Paranazzamides A and B, new cyclic dipeptides containing a C7-prenylated tryptophan, produced by pathogenic reptile fungi Paranannizziopsis sp. UH-21

J Antibiot (Tokyo). 2024 Jul;77(7):403-411. doi: 10.1038/s41429-024-00725-3. Epub 2024 May 15.

Abstract

Two new cyclic dipeptides, paranazzamides A (1) and B (2) containing a C7-prenylated tryptophan, were isolated from a culture broth of snake fungal disease-isolate Paranannizziopsis sp. UH-21. This is the first report on the new secondary metabolites from Paranannizziopsis sp. The planar structures of 1 and 2 were elucidated using various spectroscopic techniques including MS and 1D/2D NMR. The absolute configuration of 1 was assigned by comparison with the synthesized compound. Compounds 1 and 2 exhibited no antifungal activity, no antibacterial activity, and no cytotoxic activity even at a concentration of 128 µg ml-1, whereas 1 and 2 exhibited amphotericin B potentiating activity against Candida auris in combination treatment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amphotericin B / pharmacology
  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Candida / drug effects
  • Dipeptides* / chemistry
  • Dipeptides* / isolation & purification
  • Dipeptides* / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Peptides, Cyclic* / chemistry
  • Peptides, Cyclic* / isolation & purification
  • Peptides, Cyclic* / pharmacology
  • Prenylation
  • Tryptophan* / chemistry
  • Tryptophan* / metabolism

Substances

  • Tryptophan
  • Dipeptides
  • Peptides, Cyclic
  • Antifungal Agents
  • Anti-Bacterial Agents
  • Amphotericin B