Bioactive Ascochlorin Analogues from the Marine-Derived Fungus Stilbella fimetaria

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  • Karolina Subko
  • Sara Kildgaard
  • Francisca Vicente
  • Fernando Reyes
  • Olga Genilloud
  • Thomas O. Larsen

The marine-derived fungus Stilbella fimetaria is a chemically talented fungus producing several classes of bioactive metabolites, including meroterpenoids of the ascochlorin family. The targeted dereplication of fungal extracts by UHPLC-DAD-QTOF-MS revealed the presence of several new along with multiple known ascochlorin analogues (19-22). Their structures and relative configuration were characterized by 1D and 2D NMR. Further targeted dereplication based on a novel 1,4-benzoquinone sesquiterpene derivative, fimetarin A (22), resulted in the identification of three additional fimetarin analogues, fimetarins B-D (23-25), with their tentative structures proposed from detailed MS/HRMS analysis. In total, four new and eight known ascochlorin/fimetarin analogues were tested for their antimicrobial activity, identifying the analogues with a 5-chloroorcylaldehyde moiety to be more active than the benzoquinone analogue. Additionally, the presence of two conjugated double bonds at C-2'/C-3' and C-4'/C-5' were found to be essential for the observed antifungal activity, whereas the single, untailored bonds at C-4'/C-5' and C-8'/C-9' were suggested to be necessary for the observed antibacterial activity.

Original languageEnglish
Article number46
JournalMarine Drugs
Issue number2
Number of pages12
Publication statusPublished - 2021

    Research areas

  • ascochlorin, bioactivity, dereplication, meroterpenoids, MS/HRMS

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