RESUMO

Four diterpenes and a nor-diterpenoid, all of which possess unusual carbocyclic skeletons, were isolated from the hexane solubles of the West Indian gorgonian Pseudopterogorgia elisabethae. The structures and relative configurations of novel metabolites elisabethin D (2), elisabethin D acetate (3), 3-epi-elisabanolide (5), elisapterosin A (6), and elisapterosin B (7) were elucidated by interpretation of overall spectral data, which included 2D NMR correlation methods, IR, UV, and accurate mass measurements (HREI-MS and HRFAB-MS), chemical reactions, and X-ray diffraction analyses. The tetracyclic carbon skeleton of the elisapterosins is undescribed and constitutes a new class of C(20) rearranged diterpenes. Elisapterosin B displays strong in vitro anti-tuberculosis activity.

Assuntos

Cnidários/química , Diterpenos/química , Animais , Antituberculosos/química , Antituberculosos/isolamento & purificação , Antituberculosos/metabolismo , Antituberculosos/farmacologia , Hidrocarbonetos Aromáticos com Pontes/química , Cristalografia por Raios X , Diterpenos/isolamento & purificação , Diterpenos/metabolismo , Diterpenos/farmacologia , Humanos , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Conformação Molecular , Estrutura Molecular , Mycobacterium tuberculosis/efeitos dos fármacos , Compostos Policíclicos/química , Células Tumorais Cultivadas , Índias Ocidentais