Total Synthesis and Structural Reassignment of the Molt-Inhibiting Marine Alkaloid Erebusinone

J Nat Prod. 2024 Oct 25;87(10):2499-2506. doi: 10.1021/acs.jnatprod.4c00973. Epub 2024 Oct 4.

Abstract

The marine alkaloid erebusinone is a secondary metabolite isolated from the Antarctic sponge Isodictya erinacea. Initial biological assays have shown that erebusinone increases amphipod mortality, probably by inhibition of the biosynthesis of molting hormone (ecdysone). Herein, we report the first total synthesis of the proposed structure of erebusinone and a structural revision.

MeSH terms

  • Alkaloids* / chemical synthesis
  • Alkaloids* / chemistry
  • Alkaloids* / pharmacology
  • Amphipoda / drug effects
  • Animals
  • Antarctic Regions
  • Ecdysone / pharmacology
  • Marine Biology
  • Molecular Structure
  • Molting / drug effects
  • Porifera* / chemistry

Substances

  • Alkaloids
  • Ecdysone