoside) and an R group. The steroid nucleus consists of four fused rings to which other functional groups such as methyl, hydroxyl, and aldehyde groups can be attached to influence the overall molecule's biological activity. Cardiac glycosi ...
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West Indies
The West Indies is a subregion of North America, surrounded by the North Atlantic Ocean and the Caribbean Sea that includes 13 independent island countries and 18 dependencies and other territories in three major archipelagos: the Greater Antilles, the Lesser Antilles, and the Lucayan Archipelago. The subregion includes all the islands in the Antilles, plus The Bahamas and the Turks and Caicos Islands, which are in the North Atlantic Ocean. Nowadays, the term West Indies is often interchangeable with the term Caribbean, although the latter may also include some Central and South American mainland nations which have Caribbean coastlines, such as Belize, French Guiana, Guyana, and Suriname, as well as the Atlantic island nations of Barbados, Bermuda, and Trinidad and Tobago, all of which are geographically distinct from the three main island groups, but culturally related. Origin and use of the term In 1492, Christopher Columbus became the first European to record his arri ...
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Cascabela Thevetia
''Cascabela thevetia'' (syn: ''Thevetia peruviana'') is a poisonous plant native throughout Mexico and in Central America, and cultivated widely as an ornamental. It is a relative of ''Nerium oleander'', giving it a common name yellow oleander, and is also called lucky nut in the West Indies. Etymology 'Cascabel', 'cascavel' or 'cascabela' is Spanish for a small bell, a snake's rattle or a rattlesnake itself. The allusion may also be to the plant's toxicity comparable to the venom of a rattlesnake. The latin specific name ''thevetia'' commemorates André de Thevet (1516-1590), a French Franciscan priest and explorer, who explored Brazil and Guiana (where the plant is known as chapéu-de-napoleão, ie, Napoleon's hat). Description ''Cascabela thevetia'' is an evergreen tropical shrub or small tree. Its leaves are willow-like, linear-lanceolate, and glossy green in color. They are covered in waxy coating to reduce water loss (typical of oleanders). Its stem is green turning silve ...
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Dogbane
Dogbane, dog-bane, dog's bane, and other variations, some of them regional and some transient, are names for certain plants that are reputed to kill or repel dogs; "bane" originally meant "slayer", and was later applied to plants to indicate that they were poisonous to particular creatures. History of the term The earliest reference to such names in common English usage was in the 16th century, in which they were applied to various plants in the Apocynaceae, in particular ''Apocynum''. Some plants in the Asclepiadoideae, now a subfamily of the Apocynaceae, but until recently regarded as the separate family Asclepiadaceae, were also called dogbane even before the two families were united. It is not clear how much earlier the name had been in use in the English language, which originated about 1000 years earlier in mediaeval times. However, centuries before the appearance of the English language, Pedanius Dioscorides, in his ''De Materia Medica'', had already described members of ...
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Apocynaceae
Apocynaceae (from ''Apocynum'', Greek for "dog-away") is a family of flowering plants that includes trees, shrubs, herbs, stem succulents, and vines, commonly known as the dogbane family, because some taxa were used as dog poison Members of the family are native to the European, Asian, African, Australian, and American tropics or subtropics, with some temperate members. The former family Asclepiadaceae (now known as Asclepiadoideae) is considered a subfamily of Apocynaceae and contains 348 genera. A list of Apocynaceae genera may be found here. Many species are tall trees found in tropical forests, but some grow in tropical dry (xeric) environments. Also perennial herbs from temperate zones occur. Many of these plants have milky latex, and many species are poisonous if ingested, the family being rich in genera containing alkaloids and cardiac glycosides, those containing the latter often finding use as arrow poisons. Some genera of Apocynaceae, such as '' Adenium'', bleed clea ...
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Hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, 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 w ...
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Glucose
Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world. In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as starch and amylopectin, and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar. The naturally occurring form of glucose is -glucose, while -glucose is produced synthetically in comparatively small amounts and is less biologically active. Glucose is a monosaccharide containing six carbon atoms and an aldehyde group, and is therefore an aldohexose. The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) form. Gluco ...
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Digitalose
Digitalose is a deoxy sugar that is a component of various cardiac glycosides including thevetin and emicymarin. It was first reported in 1892 as being obtained by the hydrolysis of ''Digtalinum verum''. The chemical structure was first elucidated in 1943 by the German chemist Otto Schmidt. Chemically, it is a methyl ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ... of D-fucose. See also * Sarmentose, a related deoxy sugar References {{reflist Deoxy sugars Ethers ...
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Sterol
Sterol is an organic compound with formula , whose molecule is derived from that of gonane by replacement of a hydrogen atom in position 3 by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the gonane structure, additional functional groups, and/or modified ring systems derived from gonane are called steroids. Therefore, sterols are a subgroup of the steroids. They occur naturally in most eukaryotes, including plants, animals, and fungi, and can also be produced by some bacteria (however likely with different functions). The most familiar type of animal sterol is cholesterol, which is vital to cell membrane structure, and functions as a precursor to fat-soluble vitamins and steroid hormones. While technically alcohols, sterols are classified by biochemists as lipids (fats in the broader sense of the term). Types Sterols of plants are called ''phytosterols'' and sterols of animals are called ''zoosterols''. The most importa ...
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