Axiplyns A–E, new sesquiterpene isothiocyanates from the marine sponge Axinyssa aplysinoides

Five new isothiocyanate sesquiterpenes, designated axiplyns A–E (1–5) have been isolated, together with two known isothiocyanate sesquiterpenes (6, 7), from the sponge Axinyssa aplysinoides collected at Misali Island, Tanzania. Axiplyns 4 and 5 embody a new indane sesquiterpene skeleton, and compounds 1, 2, and 5 contain unprecedented ring systems, namely a 6,8-dioxabicyclo[3.2.1]octane and a 2-oxabicyclo[2.2.1]heptane. Axiplyns A, B, and C are potent brine shrimp toxins with LD50 values between 1.5 and 1.8 μg/mL.