Treasures from the Deep: Characellides as Anti-Inflammatory Lipoglycotripeptides from the Sponge Characella pachastrelloides

Org Lett. 2019 Jan 4;21(1):246-251. doi: 10.1021/acs.orglett.8b03684. Epub 2018 Dec 20.

Abstract

The chemical investigation of marine invertebrates from the deep Northeastern Atlantic revealed new lipoglycotripeptides named characellides isolated from the tetractinellid sponge Characella pachastrelloides. This new family of natural products features a central tripeptide linked to a rare sugar unit and a long alkyl chain ending with a 2,3-dimethyltetrahydropyran. The configurations of all 13 chiral centers were determined by extensive use of NMR data and circular dichroism spectra combined with calculations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Cell Line
  • Dose-Response Relationship, Drug
  • Lipoglycopeptides / chemistry*
  • Lipoglycopeptides / isolation & purification
  • Lipoglycopeptides / pharmacology
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Mice
  • Microglia / drug effects
  • Microglia / metabolism
  • Molecular Conformation
  • Porifera
  • Reactive Oxygen Species / metabolism
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Lipoglycopeptides
  • Lipopolysaccharides
  • Reactive Oxygen Species