RESUMO
A unique cytotoxic metabolite, turbinamide (1), has been isolated from the marine tunicate Sidnyum turbinatum through a bioassay-guided approach. Its structure has been elucidated by an extensive spectroscopic analysis. Turbinamide demonstrated a strong and selective cytotoxic effect against neuronal cells rather than immune system cells. Structure: see text.
Assuntos
Alcanos/isolamento & purificação , Amidas/isolamento & purificação , Antineoplásicos/isolamento & purificação , Urocordados/química , Alcanos/química , Alcanos/farmacologia , Amidas/química , Amidas/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Humanos , Camundongos , Monócitos/efeitos dos fármacos , Neurônios/efeitos dos fármacos , Ressonância Magnética Nuclear Biomolecular , Ratos , Células Tumorais Cultivadas/efeitos dos fármacosRESUMO
In addition to the known sodium 3,7,11,15-tetramethylhexadeca-1,19-diyl sulfate (4), the BuOH extract of the Mediterranean tunicate Sidnyum turbinatum was shown to contain four new metabolites: 1-heptadecanyl sulfate (1), 1-octadecanyl sulfate (2), sodium (2S)-2,6,10,14-tetramethylpentadeca-1,18-diyl sulfate (3), and 1-hexyl sulfate (5). Their structures were determined by spectroscopic and chemical methods. Compounds 1-5 exhibited in vitro antiproliferative activity estimated on the WEHI 164 cell line.
Assuntos
Sulfatos/metabolismo , Urocordados/metabolismo , Animais , Divisão Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Fibrossarcoma/metabolismo , Espectroscopia de Ressonância Magnética , Mercaptopurina , Camundongos , Modelos Químicos , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Sulfatos/farmacologia , Células Tumorais Cultivadas , Urocordados/químicaRESUMO
Three sulfated alkene and alkanes-(R)-2,6-dimethylheptyl sulfate (1), 6-methylheptyl sulfate (2a), and (E)-5-octenyl sulfate (3a)-with cytotoxic activity in vitro, have been isolated from the Mediterranean ascidian Halocynthia papillosa. The structures of the new compounds 2a and 3a have been elucidated by spectroscopic analysis.
