Prenylated quinolinone alkaloids and prenylated isoindolinone alkaloids from the fungus Aspergillus nidulans

Phytochemistry. 2020 Jan:169:112177. doi: 10.1016/j.phytochem.2019.112177. Epub 2019 Nov 8.

Abstract

Two undescribed prenylated quinolinone alkaloids, aspoquinolones E and F, and three undescribed prenylated isoindolinone alkaloids aspernidines F-H, were isolated from the fungus Aspergillus nidulans. Their structures and configurations were elucidated based on spectroscopic analyses and ECD spectra. Aspoquinolones E and F possess a C10 moiety with an unusual 2,2,4-trimethyl-3oxa-bicyclo[3.1.0]hexane unit, and aspernidines F-H own a C15 side chain. These compounds were evaluated for cytotoxic activities against five human cancer cell lines, compounds 1 and 5 exhibited strong inhibitory activities against A-549 and SW-480 cells with IC50 values of 3.50 and 4.77 μM, respectively.

Keywords: Aspergillus nidulans (Trichocomaceae); Cytotoxic activities; Isoindolinone; Quinolinone.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Aspergillus nidulans / chemistry*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Phthalimides / chemistry
  • Phthalimides / isolation & purification
  • Phthalimides / pharmacology*
  • Prenylation
  • Quinolones / chemistry
  • Quinolones / isolation & purification
  • Quinolones / pharmacology*
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Antineoplastic Agents
  • Phthalimides
  • Quinolones
  • phthalimidine