Citrifuran E-I, Five Dimeric Polyketides With Potential Anti-inflammatory Activity From Aspergillus sp. AWG 1-15
Qun-Yan Jiang1, Guo-Ping Yin1, Ran He1
1State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Bioactive Natural Product Research, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, P. R. China.
Chemistry & Biodiversity
|April 7, 2025
Summary
Five new fungal compounds, citrifurans E-I, show anti-inflammatory potential. These rare azaphilone-furanone heterodimers inhibited nitric oxide production in immune cells, indicating therapeutic promise.
Area of Science:
- Natural Product Chemistry
- Medicinal Chemistry
- Mycology
Background:
- Fungal secondary metabolites, particularly polyketides, are a rich source of novel bioactive compounds.
- Aspergillus species are known producers of diverse and complex chemical structures.
- The structural diversity of fungal polyketides offers opportunities for discovering new therapeutic agents.
Purpose of the Study:
- To isolate and characterize novel dimeric polyketides from the fungus Aspergillus sp. AWG 1-15.
- To investigate the anti-inflammatory properties of the isolated compounds.
- To elucidate the structure-activity relationship of these unique fungal metabolites.
Main Methods:
- Isolation and purification of compounds using chromatographic techniques.
- Structure elucidation employing high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and extensive nuclear magnetic resonance (NMR) spectroscopy.
- Determination of absolute configurations via electronic circular dichroism (ECD) calculations and chemical derivatization.
- In vitro anti-inflammatory assay measuring nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages.
Main Results:
- Five novel dimeric polyketides, designated citrifuran E-I (compounds 1-5), were successfully isolated.
- These compounds represent rare heterodimers of azaphilone and furanone scaffolds.
- Compounds 1-4 demonstrated moderate anti-inflammatory activity by inhibiting nitric oxide production, with IC50 values ranging from 12.6 to 37.3 µM, outperforming the positive control.
Conclusions:
- The fungus Aspergillus sp. AWG 1-15 produces unique dimeric polyketides with significant anti-inflammatory potential.
- Citrifurans E-I represent a novel class of natural products with potential for development as anti-inflammatory agents.
- Further investigation into the mechanism of action and optimization of these compounds is warranted.
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