RESUMO
The antibiotic elansolid C1 (8) was isolated from Chitinophaga sancti strain FxGBF13 after fermentation in the presence of anthranilic acid. Remarkably, 8 was also obtained by addition of anthranilic acid to a crude fermentation extract containing the macrolide elansolid A2 (1*). This Michael-type conjugate addition allowed us to generate 21 new derivatives of elansolid C1 (9-29) by using various nucleophiles. Biological activities of all derivatives were evaluated against Staphylococcus aureus, Micrococcus luteus, and the mouse cell line L929.
Assuntos
Antibacterianos/isolamento & purificação , Fibroblastos/efeitos dos fármacos , Macrolídeos/isolamento & purificação , Micrococcus luteus/efeitos dos fármacos , Staphylococcus aureus/efeitos dos fármacos , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Bactérias/química , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Misturas Complexas/química , Avaliação Pré-Clínica de Medicamentos , Fermentação , Macrolídeos/química , Macrolídeos/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Camundongos , Testes de Sensibilidade Microbiana , Micrococcus luteus/crescimento & desenvolvimento , Staphylococcus aureus/crescimento & desenvolvimento , ortoaminobenzoatos/químicaRESUMO
A new 12-membered macrolide, balticolid (1) was isolated from the EtOAc extract of the culture broth of fungal strain 222 belonging to the Ascomycota, which was found on driftwood collected from the coast of the Greifswalder Bodden, Baltic Sea, Germany. The structure of balticolid was determined to be (3R,11R), (4E,8E)-3-hydroxy-11-methyloxacyclododeca-4,8-diene-1,7-dione using extensive spectral data as well as the modified Mosher ester method. Balticolid (1) displayed anti-HSV-1 activity with an IC50 value of 0.45 µM.
Assuntos
Antivirais/isolamento & purificação , Ascomicetos/química , Macrolídeos/isolamento & purificação , Água do Mar/microbiologia , Antivirais/química , Antivirais/farmacologia , Herpesvirus Humano 1/efeitos dos fármacos , Macrolídeos/química , Macrolídeos/farmacologia , Microbiologia da ÁguaRESUMO
Six new naphthalenone derivatives, balticols A-F and the known metabolite altechromone A were isolated from the AcOEt extract of the culture broth of fungal strain 222 belonging to the Ascomycota, which was found on driftwood collected at the coast of the Greifswalder Bodden, Baltic Sea, Germany. All structures were elucidated on the basis of NMR spectroscopic data and mass spectrometric analyses. The balticols were found to exhibit inhibitory activity against influenza virus A and herpes simplex virus. The most potent antiviral activity was observed for balticol E with an IC(50) value of 0.01 microg/ml against Herpes simplex virus type I.