Aplysqualenols A and B: Squalene‐Derived Polyethers with Antitumoral and Antiviral Activity from the Caribbean Sea Slug <i>Aplysia dactylomela</i>

Abstract

The novel bromotriterpene polyethers aplysqualenol A (<b>1</b>) and aplysqualenol B (<b>2</b>) have been isolated from the Caribbean sea slug <i>Aplysia dactylomela</i> collected in Puerto Rico, and their structures and relative configurational assignments established from spectroscopic data aided by quantum mechanical calculations of NMR chemical shifts. Although both these compounds may be conceived as polyoxycyclic derivatives of the C30 squalene skeleton, remarkably <b>1</b> and <b>2</b> possess an unprecedented C15 to C24 flexible chain of 14<i>S</i>* spatial disposition that contains a unique ether bridge between C16 and C19. Biological activity screening tests revealed that, although aplysqualenol A (<b>1</b>) does not have significant anti-infective properties, it possesses potent antitumoral and antiviral activities.