Curindolizine, an Anti-Inflammatory Agent Assembled via Michael Addition of Pyrrole Alkaloids Inside Fungal Cells

Org Lett. 2016 Apr 15;18(8):1816-9. doi: 10.1021/acs.orglett.6b00549. Epub 2016 Apr 5.

Abstract

Curvularia sp. IFB-Z10, a white croaker-associated fungus, generates a skeletally unprecedented indolizine alkaloid named curindolizine (1), which displays an anti-inflammatory action in lipopolyssacharide (LPS)-induced RAW 264.7 macrophages with an IC50 value of 5.31 ± 0.21 μM. The enzymatic transformation test demonstrated that the unique curindolizine architecture was most likely produced by the regiospecific in-cell Michael addition reaction between pyrrole alkaloids, curvulamine, and 3,5-dimethylindolizin-8(5H)-one.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology*
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Fungi
  • Indole Alkaloids
  • Indolizines / chemistry*
  • Inhibitory Concentration 50
  • Lipopolysaccharides / chemistry*
  • Pyrroles / chemistry*

Substances

  • 3,5-dimethylindolizin-8(5H)-one
  • Alkaloids
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Indole Alkaloids
  • Indolizines
  • Lipopolysaccharides
  • Pyrroles
  • curvulamine