Osteoclastogenesis Inhibitory Polyketides from the Sponge-Associated Fungus Xylaria feejeensis

Chem Biodivers. 2018 Dec;15(12):e1800358. doi: 10.1002/cbdv.201800358. Epub 2018 Dec 5.

Abstract

A new ten-membered macrolide (1) and a new α-pyrone derivative, (-)-annularin C (2), together with 14 known analogs (3-16) were isolated from the AcOEt extract of the fungus Xylaria feejeensis isolated from the South China Sea sponge Stylissa massa. The structures of the new compounds were elucidated by the spectroscopic analysis and by comparison with reported data. The absolute configuration was determined by the optical rotation and ECD experiments. In an in vitro test, compounds 1, 5 and 9 exhibited significant down-regulating activity of osteoclast cell differentiation at 0.5 and 1 μm. This is the first report of the fungus X. feejeensis from a marine sponge and of osteoclastogenesis inhibitory activity for the metabolites of these kinds.

Keywords: Xylaria feejeensis; biological activity; osteoclastogenesis inhibitory activity; sponge-associated fungus; α-pyrone analogs.

MeSH terms

  • Animals
  • Ascomycota / chemistry*
  • Ascomycota / metabolism
  • Cell Differentiation / drug effects
  • Circular Dichroism
  • Macrolides / chemistry
  • Macrolides / isolation & purification
  • Macrolides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mice
  • Mice, Inbred C57BL
  • Molecular Conformation
  • Osteoclasts / cytology
  • Osteoclasts / drug effects
  • Osteoclasts / metabolism
  • Osteogenesis / drug effects
  • Polyketides / chemistry*
  • Polyketides / isolation & purification
  • Polyketides / pharmacology
  • Porifera / microbiology*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Macrolides
  • Polyketides