Enantiomeric Polyketides from the Starfish-Derived Symbiotic Fungus Penicillium sp. GGF16-1-2

Chem Biodivers. 2019 Jun;16(6):e1900052. doi: 10.1002/cbdv.201900052. Epub 2019 May 7.

Abstract

One new racemic mixture, penicilliode A (1) and four pairs of enantiomeric polyketides, penicilliode B and C (2 and 3) and coniochaetone B and C (4 and 5), were obtained from the starfish-derived symbiotic fungus Penicillium sp. GGF16-1-2. Interestingly, the strain GGF16-1-2 can produce enantiomers. The absolute configuration of 1 was determined by X-ray diffraction (XRD) analysis, and the absolute configurations of 2-4 were determined by the optical rotation (OR) values and electronic circular dichroism (ECD) calculations. Compounds 1-5 were firstly isolated from the marine-derived fungus Penicillium as racemates, and 2-5 were separated by HPLC with a chiral stationary phase. All the compounds were evaluated for their antibacterial, cytotoxic and inhibitory activities against PDE4D2.

Keywords: Penicillium sp. GGF16-1-2; antibacterial activity; cytotoxicity; enantiomers; inhibitors; starfish-derived symbiotic fungus.

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Crystallography, X-Ray
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Humans
  • Molecular Conformation
  • Penicillium / chemistry
  • Penicillium / metabolism*
  • Polyketides / chemistry*
  • Polyketides / isolation & purification
  • Polyketides / pharmacology
  • Starfish / microbiology*
  • Stereoisomerism
  • Symbiosis

Substances

  • Polyketides