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Alcalóides De Annona Foetida Mart. Com Atividade Antileishmania

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Alcalóides De Annona Foetida Mart. Com Atividade Antileishmania Alcalóides de Annona foetida Mart. com atividade antileishmania Emmanoel V. Costa (PG) * 1,, Maria Lúcia B. Pinheiro (PQ)1,Clahildek M. Xavier (IC)1, Jefferson R. de A. Silva (PQ)1, Afonso D. L. Souza(PQ)1, Ana Cláudia F. Amaral (PQ)2 Francinete Campos (PG) 3. Andersson Barison (PG) 3 e Leonor L. Leon (PQ)4 1 Departamento de Química/ICE/UFAM-Manaus , 2 LQPN/FIOCRUZ/RJ, 3 UFSCar 4 IOC/FIOCRUZ/RJ [email protected] Palavras Chave: annomontina, atividade leishmanicida, Annona foetida. sugerindo a presença de um hidrogênio indólico. Este Introdução conjunto de dados levou à suposição de que se tratava de um composto com um núcleo b-carbolínico A espécie Annona foetida Mart.(Annonaceae), substituído com um fragmento C4H4N3, compatível com um grupo aminopirimidínico. Os espectros de conhecida popularmente como envira-ata ou graviola 13 15 da mata, distribui-se na Amazônia brasileira e RMN C 1D e 2D (BB, HSQC e HMBC) e de RMN N (HSQCe HMBC), aliados a comparações com dados peruana, e de acordo com a população local 3 apresenta propriedades inseticida e antiparasitária, da literatura permitiram identificar 1 como o alcalóide 2-amino pirimidino-b-carbolínico, annomontina, principalmente as sementes. Em continuação às 1 nossas investigações sobre a espécie, neste isolado anteriormente de Annona montana . EDFB-3 trabalho, relatamos o isolamento de dois alcalóides apresentou características espectrométricas tipo pirimidino-b-carbolínicos, a annomontina 1 e um similares às de 1 e se encontra em fase de derivado em fase de determinação estrutural, assim determinação estrutural.Nas investigações de como, os resultados dos ensaios destes alcalóides ativi dade biológica foram usadas formas promastigotas de Leishmania braziliensis e L. frente a formas promastigotas de Leishmania o guyanensis e L.braziliensis, principais transmissores guyanensis. Após 24 h de incubação a 26 C os parasitas foram contados em câmara de Neubauer de leishmaniose no estado do Amazonas. com auxílio de microscópio óptico e o resultado expresso como DL /24h. Annomontina apresentou Resultados e Discussão 50 pronunciada atividade leishmanicida contra L. braziliensis (DL50 = 9,1 mg/mL) e EDFB-3 apresentou As cascas do caule foram trituradas e extraídas atividade moderada (DL50 = 70,07 mg/mL). sucessivamente a frio com hexano, diclorometano e metanol. Os extratos diclometânico e metanólico, 5 4 6 5a 4a submetidos a metodologia convencional para 3 7 alcalóides, forneceu dois sólidos cristalinos, EDFB-2 N 2 8a N 1a 1 e EDFB-3, de natureza alcaloídica.O EM/ESI de 8 + EDFB-2 apresentou íon pseudo molecular [M+H] a 6' H 1' N 5' m/z 262 sugerindo a fórmula C15H11N5. O espectro no -1 IV apresentou absorções em 3346 e 3169 cm 2' 4' H2N N típicas de NH e NH2 e em 1630, 1551, 1467 e 740 -1 7' 3' cm evidenciando a natureza aromática do composto, 1 confirmada pelas absorções em lmax em 290,91, 307,50 e 389,89 nm no espectro espectro de UV. O Conclusões espectro de RMN1H em acetona apresentou sinais para oito hidrogênios aromáticos entre d 8,40- 7,10.Foram observados quatro sinais, pertencentes a A família Annonaceae é conhecida como uma rica dois conjuntos independentes de dubletos (d 8,39 e fonte de alcalóides isoquinolínicos. A.foetida é a segunda espécie a registrar ocorrência de 8,10; d 8,34 e 7,74), com constantes de acoplamento (J) em torno de 5,0 Hz, característicos de estrutura pirimidino-b-carbolínica, não se conhecendo hidrogênios a e b de anéis piridínicos.Os sinais relato deste tipo de alcalóide em outra família da registrados em d 8,16 ( d, J =7,9 1H) , 7,56 ( dl , ordem Magnoliales. Os testes biológicos confirmam a J=7,9,1H), 7,46 (ddd, J= 7,9, 7,2 e 1,0 Hz,1H) e família como promissora em compostos 7,17, ddd, J=7,9; 7,2 e 1,0 Hz,1H), caracterizaram a antileishmania. presença de anel benzenico orto-dissubstituído.O 1Leboeuf, et al 1982.Journal of the Chemical Society, Perkin espectro de RMN 1H revelou ainda mais três sinais Transactions,1, 1205-1208. RENOR/CAPES, sendo dois em 6,24 (sl,2H) confirmando a presença UFAM/CAPES do grupo NH2, e o terceiro sinal em d 11,66 (sl, 1H) . 25a Reunião Anual da Sociedade Brasileira de Química - SBQ 2.
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