Rare Chromone Derivatives from the Marine-Derived Penicillium citrinum with Anti-Cancer and Anti-Inflammatory Activities

Mar Drugs. 2021 Jan 8;19(1):25. doi: 10.3390/md19010025.

Abstract

Three new and rare chromone derivatives, epiremisporine C (1), epiremisporine D (2), and epiremisporine E (3), were isolated from marine-derived Penicillium citrinum, together with four known compounds, epiremisporine B (4), penicitrinone A (5), 8-hydroxy-1-methoxycarbonyl-6-methylxanthone (6), and isoconiochaetone C (7). Among the isolated compounds, compounds 2-5 significantly decreased fMLP-induced superoxide anion generation by human neutrophils, with IC50 values of 6.39 ± 0.40, 8.28 ± 0.29, 3.62 ± 0.61, and 2.67 ± 0.10 μM, respectively. Compounds 3 and 4 exhibited cytotoxic activities with IC50 values of 43.82 ± 6.33 and 32.29 ± 4.83 μM, respectively, against non-small lung cancer cell (A549), and Western blot assay confirmed that compounds 3 and 4 markedly induced apoptosis of A549 cells, through Bcl-2, Bax, and caspase 3 signaling cascades.

Keywords: Penicillium citrinum; anti-cancer activity; anti-inflammatory activity; chromone derivatives.

MeSH terms

  • A549 Cells
  • Adult
  • Anti-Bacterial Agents / pharmacology
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Antibiotics, Antineoplastic / chemistry*
  • Antibiotics, Antineoplastic / pharmacology*
  • Caspase 3 / drug effects
  • Cell Line, Tumor
  • Chromones / chemistry*
  • Chromones / pharmacology*
  • Fermentation
  • Humans
  • In Vitro Techniques
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Neutrophils / drug effects
  • Neutrophils / metabolism
  • Penicillium / chemistry*
  • Proto-Oncogene Proteins c-bcl-2 / drug effects
  • Signal Transduction / drug effects
  • Superoxides / chemistry
  • Young Adult
  • bcl-2-Associated X Protein / drug effects

Substances

  • Anti-Bacterial Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antibiotics, Antineoplastic
  • Chromones
  • Proto-Oncogene Proteins c-bcl-2
  • bcl-2-Associated X Protein
  • Superoxides
  • CASP3 protein, human
  • Caspase 3

Supplementary concepts

  • Penicillium citrinum