Azacoccones F-H, new flavipin-derived alkaloids from an endophytic fungus Epicoccum nigrum MK214079
| Autor: | Harwoko Harwoko, Georgios Daletos, Tibor Kurtán, Elena Ancheeva, Marian Frank, Peter Proksch, Michael Feldbrügge, Jungho Lee, Werner E.G. Müller, Rainer Kalscheuer, Zhen Liu, Attila Mándi, Rudolf Hartmann |
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| Rok vydání: | 2020 |
| Předmět: |
Circular dichroism
Staphylococcus aureus Antifungal Agents Stereochemistry Ustilago Electrospray ionization Antineoplastic Agents Microbial Sensitivity Tests medicine.disease_cause 01 natural sciences Russia Minimum inhibitory concentration Mice Alkaloids Ascomycota Cell Line Tumor Drug Discovery medicine Endophytes Animals Pharmacology Biological Products biology Molecular Structure 010405 organic chemistry Chemistry Basidiomycota Absolute configuration Salix General Medicine biology.organism_classification 0104 chemical sciences Anti-Bacterial Agents Plant Leaves 010404 medicinal & biomolecular chemistry Antibacterial activity Epicoccum nigrum o-Phthalaldehyde |
| Zdroj: | Fitoterapia. 146 |
| ISSN: | 1873-6971 |
| Popis: | Three new flavipin-derived alkaloids, azacoccones F-H (1–3), along with six known compounds (4–9) were isolated from the endophytic fungus Epicoccum nigrum MK214079 associated with leaves of Salix sp. The structures of the new compounds were established by analysis of their 1D/2D nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HRESIMS) data. The absolute configuration of azacoccones F-H (1–3) was determined by comparison of experimental electronic circular dichroism (ECD) data with reported ones and biogenetic considerations. Epicocconigrone A (4), epipyrone A (5), and epicoccolide B (6) exhibited moderate antibacterial activity against Staphylococcus aureus ATCC 29213 with minimal inhibitory concentration (MIC) values ranging from 25 to 50 μM. Furthermore, epipyrone A (5) and epicoccamide A (7) displayed mild antifungal activity against Ustilago maydis AB33 with MIC values of 1.6 and 1.8 mM, respectively. Epicorazine A (8) showed pronounced cytotoxicity against the L5178Y mouse lymphoma cell line with an IC50 value of 1.3 μM. |
| Databáze: | OpenAIRE |
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