Serpentine (alkaloid)
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Serpentine (alkaloid)
Serpentine is a terpene indole alkaloid produced by several members of the family Apocynaceae, including ''Catharanthus roseus'' and ''Rauvolfia serpentina''. See also *Vinervine *Akuammicine References

Alkaloids found in Apocynaceae {{alkaloid-stub ...
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Terpene
Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n > 1. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes are further classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), as examples. The terpene alpha-pinene, is a major component of the common solvent, turpentine. History and terminology The term ''terpene'' was coined in 1866 by the German chemist August Kekulé to denote all hydrocarbons having the empirical formula C10H16, of which camphene was one. Previously, many hydrocarbons having the empirical formula C10H16 had been called "camphene", but many other hydrocarbons of the same composition had had different names. Kekulé coined the term "terpene" in order to reduce the confusion. The name "terpene" is a shortened form of "terpentine", an obsolete spelling of "turpentine". Although sometimes ...
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Indole
Indole is an aromatic heterocyclic organic compound with the formula C8 H7 N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environment and can be produced by a variety of bacteria. As an intercellular signal molecule, indole regulates various aspects of bacterial physiology, including spore formation, plasmid stability, resistance to drugs, biofilm formation, and virulence. The amino acid tryptophan is an indole derivative and the precursor of the neurotransmitter serotonin. General properties and occurrence Indole is a solid at room temperature. It occurs naturally in human feces and has an intense fecal odor. At very low concentrations, however, it has a flowery smell, and is a constituent of many perfumes. It also occurs in coal tar. The corresponding substituent is called indolyl. Indole undergoes electrophilic substitution, mainly at position 3 (see diagra ...
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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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Apocynaceae
Apocynaceae (from ''Apocynum'', Greek for "dog-away") is a family of flowering plants that includes trees, shrubs, herbs, stem succulents, and vines, commonly known as the dogbane family, because some taxa were used as dog poison Members of the family are native to the European, Asian, African, Australian, and American tropics or subtropics, with some temperate members. The former family Asclepiadaceae (now known as Asclepiadoideae) is considered a subfamily of Apocynaceae and contains 348 genera. A list of Apocynaceae genera may be found here. Many species are tall trees found in tropical forests, but some grow in tropical dry (xeric) environments. Also perennial herbs from temperate zones occur. Many of these plants have milky latex, and many species are poisonous if ingested, the family being rich in genera containing alkaloids and cardiac glycosides, those containing the latter often finding use as arrow poisons. Some genera of Apocynaceae, such as '' Adenium'', bleed clea ...
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Catharanthus Roseus
''Catharanthus roseus'', commonly known as bright eyes, Cape periwinkle, graveyard plant, Madagascar periwinkle, old maid, pink periwinkle, rose periwinkle, is a species of flowering plant in the family Apocynaceae. It is native and endemic to Madagascar, but grown elsewhere as an ornamental and medicinal plant. It is a source of the drugs vincristine and vinblastine, used to treat cancer. It was formerly included in the genus ''Vinca'' as ''Vinca rosea''. It has many vernacular names among which are ''arivotaombelona'' or ''rivotambelona'', ''tonga'', ''tongatse'' or ''trongatse'', ''tsimatiririnina'', and ''vonenina''. Synonyms Two varieties are recognized * ''Catharanthus roseus'' var. ''roseus'' : Synonymy for this variety ::''Catharanthus roseus'' var. ''angustus'' Steenis ex Bakhuizen f. :: ''Catharanthus roseus'' var. ''albus'' G.DonG.Don, Gen. Hist. 4(1): 95. 1837. :: ''Catharanthus roseus'' var. ''occellatus'' G.Don :: ''Catharanthus roseus'' var. ''nanus'' Markgr. :: ...
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Rauvolfia Serpentina
''Rauvolfia serpentina'', the Indian snakeroot, devil pepper, or serpentine wood, is a species of flower in the milkweed family Apocynaceae. It is native to the Indian subcontinent and East Asia (from India to Indonesia). ''Rauvolfia'' is a perennial undershrub widely distributed in India in the sub-Himalayan regions up to . Chemical composition ''Rauvolfia serpentina'' contains dozens of alkaloids of the indole alkaloid family, including ajmaline, ajmalicine, reserpine, and serpentine, among others. Research ''Rauvolfia serpentina'' may be useful in treating excitable patients with hypertension. According to a 2016 review by Canadian researchers, 4 different high-quality clinical trials on humans suggest that reserpine significantly reduces systolic blood pressure (SBP) compared to placebo. They concluded it may be as effective at reducing SBP as other front-line hypertensive drugs, but that more research is needed to determine a dose-specific safety profile. Rabbits fed ...
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Vinervine
Vinervine is a monoterpene indole alkaloid of the Vinca sub-group. It is a derivative of akuammicine, with one additional hydroxy (OH) group in the indole portion, hence it is also known as 12-hydroxyakuammicine. History The alkaloids are a large group of natural products which are classified according to the part-structure which members of a particular group contain. Vinervine is a monoterpene indole alkaloid of the Vinca sub-group which shares a common biosynthesis with other members, namely that they are derived from strictosidine. It was first characterised in 1964 and the structures of closely related materials including akuammicine were confirmed in 1983. Natural occurrence Vinervine is found in a variety of plants of the Apocynaceae family, including ''Vinca erecta'', ''Tabernaemontana divaricata'' and several other flowering plants species that are native to Africa, Asia, and Europe. Biosynthesis As with other indole alkaloids, the biosynthesis of vinervine starts fro ...
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Akuammicine
Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including ''Picralima nitida'', ''Vinca minor'' and the ''Aspidosperma''. History The alkaloids are a large group of natural products which are classified according to the part-structure which members of a particular group contain. Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group which shares a common biosynthesis with other members, namely that they are derived from strictosidine. It was first isolated in 1927 and had been investigated by Sir Robert Robinson and others before its structure was correctly deduced. This was confirmed by X-ray crystallography in 2017. Natural occurrence Akuammicine is found in plants of the Apocynaceae family and was first isolated from ''Picralima nitida''. It has also been reported in ''Catharanthus roseus''. Synthesis Biosynthesis As with other indole alkaloids, the biosynthesis of akuammicine starts from t ...
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