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Molecules 2018, 23(9), 2245; https://doi.org/10.3390/molecules23092245

Depsidone Derivatives and a Cyclopeptide Produced by Marine Fungus Aspergillus unguis under Chemical Induction and by Its Plasma Induced Mutant

1
Research Institute for Marine Drugs and Nutrition, College of Food Science and Technology, Guangdong Provincial Key Laboratory of Aquatic Product Processing and Safety, Guangdong Province Engineering Laboratory for Marine Biological Products, Guangdong Ocean University, Zhanjiang 524088, China
2
School of Environmental and Chemical Engineering, Dalian Jiaotong University, Dalian 116028, China
3
Shenzhen Institute of Guangdong Ocean University, Shenzhen 518120, China
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Francesco Epifano
Received: 17 August 2018 / Revised: 29 August 2018 / Accepted: 30 August 2018 / Published: 3 September 2018
(This article belongs to the Special Issue Natural Product Isolation, Identification and Biological Activity)
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Abstract

A new depsidone derivative (1), aspergillusidone G, was isolated from a marine fungus Aspergillus unguis, together with eight known depsidones (29) and a cyclic peptide (10): agonodepside A (2), nornidulin (3), nidulin (4), aspergillusidone F (5), unguinol (6), aspergillusidone C (7), 2-chlorounguinol (8), aspergillusidone A (9), and unguisin A (10). Compounds 14 and 79 were obtained from the plasma induced mutant of this fungus, while 5, 6, and 10 were isolated from the original strain under chemical induction. Their structures were identified using spectroscopic analysis, as well as by comparison with literature data. The HPLC fingerprint analysis indicates that chemical induction and plasma mutagenesis effectively influenced the secondary metabolism, which may be due to their regulation in the key steps in depsidone biosynthesis. In bioassays, compound 9 inhibited acetylcholinesterase (AChE) with IC50 in 56.75 μM. Compounds 1, 5, 7, 8, and 9 showed moderate to strong activity towards different microbes. Compounds 3, 4, and 5 exhibited potent larvicidality against brine shrimp. In docking studies, higher negative CDOCKER interaction energy and richer strong interactions between AChE and 9 explained the greater activity of 9 compared to 1. Chemical induction and plasma mutagenesis can be used as tools to expand the chemodiversity of fungi and obtain useful natural products. View Full-Text
Keywords: depsidones; Aspergillus unguis; chemical induction; plasma-induced mutant; docking depsidones; Aspergillus unguis; chemical induction; plasma-induced mutant; docking
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Yang, W.-C.; Bao, H.-Y.; Liu, Y.-Y.; Nie, Y.-Y.; Yang, J.-M.; Hong, P.-Z.; Zhang, Y. Depsidone Derivatives and a Cyclopeptide Produced by Marine Fungus Aspergillus unguis under Chemical Induction and by Its Plasma Induced Mutant. Molecules 2018, 23, 2245.

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