Structurally diverse vibralactones produced by the fungus Stereum hirsutum

Bioorg Chem. 2020 Jun:99:103760. doi: 10.1016/j.bioorg.2020.103760. Epub 2020 Mar 14.

Abstract

Eight unexpected vibralactone homodimers, bisvibralactones A-H (1-8), and three new vibralactone monomers, hirsutumins A-C (9-11), were isolated from the culture of Stereum hirsutum. Their structures and absolute configurations were determined by detailed analyses of NMR, optical rotations, ECD, and high-resolution mass spectra as well as chemical transformation. Compounds 1-8 are unusual vibralactone dimers formed by the esterification of two vibralactone monomers. The absolute configurations of compounds 1 and 5 were determined by chemical conversions. All of the isolated compounds were evaluated for Porcine Pancreatic Lipase (PPL) inhibitory activities, and compound 10 showed significant inhibitory activity against PPL, with an IC50 value of 8.31 ± 1.04 μM.

Keywords: Bisvibralactone; Porcine Pancreatic Lipase inhibitory activities; Stereum hirsutum; Vibralactone homodimer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Basidiomycota / chemistry*
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / metabolism
  • Enzyme Inhibitors / pharmacology*
  • Lactones / chemistry
  • Lactones / metabolism
  • Lactones / pharmacology*
  • Lipase / antagonists & inhibitors*
  • Lipase / metabolism
  • Molecular Structure
  • Pancreas / enzymology
  • Structure-Activity Relationship
  • Swine

Substances

  • Enzyme Inhibitors
  • Lactones
  • vibralactone
  • Lipase

Supplementary concepts

  • Stereum hirsutum