Rotenoid

Rotenoids are naturally occurring substances containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus. Rotenoids are related to the isoflavones.

Many plants in the subfamily Faboideae contain rotenoids. Rotenoids can be found in Lonchocarpus sp. Deguelin and tephrosin can be found in Tephrosia vogelii[1]. 6'-O-β-D-glucopyranosyl-12a-hydroxydalpanol can be found in the fruits of Amorpha fruticosa[2]. 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[3]. Deguelin, dehydrodeguelin, rotenol, rotenone, tephrosin and sumatrol can be found in Indigofera tinctoria[4]. 6aα,12aα-12a-hydroxyelliptone can be found in the stems of Derris trifoliata[5]. Amorphol, a rotenoid bioside can be isolated from plants of the genus Amorpha[6]. Deguelin, rotenone, elliptone and α-toxicarol can be found in the seeds of Lonchocarpus salvadorensis[7]. Clitoriacetal, stemonacetal, 6-deoxyclitoriacetal, 11-deoxyclitoriacetal, 9-demethylclitoriacetal and stemonal can be isolated from Clitoria fairchildiana[8].

References

  1. ^ 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
  2. ^ Effect of new rotenoid glycoside from the fruits of Amorpha fruticosa LINNE on the growth of human immune cells. Hak Ju Lee, Ha Young Kang, Cheol Hee Kim, Hyo Sung Kim, Min Chul Kwon, Sang Moo Kim, Il Shik Shin and Hyeon Yong Lee, Cytotechnology, Volume 52, Number 3, 219-226, doi:10.1007/s10616-006-9040-5
  3. ^ Rotenoid derivatives and other constituents of the twigs of Millettia duchesnei. François Ngandeu, Merhatibeb Bezabih, Dieudonne Ngamga, Alembert T. Tchinda, Bonaventure T. Ngadjui, Berhanu M. Abegaz, Hanh Dufat and François Tillequin, Phytochemistry, Volume 69, Issue 1, January 2008, Pages 258-263, doi:10.1016/j.phytochem.2007.05.038 PMID 17640692
  4. ^ 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. Kamal R. and Mangla M., Journal of biosciences, 1993, vol. 18, no1, pp. 93-101
  5. ^ Cancer chemopreventive activity of rotenoids from Derris trifoliata. Ito Chihiro, Itoigawa Masataka, Kojima Naoki, Tan Hugh T.W., Takayasu Junko, Tokuda Harukuni, Nishino Hoyoku and Furukawa Hiroshi, Planta medica, 2004, vol. 70, no1, pp. 8-11
  6. ^ Structure of amorphol — A rotenoid bioside from plants of the genus Amorpha. A. U. Kasymov, E. S. Kondratenko and N. K. Abubakirov, Chemistry of Natural Compounds, Volume 10, Number 4, 470-473, doi:10.1007/BF00563810
  7. ^ Rotenoids of Lonchocarpus salvadorensis: Their effectiveness in protecting seeds against bruchid predation. Nicholas Birch, Leslie Crombie and W. Mary Crombie, Phytochemistry, Volume 24, Issue 12, 26 November 1985, Pages 2881-2883, doi:10.1016/0031-9422(85)80019-4
  8. ^ Antiinflammatory activity of rotenoids from Clitoria fairchildiana. Pereira da Silva, B. and Paz Parente, J. (2002), Phytotherapy Research, 16: 87–88, doi:10.1002/ptr.807

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