Polyketide and Prenylxanthone Derivatives from the Endophytic Fungus Aspergillus sp. TJ23

Chem Biodivers. 2018 Dec;15(12):e1800395. doi: 10.1002/cbdv.201800395. Epub 2018 Dec 7.

Abstract

Eight secondary metabolites, including a new polyketide, named asperetide (1) and a new prenylxanthone derivative, called asperanthone (4), and six known compounds, (S)-3-butyl-7-methoxyphthalide (2), ruguloxanthone C (3), tajixanthone hydrate (5), tajixanthone methanoate (6), salimyxin B (7), and ergosterol (8), were isolated and identified from the medicinal plant-derived fungus, Aspergillus sp. TJ23. The new structures and their absolute configurations were elucidated via multiple methods, including 1D- and 2D-NMR, HR-ESI-MS, UV, IR, and the electronic circular dichroism (ECD) calculations. All of the isolates were characterized from the strain for the first time. The in vitro bioassay showed that compounds 3-5 and 8 exerted inhibitory activities against five cancer cell lines (B16, MDA-MB-231, 4T1, HepG2, and LLC) with IC50 values ranging from 5.13 to 36.8 μm.

Keywords: Aspergillus; ECD, cytotoxicity; biological activity; polyketide, prenylxanthone.

MeSH terms

  • Aspergillus / chemistry*
  • Aspergillus / metabolism
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Circular Dichroism
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Polyketides / chemistry*
  • Polyketides / isolation & purification
  • Polyketides / pharmacology
  • Spectrometry, Mass, Electrospray Ionization
  • Xanthones / chemistry*
  • Xanthones / isolation & purification
  • Xanthones / pharmacology

Substances

  • Polyketides
  • Xanthones