RESUMO
An endophytic Cryptosporiopsis sp. was isolated from Clidemia hirta and analyzed for its secondary metabolites that lead to the isolation of three bioactive molecules. The compounds were purified from the culture broth of the fungus and their structures were determined by spectroscopic methods as (R)-5-hydroxy-2-methylchroman-4-one (1), 1-(2,6-dihydroxyphenyl)pentan-1-one (2) and (Z)-1-(2-(2-butyryl-3-hydroxyphenoxy)-6-hydroxyphenyl)-3-hydroxybut-2-en-1-one (3). Compound 1 exhibited significant cytotoxic activity against the human leukemia cell line, HL-60 with an IC50 of 4 µg/ml. This compound induced G2 arrest of the HL-60 cell cycle significantly. In addition, out of these compounds, 2 and 3 were active against several bacterial pathogens. Compound 2 was active against Bacillus cereus, Escherichia coli and Staphylococcus aureus with IC50 values varying from 18 to 30 µg/ml, and compound 3 displayed activity against Pseudomonas fluorescens with an IC50 value of 6 µg/ml. Compounds 2 and 3 are novel whereas compound 1 was reported earlier but the stereochemistry of its C-2 methyl is established for the first time.
Assuntos
Ascomicetos/química , Bactérias/efeitos dos fármacos , Butirofenonas/farmacologia , Cromonas/uso terapêutico , Leucemia/tratamento farmacológico , Melastomataceae/microbiologia , Pentanonas/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Antineoplásicos/uso terapêutico , Bacillus/efeitos dos fármacos , Produtos Biológicos/química , Produtos Biológicos/farmacologia , Produtos Biológicos/uso terapêutico , Butirofenonas/química , Butirofenonas/isolamento & purificação , Pontos de Checagem do Ciclo Celular/efeitos dos fármacos , Cromonas/química , Cromonas/isolamento & purificação , Cromonas/farmacologia , Endófitos/química , Escherichia coli/efeitos dos fármacos , Células HL-60 , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Pentanonas/química , Pentanonas/isolamento & purificação , Pseudomonas fluorescens/efeitos dos fármacos , Staphylococcus aureus/efeitos dos fármacosRESUMO
From an endophytic fungus, a close relative of Talaromyces sp., found in association with Cedrus deodara, four compounds including two new ones (2 and 4) were isolated and characterized. The structures of two compounds (1 and 4) were confirmed by X-ray crystallography. The compounds displayed a range of cytotoxicities against human cancer cell lines (HCT-116, A-549, HEP-1, THP-1, and PC-3). All the compounds were found to induce apoptosis in HL-60 cells, as evidenced by fluorescence and scanning electron microscopy studies. Also, the compounds caused significant microtubule inhibition in HL-60 cells.