SciELO - Scientific Electronic Library Online

vol.49 issue2Interaction Parameter (Χ); Expansion Factor (ε); Steric Hindrance Factor (σ); and Shielding Function F(ξ); for the System PEA-Organic Solvents by Intrinsic Viscosity MeasurementsThe Solid-State and Solution-State Reassigned Structures of Tagitinin A, a 3,10-Epoxy-Germacrolide from Tithonia diversifolia, and the Interconversion of 3,10-Epoxy-Germacrolide Conformational Families via a Ring-Atom Flip Mechanism author indexsubject indexsearch form
Home Pagealphabetic serial listing  

Services on Demand




Related links

  • Have no similar articlesSimilars in SciELO


Journal of the Mexican Chemical Society

Print version ISSN 1870-249X

J. Mex. Chem. Soc vol.49 n.2 México  2005




New Pyrone and Quinoline Alkaloid from Almeidea rubra and their Trypanocidal Activity


Alessandra R. P. Ambrozina, Jair Mafezoli#,a, Paulo C. Vieria*,a, João B. Fernandesa, M. Fátima das G. F. da Silvaa , Javier A. Ellenab and Sérgio de Albuquerquec


a Departamento de Química, Universidade Federal de São Carlos, Rod. Washington Luiz, km 235, CP 676, 13565-905 São Carlos - SP, Brazil. # Present address: UNIFOR - CCS - Curso de Farmácia, Av. Washington Soares, 1321, CP 1258, 60811-341 Fortaleza - CE. * e-mail:

b Instituto de Física de São Carlos, Universidade de São Paulo, Av. Trabalhador São Carlense, 400, 13560-970 São Carlos - SP, Brazil

c Departamento de Análises Clínicas, Toxicológicas, Bromatológicas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Av. do Café, 14040-903 Ribeirão Preto - SP, Brazil


Received: December 2, 2004
Published on the web: April 12, 2005



The investigation of the ethyl acetate fraction of methanol extract from leaves of Almeidea rubra A. St.-Hil. (Rutaceae) afforded two new compounds 4-methoxy-6-[2-(methylamino)phenyl]-2H-pyran-2-oneand rel-(7R,8R)-8-[(E)-3-hydroxy-3-methyl-1-butenyl]-4,8-dimethoxy-5,6,7,8-tetrahydrofuro[2,3-b]quinoline-7-yl acetate, along with the known compounds arborinine, N-methyl-1-hydroxy-3-methoxyacridone, skimmianine, kokusagine, isodutaduprine, isoskimmianine, and isokokusagine. Their structures were established based on their spectral data, and for the new compounds these data are described herein. Additionally, these compounds were assayed on the tripomastigote forms of Trypanosoma cruzi showing moderate trypanocidal activity.

Keywords: Almeidea rubra, Rutaceae, alkaloids, trypanocidal activity



O estudo da fração acetato de etila do extrato metanólico das folhas de Almeidea rubra А. St.-Hil. (Rutaceae) permitiu o isolamento de duas substâncias inéditas: 4-metoxi-6-[2-(metilamino)fenil]-2H-piran-2-ona e acetato de rel-(7R,8R)-8-[(E)-3-hidroxi-3-metil-1-butenil]-4,8-dimetoxi-5,6,7,8-tetraidrofuro[2,3-b]quinolin-7-ila; e dos alcalóides arborinina, N-metil-1-hidroxi-3-metoxiacridona, esquimianina, cocusagina, isodutaduprina, isoesquimianina e isococusagina. Através da análise dos dados espectroscópicos foram estabelecidas as estruturas químicas das substâncias isoladas sendo que para os alcalóides inéditos tais dados são descritos pela primeira vez. Além disso, os ensaios bilógicos sobre as formas tripomastigotas do Trypanosoma cruzi das substâncias isoladas mostraram que elas possuem atividade tripanocida moderada.





1. Jay, M.; Gleye, J.; Bouillant, M.L.; Stanislas, E.; Moretti, C.; Phytochemistry 1979, 18, 184 ;         [ Links ] Moulis, C.; Wirasutisna, K.R.; Gleye, J.; Loiseau, P.; Stanislas, E.; Moretti, C.; Phytochemistry 1983, 22, 2095;         [ Links ] Wirasutisna, K.R.; Gleye, J.; Moulis, C.; Stanislas, E.; Moretti, C.; Phytochemistry 1986, 25, 558.         [ Links ]

2. Santos, C.S.; Januário, A.H.; Vieira, P.C.; Fernandes, J.B.; Da Silva, M.F.G.F.; Pirani, J.R.; J. Braz.. Chem. Soc. 1998, 9, 39.         [ Links ]

3. Januário, A.H.; PhD. Thesis, Universidade Federal de São Carlos, 1995; Mafezoli, J.; Ph D. Thesis, Universidade Federal de São Carlos, 2001.

4., accessed in May 2004.

5. Bergenthal, D.; Mester, I.; Rósza, Zs.; Reisch, J.; Phytochemistry 1979, 18, 161.         [ Links ]

6. Ahond, A.; Picot, F.; Potier, P.; Poupat, C.; Sévenet, T.; Phytochemistry 1978, 17, 166.         [ Links ]

7. Yajima, T.; Kato, N.; Munakata, K.; Agric. Biol. Chem. 1977, 41, 1263.         [ Links ]

8. Baudouin, G.; Tillequin, F.; Koch, M.; Pusset, J.; Sevenet, T.; J. Nat. Prod. 1981, 44, 546.         [ Links ]

9. Pizzolatti, M.G.; Luciano, C.; Monache, F.D.; Phytochemistry 2000, 55, 819.         [ Links ]

10. Dewick, P.M.; Medicinal Natural Products: A Biosynthetic Approach, John Wiley & Sons: England, 1997; Waterman, P.G.         [ Links ]; Phytochemistry 1999, 27, 395.         [ Links ]

11. Rózsa, Zs.; Rábik, M.; Szendrei, K.; Kálmán, A.; Argay, Gy.; Pelczer, I.; Aynechi, M.; Mester, I.; Reisch, J.; Phytochemistry 1986, 25, 2005.         [ Links ]

12. Ambrozin, A.R.P.; Vieira, P.C.; Fernandes, J.B.; da Silva, M.F.G.F.; de Albuquerque, S.; Mem. Inst. Oswaldo Cruz 2004, 99, 227.         [ Links ]

13. Bastos, J.K.; de Albuquerque, S.; Silva, M.L.A; Planta Med. 1999, 65, 541.         [ Links ]

14. Enraf-Nonius, 1997-2000. COLLECT. Nonius BV, Delft, The Netherlands.         [ Links ]

15. Otwinowski, Z.; Minor, W. In Methods in Enzymology; Carter-Jr., C.W.; Sweet, R.M.; eds., Academic Press: New York, 1997, p. 276, 307.         [ Links ]

16. Sheldrick, G. M.; SHELXS-97; Program for Crystal Structure Resolution; University of Göttingen, Germany, 1997.         [ Links ]

17. Sheldrick, G. M.; SHELXL-97; Programfor Crystal Structures Analysis; University of Göttingen, Germany, 1997.         [ Links ]

18. Farrugia, L.J.; J. Appl. Cryst. 1997, 30, 565.         [ Links ]

19. Farrugia, L.J.; WinGX; An Integrate System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-Ray Diffraction Data; University of Glasgow, 19972003.         [ Links ]

20. Brener, Z.; Rev. Inst. Med. Trop. S. Paulo 1962, 4, 389.         [ Links ]

Creative Commons License All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License