6533b7d7fe1ef96bd1268f4c

RESEARCH PRODUCT

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

Harwoko HarwokoGeorgios DaletosTibor KurtánElena AncheevaMarian FrankPeter ProkschPeter ProkschMichael FeldbrüggeJungho LeeWerner E.g. MüllerRainer KalscheuerZhen LiuAttila MándiRudolf Hartmann

subject

Circular dichroismStaphylococcus aureusAntifungal AgentsStereochemistryUstilagoElectrospray ionizationAntineoplastic AgentsMicrobial Sensitivity Testsmedicine.disease_cause01 natural sciencesRussiaMinimum inhibitory concentrationMiceAlkaloidsAscomycotaCell Line TumorDrug DiscoverymedicineEndophytesAnimalsPharmacologyBiological ProductsbiologyMolecular Structure010405 organic chemistryChemistryBasidiomycotaAbsolute configurationSalixGeneral Medicinebiology.organism_classification0104 chemical sciencesAnti-Bacterial AgentsPlant Leaves010404 medicinal & biomolecular chemistryStaphylococcus aureusAntibacterial activityEpicoccum nigrumo-Phthalaldehyde

description

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.

yearjournalcountryeditionlanguage
2020-10-01Fitoterapia
10.1016/j.fitote.2020.104698https://pubmed.ncbi.nlm.nih.gov/32745508