New pentaenes from the sponge-derived marine fungus Penicillium rugulosum: structure determination and biosynthetic studies

Seven new fungal polyketides possessing linear pentaene structures ending in cyclic moieties were isolated from the mycelium extract of a marine sponge-derived Penicillium rugulosum. Feeding of 13C-labeled acetate and l-methionine was used to verify the polyketide origin of prugosene A1. It could also be shown that prugosenes B1 and C1 were formed from prugosene A1 by hydrolysis and decarboxylation of its oxabicyclo[2.2.1]heptane unit.