Noonindoles A-F: Rare Indole Diterpene Amino Acid Conjugates from a Marine-Derived Fungus, Aspergillus noonimiae CMB-M0339

Mar Drugs. 2022 Nov 7;20(11):698. doi: 10.3390/md20110698.

Abstract

Analytical scale chemical/cultivation profiling prioritized the Australian marine-derived fungus Aspergillus noonimiae CMB-M0339. Subsequent investigation permitted isolation of noonindoles A-F (5-10) and detection of eight minor analogues (i-viii) as new examples of a rare class of indole diterpene (IDT) amino acid conjugate, indicative of an acyl amino acid transferase capable of incorporating a diverse range of amino acid residues. Structures for 5-10 were assigned by detailed spectroscopic and X-ray crystallographic analysis. The metabolites 5-14 exhibited no antibacterial properties against G-ve and G+ve bacteria or the fungus Candida albicans, with the exception of 5 which exhibited moderate antifungal activity.

Keywords: Aspergillus noonimiae; Australia; MATRIX cultivation profiling; antifungal; indole diterpene; marine-derived fungus; microbial biodiscovery; molecular network chemical profiling; noonindole.

MeSH terms

  • Amino Acids*
  • Australia
  • Candida albicans
  • Diterpenes* / pharmacology
  • Indoles / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure

Substances

  • Amino Acids
  • Diterpenes
  • Indoles

Supplementary concepts

  • Aspergillus noonimiae

Grants and funding

This research was funded in part by the Institute for Molecular Bioscience, The University of Queensland.