Herqueilenone A, a unique rearranged benzoquinone-chromanone from the Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729

Bioorg Chem. 2020 Dec:105:104397. doi: 10.1016/j.bioorg.2020.104397. Epub 2020 Oct 21.

Abstract

The study of a Hawaiian volcanic soil-associated fungal strain Penicillium herquei FT729 led to the isolation of one unprecedented benzoquinone-chromanone, herqueilenone A (1) and two phenalenone derivatives (2 and 3). Their structures were determined through extensive analysis of NMR spectroscopic data and gauge-including atomic orbital (GIAO) NMR chemical shifts and ECD calculations. Herqueilenone A (1) contains a chroman-4-one core flanked by a tetrahydrofuran and a benzoquinone with an acetophenone moiety. Plausible pathways for the biosynthesis of 1-3 are proposed. Compounds 2 and 3 inhibited IDO1 activity with IC50 values of 14.38 and 13.69 μM, respectively. Compounds 2 and 3 also demonstrated a protective effect against acetaldehyde-induced damage in PC-12 cells.

Keywords: Acetaldehyde-induced damage; Benzoquinone-chromanone; Indoleamine 2,3-dioxygenase 1; Penicillium herquei FT729; Phenalenone derivative; Soil-associated fungus.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetaldehyde / antagonists & inhibitors
  • Acetaldehyde / pharmacology
  • Animals
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Indoleamine-Pyrrole 2,3,-Dioxygenase / antagonists & inhibitors*
  • Indoleamine-Pyrrole 2,3,-Dioxygenase / metabolism
  • Microbial Sensitivity Tests
  • Molecular Structure
  • PC12 Cells
  • Penicillium / chemistry*
  • Phenalenes / chemistry
  • Phenalenes / isolation & purification
  • Phenalenes / pharmacology*
  • Rats
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • IDO1 protein, human
  • Indoleamine-Pyrrole 2,3,-Dioxygenase
  • Phenalenes
  • phenalen-1-one
  • Acetaldehyde

Supplementary concepts

  • Penicillium herquei