RESUMO
Two new pyrroloiminoquinone alkaloids of the discorhabdin class, along with 12 compounds including one previously described synthetic derivative of the same and related skeletal classes, were isolated from the sponge Sceptrella sp., collected from Gageodo, Korea. The structures of these new compounds, designated as (-)-3-dihydrodiscorhabdin D (11) and (-)-discorhabdin Z (12), were determined by combined spectroscopic analyses. Compound 12 possesses an unusual hemiaminal group among the discorhabdin alkaloids. These compounds exhibited moderate to significant cytotoxicity, antibacterial activity, and inhibitory activity against sortase A.
Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Compostos Heterocíclicos de 4 ou mais Anéis/isolamento & purificação , Compostos Heterocíclicos de 4 ou mais Anéis/farmacologia , Poríferos/química , Quinonas/isolamento & purificação , Quinonas/farmacologia , Alcaloides/química , Aminoaciltransferases/antagonistas & inibidores , Animais , Antibacterianos/química , Antineoplásicos/química , Bacillus subtilis/efeitos dos fármacos , Proteínas de Bactérias/antagonistas & inibidores , Cisteína Endopeptidases , Ensaios de Seleção de Medicamentos Antitumorais , Escherichia coli/efeitos dos fármacos , Compostos Heterocíclicos de 4 ou mais Anéis/química , Humanos , Células K562 , Biologia Marinha , Micrococcus luteus/efeitos dos fármacos , Ressonância Magnética Nuclear Biomolecular , Proteus vulgaris/efeitos dos fármacos , Quinonas/química , Salmonella typhimurium/efeitos dos fármacos , Staphylococcus aureus/efeitos dos fármacos , EstereoisomerismoRESUMO
Five new dihydroxystyrene metabolites and six known compounds of the same structural class were isolated from an association of the sponges Poecillatra wondoensis and Jaspis sp., collected from Keomun Island, Korea. The structures of novel compounds were determined to be the sodium or N, N-dimethyl guanidinium salts of a dihydroxystyrene dimer (5) and two trimers (6, 7). Two dimers (10, 11) containing imidazole moieties were also identified on the basis of the results of combined spectroscopic analyses. Several compounds exhibited weak to moderate inhibitory effects against isocitrate lyase and sortase A enzymes derived from microorganisms.
Assuntos
Aminoaciltransferases/antagonistas & inibidores , Proteínas de Bactérias/antagonistas & inibidores , Inibidores Enzimáticos/isolamento & purificação , Isocitrato Liase/antagonistas & inibidores , Poríferos/química , Estirenos/isolamento & purificação , Animais , Cisteína Endopeptidases , Ensaios de Seleção de Medicamentos Antitumorais , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Humanos , Coreia (Geográfico) , Testes de Sensibilidade Microbiana , Estrutura Molecular , Estirenos/química , Estirenos/farmacologiaRESUMO
Four sesquiterpene glucosides were isolated from Ixeris sonchifolia Hance. The structure of a new compound (1) was assigned as 9beta-monohydroxy-2,12-dioxo-guaia-3,11(13)-dien-1alpha,5alpha,6beta,7alpha,9beta,10alphaH-12,6-olide-9-O-beta-D- glucopyranoside (ixerinoside). In addition, unambiguous and complete assignments of (1)H NMR chemical shifts for crepidiaside A (2), ixerin Z (3), and 11,13alpha-dihydroixerin Z (4) are presented. The assignments were achieved by two-dimensional NMR (gCOSY, gHSQC, gHMBC, NOESY) and one-dimensional nuclear Overhauser effect (NOE) experiments.