JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 63 No 1 (2018): Journal of the Chilean Chemical Society
Original Research Papers

PRELIMINARY PHYTOCHEMICAL STUDY OF THE ECUADORIAN PLANT CROTON ELEGANS KUNTH (EUPHORBIACEAE)

Claudia Herrera
Departamento de Química y Ciencias Exactas, Universidad Técnica Particular de Loja (UTPL), Loja
Yanely Pérez
Departamento de Química y Ciencias Exactas, Universidad Técnica Particular de Loja (UTPL), Loja
Vladimir Morocho
Departamento de Química y Ciencias Exactas, Universidad Técnica Particular de Loja (UTPL), Loja
Chabaco Armijos
Departamento de Química y Ciencias Exactas, Universidad Técnica Particular de Loja (UTPL), Loja
Omar Malagón
Departamento de Química y Ciencias Exactas, Universidad Técnica Particular de Loja (UTPL), Loja
Beatriz Brito
Instituto Nacional de Investigaciones Agropecuarias (INIAP), Quito
Marcelo Tacán
Instituto Nacional de Investigaciones Agropecuarias (INIAP), Quito
Luis Cartuche
Departamento de Química y Ciencias Exactas, Universidad Técnica Particular de Loja (UTPL), Loja
Gianluca Gilardoni
Departamento de Química y Ciencias Exactas, Universidad Técnica Particular de Loja (UTPL), Loja Prometeo Project Researcher, SENESCYT, Quito
Published April 25, 2018
Keywords
  • Croton elegans,
  • alkaloid,
  • secondary metabolite,
  • Ecuador,
  • NMR,
  • mosquera,
  • friedelin,
  • cycloeucalenol,
  • ( )-pallidine,
  • ( )-O-methylpallidine
  • ...More
    Less
How to Cite
Herrera, C., Pérez, Y., Morocho, V., Armijos, C., Malagón, O., Brito, B., Tacán, M., Cartuche, L., & Gilardoni, G. (2018). PRELIMINARY PHYTOCHEMICAL STUDY OF THE ECUADORIAN PLANT CROTON ELEGANS KUNTH (EUPHORBIACEAE). Journal of the Chilean Chemical Society, 63(1). Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/590

Abstract

The species Croton elegans Kunth, belonging to the family Euphorbiaceae and known with the common name “mosquera”, is a native medicinal plant of Ecuador. Due to its medical applications, we are interested in secondary metabolite composition. After extraction with hexane and preparation of the alkaloid extract, preparative chromatographic fractionation in both normal and direct phase was performed. 1H NMR, 13C NMR, HSQC and HMBC experiments, together with polarimetric measurements, were conducted in order to characterize the purified compunds. Two triterpene metabolites (friedelin and cycloeucalenol) and two morphinan alkaloids ((+)-pallidine and (+)-O-methylpallidine) were obtained in a pure form. This work represents the first report on the phytochemistry of C. elegans and probably the second publication on the natural (+)-pallidine alkaloid.

