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Diketopiperazine and Diphenylether Derivatives from Marine Algae-Derived Aspergillus versicolor OUCMDZ-2738 by Epigenetic Activation
- Source :
- Marine Drugs, Vol 17, Iss 1, p 6 (2018), Marine Drugs
- Publication Year :
- 2018
- Publisher :
- MDPI AG, 2018.
-
Abstract
- 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 1–4, 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.
- Subjects :
- Stereochemistry
Pharmaceutical Science
Diketopiperazines
Microbial Sensitivity Tests
010402 general chemistry
Crystallography, X-Ray
01 natural sciences
Methylation
Epigenesis, Genetic
chemistry.chemical_compound
Minimum inhibitory concentration
Inhibitory Concentration 50
Ulva
Algae
enantiomer
Drug Discovery
Ic50 values
Brevianamide
Glycoside Hydrolase Inhibitors
Pharmacology, Toxicology and Pharmaceutics (miscellaneous)
lcsh:QH301-705.5
Enzyme Assays
Biological Products
Vorinostat
endophytic fungus
antimicrobial activity
biology
Molecular Structure
010405 organic chemistry
Communication
Phenyl Ethers
Stereoisomerism
alpha-Glucosidases
Chemical Engineering
biology.organism_classification
Propanamide
0104 chemical sciences
Anti-Bacterial Agents
Biosynthetic Pathways
Aspergillus
chemistry
lcsh:Biology (General)
Fermentation
Pseudomonas aeruginosa
Aspergillus versicolor
Specific rotation
chemical-epigenetic method
Enantiomer
Subjects
Details
- Language :
- English
- ISSN :
- 16603397
- Volume :
- 17
- Issue :
- 1
- Database :
- OpenAIRE
- Journal :
- Marine Drugs
- Accession number :
- edsair.doi.dedup.....c256b995e9f8ad15d66a3b6e6f326661