Names | |
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IUPAC name 4′,5′-Dimethoxy-6′′,6′′-dimethyl-6′′H-pyrano[2′′,3′′:7,8]rotenan-4-one | |
Systematic IUPAC name (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-([1]benzopyrano[4,3-e′]benzo[1,2-b:3,4-b′]dipyran)-7(7aH)-one | |
Other names Deguelin; 3H-Bis(1)benzopyrano (3,4-b:6',5'-e)pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3- dimethyl-, (7aS,13aS)-; 3H-Bis(1) benzopyrano(3,4-b:6',5'-e)pyran- 7(7aH)-one, 13,13a-dihydro- 9, 10-dimethoxy-3,3-dimethyl-, (7aS-cis)- | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
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ChemSpider | |
PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
C23H22O6 | |
Molar mass | 394.42 g/mol |
Melting point | 171 °C (340 °F; 444 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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.
Deguelin displays anti-cancer activity by inhibiting the growth of pre-cancerous and cancerous cells [2] - particularly for lung cancer. [3] So far the compound has shown no toxic effects on normal cells. However, high doses of deguelin are suspected of having negative effects on the heart, lungs and nerves. The molecular mechanisms include the induction of apoptosis, mediated through AKT/PKB signaling pathways in malignant and premalignant human bronchial epithelia (HBE) cells, with only minimal effects on normal HBE cells. Deguelin inhibits AKT by both Phosphoinositol-3-phosphate kinase (PI3K)-dependent and PI3K-independent pathways.
Research has shown a correlation between intravenous deguelin and Parkinson's disease in rats. [4] The study does not suggest that deguelin exposure is responsible for Parkinson's disease in humans, but is consistent with the belief that chronic exposure to environmental toxins can increase the likelihood of the disease.
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, 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.
A precancerous condition is a condition, tumor or lesion involving abnormal cells which are associated with an increased risk of developing into cancer. Clinically, precancerous conditions encompass a variety of abnormal tissues with an increased risk of developing into cancer. Some of the most common precancerous conditions include certain colon polyps, which can progress into colon cancer, monoclonal gammopathy of undetermined significance, which can progress into multiple myeloma or myelodysplastic syndrome. and cervical dysplasia, which can progress into cervical cancer. Bronchial premalignant lesions can progress to squamous cell carcinoma of the lung.
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Eosinophil cationic protein (ECP) also known as ribonuclease 3 is a basic protein located in the eosinophil primary matrix. In humans, the eosinophil cationic protein is encoded by the RNASE3 gene.
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.
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Mucin-4 (MUC-4) is a mucin protein that in humans is encoded by the MUC4 gene. Like other mucins, MUC-4 is a high-molecular weight glycoprotein.
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Tephrosin is rotenoid. It is a natural fish poison found in the leaves and seeds of Tephrosia purpurea and T. vogelii.
MCF-7 is a breast cancer cell line isolated in 1970 from a 69-year-old White woman. MCF-7 is the acronym of Michigan Cancer Foundation-7, referring to the institute in Detroit where the cell line was established in 1973 by Herbert Soule and co-workers. The Michigan Cancer Foundation is now known as the Barbara Ann Karmanos Cancer Institute.ESRAA AHMED
Millettia pachycarpa is a perennial climbing shrub belonging to the genus Millettia. It is one of the most well known among ~150 species of Millettia, as it is widely used in traditional practices, such as for poisoning fish, agricultural pesticide, blood tonic, and treatments of cancer and infertility. The bark fiber is used for making strong ropes.
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.
Sarcolobus globosus is a twining shrub native to tropical regions of Asia including India, China, Thailand, Malaysia, Myanmar-Burma, the Philippines and Indonesia.
In molecular biology miR-205 microRNA is a short RNA molecule. MicroRNAs function to regulate the expression levels of other genes by several mechanisms. They are involved in numerous cellular processes, including development, proliferation, and apoptosis. Currently, it is believed that miRNAs elicit their effect by silencing the expression of target genes.
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.
Edelfosine is a synthetic alkyl-lysophospholipid (ALP). It has antineoplastic (anti-cancer) effects.
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