Dichloroisocoumarins with Potential Anti-Inflammatory Activity from the Mangrove Endophytic Fungus Ascomycota sp. CYSK-4

Mar Drugs. 2018 Feb 9;16(2):54. doi: 10.3390/md16020054.

Abstract

Three new isocoumarins-dichlorodiaportintone (1), desmethyldichlorodiaportintone (2) and desmethyldichlorodiaportinol (3)-as well as six known analogues (4-9) were isolated from the culture of the mangrove endophytic fungus Ascomycota sp. CYSK-4 from Pluchea indica. Their structures were elucidated by analysis of spectroscopic data. The absolute configuration of compounds 1 and 2 were determined by the modified Mosher's method. Compound 2 showed significant anti-inflammatory activity by inhibiting the production of NO in LPS-induced RAW 264.7 cells with IC50 value of 15.8 μM, while compounds 1, 5, and 6 exhibited weak activities with IC50 values of 41.5, 33.6, and 67.2 μM, respectively. In addition, compounds 1, 5, and 6 showed antibacterial effects against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae, and Acinetobacter calcoaceticus with the MIC values in the range of 25-50 μg·mL-1.

Keywords: Ascomycota sp.; Pluchea indica; anti-inflammatory; antibacterial; endophytic fungus; isocoumarin.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Ascomycota / chemistry*
  • Fermentation
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Isocoumarins / chemistry*
  • Isocoumarins / isolation & purification
  • Isocoumarins / pharmacology*
  • Mice
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Nitric Oxide / biosynthesis
  • RAW 264.7 Cells
  • Rhizophoraceae / microbiology*

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Isocoumarins
  • Nitric Oxide