Ten ring-B aromatized ergosterols from Aspergillus spectabilis

Chin J Nat Med. 2024 Jul;22(7):654-662. doi: 10.1016/S1875-5364(24)60594-7.

Abstract

Spectasterols F-O (1-10), ten interesting ergosterols with an aromatized B ring, were obtained from Aspergillus spectabilis. Their structures and absolute configurations were determined using a combination of high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), nuclear magnetic resonance (NMR) spectroscopy, single-crystal X-ray diffraction analyses, and electronic circular dichroism (ECD) calculations. Structurally, these aromatic ergosterols feature versatile side chains. Notably, compound aromatic ergosterols featured versatile side chains, and compound 4 is an unusual C23 ergosterol characterized by a shorter side chain due to oxidative cleavage between C-23 and C-24. All compounds were evaluated for their neuroprotective activities, with compound 8 showing a dose-dependent ability to reduce apoptosis and protect mitochondrial function in glutamate-induced SH-SY5Y cells.

Keywords: Aromatic ergosterols; Aspergillus spectabilis; Neuroprotective activities; Steroids; Structure elucidation.

MeSH terms

  • Apoptosis / drug effects
  • Aspergillus* / chemistry
  • Cell Line, Tumor
  • Ergosterol* / analogs & derivatives
  • Ergosterol* / chemistry
  • Ergosterol* / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mitochondria / drug effects
  • Mitochondria / metabolism
  • Molecular Structure
  • Neuroprotective Agents* / chemistry
  • Neuroprotective Agents* / pharmacology

Substances

  • Ergosterol
  • Neuroprotective Agents