Hemiacetalmeroterpenoids A-C and Astellolide Q with Antimicrobial Activity from the Marine-Derived Fungus Penicillium sp. N-5.

Four new compounds including three andrastin-type meroterpenoids hemiacetalmeroterpenoids A-C ( 1 - 3 ), and a drimane sesquiterpenoid astellolide Q ( 15 ), together with eleven known compounds ( 4 - 14 ) were isolated from the cultures of the marine-derived fungus Penicillium sp. N-5, while compound 14 was first isolated from a natural source. The structures of the new compounds were determined by analysis of detailed spectroscopic data, and the absolute configurations were further decided by a comparison of the experimental and calculated ECD spectra. Hemiacetalmeroterpenoid A ( 1 ) possesses a unique and highly congested 6,6,6,6,5,5-hexa-cyclic skeleton. Moreover, the absolute configuration of compound 14 was also reported for the first time. Compounds 1 , 5 and 10 exhibited significant antimicrobial activities against Penicillium italicum and Colletrichum gloeosporioides with MIC values ranging from 1.56 to 6.25 μg/mL.