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

by Xiao-Dong Li 1,2, Xiao-Ming Li 1,3,4, Xiu-Li Yin 2, Xin Li 1,3,4,* and Bin-Gui Wang 1,3,4,*
1
Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China
2
Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Chunhui Road 17, Yantai 264003, China
3
Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, Wenhai Road 1, Qingdao 266237, China
4
Center for Ocean Mega-Science, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2019, 17(10), 563; https://doi.org/10.3390/md17100563
Received: 2 September 2019 / Revised: 27 September 2019 / Accepted: 28 September 2019 / Published: 29 September 2019
(This article belongs to the Special Issue Deep-Sea Natural Products II)
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 (69), 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 14 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. View Full-Text
Keywords: deep-sea sediment-derived fungus; Aspergillus versicolor; bisabolane-type sesquiterpenoids; monoterpenoids; antimicrobial activity deep-sea sediment-derived fungus; Aspergillus versicolor; bisabolane-type sesquiterpenoids; monoterpenoids; antimicrobial activity
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Li, X.-D.; Li, X.-M.; Yin, X.-L.; Li, X.; Wang, B.-G. Antimicrobial Sesquiterpenoid Derivatives and Monoterpenoids from the Deep-Sea Sediment-Derived Fungus Aspergillus versicolor SD-330. Mar. Drugs 2019, 17, 563.

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