Bioactive Monomer and Polymer Polyketides from Edible Mushroom Cortinarius caerulescens as Glutamate Dehydrogenase Inhibitors and Antioxidants

J Agric Food Chem. 2022 Jan 26;70(3):804-814. doi: 10.1021/acs.jafc.1c07119. Epub 2022 Jan 14.

Abstract

Two new polyketides named rufoolivacin E and viocristin B, a new natural product named 1-hydroxy-3,6,8-trimethoxyanthraquinone, and 13 known compounds were isolated from edible mushroom Cortinarius purpurascens in this work. Their structures were assigned on the basis of high-resolution electrospray ionization mass spectrometry, 1D and 2D nuclear magnetic resonance, and electronic circular dichroism data. Notably, the enzyme activity test on glutamate dehydrogenase indicated that 1, 3, 4, 5, 6, 10, 11, and 15 displayed an excellent inhibition effect. Further kinetic studies showed that the most potent compounds, 4 and 10, possess great potential as competitive inhibitors of glutamate dehydrogenase. Molecular docking and computational chemistry were applied to illustrate the binding mechanism in detail. 2,2-Diphenyl-1-picrylhydrazyl and reactive oxygen species assay results showed that compounds 1, 2, 3, and 8 exhibited significant antioxidant activities with IC50 values of 7.0 ± 0.3, 8.6 ± 0.1, 7.5 ± 0.1, and 2.8 ± 0.2 μg mL-1, respectively. Thus, Cortinarius caerulescens represents a novel resource of these polyketides to be utilized in food selection and drug discovery.

Keywords: Cortinarius caerulescens (Schaeff.); Edible Mushroom; antioxidants; glutamate dehydrogenase inhibitors; polyketides.

MeSH terms

  • Agaricales*
  • Antioxidants / pharmacology
  • Cortinarius
  • Glutamate Dehydrogenase
  • Kinetics
  • Molecular Docking Simulation
  • Molecular Structure
  • Polyketides* / pharmacology
  • Polymers

Substances

  • Antioxidants
  • Polyketides
  • Polymers
  • Glutamate Dehydrogenase

Supplementary concepts

  • Cortinarius caerulescens