Delcosine
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Delcosine
Delsoline and delcosine are two closely related naturally occurring diterpene alkaloids first isolated from ''Delphinium consolida''. They occur widely in the Ranunculaceae plant family. The polycyclic ring system containing nineteen carbon atoms and one nitrogen atom in these compounds is the same as in aconitine and this is reflected in their preferred IUPAC name. History Delsoline and delcosine were named in 1924 by Markwood, who isolated these alkaloids from Delphinium consolida, but their structures were in doubt until established in 1963 and later confirmed by the X-ray crystallography of delsoline. There are many other known diterpene alkaloids, some of which differ from these in only minor ways. Thus while delsoline (R=CH3) is a methylated derivative of delcosine (R=H), it is also an isomeric methyl derivative of gigactonine. Synthesis Although individual members of this class of alkaloids have been extensively studied, their chemical complexity has limited the number ...
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Diterpene
Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being a primary intermediate. Diterpenes form the basis for biologically important compounds such as retinol, retinal, and phytol. They are known to be antimicrobial and antiinflammatory. Structures As with most terpenes a huge number of potential structures exists, which may be broadly divided according to the number of rings present. Biosynthesis Diterpenes are derived from the addition of one IPP unit to FPP to form geranylgeranyl-pyrophosphate (GGPP). From GGPP, structural diversity is achieved mainly by two classes of enzymes; the diterpene synthases and cytochromes P450. Several diterpenes are produced by plants and cyanobacteria. GGPP is also the precursor for the synthesis of the phytane by the action of the enzyme geranylger ...
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Alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.Chemical Encyclopedia: alkaloids
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Alkaloids are produced by a large variety of organisms including , , Medicinal plant, plants, an ...
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Delphinium Consolida
''Consolida regalis'', known as forking larkspur, rocket-larkspur, and field larkspur, is an annual herbaceous plant belonging to the genus ''Consolida'' of the buttercup family (Ranunculaceae). Distribution ''Consolida regalis'' is native to: *Western Asia: Turkey, Georgia, western Siberia. *Northern Europe — Denmark; Finland; Sweden; Estonia; Latvia; Lithuania. *Middle Europe — Austria; Belgium; Czech Republic; Germany; Hungary; Netherlands; Poland; Slovakia; Switzerland. *East Europe — Belarus; Estonia; Latvia; Moldova; Russian Federation—European part; Ukraine. *Southeastern Europe — Albania; Bosnia and Herzegovina; Bulgaria; Croatia; Greece; Italy; Macedonia; Montenegro; Romania; Serbia; Slovenia. * Southwestern Europe — France. Habitat The plant is found growing on sandy or chalky soils. It is present at an altitude of above sea level. It grows in dry weedy places and roadside ditches, and in cereal crop fields. The plant has become quite rare in central an ...
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Ranunculaceae
Ranunculaceae (buttercup or crowfoot family; Latin "little frog", from "frog") is a family of over 2,000 known species of flowering plants in 43 genera, distributed worldwide. The largest genera are ''Ranunculus'' (600 species), ''Delphinium'' (365), ''Thalictrum'' (330), ''Clematis'' (325), and ''Aconitum'' (300). Description Ranunculaceae are mostly herbaceous annuals or perennials, but some are woody climbers (such as ''Clematis'') or shrubs (e.g. ''Xanthorhiza''). Most members of the family have bisexual flowers which can be showy or inconspicuous. Flowers are solitary, but are also found aggregated in cymes, panicles, or spikes. The flowers are usually radially symmetrical but are also found to be bilaterally symmetrical in the genera ''Aconitum'' and ''Delphinium''. The sepals, petals, stamens and carpels are all generally free (not fused), the outer flower segments typically number four or five. The outer stamens may be modified to produce only nectar, as in Aqui ...
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Polycyclic Compound
In the field of organic chemistry, a polycyclic compound is an organic compound featuring several closed rings of atoms, primarily carbon. These ring substructures include cycloalkanes, aromatics, and other ring types. They come in sizes of three atoms and upward, and in combinations of linkages that include tethering (such as in biaryls), fusing (edge-to-edge, such as in anthracene and steroids), links via a single atom (such as in spiro compounds), bridged compounds, and longifolene. Though poly- literally means "many", there is some latitude in determining how many rings are required to be considered polycyclic; many smaller rings are described by specific prefixes (e.g., bicyclic, tricyclic, tetracyclic, etc.), and so while it can refer to these, the title term is used with most specificity when these alternative names and prefixes are unavailable. In general, the term polycyclic includes polycyclic aromatic compounds, including polycyclic aromatic hydrocarbons, as well as ...
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Aconitine
Aconitine is an alkaloid toxin produced by various plant species belonging to the genus '' Aconitum'' (family Ranunculaceae), known also commonly by the names wolfsbane and monkshood. Monkshood is notorious for its toxic properties. Aconitine is also present in Yunnan Baiyao, a proprietary traditional Chinese medicine. Uses Aconitine was previously used as an antipyretic and analgesic and still has some limited application in herbal medicine, although the narrow therapeutic index makes calculating appropriate dosage difficult. Structure and reactivity Biologically active isolates from '' Aconitum'' and ''Delphinium'' plants are classified as norditerpenoid alkaloids, which are further subdivided based on the presence or absence of the C18 carbon. Aconitine is a C19-norditerpenoid, based on its presence of this C18 carbon. It is barely soluble in water, but very soluble in organic solvents such as chloroform or diethyl ether. Aconitine is also soluble in mixtures of alcohol an ...
