Tephrosin

Last updated
Tephrosin
Tephrosin.png
Names
IUPAC name
7a-Hydroxy-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H,7aH-pyrano[2,3-c;6,5-f']dichromen-7-one
Other names
12aβ-hydroxydeguelin [1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.231.407 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C23H22O7/c1-22(2)8-7-12-15(30-22)6-5-13-20(12)29-19-11-28-16-10-18(27-4)17(26-3)9-14(16)23(19,25)21(13)24/h5-10,19,25H,11H2,1-4H3/t19-,23-/m1/s1 X mark.svgN
    Key: AQBZCCQCDWNNJQ-AUSIDOKSSA-N X mark.svgN
  • InChI=1/C23H22O7/c1-22(2)8-7-12-15(30-22)6-5-13-20(12)29-19-11-28-16-10-18(27-4)17(26-3)9-14(16)23(19,25)21(13)24/h5-10,19,25H,11H2,1-4H3/t19-,23-/m1/s1
    Key: AQBZCCQCDWNNJQ-AUSIDOKSBD
  • CC1(C=CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@]4(C3=O)O)OC)OC)C
Properties
C23H22O7
Molar mass 410.41658 g/mol
Related compounds
Related compounds
Deguelin, toxicarol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tephrosin is rotenoid. It is a natural fish poison found in the leaves and seeds of Tephrosia purpurea [2] and T. vogelii . [3]

See also

Related Research Articles

Rotenone Chemical compound

Rotenone is an odorless, colorless, crystalline isoflavone used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the seeds and stems of several plants, such as the jicama vine plant, and the roots of several members of Fabaceae. It was the first described member of the family of chemical compounds known as rotenoids. Evidence has come to suggest that rotenone may cause Parkinson's disease to develop from both acute and prolonged exposure.

<i>Ipomoea purpurea</i> Species of plant

Ipomoea purpurea, the common morning-glory, tall morning-glory, or purple morning glory, is a species in the genus Ipomoea, native to Mexico and Central America.

<i>Nepenthes vogelii</i> Species of pitcher plant from Borneo

Nepenthes vogelii is a tropical pitcher plant endemic to Borneo. It is thought to be most closely related to N. fusca.

<i>Echinacea purpurea</i> Species of flowering plant in the daisy family Asteraceae

Echinacea purpurea is a North American species of flowering plant in the sunflower family. It is native to parts of eastern North America and present to some extent in the wild in much of the eastern, southeastern and midwestern United States as well as in the Canadian Province of Ontario. It is most common in the Ozarks and in the Mississippi/Ohio Valley. Its habitats include dry open woods, prairies and barrens.

Deguelin Chemical compound

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.

<i>Lonchocarpus</i> Genus of legumes

Lonchocarpus is a plant genus in the legume family (Fabaceae). The species are called lancepods due to their fruit resembling an ornate lance tip or a few beads on a string.

<i>Tephrosia</i> Genus of plants

Tephrosia is a genus of flowering plants in the pea family, Fabaceae. It is widespread in both the Eastern and Western Hemisphere, where it is found in tropical and warm-temperate regions.

<i>Tephrosia purpurea</i> Species of plant

Tephrosia purpurea is a species of flowering plant in the pea family, Fabaceae, that has a pantropical distribution. It is a common wasteland weed. In many parts it is under cultivation as green manure crop. It is found throughout India and Sri Lanka in poor soils.

Eriodictyol Chemical compound

Eriodictyol is a bitter-masking flavanone, a flavonoid extracted from yerba santa, a plant native to North America. Eriodictyol is one of the four flavanones identified in this plant as having taste-modifying properties, the other three being homoeriodictyol, its sodium salt, and sterubin.

Pelargonidin Red anthocyanidin pigment found in certain flowers and fruits

Pelargonidin is an anthocyanidin, a type of plant pigment producing a characteristic orange color used in food and industrial dyes.

Vinceria is an extinct genus of kannemeyeriiform dicynodont in the family Shansiodontidae. Fossils of the genus have been found in the Anisian Cerro de las Cabras Formation and Carnian Río Seco de la Quebrada Formation of Argentina. One species, C. argentinensis, named in 1966, was moved to its own genus, Acratophorus, in 2021. Another species, V. vieja, was merged with Acratophorus argentinensis in 2021, leaving V. andina as the only species in the genus.

Eupalitin Chemical compound

Eupalitin is an O-methylated flavonol. It can be found in Ipomopsis aggregata.

Barbigerone Chemical compound

Barbigerone is one of a few pyranoisoflavones among several groups of isoflavones. It was first isolated from the seed of a leguminous plant Tephrosia barbigera; hence the name "barbigerone". Members of the genus Millettia are now known to be rich in barbigerone, including M. dielsiena, M. ferruginea, M. usaramensis, and M. pachycarpa. It has also been isolated from the medicinal plant Sarcolobus globosus. Barbigerone from S. globosus is validated to have significant antioxidant property. Barbigerone exhibits profound antiplasmodial activity against the malarial parasite Plasmodium falciparum. It is also demonstrated that it has anti-cancer potential as it causes apoptosis of murine lung-cancer cells.

<i>Sarcolobus globosus</i> Species of shrub

Sarcolobus globosus is a twining shrub native to tropical regions of Asia including India, China, Thailand, Malaysia, Myanmar-Burma, the Philippines and Indonesia.

Rotenoid

Rotenoids are naturally occurring substances containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus. Many have insecticidal activity, such as the prototypical member of the family, rotenone. Rotenoids are related to the isoflavones.

<i>Tephrosia vogelii</i> Species of legume

Tephrosia vogelii, the Vogel's tephrosia, fish-poison-bean or Vogel tephrosia (English), tefrósia (Portuguese) or barbasco guineano (Spanish), is a flowering plant species in the genus Tephrosia.

Millettia duchesnei is a large forest liane in the genus Millettia.

Tephrosia spinosa is a flowering plant species in the genus Tephrosia native from India, Sri Lanka, Malaysia and Indonesia.

Mesophleps ioloncha is a moth of the family Gelechiidae. It is found in India, Sri Lanka, Thailand, China, Taiwan, Indonesia, the Solomon Islands and the Philippines.

<i>Tephrosia apollinea</i> Species of plant

Tephrosia apollinea is a legume species, native to southwest Asia and northeast Africa.

References

  1. Cabizza, Maddalena; Alberto Angioni; Marinella Melis; Marco Cabras; Carlo V. Tuberoso; Paolo Cabras (2004). "Rotenone and rotenoids in cubè resins, formulations, and residues on olives". Journal of Agricultural and Food Chemistry. 52 (2): 288–293. doi:10.1021/jf034987a. PMID   14733510.
  2. Ahmad, V. U.; Z. Ali; S. R. Hussaini; F. Iqbal; M. Zahid; M. Abbas; N. Saba (1999-08-01). "Flavonoids of Tephrosia purpurea". Fitoterapia. 70 (4): 443–445. doi:10.1016/S0367-326X(99)00046-5.
  3. 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, doi : 10.1016/S0031-9422(00)90838-0