Metabolitos aislados de raputia heptaphylla y esenbeckia alata (rutaceae) y síntesis de precursores de análogos de alcaloides quinolínicos

Carlos A. Coy Barrera, Luis E. Cuca Suárez


Abstract. Previous studies on the Esenbeckia alata and Raputia heptaphylla,

both species belonging to the Rutaceae family, have shown

important results with respect to their chemistry. These species have

secondary metabolites (coumarins and alkaloids mainly), which act as

chemotaxonomic markers. This paper presents, for the first time, the phytochemical

work and isolated metabolites in these species: four coumarins:

bergapten, xanthyletin, xanthotoxin, 3-isoprenyl-4-methoxy-coumarin;

four alkaloids: skinmianine, kokusaginine, dictamnine, and 1-methyl-2-

methoxy-4-quinolone; two lignans: sesamin and mesodihydroguaiaretic

acid; two sterols: -sitosterol, stigmasterol; and a pentacyclic triterpene:

lupeol that have been isolated from leaves of E. alata. Five alkaloids

7-methoxy-2,2-dimethyl-2,6-dihidro-piran[3,2,c] quinolin-5-one, flindersiamine,

skinmianine, kokusaginine and dictamnine that have been isolated

from leaves of R. heptaphylla. Moreover, it presents a new method by

obtaining quinolone alkaloid analogue precursors trough the condensations

of Mannich adduct vinylogous and aldehydes followed by radical

cyclization to obtain products with high regio- and stereoselectivity.


Palabras clave

Raputia, Rutaceae, Esenbeckia, quinolinic alkaloids

Texto completo:



(a) Pollio, A.; De Natale, A.; Appetiti, E.; Aliotta, G.; Touwaide, A. Journal of

Ethnopharmacology. 2008. 116. 469-482. (b) Cuca L.E. Tesis doctoral, Universidad

Nacional de Colombia. Sede Bogotá 1999. 1-5.

(a) Rios, M.; Aguilar-Guadarrama, B. Biochemical Systematics and Ecology. 2002.

977-979. (b) Rios, M.; Rosa-Alonso, E.; Aguilar-Guadarrama, B. Biochemical

Systematics and Ecology. 2002. 32. 817-821. (c) Rios, M; Delgado, G. Journal of Natural

Products. 1992. 55. 1307-1309.(d) Torres, A. Tesis de magíster, Departamento

de Química, Universidad Nacional de Colombia. 2001. 10-15.

Bakhtiar, A.; Gleye, J.; Moulios, C.; Foraste, I. Phytochemistry. 1991. 30. 3840-3841.

Rosas, L.; André, T.; Das G.F.; Fernandes, J.; Vieira, P.; Oliva, G.; Thiemann, O.

XXVI Reunião Anual Sobre Evolucão. Sistemática e Ecologia Micromoleculares

Instituto de Química. Universidade Federal Fluminense, 1 a 3 de dezembro de 2004.

Alvarez, B.; Ramon-Laca, L. Journal of Ethnopharmacology. 2005. 97. 89-95.

Ito, C.; Itoigawa, M.; Onoda, S.; Hosokawa, A.; Ruangrungsi, N.; Okuda, T.; Tokuda,

H.; Nishino, H.; Furukawa, H. Phytochemistry. 2005. 66. 567-572.

Chen, K.-S.; Chang, Y.-L.; Teng, C.-M.; Chen, C.; F.; and Wu, Y.-C. Planta Médica.

66. 80-81.

Hanawa, F.; Fokialakis, N.; Skaltsounis, A. Planta Medica. 2004. 70. 531-535.

Rahman, M., Gray, A... Phytochemistry. 2005. 13. 1601-1606.

Maximin K.; Ioset, J.; Ransijn, A.; Mauel, J.; Mavi, S.; Hostettmann, K. Phytochemistry.

65. 963-968.

Collet, I.; Benoit-Vical, F.; Mustofa, A.; Stanislas, E.; Mallie, M.; Fouraste, I. Planta

Médica. 2001. 68. 68-69.

