RESUMEN
Three new benzaldehyde derivatives, sporulosaldeins Aâ-âC (1: -3: ), and 3 new benzopyran derivatives, sporulosaldeins Dâ-âF (4: -6: ), were discovered from an endophytic fungus, Paraphaeosphaeria sp. F03, which was isolated from Paepalanthus planifolius leaves. Compounds 1: -6: were elucidated by 1- and 2-dimensional nuclear magnetic resonance experiments and high-resolution mass spectrometry analysis. The absolute configuration of compound 5: was determined through the comparison of experimental and calculated electronic circular dichroism data. Compounds 1: -6: were found to exhibit antifungal activity with minimum inhibitory concentration (MIC) values of 7.8â-â250 µg/mL and racemic mixture of compound 6: exhibited weak cytotoxicity against MCF-7 and LM3 with IC50 values of 34.4 and 39.2 µM, respectively.
Asunto(s)
Antibacterianos/farmacología , Antifúngicos/farmacología , Ascomicetos/química , Benzaldehídos/farmacología , Benzopiranos/farmacología , Citotoxinas/farmacología , Animales , Antibacterianos/química , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Benzaldehídos/química , Benzaldehídos/aislamiento & purificación , Benzopiranos/química , Benzopiranos/aislamiento & purificación , Línea Celular Tumoral , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Endófitos , Humanos , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Ratones , Pruebas de Sensibilidad Microbiana , Estructura MolecularRESUMEN
In the course of our continuous search for bioactive metabolites from endophytic fungi living in plants from the Brazilian flora, leaves of Alibertia macrophylla (Rubiaceae) were submitted to isolation of endophytes, and two species of Penicillium were isolated. The acetonitrile fraction obtained in corn from a culture of Penicillium sp. 1 afforded orcinol (1). On the other hand, Penicillium sp. 1 cultivated in potato-dextrose-broth furnished two different compounds, cyclo-(L-Pro-L-Val) (2) and uracil (3). The chromatographic fractionation of the acetonitrile fraction obtained from Penicillium sp. 2 led to three dihydroisocoumarins, 4-hydroxymellein (4), 8-methoxymellein (5) and 5-hydroxymellein (6). Compounds 5 and 6 were obtained from the Penicillium genus for the first time. Additionally, metabolites 1-6 were evaluated for their antifungal and acetylcholinesterase (AChE) inhibitory activities. The most active compounds 1 and 4 exhibited detection limits of 5.00 and 10.0 microg against Cladosporium cladosporioides and C. sphaerospermum, respectively. Compound 2 showed a detection limit of 10.0 microg, displaying potent AChE inhibitory activity.