Penicilazaphilone C, a new antineoplastic and antibacterial azaphilone from the Marine Fungus Penicillium sclerotiorum

Arch Pharm Res. 2016 Dec;39(12):1621-1627. doi: 10.1007/s12272-016-0828-3. Epub 2016 Sep 7.

Abstract

Two azaphilonidal derivatives [penicilazaphilones B (1) and C (2)], have been isolated from the fermented products of marine fungus strain Penicillium sclerotiorum M-22, penicilazaphilones C was a new compound. The compound's structures were identified by the analysis of spectroscopic data including 1D and 2D NMR techniques (1H-NMR, 13C-NMR, COSY, HMQC, and HMBC). Biological evaluation revealed that penicilazaphilones B and C showed selective cytotoxicity against melanoma cells B-16 and human gastric cancer cells SGC-7901 with IC50 values of 0.291, 0.449 and 0.065, 0.720 mM, respectively, while exhibiting no significant toxicity to normal mammary epithelial cells M10 at the same concentration. Moreover, penicilazaphilones C also exhibited strong antibacterial activity against Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumonia and Escherichia coli with MIC values 0.037-0.150 mM, while penicilazaphilones B's bacteriostatic action was weaker.

Keywords: Antibacterial activity; Cytotoxicity; Marine fungus; Penicilazaphilones; Penicillium sclerotiorum.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification
  • Benzopyrans / pharmacology*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Cell Survival / physiology
  • Dose-Response Relationship, Drug
  • Fungi
  • Humans
  • Melanoma, Experimental
  • Mice
  • Microbial Sensitivity Tests / methods
  • Penicillium*
  • Pigments, Biological / chemistry
  • Pigments, Biological / isolation & purification
  • Pigments, Biological / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Benzopyrans
  • Pigments, Biological
  • azaphilone