Secondary Metabolites with Nitric Oxide Inhibition from Marine-Derived Fungus Alternaria sp. 5102

Mar Drugs. 2020 Aug 14;18(8):426. doi: 10.3390/md18080426.

Abstract

Two new benzofurans, alternabenzofurans A and B (1 and 2) and two new sesquiterpenoids, alternaterpenoids A and B (3 and 4), along with 18 known polyketides (5-22), were isolated from the marine-derived fungus Alternaria sp. 5102. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HR-ESIMS, and ECD) and X-ray crystallography, as well as the modified Mosher's method. Compounds 2, 3, 5, 7, 9-18, and 20-22 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50 values in the range from 1.3 to 41.1 μM. Structure-activity relationships of the secondary metabolites were discussed.

Keywords: Alternaria; anti-inflammatory; marine-derived fungus; secondary metabolites.

MeSH terms

  • Alternaria / metabolism*
  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Benzofurans / isolation & purification
  • Benzofurans / pharmacology
  • Dose-Response Relationship, Drug
  • Down-Regulation
  • Inhibitory Concentration 50
  • Macrophages / drug effects*
  • Macrophages / metabolism
  • Mice
  • Molecular Structure
  • Nitric Oxide / metabolism*
  • Polyketides / isolation & purification
  • Polyketides / pharmacology
  • RAW 264.7 Cells
  • Secondary Metabolism
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents
  • Benzofurans
  • Polyketides
  • Sesquiterpenes
  • Nitric Oxide