New Indole Diketopiperazine Alkaloids from Soft Coral-Associated Epiphytic Fungus Aspergillus versicolor CGF 9-1-2

Chem Biodivers. 2023 Jun;20(6):e202300301. doi: 10.1002/cbdv.202300301. Epub 2023 May 17.

Abstract

Two new indole diketopiperazine alkaloids (IDAs), (+)19-epi-sclerotiamide (1) and (-)19-epi-sclerotiamide (2), along with 13 known analogs (3-15), were isolated from a soft coral-associated epiphytic fungus Aspergillus versicolor CGF 9-1-2. The structures of two new compounds were established based on the combination of HR-ESI-MS, 1D and 2D NMR spectroscopy, optical rotation measurements and quantum chemical 13 C-NMR, the absolute configurations were determined by experimental and electronic circular dichroism (ECD) calculations. The results of molecular docking showed that all the compounds had a good binding with TDP1, TDP2, TOP1, TOP2, Ache, NLRP3, EGFR, EGFR L858R, EGFR T790M and EGFR T790/L858. Biological evaluation of compounds 3, 6, 8, 11 showed that 3 exerted a strong inhibitory effect on TDP2 with a rate of 81.72 %.

Keywords: A. versicolor CGF 9-1-2; IDAs; inhibitory effect; molecular docking; soft coral-associated epiphytic fungus.

MeSH terms

  • Agaricales*
  • Animals
  • Anthozoa* / metabolism
  • Aspergillus / chemistry
  • Diketopiperazines / chemistry
  • Diketopiperazines / pharmacology
  • ErbB Receptors / metabolism
  • Indole Alkaloids / chemistry
  • Lung Neoplasms*
  • Molecular Docking Simulation
  • Molecular Structure
  • Mutation
  • Protein Kinase Inhibitors / metabolism

Substances

  • sclerotiamide
  • Diketopiperazines
  • ErbB Receptors
  • Protein Kinase Inhibitors
  • Indole Alkaloids

Supplementary concepts

  • Aspergillus versicolor