Marine Longilenes, Oxasqualenoids with Ser-Thr Protein Phosphatase 2A Inhibition Activity

Mar Drugs. 2018 Apr 17;16(4):131. doi: 10.3390/md16040131.

Abstract

The red seaweed Laurencia viridis is a rich source of oxygenated secondary metabolites that were derived from squalene. We report here the structures of three novel compounds, (+)-longilene peroxide (1), longilene (2), and (+)-prelongilene (3) that were isolated from this alga, in addition to other substances, 4 and 5, resulting from their acid-mediated degradation. The effect of compounds 1 and 3 against Ser-Thr protein phosphatase type 2A (PP2A) was evaluated, showing that (+)-longilene peroxide (1) inhibited PP2A (IC50 11.3 μM). In order to explain the interaction between PP2A and compounds 1 and 3, molecular docking simulations onto the PP2A enzyme-binding region were used.

Keywords: Laurencia viridis; docking simulation; longilenes; marine polyether; phosphatase inhibition; red alga.

MeSH terms

  • Aquatic Organisms / chemistry*
  • Biological Products / chemistry*
  • Biological Products / pharmacology
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Laurencia / chemistry*
  • Molecular Docking Simulation
  • Protein Binding
  • Protein Phosphatase 2 / antagonists & inhibitors*
  • Seaweed / chemistry*
  • Squalene / chemistry
  • Structure-Activity Relationship

Substances

  • Biological Products
  • Enzyme Inhibitors
  • Squalene
  • Protein Phosphatase 2