Terpenoids with alpha-glucosidase inhibitory activity from the submerged culture of Inonotus obliquus

Phytochemistry. 2014 Dec;108:171-6. doi: 10.1016/j.phytochem.2014.09.022. Epub 2014 Oct 18.

Abstract

Lanostane-type triterpenoids, inotolactones A and B, a drimane-type sesquiterpenoid, inotolactone C, and five known terpenoids 6β-hydroxy-trans-dihydroconfertifolin, inotodiol, 3β,22-dihydroxyanosta-7,9(11),24-triene, 3β-hydroxycinnamolide, and 17-hydroxy-ent-atisan-19-oic acid, were isolated from the submerged culture of chaga mushroom, Inonotus obliquus. Their structures were characterized by spectroscopic methods, including MS and NMR (1D and 2D) spectroscopic techniques. Inotolactones A and B, examples of lanostane-type triterpenoids bearing α,β-dimethyl, α,β-unsaturated δ-lactone side chains, exhibited more potent alpha-glucosidase inhibitory activities than the positive control acarbose. This finding might be related to the anti-hyperglycemic properties of the fungus and to its popular role as a diabetes treatment. In addition, a drimane-type sesquiterpenoid and an atisane-type diterpenoid were isolated from I. obliquus.

Keywords: Alpha-glucosidase; Chaga mushroom; Drimane; Hymenochaetaceae; Inonotus obliquus; Lanostane; Triterpenoids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / chemistry*
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / isolation & purification*
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Heterocyclic Compounds, 3-Ring / isolation & purification
  • Heterocyclic Compounds, 3-Ring / pharmacology
  • Lanosterol* / analogs & derivatives
  • Lanosterol* / chemistry
  • Lanosterol* / isolation & purification
  • Lanosterol* / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • alpha-Glucosidases / drug effects

Substances

  • 3-hydroxycinnamolide
  • Glycoside Hydrolase Inhibitors
  • Heterocyclic Compounds, 3-Ring
  • inotodiol
  • Lanosterol
  • alpha-Glucosidases