Rotenoid

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

Natural occurrences[edit]

Many plants in the subfamily Faboideae contain rotenoids. Rotenoids can be found in Lonchocarpus sp. Deguelin and tephrosin can be found in Tephrosia vogelii.[2] 6'-O-β-D-glucopyranosyl-12a-hydroxydalpanol can be found in the fruits of Amorpha 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 and 12a-hydroxyelliptone can be isolated from the twigs of Millettia duchesnei.[4] Deguelin, dehydrodeguelin, rotenol, rotenone, tephrosin and sumatrol can be found in Indigofera tinctoria.[5] 6aα,12aα-12a-hydroxyelliptone can be found in the stems of Derris trifoliata.[6] Amorphol, a rotenoid bioside, can be isolated from plants of the genus Amorpha.[7] Deguelin, rotenone, elliptone and α-toxicarol can be found in the seeds of Lonchocarpus salvadorensis.[8] Clitoriacetal, stemonacetal, 6-deoxyclitoriacetal, 11-deoxyclitoriacetal, 9-demethylclitoriacetal and stemonal can be isolated from Clitoria fairchildiana.[9]

Rotenoids can also be found in the plant family Nyctaginaceae. Mirabijalone A, B, C and D, 9-O-methyl-4-hydroxyboeravinone B, boeravinone C and F, and 1,2,3,4-tetrahydro-1-methylisoquinoline-7,8-diol) can be isolated from the roots of Mirabilis jalapa.[10] Boeravinones G and H are two rotenoids isolated from Boerhavia diffusa.[11] Abronione and boeravinone C can be found in the desert annual Abronia villosa.[12] In 2015, a new rotenoid called crocetenone was extracted from the rhizome of Iris crocea.[13]

References[edit]

  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 3449409Freely accessible. 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. 
  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. 
  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. 
  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 3099468Freely accessible. 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.