Three New Indole Diketopiperazine Alkaloids from Aspergillus ochraceus

Chem Biodivers. 2018 Apr;15(4):e1700550. doi: 10.1002/cbdv.201700550. Epub 2018 Apr 17.

Abstract

Asperochramides A - D (1 - 4), a new natural product and three new indole diketopiperazine alkaloids, along with seven known analogs (5 - 11), were isolated from the ethyl acetate extract of Aspergillus ochraceus. Their structures were elucidated by extensive spectroscopic analyses, ECD calculation, and single-crystal X-ray diffraction analysis. Compounds 3 and 4 represent a rare group of indole diketopiperazine alkaloid with a 3-hydroxyl-2-indolone moiety. The in vitro anti-inflammatory effects of compounds 1 and 3 - 11 were investigated by using LPS-stimulated murine macrophage RAW 264.7 cells. Compounds 1, 8, 10, and 11 showed potential anti-inflammatory activities.

Keywords: Aspergillus ochraceus; ECD calculation; X-ray diffraction; asperochramides A - D; indole diketopiperazine alkaloids.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Aspergillus ochraceus / chemistry*
  • Crystallography, X-Ray
  • Diketopiperazines / chemistry
  • Diketopiperazines / isolation & purification
  • Diketopiperazines / pharmacology*
  • Dose-Response Relationship, Drug
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects*
  • Mice
  • Models, Molecular
  • Molecular Conformation
  • RAW 264.7 Cells
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Anti-Inflammatory Agents
  • Diketopiperazines
  • Lipopolysaccharides