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Skimmianine
Skimmianine is a furoquinoline alkaloid found in '' Skimmia japonica'', a flowering plant in family Rutaceae that is native to Japan and China. It is a known acetylcholinesterase inhibitor. Biosynthesis The biosynthesis of skimmianine starts from anthranilic acid, which is very abundant in the family Rutaceae. By combining anthranilic acid acetate, anthraniloyl-CoA is formed as a starting unit and able to extend side chain by adding malonyl-CoA by Claisen condensation The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base. The reaction produces a β-keto ester or a β- diketone. It is named .... Next, lactam is formed through the cyclization and generate a heterocyclic system, leading the dienol tautomer adopt the 4-hydroxy quinolone tautomer, which is 4-hydroxy-2-quinolone. With the formation of quinolone, alkylation is happening at C-3 position by intro ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Furoquinoline Alkaloid
Furoquinoline alkaloids are a group of alkaloids with simple structure. Distribution of this group of alkaloids is essentially limited to plant family Rutaceae. The simplest member of this group is dictamnine and most widespread member is skimmianine. A furoquinoline alkaloid, dictamnine, is very common within the family Rutaceae. It is the main alkaloid in the roots of ''Dictamnus albus'' and responsible for the mutagenicity of the drug derived from crude extracts. Dictamnine was also reported to be a phototoxic and photomutagenic compound. It participates in the severe skin phototoxicity of the plant. Another furoquinoline alkaloid, skimmianine, has strong antiacetylcholinesterase activity. Chemistry Thomas first isolated dictamnine from Rutaceae in 1923. It is very weak base, shows similar reaction with methyl iodide and dimethyl sulfate or diazomethane, does not form a derivative but go through isomerization to isodictamnine. Dictamine have linear structure which is confirm ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Skimmianine Biosynthesis
Skimmianine is a furoquinoline alkaloid found in ''Skimmia japonica'', a flowering plant in family Rutaceae that is native to Japan and China. It is a known acetylcholinesterase inhibitor. Biosynthesis The biosynthesis of skimmianine starts from anthranilic acid, which is very abundant in the family Rutaceae. By combining anthranilic acid acetate, anthraniloyl-CoA is formed as a starting unit and able to extend side chain by adding malonyl-CoA by Claisen condensation The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base. The reaction produces a β-keto ester or a β- diketone. It is named .... Next, lactam is formed through the cyclization and generate a heterocyclic system, leading the dienol tautomer adopt the 4-hydroxy quinolone tautomer, which is 4-hydroxy-2-quinolone. With the formation of quinolone, alkylation is happening at C-3 position by introdu ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Skimmia Japonica
''Skimmia japonica'', the Japanese skimmia, is a species of flowering plant in the family Rutaceae, native to Japan, China, and Southeast Asia. Growing to tall and wide, it is a rounded evergreen shrub with glossy, leathery leaves. It is widely cultivated as an ornamental plant in gardens and parks. Its fragrant flowers are cream-yellow or white, followed on female plants by small, round, red fruits. The plant tolerates a wide range of conditions, including frost, drought, and atmospheric pollution. It is suitable for bonsai and for Chinese gardens. Many cultivars have been developed for ornamental garden use, including varieties which are significantly more compact than their parents. These cultivars have gained the Royal Horticultural Society's Award of Garden Merit:- *'Fragrans' *'Nymans' *'Rubella' *''Skimmia'' × ''confusa'' 'Kew Green Kew Green is a large open space in Kew in west London. Owned by the Crown Estate, it is leased to the London Borough of Richmond-upon-T ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Rutaceae
The Rutaceae () is a family (biology), family, commonly known as the rueRUTACEAE in BoDD – Botanical Dermatology Database or citrus family, of flowering plants, usually placed in the order (biology), order Sapindales. Species of the family generally have flowers that divide into four or five parts, usually with strong scents. They range in form and size from Herbaceous plant, herbs to shrubs and large trees. The most economically important genus in the family is ''Citrus'', which includes the Orange (fruit), orange (''C.'' × ''sinensis''), lemon (''C.'' × ''limon''), grapefruit (''C.'' × ''paradisi''), and Lime (fruit), lime (various). ''Boronia'' is a large Australian genus, some members of which are plants with highly fragrant flowers and are used in commercial Essential oil, oil production. Other l ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acetylcholinesterase Inhibitor
Acetylcholinesterase inhibitors (AChEIs) also often called cholinesterase inhibitors, inhibit the enzyme acetylcholinesterase from breaking down the neurotransmitter acetylcholine into choline and acetate, thereby increasing both the level and duration of action of acetylcholine in the central nervous system, autonomic ganglia and neuromuscular junctions, which are rich in acetylcholine receptors. Acetylcholinesterase inhibitors are one of two types of cholinesterase inhibitors; the other being butyryl-cholinesterase inhibitors. Acetylcholinesterase is the primary member of the cholinesterase enzyme family. Acetylcholinesterase inhibitors are classified as reversible, irreversible, or quasi-irreversible (also called pseudo-irreversible). Mechanism of action Organophosphates Organophosphates like tetraethyl pyrophosphate (TEPP) and sarin inhibit cholinesterases, enzymes that hydrolyze the neurotransmitter acetylcholine. The active centre of cholinesterases feature ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Medicinal Chemistry Research
