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4-hydroxycoumarin
4-Hydroxycoumarin is a coumarin derivative with a hydroxy group at the 4-position. Occurrence 4-Hydroxycoumarin is an important fungal metabolite from the precursor coumarin, and its production leads to further fermentative production of the natural anticoagulant dicoumarol. This happens in the presence of naturally occurring formaldehyde, which allows attachment of a second 4-hydroxycoumarin molecule through the linking carbon of the formaldehyde, to the 3-position of the first 4-hydroxycoumarin molecule, to give the semi-dimer the motif of the drug class. Dicoumarol appears as a fermentation product in spoiled sweet clover silages and is considered a mycotoxin. 4-Hydroxycoumarin is biosynthesized from malonyl-CoA and 2-hydroxybenzoyl-CoA by the enzyme 4-hydroxycoumarin synthase. Anticoagulants After the identification of dicoumarol and its anticoagulant activity, it became the prototype for a class of drugs. 4-Hydroxycoumarin forms the core of the chemical structure of an ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
4-Hydroxycoumarins
4-Hydroxycoumarins belong to a class of vitamin K antagonist (VKA) anticoagulant drug molecules derived from coumarin by adding a hydroxy group at the 4 position to obtain 4-hydroxycoumarin, then adding a large aromatic substituent at the 3-position (the ring-carbon between the hydroxyl and the carbonyl). The large 3-position substituent is required for anticoagulant activity. The primary mechanism of the 4-hydroxycoumarin drugs is the inhibition of vitamin K epoxide reductase. These compounds are not direct antagonists (in the pharmaceutical sense) of vitamin K, but rather act to deplete reduced vitamin K in tissues. For this reason vitamin K antagonizes their effect, and this has led to the loose terminology of vitamin K antagonism. Origin Although 4-hydroxycoumarin itself is not an anticoagulant, it is an important fungal metabolite from the precursor coumarin, which is also not an anticoagulant, and its production leads to further fermentative production of the natural antic ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Warfarin
Warfarin, sold under the brand name Coumadin among others, is a medication that is used as an anticoagulant (blood thinner). It is commonly used to prevent blood clots such as deep vein thrombosis and pulmonary embolism, and to prevent stroke in people who have atrial fibrillation, valvular heart disease, or artificial heart valves. Less commonly, it is used following ST-segment elevation myocardial infarction and orthopedic surgery. It is generally taken by mouth, but may also be used intravenously. The common side effect is bleeding. Less common side effects may include areas of tissue damage and purple toes syndrome. Use is not recommended during pregnancy. The effects of warfarin typically should be monitored by checking prothrombin time (INR) every one to four weeks. Many other medications and dietary factors can interact with warfarin, either increasing or decreasing its effectiveness. The effects of warfarin may be reversed with phytomenadione (vitamin K1), fresh f ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Coumarin
Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain , forming a second six-membered heterocycle that shares two carbons with the benzene ring. It can be placed in the benzopyrone chemical class and considered as a lactone. Coumarin is a colorless crystalline solid with a sweet odor resembling the scent of vanilla and a bitter taste. It is found in many plants, where it may serve as a chemical defense against predators. By inhibiting synthesis of vitamin K, a related compound is used as the prescription drug warfarin – an anticoagulant – to inhibit formation of blood clots, deep vein thrombosis, and pulmonary embolism. Etymology Coumarin is derived from ''coumarou'', the French word for the tonka bean. The word ''tonka'' for the tonka bean is taken from the Galibi (Carib) tongue spoken by natives of French G ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Coumarin
Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain , forming a second six-membered heterocycle that shares two carbons with the benzene ring. It can be placed in the benzopyrone chemical class and considered as a lactone. Coumarin is a colorless crystalline solid with a sweet odor resembling the scent of vanilla and a bitter taste. It is found in many plants, where it may serve as a chemical defense against predators. By inhibiting synthesis of vitamin K, a related compound is used as the prescription drug warfarin – an anticoagulant – to inhibit formation of blood clots, deep vein thrombosis, and pulmonary embolism. Etymology Coumarin is derived from ''coumarou'', the French word for the tonka bean. The word ''tonka'' for the tonka bean is taken from the Galibi (Carib) tongue spoken by natives of French G ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Brodifacoum
Brodifacoum is a highly lethal 4-hydroxycoumarin vitamin K antagonist anticoagulant poison. In recent years, it has become one of the world's most widely used pesticides. It is typically used as a rodenticide, but is also used to control larger pests such as possum.Eason, C.T. and Wickstrom, M. ''Vertebrate pesticide toxicology manual'', New Zealand Department of Conservation Brodifacoum has an especially long half-life in the body, which ranges up to nine months, requiring prolonged treatment with antidotal vitamin K for both human and pet poisonings. It has one of the highest risks of secondary poisoning to both mammals and birds.Rodenticides: Topic Fact Sheet |
Dicumarol
Dicoumarol (INN) or dicumarol (USAN) is a naturally occurring anticoagulant drug that depletes stores of vitamin K (similar to warfarin, a drug that dicoumarol inspired). It is also used in biochemical experiments as an inhibitor of reductases. Dicoumarol is a natural chemical substance of combined plant and fungal origin. It is a derivative of coumarin, a bitter-tasting but sweet-smelling substance made by plants that does not itself affect coagulation, but which is (classically) transformed in mouldy feeds or silages by a number of species of fungi, into active dicoumarol. Dicoumarol does affect coagulation, and was discovered in mouldy wet sweet-clover hay, as the cause of a naturally occurring bleeding disease in cattle. See warfarin for a more detailed discovery history. Identified in 1940, dicoumarol became the prototype of the 4-hydroxycoumarin anticoagulant drug class. Dicoumarol itself, for a short time, was employed as a medicinal anticoagulant drug, but since the mid ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dicoumarol
