[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/en\/wiki2\/deguelin-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/en\/wiki2\/deguelin-wikipedia\/","headline":"Deguelin – Wikipedia","name":"Deguelin – Wikipedia","description":"before-content-x4 From Wikipedia, the free encyclopedia Deguelin Names Preferred IUPAC name after-content-x4 (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-([1]benzopyrano[4,3-e\u2032]benzo[1,2-b:3,4-b\u2032]dipyran)-7(7aH)-one after-content-x4 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,","datePublished":"2016-03-03","dateModified":"2016-03-03","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/en\/wiki2\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/en\/wiki2\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/8\/83\/Deguelin.png\/200px-Deguelin.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/8\/83\/Deguelin.png\/200px-Deguelin.png","height":"143","width":"200"},"url":"https:\/\/wiki.edu.vn\/en\/wiki2\/deguelin-wikipedia\/","wordCount":3208,"articleBody":"     (adsbygoogle = window.adsbygoogle || []).push({});before-content-x4From Wikipedia, the free encyclopediaDeguelinNamesPreferred IUPAC name       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4(7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-([1]benzopyrano[4,3-e\u2032]benzo[1,2-b:3,4-b\u2032]dipyran)-7(7aH)-one       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4Other namesDeguelin; 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)-IdentifiersChEBIChEMBLChemSpiderUNIIInChI=1S\/C23H22O6\/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13\/h5-10,19-20H,11H2,1-4H3\/t19-,20+\/m1\/s1\u00a0NKey:\u00a0ORDAZKGHSNRHTD-UXHICEINSA-N\u00a0NInChI=1\/C23H22O6\/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13\/h5-10,19-20H,11H2,1-4H3\/t19-,20+\/m1\/s1Key:\u00a0ORDAZKGHSNRHTD-UXHICEINBW       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4O=C2c5c(O[C@@H]3COc1cc(OC)c(OC)cc1[C@H]23)c4C=C\/C(Oc4cc5)(C)CPropertiesC23H22O6Molar mass394.42 g\/molMelting point171\u00a0\u00b0C (340\u00a0\u00b0F; 444\u00a0K)Except where otherwise noted, data are given for materials in their standard state (at 25\u00a0\u00b0C [77\u00a0\u00b0F], 100\u00a0kPa).Chemical compoundDeguelin 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.Cub\u00e9 resin, the root extract from cub\u00e9 (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) cub\u00e9 resin is no longer considered environmentally safe.Table of ContentsRat pharmacokinetics[edit]Deguelin and anti-cancer activity[edit]Deguelin and Parkinson’s disease[edit]References[edit]External links[edit]Rat pharmacokinetics[edit]Mean residence time (MRT) = 6.98 h[1]Terminal half-life (t1\/2(gamma)) = 9.26 hArea under the curve (AUC) = 57.3\u00a0ng h\/mlTotal clearance (Cl) = 4.37 L\/h per kgApparent volume of distribution (V) = 3.421 L\/kgVolume of distribution at steady-state (Vss) = 30.46 L\/kgTissue distributions after i.v. (intravenous) administration: heart > fat > mammary gland > colon > liver > kidney > brain > lung.Tissue distributions after i.g. (intragastric) administration: perirenal fat > heart > mammary gland > colon > kidney > liver > lung > brain > skin.Elimination: Within 5 days of i.g. administration, about 58.1% of the [3H]deguelin was eliminated via the feces and 14.4% via the urine. Approximately 1.7% of unchanged deguelin was found in the feces, and 0.4% in the urine.Deguelin and anti-cancer activity[edit]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.Deguelin and Parkinson’s disease[edit]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.References[edit]^ Udeani GO, Zhao GM, Shin YG,  et\u00a0al. (March 2001). “Pharmacokinetics of deguelin, a cancer chemopreventive agent in rats”. Cancer Chemother. Pharmacol. 47 (3): 263\u20138. doi:10.1007\/s002800000187. PMID\u00a011320671. S2CID\u00a06301221. Archived from the original on 2002-01-24.^ Lee HY (September 2004). “Molecular mechanisms of deguelin-induced apoptosis in transformed human bronchial epithelial cells”. Biochem. Pharmacol. 68 (6): 1119\u201324. doi:10.1016\/j.bcp.2004.05.033. PMID\u00a015313408.^ Chun KH, Kosmeder JW, Sun S,  et\u00a0al. (February 2003). “Effects of deguelin on the phosphatidylinositol 3-kinase\/Akt pathway and apoptosis in premalignant human bronchial epithelial cells”. J. Natl. Cancer Inst. 95 (4): 291\u2013302. doi:10.1093\/jnci\/95.4.291. PMID\u00a012591985.^ Caboni P, Sherer TB, Zhang N,  et\u00a0al. (November 2004). “Rotenone, deguelin, their metabolites, and the rat model of Parkinson’s disease”. Chem. Res. Toxicol. 17 (11): 1540\u20138. doi:10.1021\/tx049867r. PMID\u00a015540952.External links[edit]Fang N, Casida JE (May 1999). “Cub\u00e9 resin insecticide: identification and biological activity of 29 rotenoid constituents”. J. Agric. Food Chem. 47 (5): 2130\u20136. doi:10.1021\/jf981188x. PMID\u00a010552508.Udeani GO, Gerhauser C, Thomas CF,  et\u00a0al. (August 1997). “Cancer chemopreventive activity mediated by deguelin, a naturally occurring rotenoid”. Cancer Res. 57 (16): 3424\u20138. PMID\u00a09270008.Lee HY, Suh YA, Kosmeder JW, Pezzuto JM, Hong WK, Kurie JM (February 2004). “Deguelin-induced inhibition of cyclooxygenase-2 expression in human bronchial epithelial cells”. Clin. Cancer Res. 10 (3): 1074\u20139. doi:10.1158\/1078-0432.CCR-0833-3. PMID\u00a014871987.Fang N, Casida JE (March 1998). “Anticancer action of cub\u00e9 insecticide: correlation for rotenoid constituents between inhibition of NADH:ubiquinone oxidoreductase and induced ornithine decarboxylase activities”. Proc Natl Acad Sci USA. 95 (7): 3380\u20134. Bibcode:1998PNAS…95.3380F. doi:10.1073\/pnas.95.7.3380. PMC\u00a019844. PMID\u00a09520374.     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