Matsutakone and Matsutoic Acid, Two (Nor)steroids with Unusual Skeletons from the Edible Mushroom Tricholoma matsutake

J Org Chem. 2017 Aug 4;82(15):7974-7979. doi: 10.1021/acs.joc.7b01230. Epub 2017 Jul 19.

Abstract

Matsutakone (1), a novel sterol with an unprecedented polycyclic ring system, together with a new norsteroid matsutoic acid (2) were isolated from the fruiting bodies of Tricholoma matsutake. Their structures and absolute configurations were assigned by extensive spectroscopic analyses and computational methods. Bioassay results showed that compounds 1 and 2 exhibited inhibitory activities against acetylcholinesterase (IC50 20.9 μM for 1).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / metabolism*
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification
  • Cholinesterase Inhibitors / pharmacology*
  • Dose-Response Relationship, Drug
  • Erythrocytes / enzymology
  • Humans
  • Molecular Conformation
  • Norsteroids / chemistry
  • Norsteroids / isolation & purification
  • Norsteroids / pharmacology*
  • Sterols / chemistry
  • Sterols / isolation & purification
  • Sterols / pharmacology*
  • Structure-Activity Relationship
  • Tricholoma / chemistry*

Substances

  • Cholinesterase Inhibitors
  • Norsteroids
  • Sterols
  • matsutakone
  • matsutoic acid
  • Acetylcholinesterase