Pallidopenillines: Polyketides from the Alga-Derived Fungus Penicillium thomii Maire KMM 4675

J Nat Prod. 2016 Dec 23;79(12):3031-3038. doi: 10.1021/acs.jnatprod.6b00624. Epub 2016 Nov 29.

Abstract

Eleven new polyketides, pallidopenillines 1-11, were isolated from the alga-derived fungus Penicillium thomii. The structures of these compounds were established based on spectroscopic methods. The absolute configuration of pallidopenilline A (1) as 4R, 5S, 8S, 9R, 10R, 13R was established using a combination of the modified Mosher's method, X-ray analysis, and NOESY data. The absolute configurations of 2-5 were determined by time-dependent density functional theory calculations of the ECD spectra and ECD and NOESY data. It was shown that 1-acetylpallidopenilline A (2) and pallidopenilline G (10) inhibit the growth of colonies of 22Rv1 cells by 40% at 2 and 1 μM, respectively.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Drug Screening Assays, Antitumor
  • HCT116 Cells
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Penicillium / chemistry*
  • Polyketides / chemistry
  • Polyketides / isolation & purification*
  • Polyketides / pharmacology
  • Sargassum / microbiology

Substances

  • Antineoplastic Agents
  • Polyketides