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Preferred IUPAC Name
In chemical nomenclature, a preferred IUPAC name (PIN) is a unique name, assigned to a chemical substance and preferred among the possible names generated by IUPAC nomenclature. The "preferred IUPAC nomenclature" provides a set of rules for choosing between multiple possibilities in situations where it is important to decide on a unique name. It is intended for use in legal and regulatory situations. Preferred IUPAC names are applicable only for organic compounds, to which the IUPAC has the definition as compounds which contain at least a single carbon atom but no alkali, alkaline earth or transition metals and can be named by the nomenclature of organic compounds (see below). Rules for the remaining organic and inorganic compounds are still under development. The concept of PINs is defined in the introductory chapter (freely accessible) and chapter 5 of the ''"Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013"'', which replace two former publicat ...
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Consolida Regalis 030705
''Consolida'' is a genus of about 40 species of annual flowering plants in the family Ranunculaceae, native to western Europe, the Mediterranean and Asia. Phylogenetic studies show that ''Consolida'' is actually an annual clade nested within the genus ''Delphinium'' and it has been treated as a synonym of ''Delphinium'' in Kew's Plants of the World Online. ''Consolida'' differs from other species of ''Delphinium'' (mostly perennials) in the flower structure, with only one united petal, rather than the four separate petals (or more in cultivars) found in other delphiniums, and in the fruit, which comprises a single follicle, instead of a cluster of 3~5 together. It is a popular garden plant and cut flower, grown from seed every year, with numerous cultivars in shades of pink, blue, purple and white. In seed catalogues it is usually labelled as larkspur, a common name referring to the shape of the spurred calyx, with "delphinium" reserved for its perennial relatives. Species Th ...
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X-ray Crystallography
X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles and intensities of these diffracted beams, a crystallographer can produce a three-dimensional picture of the density of electrons within the crystal. From this electron density, the mean positions of the atoms in the crystal can be determined, as well as their chemical bonds, their crystallographic disorder, and various other information. Since many materials can form crystals—such as salts, metals, minerals, semiconductors, as well as various inorganic, organic, and biological molecules—X-ray crystallography has been fundamental in the development of many scientific fields. In its first decades of use, this method determined the size of atoms, the lengths and types of chemical bonds, and the atomic-scale differences among various mat ...
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Methylated
In the chemical sciences, methylation denotes the addition of a methyl group on a substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These terms are commonly used in chemistry, biochemistry, soil science, and the biological sciences. In biological systems, methylation is catalyzed by enzymes; such methylation can be involved in modification of heavy metals, regulation of gene expression, regulation of protein function, and RNA processing. In vitro methylation of tissue samples is also one method for reducing certain histological staining artifacts. The reverse of methylation is demethylation. In biology In biological systems, methylation is accomplished by enzymes. Methylation can modify heavy metals, regulate gene expression, RNA processing and protein function. It has been recognized as a key process underlying epigenetics. Methanogenesis Methanogenesis, the process th ...
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Gigactonine
Gigactonine is a naturally occurring diterpene alkaloid first isolated from '' Aconitum gigas''. It occurs widely in the Ranunculaceae plant family. The polycyclic ring system of this chemical compound contains nineteen carbon atoms and one nitrogen atom, which is the same as in aconitine and this is reflected in its preferred IUPAC name. History Gigactonine was reported in 1978 after its isolation from ''Aconitum gigas''. Although a novel structure at that time, it was recognised to be related to known diterpene alkaloids including delsoline, which is methylated on its 4-hydroxymethyl primary alcohol sidechain. Synthesis Although individual members of this class of alkaloids have been extensively studied, their chemical complexity has limited the number which have been individually synthesised. Similarly, their full biosynthetic pathway is only known in outline in most cases. Natural occurrence Gigactonine has been reported as the main alkaloid in the flowers of Aconitum lycoct ...
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Aconitum
''Aconitum'' (), also known as aconite, monkshood, wolf's-bane, leopard's bane, mousebane, women's bane, devil's helmet, queen of poisons, or blue rocket, is a genus of over 250 species of flowering plants belonging to the family Ranunculaceae. These herbaceous perennial plants are chiefly native to the mountainous parts of the Northern Hemisphere in North America, Europe, and Asia; growing in the moisture-retentive but well-draining soils of mountain meadows. Most ''Aconitum'' species are extremely poisonous and must be handled very carefully. Several ''Aconitum'' hybrids, such as the Arendsii form of ''Aconitum carmichaelii'', have won gardening awards—such as the Royal Horticultural Society's Award of Garden Merit. Some are used by florists. Etymology The name ''aconitum'' comes from the Greek word , which may derive from the Greek ''akon'' for dart or javelin, the tips of which were poisoned with the substance, or from ''akonae'', because of the rocky ground on which th ...
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