Bioactive Ascochlorin Analogues from the Marine-Derived Fungus Stilbella fimetaria

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

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

6 Downloads (Pure)

Abstract

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
Volume19
Issue number2
Number of pages14
ISSN1660-3397
DOIs
Publication statusPublished - 2021

Keywords

  • Meroterpenoids
  • Ascoclhorin
  • Bioactivity
  • Dereplication
  • MS/HRMS

Fingerprint Dive into the research topics of 'Bioactive Ascochlorin Analogues from the Marine-Derived Fungus Stilbella fimetaria'. Together they form a unique fingerprint.

Cite this