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Acetogenin
Acetogenins are a class of polyketide natural products found in plants of the family Annonaceae. They are characterized by linear 32- or 34-carbon chains containing oxygenated functional groups including hydroxyls, ketones, epoxides, tetrahydrofurans and tetrahydropyrans. They are often terminated with a lactone or butenolide. Over 400 members of this family of compounds have been isolated from 51 different species of plants. Many acetogenins are characterized by neurotoxicity. Examples include: * Annonacin * Annonins * Bullatacin * Uvaricin Structure Structurally, acetogenins are a series of C-35/C-37 compounds usually characterized by a long aliphatic chain bearing a terminal methyl-substituted α,β-unsaturated γ-lactone ring, as well as one to three tetrahydrofuran (THF) rings. These THF rings are located along the hydrocarbon chain, along with a number of oxygenated moieties (hydroxyls, acetoxyls, ketones, epoxides) and/or double bonds. Research Acetogenins have ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Asimina Triloba
''Asimina triloba'', the American papaw, pawpaw, paw paw, or paw-paw, among many regional names, is a small deciduous tree native to the eastern United States and Canada, producing a large, yellowish-green to brown fruit. ''Asimina'' is the only temperate genus in the tropical and subtropical flowering plant family Annonaceae, and ''Asimina triloba'' has the most northern range of all. Well-known tropical fruits of different genera in family Annonaceae include the custard-apple, cherimoya, Sugar-apple, sweetsop, ylang-ylang, and soursop. The pawpaw is a cloning, patch-forming (clonal) understory tree of hardwood forests, which is found in well-drained, deep, fertile bottomland and also hilly upland habitat. It has large, simple leaves with drip tips, more characteristic of plants in tropical rainforest, tropical rainforests than within this species' temperate climate, temperate range. Pawpaw fruits are the largest edible fruit Indigenous (ecology), indigenous to the United State ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acetogenin 2
Acetogenins are a class of polyketide natural products found in plants of the family Annonaceae. They are characterized by linear 32- or 34-carbon chains containing oxygenated functional groups including hydroxyls, ketones, epoxides, tetrahydrofurans and tetrahydropyrans. They are often terminated with a lactone or butenolide. Over 400 members of this family of compounds have been isolated from 51 different species of plants. Many acetogenins are characterized by neurotoxicity. Examples include: * Annonacin * Annonins * Bullatacin * Uvaricin Structure Structurally, acetogenins are a series of C-35/C-37 compounds usually characterized by a long aliphatic chain bearing a terminal methyl-substituted α,β-unsaturated γ-lactone ring, as well as one to three tetrahydrofuran (THF) rings. These THF rings are located along the hydrocarbon chain, along with a number of oxygenated moieties (hydroxyls, acetoxyls, ketones, epoxides) and/or double bonds. Research Acetogenins have ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Annonaceae
The Annonaceae are a Family (biology), family of flowering plants consisting of trees, shrubs, or rarely lianas commonly known as the custard apple family or soursop family. With 108 accepted genera and about 2400 known species, it is the largest family in the Magnoliales. Several genera produce edible fruit, most notably ''Annona'', ''Anonidium'', ''Asimina'', ''Rollinia'', and ''Uvaria''. Its type genus is ''Annona''. The family is concentrated in the tropics, with few species found in temperate regions. About 900 species are Neotropical, 450 are Afrotropical, and the remaining are Indomalayan. Description The species are mostly tropical, some are mid-latitude, deciduous or evergreen trees and shrubs, with some lianas, with aromatic bark, leaves, and flowers. ; Stems, stalks and leaves: Bark is fibrous and aromatic. Pith septate (fine tangential bands divided by partitions) to diaphragmed (divided by thin partitions with openings in them). Branching distichous (arranged in two ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Annonacin
Annonacin is a chemical compound with toxic effects, especially in the nervous system, found in some fruits such as the paw paw, custard apples, soursop, and others from the family ''Annonaceae''. It is a member of the class of compounds known as acetogenins. Annonacin-containing fruit products are regularly consumed throughout the West Indies for their traditional medicine uses. Traditional medicine Historically, plants and fruits of Annonaceae (particularly '' Annona muricata'' and ''Annona squamosa'') have been consumed in various forms throughout the West Indies, usually as hot water extracts of leaves.Ross, I. A. (2003). Annona muricata L. Medicinal Plants of the World, Vol. 1: Chemical Constituents, Traditional and Modern Medicinal Uses,1, 133-142. These annonacin-containing herbal teas are thought to be useful in folk medicine. On the Caribbean island of Guadeloupe, such teas are consumed mainly for their sedative qualities. Use of annonacin products in Guadeloupe of ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tetrahydrofuran
Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. Production About 200,000 tonnes of tetrahydrofuran are produced annually. The most widely used industrial process involves the acid-catalyzed dehydration of 1,4-butanediol. Ashland/ISP is one of the biggest producers of this chemical route. The method is similar to the production of diethyl ether from ethanol. The butanediol is derived from condensation of acetylene with formaldehyde followed by hydrogenation. DuPont developed a process for producing THF by oxidizing ''n''-butane to crude maleic anhydride, followed by catalytic hydrogenation. A third major industrial route entails hydroformylation of allyl alcohol followed by ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bullatacin
