Estudo químico e biológico dos fungos endofílicos associados com a espécie vegetal Alibertia macrophylla (Rubiaceae)
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Data
2009-04-17
Autores
Oliveira, Camila Martins de [UNESP]
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Editor
Universidade Estadual Paulista (Unesp)
Resumo
Este trabalho, descreve a busca de substâncias bioativas a partir do estudo químico e biológico dos extratos brutos produzidos pelos fungos endofíticos AM-01 identificado como Penicillium sp1, AM-02 e AM-03 não identificados e AM-04, também pertencente ao gênero Penicillium, que foram isolados das folhas de Alibertia macrophylla. Os fungos endofíticos isolados, foram cultivados em meio líquido MBD, e sólido (milho) a 25oC, sob agitação, e no modo estático, respectivamente. Para o meio líquido, o caldo foi separado do micélio e submetido à partição com AcOEt, fornecendo os extratos brutos após a evaporação do solvente. Para o meio sólido, foi realizado uma extração com metanol, seguido de filtração e evaporação do solvente, originando os extratos brutos. Após análises por RMN de ¹H e CLAE-DAD, os extratos brutos obtidos em milho, foram fracionados por cromatografia em coluna, seguida de separação via Cromatografia Líquida de Alta Eficiência (CLAEprep.). O extrato bruto de AM-01 (Penicillium sp1) forneceu seis substâncias da classe das isocumarinas, sendo duas inéditas. O fracionamento cromatográfico do extrato bruto de AM-02, conduziu ao isolamento de três sesquiterpenos inéditos identificados como Xylarenonas C, D e E. Também do extrato bruto de AM-02 foi isolado um composto furânico identificado como (E)-5-(1- hidroxialil)-4-(pent-1-enil)-2,5-diidrofurano-3-ácido carboxílico. O fracionamento cromatográfico de AM-04, permitiu o isolamento de um benzenóide, identificado como orcinol. O estudo químico dos extratos brutos obtidos em MBD, de AM-03 e AM-04, permitiram o isolamento das dicetopiperazinas ciclo (Pro-Try) e ciclo (L-Pro- L-Val), além da uracila. As substâncias isoladas foram identificadas por análises de RMN 1D e 2D e espectrometria de massas, bem como por comparação com dados da literatura...
This work describes the search for bioactive substances from the chemical/biological of the crude extracts produced by endophytic fungi AM-01 identified as Penicillium sp1, AM-02, AM-03 and AM-04 also belonging to the genus Penicillium isolated from the leaves of Alibertia macrophylla. The endophytic fungal isolates were grown in liquid medium and solid MBD to 25 °C under shaking and static mode, respectively. For the liquid medium the mycelium was separated from the broth and subjected to partition with AcOEt, giving the crude extracts after evaporation of the solvent. For solid medium, the extraction was performed with MeOH, followed by filtration and evaporation of the solvent yielding the crude extracts. After analysis by the ¹H NMR and HPLC-DAD, the crude extracts from maize were fractionated by chromatography on a column followed by separation using High Performance Liquid Chromatography (HPLCprep.). The crude extract of AM-01 (Penicillium sp1) provided six isocoumarins, two news. Chromatographic fractionation of the crude extract of AM-02 led to the isolation of three novel sesquiterpenes identified as Xylarenonas C, D and E and a furanic compound identified as 2,5-dihydro-5-(1-hydroxyallyl)-4-(E)-pent-1-enyl)furan-3-carboxylic acid. Chromatographic fractionation of AM-04 allowed the isolation of a benzenoid, identified as orcinol. The chemical study of AM-03 crude extracts and AM-04 cultivated in MDB allowed the isolation of diketopiperazines cyclo (Pro-Try), cyclo (L-Pro-L-Val), and uracil. The substances isolated were identified through analysis of 1H NMR, mass spectrometry and by comparison with literature data. The crude extracts and pure substances were submited for trials for antifungal agents, antioxidants, anticholinesterasic and inhibition of protease. All substances showed biological activities.
This work describes the search for bioactive substances from the chemical/biological of the crude extracts produced by endophytic fungi AM-01 identified as Penicillium sp1, AM-02, AM-03 and AM-04 also belonging to the genus Penicillium isolated from the leaves of Alibertia macrophylla. The endophytic fungal isolates were grown in liquid medium and solid MBD to 25 °C under shaking and static mode, respectively. For the liquid medium the mycelium was separated from the broth and subjected to partition with AcOEt, giving the crude extracts after evaporation of the solvent. For solid medium, the extraction was performed with MeOH, followed by filtration and evaporation of the solvent yielding the crude extracts. After analysis by the ¹H NMR and HPLC-DAD, the crude extracts from maize were fractionated by chromatography on a column followed by separation using High Performance Liquid Chromatography (HPLCprep.). The crude extract of AM-01 (Penicillium sp1) provided six isocoumarins, two news. Chromatographic fractionation of the crude extract of AM-02 led to the isolation of three novel sesquiterpenes identified as Xylarenonas C, D and E and a furanic compound identified as 2,5-dihydro-5-(1-hydroxyallyl)-4-(E)-pent-1-enyl)furan-3-carboxylic acid. Chromatographic fractionation of AM-04 allowed the isolation of a benzenoid, identified as orcinol. The chemical study of AM-03 crude extracts and AM-04 cultivated in MDB allowed the isolation of diketopiperazines cyclo (Pro-Try), cyclo (L-Pro-L-Val), and uracil. The substances isolated were identified through analysis of 1H NMR, mass spectrometry and by comparison with literature data. The crude extracts and pure substances were submited for trials for antifungal agents, antioxidants, anticholinesterasic and inhibition of protease. All substances showed biological activities.
Descrição
Palavras-chave
Quimica organica, Penicillium, Atividade biológica, Fungos endofíticos, Endophytic fungus, Penicillium
Como citar
OLIVEIRA, Camila Martins de. Estudo químico e biológico dos fungos endofílicos associados com a espécie vegetal Alibertia macrophylla (Rubiaceae). 2009. 288 f. Tese (doutorado) - Universidade Estadual Paulista, Instituto de Química, 2009.