5-Hydroxycyclopenicillone, a New β-Amyloid Fibrillization Inhibitor from a Sponge-Derived Fungus Trichoderma sp. HPQJ-34

Mar Drugs. 2017 Aug 19;15(8):260. doi: 10.3390/md15080260.

Abstract

Abstract: A new cyclopentenone, 5-hydroxycyclopeni cillone (1), was isolated together with three known compounds, ar-turmerone (2), citreoisocoumarin (3), and 6-O-methyl-citreoisocoumarin (4), from a culture of the sponge-derived fungus Trichoderma sp. HPQJ-34. The structures of 1-4 were characterized using comprehensive spectroscopic analyses. The absolute configuration of 1 was determined by comparison of electronic circular dichroism (ECD) spectra with literature values used for the reported analogue, cyclopenicillone (5), which was not isolated in this research. Compound 1 was shown to scavenge 2,2-diphenyl-1-picrylhydrazyl free radicals, and decrease β-amyloid (Aβ) fibrillization in vitro. Moreover, 1 significantly reduced H₂O₂-induced neurotoxicity in SH-SY5Y cells. These findings suggested that compound 1, a newly discovered cyclopentenone, has moderate anti-oxidative, anti-Aβ fibrillization properties and neuroprotective effects, and might be a good free radical scavenger.

Keywords: Alzheimer’s disease; Trichoderma sp. HPQJ-34; cyclopentenone; sponge-derived fungus.

MeSH terms

  • Amyloid / drug effects*
  • Animals
  • Biphenyl Compounds / chemistry*
  • Cell Line / drug effects
  • Circular Dichroism
  • Cyclopentanes / chemistry
  • Cyclopentanes / pharmacology*
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology*
  • Humans
  • Phytotherapy
  • Picrates / chemistry*
  • Porifera / microbiology*
  • Trichoderma*

Substances

  • Amyloid
  • Biphenyl Compounds
  • Cyclopentanes
  • Free Radical Scavengers
  • Picrates
  • 1,1-diphenyl-2-picrylhydrazyl
  • cyclopentenone