References

  1. http://www.biodiversitya-z.org/content/megadiverse-countries.
  2. O. Malagón, J. Ramírez, J.M. Andrade, V. Morocho, C. Armijos, G. Gilardoni, Nat. Prod. Comm. 11, 297 (2016).
  3. P.M. Jørgensen, S. León-Yánez, Catalogue of the Vascular Plants of Ecuador, Missouri Botanical Garden Press, St. Louis, 1999.
  4. S. León-Yánez, R. Valencia, N. Pitman, L. Endara, C. Ulloa Ulloa, H. Navarrete (eds.) Libro rojo de las plantas endémicas del Ecuador, 2a edición. Publicaciones del Herbario QCA, Pontificia Universidad Católica del Ecuador, Quito, 2011.
  5. A. Salatino, M.L. Faria Salatino, G. Negri, J. Braz. Chem. Soc. 18, 11 (2007).
  6. H. Wagner, S. Bladt, Plant Drug Analysis - A Thin Layer Chromatography Atlas, Springer, Berlin, Heidelberg, 1996.
  7. E.J. Corey, J.J. Ursprung, J. Am. Chem. Soc. 78, 5041 (1956).
  8. Z. Wang, T. Yeats, H. Han, R. Jetter, J. Biol. Chem. 285, 29703 (2010).
  9. Y. Ding, C. Liang, J. Kim, Y.M. Lee, J.H. Hyun, H.K. Kang, J.A. Kim, B.S. Min, Y.H. Kim, Bioorg. Med. Chem. Letters 20, 1528 (2010).
  10. S. Martucciello, M.L. Balestrieri, F. Felice, C. Estevam, A.E. Goulart Sant’Ana, C. Pizza, S. Piacente, Chem. Biol. Inter. 183, 450 (2010).
  11. P. Antonisamy, V. Duraipandiyan, S. Ignacimuthu, J. Pharm. Pharmacol. 63, 1070 (2011).
  12. N. Ouédraogo, R.W. Sawadogo, A. Tibiri, C. Bayet, M. Lompo, A.E. Hay, J. Koudou, M.G. Dijoux, I.P. Guissou, Asian Pac. J. Trop. Med. , 46 (2012).
  13. E.A. Adewusi, P. Steenkamp, G. Fouche, V. Steenkamp, Nat. Prod. Comm. 8, 1213 (2013).
  14. H.F. Pi, P. Zhang, H.L. Ruan, Y.H. Zhang, H.D. Sun, J.Z. Wu, J. Asian Nat. Prod. Res. 11, 779 (2009).
  15. Y.H. Li, Y.F. Yang, K. Li, L.L. Jin, N.Y. Yang, D.Y. Kong, Chem. Pharm. Bull. 57, 401 (2009).
  16. T. Rukachaisirikul, A. Saekee, C. Tharibun, S. Watkuolham, A. Suksamrarn, Arch. Pharm. Res. 30, 1389 (2007).
  17. D. Menezes de Oliveira, W. da Nova Mussel, L.P. Duarte, G.D. Silva, H.A. Duarte, E. C. de Lima Gomes , L. Guimarães, S.A. Vieira Filho , Quim. Nova 35, 1916 (2012).
  18. T. Kikuchi, S. Kadota, K. Tsubono, Chem. Pharm. Bull. 34, 2479 (1986).
  19. K.L. Stuart, Chem. Rev. 71, 47 (1971).
  20. J. Liu, H. Wu, F. Zheng, W. Liu, F. Feng, N. Xie, J. Sep. Sci. 37, 2513 (2014).
  21. N. Ahmat Abdul Hamid, J. Latip, I.M. Said, L.B. Din, Malaysian J. Sci. 24, 33 (2005).
  22. J.P. Bartley, L.T. Baker, C.F. Carvalho, Phytochemistry 36, 1327 (1994).
  23. Z. Zhang, H.N. El Sohly, M.R. Jacob, D.S. Pasco, L.A. Walker, A.M. Clark, J. Nat. Prod. 65, 856 (2002).
  24. V. Vecchietti, C. Casagrande, G. Ferrari, B. Danieli, G. Palmisano, J. Chem. Soc. Perkin Trans. 1, 578 (1981).
  25. K.L. Stuart, C. Chambers, D. Byfield, J. Chem. Soc. (C), 1681 (1969).
  26. W.J. Eisenreich, G. Höfner, F. Bracher, Nat. Prod. Res. 17, 437 (2003).
  27. T. Kametani, M. Ihara, T. Honda, Chem Comm., 1301 (1969).
  28. X. Cheng, D. Wang, L. Jiang, D. Yang, Chem. Biodiv. 5, 1335 (2008).
  29. S.R. Hemingway, J.D. Phillipson, R. Verpoorte, J. Nat. Prod. 44, 67 (1981).
  30. M. Shamma, P. Chinnasami, S.F. Hussain, F. Khan, Phytochemistry 15, 1802 (1976).
  31. B. Franck, G. Dunkelinann, H.J. Lubs, Angew. Chem. 79, 1066 (1967).
  32. M. Bittner, M. Silva, P. Aqueveque, J. Kufer, J. Jakupovic, R. Murillo, Bol. Soc. Chil. Quim. 42, 223 (1997).
  33. M. Bittner, J. Alarcón, P. Aqueveque, J. Becerra, V. Hernández, M. Hoeneisen, M. Silva, Bol. Soc. Chil. Quim. 46, 419 (2001).

Copyright @2019 | Designed by: Open Journal Systems Chile Logo Open Journal Systems Chile Support OJS, training, DOI, Indexing, Hosting OJS

Code under GNU license: OJS PKP