Rotenoids
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Rotenoids
Rotenoids are naturally occurring substances containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus. Many have insecticidal and piscicidal activity, such as the prototypical member of the family, rotenone. Rotenoids are related to the isoflavones. Natural occurrences Many plants in the subfamily Faboideae contain rotenoids. Rotenoids can be found in ''Lonchocarpus sp''. Deguelin and tephrosin can be found in ''Tephrosia vogelii''. 6'-O-β-D-glucopyranosyl-12a-hydroxydalpanol can be found in the fruits of ''Amorpha fruticosa''. Elliptol, 12-deoxo-12alpha-methoxyelliptone, 6-methoxy-6a,12a-dehydrodeguelin, 6a,12a-dehydrodeguelin, 6-hydroxy-6a,12a-dehydrodeguelin, 6-oxo-6a,12a-dehydrodeguelin and 12a-hydroxyelliptone can be isolated from the twigs of ''Millettia duchesnei''. Deguelin, dehydrodeguelin, rotenol, rotenone, tephrosin and sumatrol can be found in ''Indigofera tinctoria''. 6aα,12aα-12a-hydroxyelliptone can be found in the stems of ''Derris trifoliata''. Amorp ...
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Rotenone
Rotenone is an odorless, colorless, crystalline isoflavone. It occurs naturally in the seeds and stems of several plants, such as the jicama vine, and in the roots of several other members of the Fabaceae. It was the first-described member of the family of chemical compounds known as rotenoids. Rotenone is approved for use as a piscicide to remove alien fish species, see ''Uses.'' It has also been used as a broad-spectrum insecticide, but its use as an insecticide has been banned in many countries. Discovery The earliest written record of the now-known rotenone-containing plants used for killing leaf-eating caterpillars was in 1848; for centuries, these same plants had been used to poison fish. The active chemical component was first isolated in 1895 by a French botanist, Emmanuel Geoffroy, who called it ''nicouline'', from a specimen of ''Robinia nicou'', now called '' Deguelia utilis'', while traveling in French Guiana. He wrote about this research in his thesis, publishe ...
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Deguelin
Deguelin is a derivative of rotenone. Both are compounds classified as rotenoids of the flavonoid family and are naturally occurring insecticides. They can be produced by extraction from several plant species belonging to three genera of the legume family, Fabaceae: ''Lonchocarpus'', '' Derris'', or ''Tephrosia''. Cubé resin, the root extract from cubé ('' Lonchocarpus utilis'') and from barbasco ('' Lonchocarpus urucu''), is used as a commercial insecticide and piscicide (fish poison). The major active ingredients are rotenone and deguelin. Although "organic" (produced by nature) cubé resin is no longer considered environmentally safe. Rat pharmacokinetics * Mean residence time (MRT) = 6.98 h * Terminal half-life (t1/2(gamma)) = 9.26 h * Area under the curve (AUC) = 57.3 ng h/ml * Total clearance (Cl) = 4.37 L/h per kg * Apparent volume of distribution (V) = 3.421 L/kg * Volume of distribution at steady-state (Vss) = 30.46 L/kg * Tissue distributions after i.v. (intr ...
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Tephrosin
Tephrosin is rotenoid. It is a natural fish poison found in the leaves and seeds of ''Tephrosia purpurea ''Tephrosia purpurea'' is a species of flowering plant in the family Fabaceae. It grows in poor soils as a common wasteland weed and has a pantropical distribution. It is a type of legume native to south-western Asia (the Levant, Arabian Penins ...'' and '' T. vogelii''.Production of rotenoids by heterotrophic and photomixotrophic cell cultures of tephrosia vogelii. Nadine Lambert, Marie-France Trouslot, Claudine Nef-Campa and Hervé Chrestin, Phytochemistry, Volume 34, Issue 6, December 1993, Pages 1515-1520, See also * Cubé resin References Pesticides Phenol ethers Acyloins Tertiary alcohols Rotenoids Cyclic ethers Heterocyclic compounds with 5 rings Pyranochromenes Methoxy compounds {{heterocyclic-stub ...
