RESUMO
Endophytic fungi are fungi that colonize internal tissues of plants; several biologically active compounds have been isolated from these fungi. There are few studies of compounds isolated from endophytic fungi of Amazon plants. Thus, this study aimed the isolation and structural identification of ergosterol (1), ergosterol peroxide (2), mevalonolactone (3), cytochalasin B (4) and cytochalasin H (5) from Aspergillus sp. EJC 04, an endophytic fungus from Bauhinia guianensis. The cytochalasin B (4) and the diacetate derivative of cytochalasin B (4a) showed high lethality in the brine shrimp assay. This is the first occurrence of cytochalasins in Amazonian endophytic fungi from B. guianensis.
Assuntos
Artemia/efeitos dos fármacos , Aspergillus/química , Citocalasina B/toxicidade , Citocalasinas/toxicidade , Endófitos/química , Ergosterol/análogos & derivados , Fabaceae/microbiologia , Ácido Mevalônico/análogos & derivados , Acetilação , Animais , Argentina , Aspergillus/isolamento & purificação , Citocalasina B/química , Citocalasina B/isolamento & purificação , Citocalasinas/química , Citocalasinas/isolamento & purificação , Endófitos/isolamento & purificação , Ergosterol/química , Ergosterol/isolamento & purificação , Ergosterol/toxicidade , Dose Letal Mediana , Ácido Mevalônico/química , Ácido Mevalônico/isolamento & purificação , Ácido Mevalônico/toxicidade , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Espectrometria de Massas por Ionização por Electrospray , Relação Estrutura-AtividadeRESUMO
Biotransformations are reactions mediated by microorganisms, such as fungi. These bioreactions have high chemo- and stereoselectivity on organic substrates and can be applied in the search for new bioactive compounds. In this study, acanthoic acid (AA) was biotransformed using the fungus Xylaria sp., giving the novel compound 3ß,7ß-dihydroxyacanthoic acid (S1). Both the AA and the product S1 were tested against Gram-positive and Gram-negative bacteria. To identify and validate possible biological targets as enzymes or proteins involved in the activity observed in vitro, we used the molecular docking method. Hydroxylation at the C-3 and C-7 positions of the biotransformation product enhanced its activity against Escherichia coli as well as its binding affinity and interactions with superoxide dismutase 1 (SOD1; PDB ID 4A7G). Based on our results, the SOD1 enzyme was suggested to be a possible target for the antioxidant activity of product S1.
RESUMO
Los hongos endofíticos son hongos que colonizan los tejidos internos de las plantas; varios compuestos biológicamente activos se han aislado a partir de estos hongos. Existen pocos estudios de compuestos aislados de hongos endófitos de plantas amazónicas. Por lo tanto, este estudio tuvo como objetivo el aislamiento y la identificación estructural de ergosterol (1), peróxido de ergosterol (2), mevalonolactona (3), citocalasina B (4) y citocalasina H (5) a partir de Aspergillus spp. EJC 04, un hongo endofítico de Bauhinia guianensis. La citocalasina B (4) y el derivado diacetato de citocalasina B (4a) mostraron una alta letalidad en el ensayo de Artemia salina. Esta es la primera aparición de citocalasinas en hongos endófitos amazónica de B. guianensis
Endophytic fungi are fungi that colonize internal tissues of plants; several biologically active compounds have been isolated from these fungi. There are few studies of compounds isolated from endophytic fungi of Amazon plants. Thus, this study aimed the isolation and structural identification of ergosterol (1), ergosterol peroxide (2), mevalonolactone (3), cytochalasin B (4) and cytochalasin H (5) from Aspergillus sp. EJC 04, an endophytic fungus from Bauhinia guianensis. The cytochalasin B (4) and the diacetate derivative of cytochalasin B (4a) showed high lethality in the brine shrimp assay. This is the first occurrence of cytochalasins in Amazonian endophytic fungi from B. guianensis