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Chemical examination of the EtOAc extract of the deep sea-derived fungus Penicillium sp . YPGA11 resulted in the isolation of four new farnesylcyclohexenones, peniginsengins B⁻E ( 1 ⁻ 4 ), and a known analog peniginsengin A ( 5 ). The structures of compounds 1 ⁻ 4 were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of 1 , 2 , and 4 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compounds 1 ⁻ 5 , characterized by a highly oxygenated 1-methylcyclohexene unit and a (4 E ,8 E )-4,8-dimethyldeca-4,8-dienoic acid side chain, are rarely found in nature. Compounds 2 ⁻ 4 exhibited antibacterial activity against Staphylococcus aureus .

Peniginsengins B–E, New Farnesylcyclohexenones from the Deep Sea-Derived Fungus Penicillium sp. YPGA11