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

Org Biomol Chem. 2022 Feb 2;20(5):1031-1040. doi: 10.1039/d1ob02297k.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology*
  • Candida / drug effects
  • Cell Line, Tumor
  • Cyclohexylamines / chemical synthesis
  • Cyclohexylamines / isolation & purification
  • Cyclohexylamines / pharmacology*
  • Humans
  • Islands
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Monocyclic Sesquiterpenes / chemistry
  • Monocyclic Sesquiterpenes / isolation & purification
  • Monocyclic Sesquiterpenes / pharmacology*
  • Pacific Ocean
  • Porifera / chemistry*

Substances

  • Antifungal Agents
  • Cyclohexylamines
  • Monocyclic Sesquiterpenes