A New Brominated Isocoumarin from the Marine Starfish-Associated Fungus Aspergillus sp. WXF1904

Chem Biodivers. 2024 Feb;21(2):e202301706. doi: 10.1002/cbdv.202301706. Epub 2023 Dec 15.

Abstract

Based on the one strain many compounds strategy, a new brominated isocoumarin, 5-bromo-6,8-dihydroxy-3,7-dimethylisocoumarin (1), along with four new natural products, methyl 3-bromo-2,4-dihydroxy-6-methylbenzoate (2), methyl 2-bromo-4,6-dihydroxybenzoate (3), (E)-3-(3-bromo-4-hydroxyphenyl) acrylic acid (4) and 4-hydroxy-3-methyl-6-phenyl-2H-pyran-2-one (5), and four known compounds, methyl orsellinate (6), 4-hydroxy-3-methyl-6-(1-methyl-1-propenyl)-2H-pyran-2-one (7), pilobolusate (8) and cis-ferulic acid (9), were isolated from the ethyl acetate extract of the fungus Aspergillus sp. WXF1904 under the condition of adding bromine salt to the production medium. The structures of the new compounds were established by analysis of NMR and MS data. Compounds (1-9) were evaluated for inhibitory activity of acetylcholinesterase and pancreatic lipase, the new compound 1, known compounds 6 and 7 displayed weak inhibitory activity against acetylcholinesterase, compounds 2, 5, 7 and 8 showed weak inhibitory activity against pancreatic lipase.

Keywords: Aspergillus sp. WXF1904; bromine salt; isocoumarin; secondary metabolite; starfish-associated fungus.

MeSH terms

  • Acetylcholinesterase*
  • Aspergillus / chemistry
  • Benzoates / chemistry
  • Fungi
  • Isocoumarins* / chemistry
  • Lipase
  • Molecular Structure

Substances

  • Acetylcholinesterase
  • Isocoumarins
  • Lipase
  • Benzoates