Isolation, Structural Elucidation, and α-Glucosidase Inhibitory Activities of Triterpenoid Lactones and Their Relevant Biogenetic Constituents from Ganoderma resinaceum

Molecules. 2018 Jun 8;23(6):1391. doi: 10.3390/molecules23061391.

Abstract

Ganoderma resinaceum has been used as an ethnomedicine for lowering blood sugar. To clarify the bioactive chemical constituents contributing to lower blood sugar, chemical investigation on the fruiting bodies of Ganoderma resinaceum was conducted by chromatographic techniques, and led to the isolation of 14 compounds. Their structures were elucidated as triterpenoid lactones (14 and 8) and ganoderma acids (57 and 914) based on the analysis of extensive spectroscopy (mass spectrometry (MS), nuclear magnetic resonance (NMR), infrared (IR), and ultraviolet (UV)) and comparison with literature data. Compounds 3, 5, 6, and 914 were evaluated for α-glucosidase inhibitory activity. Compounds 17 are new compounds. Compounds 14 and 8 were characteristic of an oxaspirolactone moiety, consisting of a five-membered ether ring, a five-membered lactone ring, and a characteristic C-23 spiro carbon. It is rare for natural products that such an oxaspirolactone moiety occurred in the lanostane-type triterpenoids. Compounds 57 and 914 may be important intermediates of the biosynthetic pathways of 14 and 8. Compounds 1 and 2 showed more potent inhibitory activity against α-glucosidase compared with the positive control drug acarbose with IC50 value of 0.75 ± 0.018 mM and 1.64 ± 0.022 mM, respectively.

Keywords: Ganoderma resinaceum; oxaspirolactone; triterpenoid; triterpenoid lactone; α-glucosidase inhibitory activity.

MeSH terms

  • Ganoderma / chemistry*
  • Glycoside Hydrolase Inhibitors / chemistry*
  • Glycoside Hydrolase Inhibitors / isolation & purification
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Lactones / chemistry
  • Lactones / isolation & purification
  • Lactones / pharmacology*
  • Molecular Structure
  • Spectrum Analysis / methods
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*

Substances

  • Glycoside Hydrolase Inhibitors
  • Lactones
  • Triterpenes