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Bufanolide
Bufanolide is a C24 steroid and, indirectly, a parent structure of bufadienolide. Its derivatives was found in ''Bufo'' and ''Scilla'', as an aglycone of cardiac glycosides and is usually toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst .... References {{Cardiac glycosides Bufanolides ...
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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 bufanolides ...
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Steroid
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and as signaling molecules. Hundreds of steroids are found in plants, animals and fungi. All steroids are manufactured in cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene. The steroid core structure is typically composed of seventeen carbon atoms, bonded in four " fused" rings: three six-member cyclohexane rings (rings A, B and C in the first illustration) and one five-member cyclopentane ring (the D ring). Steroids vary by the functional groups attached to this four-ring core and by the oxidation state of the rings. Sterols are forms of steroids with a hydroxy group at position three and a skeleton derived from cholestane. ''A ...
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Parent Structure
In chemistry, a parent structure is the Chemical structure, structure of an unadorned ion or molecule from which Derivative (chemistry), derivatives can be visualized. Parent structures underpin systematic nomenclature and facilitate classification. Fundamental parent structures have one or no functional groups and often have various types of symmetry. Benzene () is a chemical itself consisting of a hexagonal Ring (chemistry), ring of carbon atoms with a hydrogen atom attached to each, and is the parent of many derivatives that have substituent atoms or groups replacing one or more of the hydrogens. Some parents are rare or nonexistent themselves, as in the case of porphine, though many simple and complex derivatives are known. File:Benzene circle.png, Benzene is the parent. File:Toluene-vec.svg, Toluene is a derivative of benzene. File:Porphyrin.svg, Porphine is the parent of porphyrins. File:PPIXtransH.png, Protoporphyrin IX is a natural derivative of the parent porphine. Fi ...
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Bufo
''Bufo'' is a genus of true toads in the amphibian family Bufonidae. As traditionally defined, it was a wastebasket genus containing a large number of toads from much of the world, but following taxonomic reviews most of these have been moved to other genera, leaving only seventeen extant (living) species from Europe, northern Africa and Asia in this genus, including the well-known common toad (''B. bufo''). Some of the genera that contain species formerly placed in ''Bufo'' are ''Anaxyrus'' (many North American species), ''Bufotes'' (European green toad and relatives), ''Duttaphrynus'' (many Asian species, including the Asian common toad introduced elsewhere), ''Epidalea'' (natterjack toad) and ''Rhinella'' (many Latin American species, including the cane toad introduced elsewhere). Description True toads have in common stocky figures and short legs, which make them relatively poor jumpers. Their dry skin is thick and "warty". Behind their eyes, ''Bufo'' species have wart-li ...
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Scilla
''Scilla'' () is a genus of about 30 to 80 species of bulb-forming perennial herbaceous plants in the family Asparagaceae, subfamily Scilloideae. Sometimes called the squills in English, they are native to woodlands, subalpine meadows, and seashores throughout Europe, Africa and the Middle East. A few species are also naturalized in Australasia and North America. Their flowers are usually blue, but white, pink, and purple types are known; most flower in early spring, but a few are autumn-flowering. Several ''Scilla'' species are valued as ornamental garden plants. Taxonomy Species of ''Scilla'' have been known since classical antiquity, being described by both Greek (Theophrastus (371–287 BC) and Discorides (40–90 AD)) and Roman (Pliny (23–79 AD)) writers. Theophrastus described ''Scilla hyacinthoides'' (''skilla''), and more briefly '' S. autumnalis'' and '' S. bifolia'' in his ''Historia plantarum'', where he mentions "those of squill" (σκῐ́λ ...
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Aglycone
An aglycone (aglycon or genin) is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid molecule. Detection A way to identify aglycone is proposed to extract it from Agave spp. by using H-NMR and Heteronuclear multiple bond correlation (HMBC) experiments. The HMBC experiment can be combined with other techniques such as mass spectrometry to further examine the structure and the function of aglycone. Samples of glycones and glycosides from limonoids can be simultaneously quantified through a high performance liquid chromatography (HPLC) method, where a binary solvent system and a diode array detector separate and detect them at a sensitivity of 0.25-0.50 µg. Clinical significance A study on molecular markers in human aortic endothelial cells published that aglycone stopped cell migration but not monocyte adhesion, which is the initial step of atherosclerotic plaq ...
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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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Toxic
Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a substructure of the organism, such as a cell ( cytotoxicity) or an organ such as the liver (hepatotoxicity). By extension, the word may be metaphorically used to describe toxic effects on larger and more complex groups, such as the family unit or society at large. Sometimes the word is more or less synonymous with poisoning in everyday usage. A central concept of toxicology is that the effects of a toxicant are dose-dependent; even water can lead to water intoxication when taken in too high a dose, whereas for even a very toxic substance such as snake venom there is a dose below which there is no detectable toxic effect. Toxicity is species-specific, making cross-species analysis problematic. Newer paradigms and metrics are evolving to bypass ...
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