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Cardenolide
A cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides (cardenolides that contain structural groups derived from sugars). Cardenolide glycosides are often toxic; specifically, they are heart-arresting. Cardenolides are toxic to animals through inhibition of the enzyme Na+/K+‐ATPase, which is responsible for maintaining the sodium and potassium ion gradients across the cell membranes. Etymology The term derives from ''card-'' "heart" (from Greek καρδία ''kardiā'') and the suffix ''-enolide'', referring to the lactone ring at C17. Cardenolides are a class of steroids (or aglycones if viewed as cardiac glycoside constituents), and cardenolides are a subtype of this class (see MeSH D codes list). Structure Cardenolides are C(23)-steroids with methyl groups at C-10 and C-13 and a five-membered lactone (specifically a butenolide) at C-17. They are aglycone constituents o ...
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Monarch Butterfly
The monarch butterfly or simply monarch (''Danaus plexippus'') is a milkweed butterfly (subfamily Danainae) in the family Nymphalidae. Other common names, depending on region, include milkweed, common tiger, wanderer, and black-veined brown. It is amongst the most familiar of North American butterflies and an iconic pollinator, although it is not an especially effective pollinator of milkweeds. Its wings feature an easily recognizable black, orange, and white pattern, with a wingspan of . A Müllerian mimic, the viceroy butterfly, is similar in color and pattern, but is markedly smaller and has an extra black stripe across each hindwing. The eastern North American monarch population is notable for its annual southward late-summer/autumn instinctive migration from the northern and central United States and southern Canada to Florida and Mexico. During the fall migration, monarchs cover thousands of miles, with a corresponding multigenerational return north in spring. The wes ...
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Queen (butterfly)
The queen butterfly (''Danaus gilippus'') is a North and South American butterfly in the family Nymphalidae with a wingspan of . It is orange or brown with black wing borders and small white forewing spots on its dorsal wing surface, and reddish ventral wing surface fairly similar to the dorsal surface. The ventral hindwings have black veins and small white spots in a black border. The male has a black androconial scent patch on its dorsal hindwings. It can be found in meadows, fields, marshes, deserts, and at the edges of forests. This species is possibly a close relative to the similarly colored soldier butterfly (or tropical queen, '' D. eresimus''), in any case, it is not close to the plain tiger ('' D. chrysippus'', African queen) as was long believed. There are seven subspecies. Females lay one egg at a time on larval host plants. Larvae use these plants as a food source, whereas adult butterflies feed mainly on nectar from flowers. Unpalatability to avian predators is a f ...
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Milkweeds
''Asclepias'' is a genus of herbaceous, perennial, flowering plants known as milkweeds, named for their latex, a milky substance containing cardiac glycosides termed cardenolides, exuded where cells are damaged. Most species are toxic to humans and many other species, primarily due to the presence of cardenolides, although, as with many such plants, there are species that feed upon them (e.g. their leaves) and from them (e.g. their nectar). Most notable are monarch butterflies, who use and require certain milkweeds as host plants for their larvae. The genus contains over 200 species distributed broadly across Africa, North America, and South America. It previously belonged to the family Asclepiadaceae, which is now classified as the subfamily Asclepiadoideae of the dogbane family, Apocynaceae. The genus was formally described by Carl Linnaeus in 1753, who named it after Asclepius, the Greek god of healing. Flowers Members of the genus produce some of the most complex flowe ...
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Danaus Chrysippus
''Danaus chrysippus'', also known as the plain tiger, African queen, or African monarch, is a medium-sized butterfly widespread in Asia, Australia and Africa. It belongs to the Danainae subfamily of the brush-footed butterfly family Nymphalidae. Danainae primarily consume plants in the genus ''Asclepias'', more commonly called milkweed. Milkweed contains toxic compounds, cardenolides, which are often consumed and stored by many butterflies. Because of their emetic properties, the plain tiger is unpalatable to most predators. As a result, its coloration is widely mimicked by other species of butterflies. The plain tiger inhabits a wide variety of habitats, although it is less likely to thrive in jungle-like conditions and is most often found in drier, wide-open areas. ''D. chrysippus'' encompasses three main subspecies: ''D. c. alcippus, D. c. chrysippus,'' and ''D. c. orientis.'' These subspecies are found concentrated in specific regions within the larger range of the entire sp ...