Bullatacin is a bis(tetrahydrofuranoid) fatty acid lactone found in some fruits from Annonaceae family. It is a member of the class of compounds known as acetogenin Acetogenins are a class of polyketide natural products found in plants of the family Annonaceae. They are characterized by linear 32- or 34-carbon chains containing oxygenated functional groups including hydroxyls, ketones, epoxides, tetrahydro ...s. References Furanones Tetrahydrofurans Secondary alcohols Polyketides NADH dehydrogenase inhibitors {{organic-compound-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Annonin
Annonins are a group of chemical compounds classified as acetogenins. They are found in the extracts of '' Annona'' seeds ('' A. squamosa'' and '' A. muricata''). Annonin-based bioinsecticides are used to control Coleoptera (beetle) pests commonly found in stored organic cereal and beans in the country of Brazil. Other different types of annonin-based insecticides, derived from ''A. mucosa,'' fight off lepidopteran (moth) pests that infest cabbage leaves, also found in the tropical climates of Brazil. The benefit of using these bioinsecticides is their relatively low cost and no phytotoxicity Phytotoxicity describes any adverse effects on plant growth, physiology, or metabolism caused by a chemical substance, such as high levels of fertilizers, herbicides, heavy metals, or nanoparticles. General phytotoxic effects include altered plan .... These annonin molecules act as overpowering inhibitors of complex I (NADH: ubiquinone oxidoreductase) in the electron-transport chain in th ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Uvaricin
Uvaricin is a bis(tetrahydrofuranoid) fatty acid lactone that was first isolated in 1982 from the roots of the Annonaceae ''Uvaria acuminata''. Uvaricin was the first known example in a class of compounds known as acetogenins. Acetogenins, which are found in plants of the family Annonaceae, seem to kill cells by inhibiting NADH dehydrogenase in the mitochondrion. A method to synthesize uvaricin was first published in 1998, and an improved stereoselective In chemistry, stereoselectivity is the property of a chemical reaction in which a single reactant forms an unequal mixture of stereoisomers during a non-stereospecific creation of a new stereocenter or during a non-stereospecific transformation of ... synthesis published in 2001. References Acetate esters Tetrahydrofurans Furanones Polyketides {{organic-compound-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tetrahydropyran
Tetrahydropyran (THP) is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. It is named by reference to pyran, which contains two double bonds, and may be produced from it by adding four hydrogens. In 2013, its preferred IUPAC name was established as oxane. The compound is a colourless volatile liquid. Derivatives of tetrahydropyran are, however, more common. 2-Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and 3,4-dihydropyran are commonly used as protecting groups in organic synthesis. Furthermore, a tetrahydropyran ''ring system'', i.e., five carbon atoms and an oxygen, is the core of pyranose sugars, such as glucose. Structure and preparation In gas phase, the THP exists in its lowest energy Cs symmetry chair conformation. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel. Tetrahydropyranyl deri ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acetoxy
In organic chemistry, the acetoxy group (abbr. AcO or OAc; IUPAC name: acetyloxy), is a functional group with the formula and the structure . As the ''-oxy'' suffix implies, it differs from the acetyl group () by the presence of an additional oxygen atom. The name acetoxy is the short form of ''acetyl-oxy''. Functionality An acetoxy group may be used as a protection for an alcohol functionality in a synthetic route although the protecting group itself is called an acetyl group. Alcohol protection There are several options of introducing an acetoxy functionality in a molecule from an alcohol (in effect protecting the alcohol by acetylation): * Acetyl halide, such as acetyl chloride in the presence of a base like triethylamine * Activated ester form of acetic acid, such as a N-hydroxysuccinimide ester, although this is not advisable due to higher costs and difficulties. * Acetic anhydride in the presence of base with a catalyst such as pyridine with a bit of DMAP added. ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Polyketides
Polyketides are a class of natural products derived from a precursor molecule consisting of a chain of alternating ketone (or reduced forms of a ketone) and methylene groups: (-CO-CH2-). First studied in the early 20th century, discovery, biosynthesis, and application of polyketides has evolved. It is a large and diverse group of secondary metabolites caused by its complex biosynthesis which resembles that of fatty acid synthesis. Because of this diversity, polyketides can have various medicinal, agricultural, and industrial applications. Many polyketides are medicinal or exhibit acute toxicity. Biotechnology has enabled discovery of more naturally-occurring polyketides and evolution of new polyketides with novel or improved bioactivity. History Naturally produced polyketides by various plants and organisms have been used by humans since before studies on them began in the 19th and 20th century. In 1893, J. Norman Collie synthesized detectable amounts of orcinol by heating dehy ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fatty Alcohols
Fatty alcohols (or long-chain alcohols) are usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils. The precise chain length varies with the source. Some commercially important fatty alcohols are lauryl, stearyl, and oleyl alcohols. They are colourless oily liquids (for smaller carbon numbers) or waxy solids, although impure samples may appear yellow. Fatty alcohols usually have an even number of carbon atoms and a single alcohol group (–OH) attached to the terminal carbon. Some are unsaturated and some are branched. They are widely used in industry. As with fatty acids, they are often referred to generically by the number of carbon atoms in the molecule, such as "a C12 alcohol", that is an alcohol having 12 carbons, for example dodecanol. Production and occurrence Most fatty alcohols in nature are found as waxes which are esters of fatty acids and fatty alcohols. T ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
