RESUMO
Tripartin (1), a new dichlorinated indanone, was isolated from the culture broth of the Streptomyces sp. associated with a larva of the dung beetle Copris tripartitus Waterhouse. The planar structure of tripartin (1) was identified by the spectroscopic analyses of NMR, mass, UV, and IR data. The structure was confirmed, and the absolute configuration of 1 was determined by X-ray crystallography. Tripartin displayed specific activity as an inhibitor of the histone H3 lysine 9 demethylase KDM4 in HeLa cells.
Assuntos
Besouros/microbiologia , Histona Desmetilases/antagonistas & inibidores , Hidrocarbonetos Clorados/isolamento & purificação , Hidrocarbonetos Clorados/farmacologia , Indanos/isolamento & purificação , Indanos/farmacologia , Animais , Cristalografia por Raios X , Células HeLa , Humanos , Hidrocarbonetos Clorados/química , Indanos/química , Larva/microbiologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Streptomyces/químicaRESUMO
Bahamaolides A and B (1 and 2), two new 36-membered macrocyclic lactones, were isolated from the culture of the marine actinomycete Streptomyces sp. derived from a sediment sample collected at North Cat Cay in the Bahamas. The planar structures of 1 and 2, bearing a hexaenone and nine consecutive skipped hydroxy groups, were determined by 1D and 2D NMR, mass, IR, and UV spectra. The absolute configurations of the bahamaolides were established by combined multistep chemical reactions and spectroscopic analysis. Bahamaolide A displayed significant inhibitory activity against Candida albicans isocitrate lyase and antifungal activity against various pathogenic fungi.
Assuntos
Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Lactonas/isolamento & purificação , Lactonas/farmacologia , Macrolídeos/isolamento & purificação , Macrolídeos/farmacologia , Polienos/isolamento & purificação , Polienos/farmacologia , Streptomyces/química , Antifúngicos/química , Bahamas , Candida albicans/enzimologia , Fungos/efeitos dos fármacos , Isocitrato Liase/efeitos dos fármacos , Isocitrato Liase/metabolismo , Lactonas/química , Macrolídeos/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Polienos/químicaRESUMO
Tripartilactam, a structurally unprecedented cyclobutane-bearing tricyclic lactam metabolite, was discovered from Streptomyces sp. isolated from a brood ball of the dung beetle, Copris tripartitus. The structure of this compound was elucidated by the combination of NMR, MS, UV, and IR spectroscopy and multistep chemical derivatization. Tripartilactam was evaluated as a Na(+)/K(+) ATPase inhibitor (IC(50) = 16.6 µg/mL).
Assuntos
Besouros/microbiologia , Ciclobutanos/química , Fezes/microbiologia , Lactamas/química , Inibidores de Simportadores de Cloreto de Sódio e Potássio/química , Streptomyces/química , Animais , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Ciclobutanos/isolamento & purificação , Ciclobutanos/farmacologia , Humanos , Lactamas/isolamento & purificação , Lactamas/farmacologia , Estrutura Molecular , Inibidores de Simportadores de Cloreto de Sódio e Potássio/isolamento & purificação , Inibidores de Simportadores de Cloreto de Sódio e Potássio/farmacologia , Streptomyces/isolamento & purificaçãoRESUMO
Two new phenylpyridines, named coprismycins A and B (1 and 2), and previously reported dipyridines (3-6) were isolated from a culture of Streptomyces sp. associated with the dung beetle, Copris tripartitus. The structures of the coprismycins (1 and 2) were elucidated by the analysis of 1D and 2D NMR spectra and mass, UV, and IR spectra. Coprismycins A-B (1 and 2) and dipyridines (5 and 6) displayed comparable neuroprotective effects against MPP(+) (1-methyl-4-phenylpyrimidium)-induced neurotoxicity in neuroblastoma SH-SY5Y cells.