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Lonchocarpus Salvadorensis
''Lonchocarpus salvadorensis'', the Sangre de Chucho, is a plant species in the genus ''Lonchocarpus''. The rotenoids deguelin, rotenone Rotenone is an odorless, colorless, crystalline isoflavone. It occurs naturally in the seeds and stems of several plants, such as the jicama vine, and in the roots of several other members of the Fabaceae. It was the first-described member of the ..., elliptone and α-toxicarol can be found in the seeds of ''L. salvadorensis''.Rotenoids of Lonchocarpus salvadorensis: Their effectiveness in protecting seeds against bruchid predation. Nicholas Birch, Leslie Crombie and W. Mary Crombie, Phytochemistry, Volume 24, Issue 12, 26 November 1985, Pages 2881-2883, References salvadorensis {{Millettieae-stub ...
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Rotenone
Rotenone is an odorless, colorless, crystalline isoflavone. It occurs naturally in the seeds and stems of several plants, such as the jicama vine, and in the roots of several other members of the Fabaceae. It was the first-described member of the family of chemical compounds known as rotenoids. Rotenone is approved for use as a piscicide to remove alien fish species, see ''Uses.'' It has also been used as a broad-spectrum insecticide, but its use as an insecticide has been banned in many countries. Discovery The earliest written record of the now-known rotenone-containing plants used for killing leaf-eating caterpillars was in 1848; for centuries, these same plants had been used to poison fish. The active chemical component was first isolated in 1895 by a French botanist, Emmanuel Geoffroy, who called it ''nicouline'', from a specimen of ''Robinia nicou'', now called '' Deguelia utilis'', while traveling in French Guiana. He wrote about this research in his thesis, publishe ...
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Isoflavone
Isoflavones are a type of naturally-occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones occur in many plant species, but are especially high in soybeans. Although isoflavones and closely-related phytoestrogens are sold as dietary supplements, there is little scientific evidence for either the safety of long-term supplementation or of health benefits from these compounds. Some studies indicate that isoflavone supplementation may help lower the risk of hormone-related cancers. Organic chemistry and biosynthesis Isoflavone is an isomer of flavone, which is chromone substituted with a phenyl group in the 2-position. In isoflavone, the phenyl group is in the 3-position. Substituted isoflavone derivatives are related to the parent by the replacement of two or three hydrogen atoms with hydroxyl groups. Isoflavone differs from flavone (2-phenyl-4''H''-1-benzopyr-4-one) in location of the phenyl group. Isoflavones are produced via a branch of the ...
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Millettia Duchesnei
''Millettia duchesnei'' is a large forest liana in the genus ''Millettia''. The rotenoids elliptol, , , , , , and the flavanone eriodictyol Eriodictyol is a bitter-masking flavanone, a flavonoid extracted from yerba santa ('' Eriodictyon californicum''), a plant native to North America. Eriodictyol is one of the four flavanones identified in this plant as having taste-modifying prop ... can be isolated from the twigs of ''M. duchesnei''.Rotenoid derivatives and other constituents of the twigs of Millettia duchesnei. François Ngandeu, Merhatibeb Bezabih, Dieudonne Ngamga, Alembert T. Tchinda, Bonaventure T. Ngadjui, Berhanu M. Abegaz, Hanh Dufat and François Tillequin, Phytochemistry, Volume 69, Issue 1, January 2008, Pages 258-263, References External links duchesnei Taxa named by Émile Auguste Joseph De Wildeman {{Millettieae-stub ...
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Amorpha
''Amorpha'' is a genus of plants in the pea family, Fabaceae. All the species are native to North America, from southern Canada, most of the United States (US), and northern Mexico. They are commonly known as false indigo. The name ''Amorpha'' means "deformed" or "without form" in Greek and was given because flowers of this genus only have one petal, unlike the usual "pea-shaped" flowers of the Faboideae subfamily. ''Amorpha'' is missing the wing and keel petals. The desert false indigo or indigo bush ('' Amorpha fruticosa''), is a shrub that grows from 3 m to 5 m tall. The species is considered a rare species in the US state of West Virginia and in the Canadian provinces of Manitoba and Ontario, but is considered an invasive plant in some areas of the northeastern and northwestern United States and in southeastern Canada, beyond its native range, and has also been introduced into Europe. The lead plant ('' Amorpha canescens''), a bushy shrub, is an important North A ...
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Bioside
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of ''Heliconius'' butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body. In formal terms, a glycoside is any molecule in which a sugar group is bonded through its anomeric carbon to another group via a glycosidic bond. Glycosides can be linked by an O- (an ''O-glycoside''), N- (a ''glycosylamine''), S-(a ''thioglycoside''), or C- (a ''C-glycoside'') glycosidic bond. According to the ...
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