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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 glyco ...
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Cardiac Glycosides
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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Strophanthidin
k-Strophanthidin is a cardenolide found in species of the genus ''Strophanthus''. It is the aglycone of k-strophanthin, an analogue of ouabain. k-strophanthin is found in the ripe seeds of Strophanthus kombé and in the lily Convallaria. K-Strophantidin can be differentiated into: * k-Strophanthin-α, h-Strophanthin, Cymarin, Strophanthidin-D-cymarosid (CAS: 508-77-0) * k-Strophanthin-β, k-Strophanthin, Strophosid, Strophanthidin-glucocymarosid (CAS: 560-53-2) * k-Strophanthin-γ,k-Strophanthosid, Strophanthidin-diglucocymarosid (CAS: 33279-57-1) * Convallatoxin or Strophanthidin-L-rhamnosid (CAS: 508-75-8) * Convallosid or Strophanthidin-glucorhamnosid (CAS: 13473-51-3) Strophantidin is a cardiac glycoside which mechanism of action is similar to Digitalis, Ouabain and digitoxin. It specifically inhibits the membrane protein Na+/ K+ ATPase in muscle tissue (heart) which can lead to Ca2+ overload, diastolic dysfunction, arrythmias and ultimately to heart failure and death. Nat ...
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Ouabain
Ouabain or (from Somali ''waabaayo'', "arrow poison" through French ''ouabaïo'') also known as g-strophanthin, is a plant derived toxic substance that was traditionally used as an arrow poison in eastern Africa for both hunting and warfare. Ouabain is a cardiac glycoside and in lower doses, can be used medically to treat hypotension and some arrhythmias. It acts by inhibiting the Na/K-ATPase, also known as the sodium-potassium ion pump. However, adaptations to the alpha-subunit of the Na+/K+-ATPase via amino acid substitutions, have been observed in certain species, namely some herbivore- insect species, that have resulted in toxin resistance. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities. Sources Ouabain can be found in ...
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Neoconvalloside
Neoconvalloside is a cardenolide glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ... extracted from '' Convallaria majalis''. References Cardenolides Aldehydes Rhamnosides {{steroid-stub ...
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Digitoxigenin
Digitoxigenin, a cardenolide, is the aglycone of digitoxin. Digitoxigenin can be used to prepare actodigin. In Lednicer's book on steroids, it is made from deoxycholic acid Deoxycholic acid is a bile acid. Deoxycholic acid is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The two primary bile acids secreted by the liver are cholic acid and chenodeoxycholic acid. Bacteria .... References Cardenolides Diols {{steroid-stub ...
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Digitoxin
Digitoxin is a cardiac glycoside used for the treatment of heart failure and certain kinds of heart arrhythmia. It is a phytosteroid and is similar in structure and effects to digoxin, though the effects are longer-lasting. Unlike digoxin, which is eliminated from the body via the kidneys, it is eliminated via the liver, and so can be used in patients with poor or erratic kidney function. While several controlled trials have shown digoxin to be effective in a proportion of patients treated for heart failure, the evidence base for digitoxin is not as strong, although it is presumed to be similarly effective. Medical uses Digitoxin is used for the treatment of heart failure, especially in people with impaired kidney function. It is also used to treat certain kinds of heart arrhythmia, such as atrial fibrillation. Contraindications Contraindications include * problems with the heart rhythm, such as severe bradycardia (slow heartbeat), ventricular tachycardia (fast heartbeat c ...
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Bufadienolide
Bufadienolide is a chemical compound with steroid structure. Its derivatives are collectively known as bufadienolides, including many in the form of bufadienolide glycosides (bufadienolides that contain structural groups derived from sugars). These are a type of cardiac glycoside, the other being the cardenolide glycosides. Both bufadienolides and their glycosides are toxic; specifically, they can cause an atrioventricular block, bradycardia (slow heartbeat), ventricular tachycardia (a type of rapid heartbeat), and possibly lethal cardiac arrest. Etymology The term derives from the toad genus '' Bufo'' that contains bufadienolide glycosides, the suffix ''-adien-'' that refers to the two double bonds in the lactone ring, and the ending ''-olide'' that denotes the lactone structure. Consequently, related structures with only one double bond are called ''bufenolides'', and the saturated equivalent is ''bufanolide''. Classification According to MeSH, bufadienolides and buf ...
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