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Journal of the Mexican Chemical Society

Print version ISSN 1870-249X

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

 

Article

 

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: paulo@dq.ufscar.br

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

 

Abstract

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

 

Resumo

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.

 

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