Chromone Derivatives with α-Glucosidase Inhibitory Activity from the Marine Fungus Penicillium thomii Maire

Molecules. 2021 Aug 31;26(17):5273. doi: 10.3390/molecules26175273.

Abstract

The fungal strain YPGA3 was isolated from the sediments of the Yap Trench and identified as Penicillium thomii. Eight new chromone derivatives, named penithochromones M-T (1-8), along with two known analogues, 9 and 10, were isolated from the strain. The structures were established by detailed analyses of the spectroscopic data. The absolute configuration of the only chiral center in compound 1 was tentatively determined by comparing the experimental and the calculated specific rotations. Compounds 7 and 8 represent the first examples of chromone derivatives featuring a 5,7-dioxygenated chromone moiety with a 9-carbon side chain. Bioassay study revealed that compounds 6-10 exhibited remarkable inhibition against α-glucosidase with IC50 values ranging from 268 to 1017 μM, which are more active than the positive control acarbose (1.3 mmol).

Keywords: chromone derivatives; inhibitions on α-glucosidase; structural elucidation.

MeSH terms

  • Chromones / chemistry
  • Chromones / metabolism*
  • Enzyme Activation / drug effects
  • Glycoside Hydrolase Inhibitors / chemistry*
  • Glycoside Hydrolase Inhibitors / metabolism
  • Glycoside Hydrolase Inhibitors / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Penicillium / metabolism*
  • alpha-Glucosidases / metabolism*

Substances

  • Chromones
  • Glycoside Hydrolase Inhibitors
  • alpha-Glucosidases

Supplementary concepts

  • Penicillium thomii