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Three novel monomeric naphtho-γ-pyrones, peninaphones A-C (compounds 1 - 3 ), along with two known bis-naphtho-γ-pyrones (compounds 4 and 5 ) were isolated from mangrove rhizosphere soil-derived fungus Penicillium sp. HK1-22. The absolute configurations of compounds 1 and 2 were determined by electronic circular dichroism (ECD) spectra, and the structure of compound 3 was confirmed by single-crystal X-ray diffraction analysis. Compounds 4 and 5 are a pair of hindered rotation isomers. A hypothetical biosynthetic pathway for the isolated monomeric and dimeric naphtho-γ-pyrones is also discussed in this study. Compounds 1 - 3 showed antibacterial activity against Staphylococcus aureus (ATCC 43300, 33591, 29213, and 25923) with minimum inhibitory concentration (MIC) values in the range of 12.5-50 μg/mL. Compound 3 exhibited significant activity against the rice sheath blight pathogen Rhizoctonia solani .

New Naphtho-γ-Pyrones Isolated from Marine-Derived Fungus Penicillium sp. HK1-22 and Their Antimicrobial Activities