Ene-yne Hydroquinones from a Marine-derived Strain of the Fungus Pestalotiopsis neglecta with Effects on Liver X Receptor Alpha

J Nat Prod. 2020 Apr 24;83(4):1258-1264. doi: 10.1021/acs.jnatprod.0c00050. Epub 2020 Apr 13.

Abstract

Seven unusual new ene-yne hydroquinones (1-3, 5-8), including three rare glycosylated derivatives named pestalotioquinosides A-C (6-8), were obtained from the marine-derived strain SCSIO41403 of the fungus Pestalotiopsis neglecta. Their structures including absolute configurations were elucidated by spectroscopic analysis and induced electronic circular dichroism experiments. In silico molecular docking and in vitro surface plasmon resonance studies showed that pestalotioquinoside C (8) could act as a liver X receptor alpha (LXRα) modulator. Further study showed that LXR target gene ABCA1 was significantly upregulated by 8, which revealed 8 as a potential LXRα agonist.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP Binding Cassette Transporter 1 / chemistry*
  • ATP Binding Cassette Transporter 1 / isolation & purification
  • ATP Binding Cassette Transporter 1 / pharmacokinetics
  • Hydroquinones / chemistry*
  • Liver X Receptors / chemistry*
  • Liver X Receptors / isolation & purification
  • Liver X Receptors / metabolism
  • Molecular Docking Simulation
  • Molecular Structure
  • Neglecta / chemistry
  • Pestalotiopsis / chemistry
  • Xylariales / chemistry

Substances

  • ABCA1 protein, human
  • ATP Binding Cassette Transporter 1
  • Hydroquinones
  • Liver X Receptors
  • NR1H3 protein, human