New Antibacterial Thiodiketopiperazines from the Deep Sea Sediment-Derived Fungus Epicoccum nigrum SD-388

Chem Biodivers. 2020 Aug;17(8):e2000320. doi: 10.1002/cbdv.202000320. Epub 2020 Jul 20.

Abstract

Two new antibacterial thiodiketopiperazine derivatives (TDKPs), 7-dehydroxyepicoccin H and 7-hydroxyeutypellazine F, along with seven known TDKP analogs, were isolated and identified from Epicoccum nigrum SD-388, a deep-sea-sediment-derived fungus. The structures of these compounds were elucidated on the basis of detailed spectroscopic analysis. The absolute configuration of 7-dehydroxyepicoccin H was established by X-ray crystallographic analysis, while 7-hydroxyeutypellazine F was determined by ECD experiment and TDDFT-ECD calculation. The antibacterial activities against human and aquatic pathogens were evaluated. 7-Dehydroxyepicoccin H and 7-hydroxyeutypellazine F displayed inhibitory activities against aquatic pathogens Vibrio vulnificus, V. alginolyticus, and Edwardsiella tarda, with MIC values ranging from 4.0 to 8.0 μg/mL.

Keywords: Epicoccum nigrum; antibacterial activity; deep sea-derived fungus; thiodiketopiperazines.

MeSH terms

  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Ascomycota / chemistry*
  • Geologic Sediments / chemistry*
  • Microbial Sensitivity Tests
  • Piperazines / isolation & purification*
  • Piperazines / pharmacology
  • Spectrum Analysis / methods

Substances

  • Anti-Bacterial Agents
  • Piperazines

Supplementary concepts

  • Epicoccum nigrum