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Open AccessArticle

New Thiodiketopiperazine and 3,4-Dihydroisocoumarin Derivatives from the Marine-Derived Fungus Aspergillus terreus

1
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, China
2
Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237, China
3
Institute of Oceanography, Minjiang University, Fuzhou 350108, China
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2020, 18(3), 132; https://doi.org/10.3390/md18030132
Received: 7 February 2020 / Revised: 24 February 2020 / Accepted: 24 February 2020 / Published: 26 February 2020
(This article belongs to the Special Issue Bioactive Molecules from Marine Microorganisms)
Aspergillus terreus has been reported to produce many secondary metabolites that exhibit potential bioactivities, such as antibiotic, hypoglycemic, and lipid-lowering activities. In the present study, two new thiodiketopiperazines, emestrins L (1) and M (2), together with five known analogues (37), and five known dihydroisocoumarins (812), were obtained from the marine-derived fungus Aspergillus terreus RA2905. The structures of the new compounds were elucidated by analysis of the comprehensive spectroscopic data, including high-resolution electrospray ionization mass spectrometry (HRESIMS), one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR), and electronic circular dichroism (ECD) data. This is the first time that the spectroscopic data of compounds 3, 8, and 9 have been reported. Compound 3 displayed antibacterial activity against Pseudomonas aeruginosa (minimum inhibitory concentration (MIC) = 32 μg/mL) and antifungal activity against Candida albicans (MIC = 32 μg/mL). In addition, compound 3 exhibited an inhibitory effect on protein tyrosine phosphatase 1 B (PTP1B), an important hypoglycemic target, with an inhibitory concentration (IC)50 value of 12.25 μM. View Full-Text
Keywords: marine-derived fungus; Aspergillus terreus; thiodiketopiperazines; dihydroisocoumarins marine-derived fungus; Aspergillus terreus; thiodiketopiperazines; dihydroisocoumarins
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Wu, J.-S.; Shi, X.-H.; Yao, G.-S.; Shao, C.-L.; Fu, X.-M.; Zhang, X.-L.; Guan, H.-S.; Wang, C.-Y. New Thiodiketopiperazine and 3,4-Dihydroisocoumarin Derivatives from the Marine-Derived Fungus Aspergillus terreus. Mar. Drugs 2020, 18, 132.

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