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Published on: May 16, 2020
Antimicrobial metabolites from the marine-derived fungus Aspergillus sp. ZZ1861
Yura Ha1, Yufang Zhou2, Mingzhu Ma2
1Ocean College, Zhoushan Campus, Zhejiang University, Zhoushan, 316021, China.
Abstract:
Fungi from the genus Aspergillus are important resources for the discovery of bioactive agents. This investigation characterized the isolation, structural elucidation, and antimicrobial evaluation of 46 metabolites produced by the marine-derived fungus Aspergillus sp. ZZ1861 in rice solid and potato dextrose broth liquid media. The structures of these isolated compounds were determined based on their HRESIMS data, NMR spectral analyses, and data from ECD, NMR, and optical rotation calculations. Emericelactones F and G, 20R,25S-preshamixanthone, 20R,25R-preshamixanthone, phthalimidinic acid A, phthalimidinic acid B, aspergilol G, and 2-hydroxyemodic amide are eight previously undescribed compounds and (S)-2-(5-hydroxymethyl-2-formylpyrrol-1-yl) propionic acid lactone is reported from a natural resource for the first time. It is also the first report of the configurations of 25S-O-methylarugosin A, 25R-O-methylarugosin A, 5R-(+)-9-hydroxymicroperfuranone, and 5R-(+)-microperfuranone. Phthalimidinic acid A, phthalimidinic acid B, aspergilol G, and 2-hydroxyemodic amide have antifungal activity against Candida albicans with MIC values of 1.56, 3.12, 1.56, and 12.5 μg/mL, respectively, 20R,25S-preshamixanthone (MIC 25 μg/mL) shows antibacterial activity against Escherichia coli, and 20R,25R-preshamixanthone exhibits antimicrobial activity against all three tested pathogens of methicillin-resistant Staphylococcus aureus, E. coli, and C. albicans with MIC values of 50, 25, 25 μg/mL, respectively.
Insights
Marine fungus Aspergillus sp. ZZ1861 yielded 46 bioactive metabolites, including eight new compounds. Several compounds showed significant antifungal and antibacterial activities against pathogens like Candida albicans and Escherichia coli.
Area of Science:
- Marine natural products chemistry
- Mycology
- Medicinal chemistry
Background:
- Fungi, particularly from the genus Aspergillus, are a rich source of novel bioactive compounds.
- Marine-derived microorganisms offer unique chemical diversity for drug discovery.
Purpose of the Study:
- To isolate, elucidate the structures of, and evaluate the antimicrobial potential of metabolites from the marine fungus Aspergillus sp. ZZ1861.
- To identify new bioactive natural products for potential therapeutic applications.
Main Methods:
- Cultivation of Aspergillus sp. ZZ1861 in solid rice and liquid potato dextrose broth media.
- Structure determination using High-Resolution Electrospray Ionization Mass Spectrometry (HRESIMS), Nuclear Magnetic Resonance (NMR) spectral analyses, Electronic Circular Dichroism (ECD), and optical rotation calculations.
- Antimicrobial activity assessment using Minimum Inhibitory Concentration (MIC) assays against selected pathogens.
Main Results:
- Isolation and characterization of 46 metabolites, including eight previously undescribed compounds: Emericelactones F and G, 20R,25S-preshamixanthone, 20R,25R-preshamixanthone, phthalimidinic acid A, phthalimidinic acid B, aspergilol G, and 2-hydroxyemodic amide.
- First report of (S)-2-(5-hydroxymethyl-2-formylpyrrol-1-yl) propionic acid lactone from a natural source and the configurations of several other compounds.
- Phthalimidinic acid A, phthalimidinic acid B, and aspergilol G exhibited potent antifungal activity against Candida albicans (MICs 1.56–3.12 μg/mL).
- 20R,25S-preshamixanthone showed antibacterial activity against Escherichia coli (MIC 25 μg/mL).
- 20R,25R-preshamixanthone displayed broad-spectrum antimicrobial activity against methicillin-resistant Staphylococcus aureus, E. coli, and C. albicans (MICs 25–50 μg/mL).
Conclusions:
- The marine-derived fungus Aspergillus sp. ZZ1861 is a prolific source of structurally diverse metabolites with significant antimicrobial properties.
- New compounds like phthalimidinic acids A and B, aspergilol G, and 20R,25R-preshamixanthone demonstrate potential as leads for developing new antifungal and antibacterial agents.
