Further dibromotyrosine-derived metabolites from the marine sponge Aplysina caissara

Abstract

A re-investigação química do extrato bruto da esponja Aplysina caissara levou ao isolamento de cinco novos derivados da dibromotirosina, denominados agelocaissarinas A1, A2, B1, B2 e caissarina C, além dos já conhecidos fistularina-3 e 11-hidroxiaerotionina. Os compostos isolados tiveram suas estruturas determinadas pela análise de seus espectros de RMN mono-e bidimensionais, espectro de massas de alta resolução, infravermelho e ultravioleta. A configuração relativa das agelocaissarinas pôde ser estabelecida por análise dos espectros de RMN-1 H e modelagem molecular, enquanto que a configuração absoluta do sistema espiroxazolidínico da fistularina-3, da caissarina C e da 11-hidroxiaerotionina pôde ser estabelecida pela análise de seus espectros de dicroísmo circular. A fistularina-3 e a 11-hidroxiaerotionina apresentaram atividade antibiótica moderada contra várias linhagens de bactérias patogênicas.The re-investigation of the crude extract obtained from the sponge Aplysina caissara led to the isolation of five new dibromotyrosine derivatives, named agelocaissarines A1, A2, B1, B2 and caissarine C, along with the already known fistularin-3 and 11-hydroxyaerothionin. All compounds were identified by analysis of mono-and bidimensional NMR spectra, high resolution mass spectra, infrared and ultraviolet spectra. The relative stereochemistry of agelocaissarines could be established by analysis of 1 H NMR spectra and molecular modeling, while the absolute configuration of the spiroxazolidine moieties of fistularin-3, caissarine C and 11-hydroxyaerothionin was established by analysis of 1 H NMR and circular dichroism spectra. Fistularin-3 and 11-hydroxyaerothionin displayed moderate antibiotic activity against several pathogenic bacteria.

Isolamento e atividades biológicas de produtos naturais das esponjas monanchora arbuscula, aplysina sp. petromica ciocalyptoides e topsentia ophiraphidites, da ascídia didemnum ligulum e do octocoral carijoa riisei

“…O gênero Aplysina pertence à ordem Verongida, conhecido como sendo fonte de substâncias bromadas derivadas da tirosina 7 . Espécimens de Aplysina sp., recentemente descrita como sendo uma espécie nova de esponja do litoral baiano 8 , foram obtidos na Baía de Todos os Santos, Salvador (BA) em 1999.…”

“…13 sugere que esta seja um artefato de isolamento formado pela condensação do ácido correspondente com EtOH durante o processo de armazenamento. O espectro de dicroísmo circular de 4 apresentou efeito Cotton positivo em λ max 255 e 290 nm, indicando configuração absoluta 1(R), 6(S) 7 .…”

Cytotoxic effects of Fisturalin-3 and 11-Deoxyfisturalin-3 on Jurkat and U937 cell lines

“…Sponges of the Aplysinidae family are a rich source of microorganisms. They also contain high concentrations of brominated alkaloids 2,[7][8][9][10][11][12][13] . Of these alkaloids Compagnone RS et al 9 identified 11-Deoxyfistularin-3 (DF) and Fistularin (F), (the structures are illustrated in Fig.…”

“…1). The compounds have been shown to have wide biological activity including anti bacterial and anti viral effects [7][8][9][10][11][12][13] . In addition, DF has been reported to inhibit cell proliferation of MCF-7 cells with an IC 50 of 17 μM; however, the mechanism by which the decrease in cell viability occurs is not known 9 .…”

Aplysfistularine: a novel dibromotyrosine derivative isolated from Aplysina fistularis

“…16 The richest sources of biogenetically, tyrosine--derived bromo-containing amines, are members of the Verongida order, and the genus Aplysina. [17][18][19][20] Previous and recent reports of Aplysina fistularis have documented the presence of a large number of brominated metabolites including: fistularines, aerothionines, ceratinamines, aplysamines, anamonianes and psammaplysines. [21][22][23] The diversity of biological activity found in compounds isolated from marine sponges is due to the presence of bromotyrosine derivatives.…”