Bioactive halogenated dihydroisocoumarins produced by the endophytic fungus Lachnum palmae isolated from Przewalskia tangutica

Phytochemistry. 2018 Apr:148:97-103. doi: 10.1016/j.phytochem.2018.01.018. Epub 2018 Feb 6.

Abstract

Guided by the UPLC-ESIMS profile, seven previously undescribed halogenated dihydroisocoumarins, palmaerones A-G, along with eleven known dihydroisocoumarins, were isolated from Lachnum palmae, an endophytic fungus from Przewalskia tangutica by exposure to a histone deacetylase inhibitor SAHA. Structures of the isolates were elucidated by analysis of their NMR, MS and optical rotation values. The antimicrobial, anti-inflammatory and cytotoxic activities of palmaerones A-G were evaluated. Palmaerones A-G showed antimicrobial activities against the strains (C. neoformans, Penicillium sp., C. albicans, B. subtilis and S. aureus), and palmaerone E exhibited potential antimicrobial activities against all the test strains with the MIC value in the range of 10-55 μg/mL. Palmaerones A and E exhibited moderate inhibitory effects on NO production in LPS-induced RAW 264.7 cells, with the IC50 values of 26.3 and 38.7 μM, respectively and no obvious toxicities were observed at 50 μM. Palmaerone E showed weak cytotoxicity against HepG2 with the IC50 value of 42.8 μM. This work provides an effective strategy for expanding natural product resource.

Keywords: Chemical epigenetic manipulation; Dihydroisocoumarins; Hyaloscyphaceae; Lachnum palmae; Przewalskia tangutica; Solanaceae.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Anti-Inflammatory Agents / pharmacology
  • Ascomycota / chemistry*
  • Coumarins / chemistry
  • Coumarins / isolation & purification*
  • Coumarins / pharmacology*
  • Hep G2 Cells
  • Histone Deacetylase Inhibitors / pharmacology
  • Humans
  • Hydrocarbons, Halogenated / chemistry
  • Hydrocarbons, Halogenated / isolation & purification*
  • Hydrocarbons, Halogenated / pharmacology*
  • Inhibitory Concentration 50
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Penicillium / chemistry
  • Solanaceae / microbiology*
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Bacterial Agents
  • Anti-Inflammatory Agents
  • Coumarins
  • Histone Deacetylase Inhibitors
  • Hydrocarbons, Halogenated