2 H-Pyranone and isocoumarin derivatives isolated from the plant pathogenic fungus Leptosphaena maculans

J Asian Nat Prod Res. 2019 Oct;21(10):939-946. doi: 10.1080/10286020.2018.1485661. Epub 2018 Jul 2.

Abstract

Two new 2H-pyranones and two new isocoumarin derivatives, maculanslines A-D (1-4), together with seven known compounds (5-11), were isolated from the plant pathogenic fungus Leptosphaena maculans. Their planar structures and absolute configuration were elucidated by comprehensive spectroscopic techniques including high-resolution electrospray ionization mass spectrum, 1D and 2D nuclear magnetic resonance, as well as electronic circular dichroism. All 11 compounds were tested for their inhibitory activity against α-glucosidase. Compound 1 showed moderate inhibitory activity against α-glucosidase with IC50 of 74.35 μM.

Keywords: 2-pyranones; inhibition of -glucosidase; isocoumarins.

MeSH terms

  • Circular Dichroism
  • Fungi / chemistry*
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / pharmacology
  • Isocoumarins / analysis*
  • Isocoumarins / isolation & purification
  • Isocoumarins / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plant Diseases
  • Pyrans / analysis*
  • Pyrans / pharmacology
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Glycoside Hydrolase Inhibitors
  • Isocoumarins
  • Pyrans