Antifungal mono- and dimeric nitrogenous bisabolene derivatives from a sponge in the order Bubarida from Futuna Islands

An abundant sponge of the order Bubarida was selected for further chemical investigation following biological and chemical screening of sponges collected from Futuna Islands in the Indo-Pacific. Ten new nitrogenous bisabolene derivatives were isolated and identified: the monomeric theonellin formamide analogues named bubaridins A-F (1-6) with unusual oxidised linear chains, and the first isocyanide/formamide dimeric and cyclised bisabolenes 7-9. The structure elucidation of these nitrogenous bisabolenes involved HRESIMS, NMR, and ECD analyses, and the chiral compounds were found to be racemates. A biosynthetic hypothesis for the production of these metabolites is proposed and some chemotaxonomic considerations are discussed. Furthermore, the antimicrobial and antitumoral activity were evalutated and the trans-dimer theonellin isocyanide (7) was shown to exhibit potent and selective antifungal activity.

Automated summary

In this study, ten new nitrogenous bisabolene derivatives were isolated from a sponge collected from the Futuna Islands. These compounds include monomeric theonellin formamide analogues with unusual oxidised linear chains and the first isocyanide/formamide dimeric and cyclised bisabolenes. The structure elucidation involved various analysis methods, and a biosynthetic hypothesis was proposed. The antimicrobial and antitumoral activity of these compounds were evaluated, and the trans-dimer theonellin isocyanide was shown to exhibit potent and selective antifungal activity.