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Rotenoid

From Wikipedia, the free encyclopedia
Naturally occurring substance
Rotenone

Rotenoids are naturally occurring substances containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus.[1] Many haveinsecticidal andpiscicidal activity, such as the prototypical member of the family,rotenone. Rotenoids are related to theisoflavones.

Natural occurrences

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Many plants in the subfamilyFaboideae contain rotenoids. Rotenoids can be found inLonchocarpus sp.Deguelin andtephrosin can be found inTephrosia vogelii.[2]6'-O-β-D-glucopyranosyl-12a-hydroxydalpanol can be found in the fruits ofAmorpha fruticosa.[3]Elliptol,12-deoxo-12alpha-methoxyelliptone,6-methoxy-6a,12a-dehydrodeguelin,6a,12a-dehydrodeguelin,6-hydroxy-6a,12a-dehydrodeguelin,6-oxo-6a,12a-dehydrodeguelin and12a-hydroxyelliptone can be isolated from the twigs ofMillettia duchesnei.[4] Deguelin,dehydrodeguelin,rotenol,rotenone,tephrosin andsumatrol can be found inIndigofera tinctoria.[5]6aα,12aα-12a-hydroxyelliptone can be found in the stems ofDerris trifoliata.[6]Amorphol, a rotenoidbioside, can be isolated from plants of the genusAmorpha.[7] Deguelin, rotenone,elliptone andα-toxicarol can be found in the seeds ofLonchocarpus salvadorensis.[8]Clitoriacetal,stemonacetal,6-deoxyclitoriacetal,11-deoxyclitoriacetal,9-demethylclitoriacetal andstemonal can be isolated fromClitoria fairchildiana.[9]

Rotenoids can also be found in the plant familyNyctaginaceae.Mirabijalone A,B,C andD,9-O-methyl-4-hydroxyboeravinone B,boeravinone C andF, and1,2,3,4-tetrahydro-1-methylisoquinoline-7,8-diol) can be isolated from the roots ofMirabilis jalapa.[10]Boeravinones G andH are two rotenoids isolated fromBoerhavia diffusa.[11]Abronione andboeravinone C can be found in the desert annualAbronia villosa.[12] In 2015, a new rotenoid calledcrocetenone was extracted from the rhizome ofIris crocea.[13]

References

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  1. ^Rotenoids on www.chemicool.com
  2. ^Lambert, Nadine; Trouslot, Marie-France; Nef-Campa, Claudine; Chrestin, Hervé (1993). "Production of rotenoids by heterotrophic and photomixotrophic cell cultures of tephrosia vogelii".Phytochemistry.34 (6):1515–1520.doi:10.1016/S0031-9422(00)90838-0.
  3. ^Lee, Hak Ju; Kang, Ha Young; Kim, Cheol Hee; Kim, Hyo Sung; Kwon, Min Chul; Kim, Sang Moo; Shin, Il Shik; Lee, Hyeon Yong (2007)."Effect of new rotenoid glycoside from the fruits of Amorpha fruticosa LINNE on the growth of human immune cells".Cytotechnology.52 (3):219–26.doi:10.1007/s10616-006-9040-5.PMC 3449409.PMID 19002880.
  4. ^Ngandeu, François; Bezabih, Merhatibeb; Ngamga, Dieudonne; Tchinda, Alembert T.; Ngadjui, Bonaventure T.; Abegaz, Berhanu M.; Dufat, Hanh; Tillequin, François (2008). "Rotenoid derivatives and other constituents of the twigs of Millettia duchesnei".Phytochemistry.69 (1):258–63.doi:10.1016/j.phytochem.2007.05.038.PMID 17640692.
  5. ^Kamal, R.; Mangla, M. (1993). "In vivo and in vitro investigations on rotenoids from Indigofera tinctoria and their bioefficacy against the larvae of Anopheles stephensi and adults of Calmlosobruchus chinensis".Journal of Biosciences.18:93–101.doi:10.1007/BF02703041.S2CID 28058102.
  6. ^Ito, C; Itoigawa, M; Kojima, N; Tan, HT; Takayasu, J; Tokuda, H; Nishino, H; Furukawa, H (2004). "Cancer chemopreventive activity of rotenoids from Derris trifoliata".Planta Medica.70 (6):585–8.doi:10.1055/s-2004-815447.PMID 15229812.
  7. ^Kasymov, A. U.; Kondratenko, E. S.; Abubakirov, N. K. (1974). "Structure of amorphol — A rotenoid bioside from plants of the genus Amorpha".Chemistry of Natural Compounds.10 (4):470–473.doi:10.1007/BF00563810.S2CID 4821283.
  8. ^Birch, Nicholas; Crombie, Leslie; Crombie, W.Mary (1985). "Rotenoids of Lonchocarpus salvadorensis: Their effectiveness in protecting seeds against bruchid predation".Phytochemistry.24 (12):2881–2883.doi:10.1016/0031-9422(85)80019-4.
  9. ^Pereira Da Silva, Bernadete; Paz Parente, José (2002). "Antiinflammatory activity of rotenoids from Clitoria fairchildiana".Phytotherapy Research.16:87–88.doi:10.1002/ptr.807.PMID 11933150.
  10. ^Yi-Fen, Wang; Ji-Jun, Chen; Yan, Yang; Yong-Tang, Zheng; Shao-Zong, Tang; Shi-De, Luo (2002). "New Rotenoids from Roots of Mirabilis jalapa".Helvetica Chimica Acta.85 (8):2342–2348.doi:10.1002/1522-2675(200208)85:8<2342::AID-HLCA2342>3.0.CO;2-S.
  11. ^Ahmed-Belkacem, A; MacAlou, S; Borrelli, F; Capasso, R; Fattorusso, E; Taglialatela-Scafati, O; Di Pietro, A (2007). "Nonprenylated rotenoids, a new class of potent breast cancer resistance protein inhibitors".Journal of Medicinal Chemistry.50 (8):1933–8.doi:10.1021/jm061450q.PMID 17341062.
  12. ^Starks, CM; Williams, RB; Norman, VL; Lawrence, JA; Goering, MG; O'Neil-Johnson, M; Hu, JF; Rice, SM; Eldridge, GR (2011)."Abronione, a rotenoid from the desert annual Abronia villosa".Phytochemistry Letters.4 (2):72–74.doi:10.1016/j.phytol.2010.08.004.PMC 3099468.PMID 21617767.
  13. ^Bhat, G.A.; Mir, F.; Shawl, A.S.; Ganai, B.A.; Kamili, A.N.; Masood, A.; Tantry, M.A. (March 2015). "Crocetenone, a new rotenoid with an unusual trans-fused ring system from Iris crocea".Nat Prod Commun.10 (3):503–4.PMID 25924539.
Isoflavones and theirglycosides
Isoflavones
O-methylated isoflavones
Glycosides
Prenylated isoflavones
Pyranoisoflavones
Derivatives
Synthetic
Rotenoids and theirglycosides
Rotenoids
Glycosides
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