Azacoccones F-H, new flavipin-derived alkaloids from an endophytic fungus Epicoccum nigrum MK214079.

Abstract

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.

• Authors: Harwoko Harwoko, Jungho Lee, Rudolf Hartmann, Attila Mándi, Tibor Kurtán, Werner E G Müller, Michael Feldbrügge, Rainer Kalscheuer, Elena Ancheeva, Georgios Daletos, Marian Frank, Zhen Liu, Peter Proksch
• Journal: Fitoterapia (Fitoterapia) Vol. 146 Pg. 104698 (Oct 2020) ISSN: 1873-6971 [Electronic] Netherlands
• PMID: 32745508 (Publication Type: Journal Article)
• Copyright: Copyright © 2020 Elsevier B.V. All rights reserved.

Chemical References

• Alkaloids
• Anti-Bacterial Agents
• Antifungal Agents
• Antineoplastic Agents
• Biological Products
• flavipin
• o-Phthalaldehyde

Topics

• Alkaloids (isolation & purification, pharmacology)
• Animals
• Anti-Bacterial Agents (isolation & purification, pharmacology)
• Antifungal Agents (isolation & purification, pharmacology)
• Antineoplastic Agents (isolation & purification, pharmacology)
• Ascomycota (chemistry)
• Basidiomycota
• Biological Products (isolation & purification, pharmacology)
• Cell Line, Tumor
• Endophytes (chemistry)
• Mice
• Microbial Sensitivity Tests
• Molecular Structure
• Plant Leaves (microbiology)
• Russia
• Salix (microbiology)
• Staphylococcus aureus (drug effects)
• o-Phthalaldehyde (analogs & derivatives, isolation & purification, pharmacology)