''Medicinal Chemistry Research'' is a peer-reviewed scientific journal of medicinal chemistry emphasizing the structure-activity relationships of biologically active compounds. It was founded in 1991 by Alfred Burger (University of Virginia), who also founded the ''Journal of Medicinal Chemistry''. Editors Alfred Burger served as its first Editor-in-Chief before passing on the mantle to Richard Glennon (Virginia Commonwealth University). Stephen J. Cutler (University of South Carolina) then took over and served as the Editor-in-Chief between 2002 and 2019. Longqin Hu (Rutgers University–New Brunswick) became the current Editor-in-Chief in 2020. The current Associate Editors include Esperanza J. Carcache de Blanco (Ohio State University), Bowen Ke ( West China Hospital and Sichuan University), Amol Kulkarni (University of Texas at El Paso) and Marco Pieroni (University of Parma), supported by a 50-member international editorial board. Scope of the journal ''Medicinal Chemistr ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Anthranilic Acid
Anthranilic acid is an aromatic acid with the formula C6H4(NH2)(CO2H) and has a sweetish taste. The molecule consists of a benzene ring, ''ortho''-substituted with a carboxylic acid and an amine. As a result of containing both acidic and basic functional groups, the compound is amphoteric. Anthranilic acid is a white solid when pure, although commercial samples may appear yellow. The anion 6H4(NH2)(CO2)sup>−, obtained by the deprotonation of anthranilic acid, is called anthranilate. Anthranilic acid was once thought to be a vitamin and was referred to as vitamin L1 in that context, but it is now known to be non-essential in human nutrition. Structure Although not usually referred to as such, it is an amino acid. Solid anthranilic acid typically consists of both the amino-carboxylic acid and the zwitterionic ammonium carboxylate forms, and has a monoclinic crystal structure with space group P21. It is triboluminescent. Above , it converts to an orthorhombic form with spa ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Claisen Condensation
The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base. The reaction produces a β-keto ester or a β- diketone. It is named after Rainer Ludwig Claisen, who first published his work on the reaction in 1887. The reaction has often been displaced by diketene-based chemistry, which affords acetoacetic esters. Requirements At least one of the reagents must be enolizable (have an α-proton and be able to undergo deprotonation to form the enolate anion). There are a number of different combinations of enolizable and nonenolizable carbonyl compounds that form a few different types of Claisen. The base used must not interfere with the reaction by undergoing nucleophilic substitution or addition with a carbonyl carbon. For this reason, the conjugate sodium alkoxide base of the alcohol formed (e.g. sodium ethoxide if ethanol is formed) is often used, since the a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Quinoline Alkaloids
Quinoline alkaloids are naturally occurring chemical compounds from the group of alkaloids, which are chemically derived from quinoline. Some quinoline alkaloids show antiseptic, Convulsion, convulsive or antineoplastic effects. Examples Alkaloids with a quinoline partial structure are widespread and are usually further subdivided according to their occurrence and biogenetic origin. Among the quinoline alkaloids are the cinchona alkaloids quinine and quinidine, which are important due to their therapeutic potential, furthermore cinchonine and cinchonidine, as well as some furoquinoline alkaloids and acridine alkaloids. Strychnine and brucine, alkaloids of the Nux-vomica, nux vomica, which have a hydrogenated quinoline system, are also counted among the quinoline alkaloids. Also nitramarine (1-(2-quinolinyl)-β-carboline) belongs to the quinoline alkaloids. File:Quinine.svg, Quinine File:Cinchonidine.svg, Cinchonidine File:Cinchonine.svg, Cinchonine File:Quinidine.svg, Quinidine ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Furans
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans. Furan is a colorless, flammable, highly volatile liquid with a boiling point close to room temperature. It is soluble in common organic solvents, including alcohol, ether, and acetone, and is slightly soluble in water. Its odor is "strong, ethereal; chloroform-like". It is toxic and may be carcinogenic in humans. Furan is used as a starting point for other speciality chemicals. History The name "furan" comes from the Latin ''furfur'', which means bran (furfural is produced from bran). The first furan derivative to be described was 2-furoic acid, by Carl Wilhelm Scheele in 1780. Another important derivative, furfural, was reported by Johann Wolfgang Döbereiner in 1831 and characterised nine years later by John Stenhouse. Furan itself was first prepared by Heinrich Limpr ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Plant Toxins
A toxin is a naturally occurring poison produced by metabolic activities of living cells or organisms. They occur especially as proteins, often conjugated. The term was first used by organic chemist Ludwig Brieger (1849–1919), derived from '' toxic''. Toxins can be small molecules, peptides, or proteins that are capable of causing disease on contact with or absorption by body tissues interacting with biological macromolecules such as enzymes or cellular receptors. They vary greatly in their toxicity, ranging from usually minor (such as a bee sting) to potentially fatal even at extremely low doses (such as botulinum toxin). Terminology Toxins are often distinguished from other chemical agents strictly based on their biological origin. Less strict understandings embrace naturally occurring inorganic toxins, such as arsenic. Other understandings embrace synthetic analogs of naturally occurring organic poisons as toxins, and may or may not embrace naturally oc ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methoxy Compounds
In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position as an electron-donating group, but as an electron-withdrawing group if at the ''meta'' position. At the ''ortho'' position, steric effects are likely to cause a significant alteration in the Hammett equation prediction, which otherwise follows the same trend as that of the ''para'' position. Occurrence The simplest of methoxy compounds are methanol and dimethyl ether. Other methoxy ethers include anisole and vanillin. Many metal alkoxides contain methoxy groups, such as tetramethyl orthosilicate and titanium methoxide. Esters with a methoxy group can be referred to as methyl esters, and the —COOCH3 substituent is called a methoxycarbonyl. Biosynthesis In nature, methoxy groups are found on nucleosides subjected to 2′-''O''-methyla ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