Dicoumarol (INN) or dicumarol (USAN) is a naturally occurring anticoagulant drug that depletes stores of vitamin K (similar to warfarin, a drug that dicoumarol inspired). It is also used in biochemical experiments as an inhibitor of reductases. Dicoumarol is a natural chemical substance of combined plant and fungal origin. It is a derivative of coumarin, a bitter-tasting but sweet-smelling substance made by plants that does not itself affect coagulation, but which is (classically) transformed in mouldy feeds or silages by a number of species of fungi, into active dicoumarol. Dicoumarol does affect coagulation, and was discovered in mouldy wet sweet-clover hay, as the cause of a naturally occurring bleeding disease in cattle. See warfarin for a more detailed discovery history. Identified in 1940, dicoumarol became the prototype of the 4-hydroxycoumarin anticoagulant drug class. Dicoumarol itself, for a short time, was employed as a medicinal anticoagulant drug, but since the mid ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Rodenticide
Rodenticides are chemicals made and sold for the purpose of killing rodents. While commonly referred to as "rat poison", rodenticides are also used to kill mice, squirrels, woodchucks, chipmunks, porcupines, nutria, beavers, and voles. Despite the crucial roles that rodents play in nature, there are times when they need to be controlled. Some rodenticides are lethal after one exposure while others require more than one. Rodents are disinclined to gorge on an unknown food (perhaps reflecting an adaptation to their inability to vomit), preferring to sample, wait and observe whether it makes them or other rats sick. This phenomenon of poison shyness is the rationale for poisons that kill only after multiple doses. Besides being directly toxic to the mammals that ingest them, including dogs, cats, and humans, many rodenticides present a secondary poisoning risk to animals that hunt or scavenge the dead corpses of rats. Classes of rodenticides Anticoagulants Anticoagulant ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sweet Clover
''Melilotus'', known as melilot, sweet clover, and kumoniga (from the Cumans),Bulgarian Folk Customs, Mercia MacDermott, pg 27 is a genus in the family Fabaceae (the same family that also includes the ''Trifolium'' clovers). Members are known as common grassland plants and as weeds of cultivated ground. Originally from Europe and Asia, it is now found worldwide. This legume is commonly named for its sweet smell, which is due to the presence of coumarin in its tissues. Coumarin, though responsible for the sweet smell of hay and newly mowed grass, has a bitter taste, and, as such, possibly acts as a means for the plant to discourage consumption by animals. Fungi (including ''Penicillium, Aspergillus, Fusarium'', and ''Mucor'') can convert coumarin into dicoumarol, a toxic anticoagulant. Consequently, dicoumarol may be found in decaying sweet-clover, and was the cause of the so-called sweet-clover disease, recognized in cattle in the 1920s. A few varieties of sweet clover have bee ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mycotoxin
A mycotoxin (from the Greek μύκης , "fungus" and τοξίνη , "toxin") is a toxic secondary metabolite produced by organisms of kingdom Fungi and is capable of causing disease and death in both humans and other animals. The term 'mycotoxin' is usually reserved for the toxic chemical products produced by fungi that readily colonize crops. Examples of mycotoxins causing human and animal illness include aflatoxin, citrinin, fumonisins, ochratoxin A, patulin, trichothecenes, zearalenone, and ergot alkaloids such as ergotamine. One mold species may produce many different mycotoxins, and several species may produce the same mycotoxin. Production Most fungi are aerobic (use oxygen) and are found almost everywhere in extremely small quantities due to the diminute size of their spores. They consume organic matter wherever humidity and temperature are sufficient. Where conditions are right, fungi proliferate into colonies and mycotoxin levels become high. The reason for the product ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Biosynthesis
Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. This process often consists of metabolic pathways. Some of these biosynthetic pathways are located within a single cellular organelle, while others involve enzymes that are located within multiple cellular organelles. Examples of these biosynthetic pathways include the production of lipid membrane components and nucleotides. Biosynthesis is usually synonymous with anabolism. The prerequisite elements for biosynthesis include: precursor compounds, chemical energy (e.g. ATP), and catalytic enzymes which may require coenzymes (e.g.NADH, NADPH). These elements create monomers, the building blocks for macromolecules. Some important biological macromolecules include: proteins, which are composed of amino acid monomers joined via peptide bon ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Derivative (chemistry)
In chemistry, a derivative is a compound that is derived from a similar compound by a chemical reaction. In the past, derivative also meant a compound that ''can be imagined to'' arise from another compound, if one atom or group of atoms is replaced with another atom or group of atoms, but modern chemical language now uses the term structural analog for this meaning, thus eliminating ambiguity. The term "structural analogue" is common in organic chemistry. In biochemistry, the word is used for compounds that at least theoretically can be formed from the precursor compound. Chemical derivatives may be used to facilitate analysis. For example, melting point (MP) analysis can assist in identification of many organic compounds. A crystalline derivative may be prepared, such as a semicarbazone or 2,4-dinitrophenylhydrazone (derived from aldehydes or ketones), as a simple way of verifying the identity of the original compound, assuming that a table of derivative MP values is available ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
