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Depsidone Derivatives and a Cyclopeptide Produced by Marine Fungus Aspergillus unguis under Chemical Induction and by Its Plasma Induced Mutant.
- Source :
-
Molecules (Basel, Switzerland) [Molecules] 2018 Sep 03; Vol. 23 (9). Date of Electronic Publication: 2018 Sep 03. - Publication Year :
- 2018
-
Abstract
- A new depsidone derivative ( 1 ), aspergillusidone G, was isolated from a marine fungus Aspergillus unguis , together with eight known depsidones ( 2 ‒ 9 ) 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 1 ‒ 4 and 7 ‒ 9 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 IC <subscript>50</subscript> 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.
- Subjects :
- Acetylcholinesterase chemistry
Acetylcholinesterase metabolism
Anti-Infective Agents chemistry
Anti-Infective Agents pharmacology
Aspergillus metabolism
Candida albicans drug effects
Cholinesterase Inhibitors chemistry
Cholinesterase Inhibitors pharmacology
Depsides chemistry
Depsides pharmacology
Microbial Sensitivity Tests
Models, Molecular
Molecular Docking Simulation
Molecular Structure
Mutation
Peptides, Cyclic chemistry
Peptides, Cyclic pharmacology
Plasma Gases pharmacology
Secondary Metabolism
Staphylococcus aureus drug effects
Vibrio parahaemolyticus drug effects
Anti-Infective Agents isolation & purification
Aspergillus genetics
Cholinesterase Inhibitors isolation & purification
Depsides isolation & purification
Peptides, Cyclic isolation & purification
Subjects
Details
- Language :
- English
- ISSN :
- 1420-3049
- Volume :
- 23
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- Molecules (Basel, Switzerland)
- Publication Type :
- Academic Journal
- Accession number :
- 30177651
- Full Text :
- https://doi.org/10.3390/molecules23092245