Bergamotane Sesquiterpenes with Alpha-Glucosidase Inhibitory Activity from the Plant Pathogenic Fungus Penicillium expansum

Chem Biodivers. 2017 Jan;14(1). doi: 10.1002/cbdv.201600184. Epub 2016 Dec 19.

Abstract

Two new bergamotane sesquiterpene lactones, named expansolides C and D (1 and 2), together with two known compounds expansolides A and B (3 and 4), were isolated from the plant pathogenic fungus Penicillium expansum ACCC37275. The structures of the new compounds were established by detailed analyses of the spectroscopic data, especially 1D-, 2D-NMR, and HR-ESI-MS. In an in vitro bioassay, the epimeric mixture of expansolides C and D (1 and 2) (in a ratio of 2:1 at the temprature of the bioassay) exhibited more potent α-glucosidase inhibitory activity (IC50 =0.50 ± 0.02 mm) as compared with the positive control acarbose (IC50 = 1.90 ± 0.05 mm). To the best of our knowledge, it was the first report on the α-glucosidase inhibitory activity of bergamotane sesquiterpenes.

Keywords: Penicillium expansum; Bergamotane; Expansolides C and D; Sesquiterpenes; α-Glucosidase inhibitory activities.

MeSH terms

  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology
  • Inhibitory Concentration 50
  • Lactones / isolation & purification
  • Lactones / pharmacology
  • Molecular Structure
  • Penicillium / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*
  • alpha-Glucosidases / drug effects*

Substances

  • Enzyme Inhibitors
  • Lactones
  • Sesquiterpenes
  • alpha-Glucosidases