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Open AccessCommunication

Diketopiperazine and Diphenylether Derivatives from Marine Algae-Derived Aspergillus versicolor OUCMDZ-2738 by Epigenetic Activation

by Wen Liu 1,2,†, Liping Wang 2,†, Bin Wang 1, Yanchao Xu 2, Guoliang Zhu 3,4, Mengmeng Lan 3, Weiming Zhu 2,3,5,* and Kunlai Sun 1,*
1
Zhejiang Provincial Engineering Technology Research Center of Marine Biomedical Products, School of Food and Pharmacy, School of Marine Science and Technology, Zhejiang Ocean University, Zhoushan 316022, China
2
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China
3
Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
4
State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China
5
Open Studio for Druggability Research of Marine Natural Products, Pilot National Laboratory for Marine Science and Technology (Qingdao), Qingdao, 266237, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this paper.
Mar. Drugs 2019, 17(1), 6; https://doi.org/10.3390/md17010006
Received: 28 November 2018 / Revised: 17 December 2018 / Accepted: 20 December 2018 / Published: 22 December 2018
(This article belongs to the Special Issue Isolation and Structure Elucidation of Marine Secondary Metabolites)
A chemical-epigenetic method was used to enhance the chemodiversity of a marine algicolous fungus. Apart from thirteen known compounds, (+)-brevianamide R ((+)-3), (‒)-brevianamide R ((‒)-3), (+)-brevianamide Q ((+)-4), (‒)-brevianamide Q ((‒)-4), brevianamide V ((+)-5), brevianamide W ((‒)-5), brevianamide K (6), diorcinol B (7), diorcinol C (8), diorcinol E (9), diorcinol J (10), diorcinol (11), 4-methoxycarbonyldiorcinol (12), two new compounds, (+)- and (‒)-brevianamide X ((+)- and (‒)- 2)), as well as a new naturally occurring one, 3-[6-(2-methylpropyl)-2-oxo-1H-pyrazin-3-yl]propanamide (1), were isolated from chemical-epigenetic cultures of Aspergillus versicolor OUCMDZ-2738 with 10 µM vorinostat (SAHA). Compared to cultures in the same medium without SAHA, compounds 14, 8, 9, 11, and 12 were solely observed under SAHA condition. The structures of these compounds were elucidated based on spectroscopic analysis, specific rotation analysis, ECD, and X-ray crystallographic analysis. (±)-3, (±)-4, and (±)-5 were further resolved into the corresponding optically pure enantiomers and their absolute configurations were determined for the first time. Compounds 11 and 12 showed selective antibacterial against Pseudomonas aeruginosa with a minimum inhibitory concentration (MIC) of 17.4 and 13.9 μM, respectively. Compound 10 exhibited better α-glucosidase inhibitory activity than the assay control acarbose with IC50 values of 117.3 and 255.3 μM, respectively. View Full-Text
Keywords: chemical-epigenetic method; endophytic fungus; Aspergillus versicolor; enantiomer; antimicrobial activity chemical-epigenetic method; endophytic fungus; Aspergillus versicolor; enantiomer; antimicrobial activity
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MDPI and ACS Style

Liu, W.; Wang, L.; Wang, B.; Xu, Y.; Zhu, G.; Lan, M.; Zhu, W.; Sun, K. Diketopiperazine and Diphenylether Derivatives from Marine Algae-Derived Aspergillus versicolor OUCMDZ-2738 by Epigenetic Activation. Mar. Drugs 2019, 17, 6.

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