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. 2019 Sep 29;17(10):563.
doi: 10.3390/md17100563.

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

Affiliations

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

Xiao-Dong Li et al. Mar Drugs. .

Abstract

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.

Keywords: Aspergillus versicolor; antimicrobial activity; bisabolane-type sesquiterpenoids; deep-sea sediment-derived fungus; monoterpenoids.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of compounds 19.
Figure 2
Figure 2
Key COSY (bold lines) and HMBC (arrows) correlations for compounds 14.
Figure 3
Figure 3
Experimental and calculated ECD spectra of compounds 1 and 2.
Figure 4
Figure 4
Key NOESY correlations (blue lines: β-orientation; blue dotted lines: α-orientation) for compounds 35.
Figure 5
Figure 5
X-ray structures of compounds 3 and 5.
Figure 6
Figure 6
Experimental and calculated ECD spectra of compounds 35.

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