Anaya, A.; Macias-Rubacava, M.; Cruz-Ortega, R.; García-Santana, C.; Sánchez-

Monterrubio, P.; Hernández-Bautista, B.; Mata, R. Phytochemistry. 2005. 66.


(a) Bertani, S. ; Bourdy, G. ; Landau, I. ; Robinson, J. ; Esterre, P. ; Deharo,

E. Journal of Ethnopharmacology. 2005. 98. 45-54. (b) Dolabela, M.; Oliveira, S.;

Nascimento, J.; Peres, J.M,; Wagner, H,; Povoa, M.; de Oliveira, A. Phytomedicine.

15. 367-372.

Michael, J.; Natural Products Reports. 2008. 25. 166-167.

(a) Aurrecoechea, J. M.; Gorgojo, J. M.; Saornil, C. Journal Organic Chemistry.

70. 9640-9643. (b) Aurrecoechea, J, M., Suero, R., De Torre, E.. Journal

Organic Chemistry. 2006. 71. 8767-8777.

Reviews: (a) Parsons, A. F.C.R. Academic Sciences. II. 2001, 391-400. (b) Clarck,

A.J. Journal Chemical Society. Reviews. 2002. 31. 1-12

(a) Khan, F. A.; Dash, J.Journal Organic Chemistry. 2003. 68. 4556-4559.(b) Abe,

H,; Aoyagi, S,; Kibayashi, S. Journal of the American Chemical Society. 2000. 122.


(a) Parsons,; Penckett, C.S,; Cramp, M.C,; West, R.I,; Warrington, J,; Saraiva,

M.C. Tetrahedron. 1996. 52.647-660.

Ahman, J,; Somfai, P,; Journal Chemical Society Perkin Trans I. 1994. 1072-1082.

(a) Yang, C. C,; Chang, H. T,; Fang, J.M. Journal Organic Chemistry. 1998. 58.

-3105. (b) Flanagan, S,; Harrowven, D.C,; Bradley, M. Tetrahedron Letters.


Joucla, L,; Putey, A,; Joseph, B. Tetrahedron Letters. 2005. 46, 8177-8179.

(a) Coy, C.A and Cuca, L.E. Scientia et Technica. 2007. 33. 337-338. (b) Cuca, L.E

and Coy, C.A. Biochemical Systematics and Ecology. 2007. 35. 386-388.

Hwu, J.; Tseng, W.; Gnabre, J.; Giza, P.; Huang, R. Journal of Medical Chemistry.

41. 2994-3000.

Pusset, J.; Lopez, J.; Neirabeyeh, M.; Veillon, J. Planta Medica. 1991. 57. 153-155.

Forgo, P.; Kuver, K. Steroids. 2004. 69.43-50.

Djilani, A., Legseir, B., Soulimani, R., Dicko, A., Younos, C. Journal of the Brazilian

Chemical Society, 2006. 17. 518-520.

Merck. Reactivos de Coloración para Cromatografía en Capa Fina y en Papel. E.

Merck, Darmstadt (R.F. de Alemania). 1965. 27-332.

Campbell, W,; Davidowitz, B,; Jackson, G. Phytochemistry. 1990. 4. 1304-1306.

Biavatti, M.; Vieira, P,; Da Silva, M,; Fernandes, J,; Victor, S,; Pagnocca, F,;

Albuquerque, S,; Caracelli, I,; Scpector, J. Journal of the Brazilian Chemical

Society. 2002.13. 66-70

Hon, Y., Chang, F., Lu, L., Lin, W. Tetrahedron. 1998. 5233-5246.

Ripa, L.; Hallberg, A. Journal of Organic Chemistry. 1998. 63.84- 91.

Brevion, F., Vitale, M., Fensterbank, L., Malacria, M. Tetrahedron Asymmetry.

14. 2889-2896.

Aurrecoechea, J. M.; Coy, C.A., Patiño, O. Journal of Organic Chemistry. 2008. 73,



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