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Two new antimicrobial bisabolane-type sesquiterpenoid derivatives, ent -aspergoterpenin C (compound 1 ) and 7- O -methylhydroxysydonic acid ( 2 ), and two new butyrolactone-type monoterpenoids, pestalotiolactones C ( 3 ) and D ( 4 ), along with a known monoterpenoid pestalotiolactone A ( 5 ) and four known bisabolane sesquiterpenoids ( 6 - 9 ), were isolated and identified from the deep-sea sediment-derived fungus Aspergillus versicolor SD-330. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and the absolute configurations of the new compounds 1 - 4 were determined by the combination of NOESY and TDDFT-ECD calculations and X-ray crystallographic analysis. Additionally, we first determined and reported the absolute configuration of the known monoterpenoid pestalotiolactone A ( 5 ) through the X-ray crystallographic experiment. All of these isolated compounds were evaluated for antimicrobial activities against human and aquatic pathogenic bacteria. Compounds 1 , 2 , 6 and 9 exhibited selective inhibitory activities against zoonotic pathogenic bacteria such as Escherichia coli , Edwardsiella tarda , Vibrio anguillarum and V. harveyi , with MIC values ranging from 1.0 to 8.0 μg/mL.

Antimicrobial Sesquiterpenoid Derivatives and Monoterpenoids from the Deep-Sea Sediment-Derived Fungus Aspergillus versicolor SD-330