5-Hydroxycyclopenicillone Inhibits β-Amyloid Oligomerization and Produces Anti-β-Amyloid Neuroprotective Effects In Vitro

Molecules. 2017 Oct 1;22(10):1651. doi: 10.3390/molecules22101651.

Abstract

The oligomer of β-amyloid (Aβ) is considered the main neurotoxin in Alzheimer's disease (AD). Therefore, the inhibition of the formation of Aβ oligomer could be a target for AD therapy. In this study, with the help of the dot blotting assay and transmission electronic microscopy, it was have discovered that 5-hydroxycyclopenicillone, a cyclopentenone recently isolated from a sponge-associated fungus, effectively reduced the formation of Aβ oligomer from Aβ peptide in vitro. Molecular dynamics simulations suggested hydrophobic interactions between 5-hydroxycyclopenicillone and Aβ peptide, which might prevent the conformational transition and oligomerization of Aβ peptide. Moreover, Aβ oligomer pre-incubated with 5-hydroxycyclopenicillone was less toxic when added to neuronal SH-SY5Y cells compared to the normal Aβ oligomer. Although 5-hydroxycyclopenicillone is not bioavailable in the brain in its current form, further modification or encapsulation of this chemical might improve the penetration of 5-hydroxycyclopenicillone into the brain. Based on the current findings and the anti-oxidative stress properties of 5-hydroxycyclopenicillone, it is suggested that 5-hydroxycyclopenicillone may have potential therapeutic efficacy in treating AD.

Keywords: 5-hydroxycyclopenicillone; Alzheimer’s disease; oligomer; sponge-associated fungus; β-amyloid.

MeSH terms

  • Alzheimer Disease / drug therapy
  • Amyloid beta-Peptides / antagonists & inhibitors*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Cyclopentanes / chemistry*
  • Cyclopentanes / pharmacology*
  • Fungi / chemistry
  • Humans
  • Molecular Dynamics Simulation
  • Neurons / drug effects*
  • Neurons / pathology
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / pharmacology*
  • Neuroprotective Agents / therapeutic use

Substances

  • Amyloid beta-Peptides
  • Cyclopentanes
  • Neuroprotective Agents
  • cyclopentenone