Solomonamides A and B, new anti-inflammatory peptides from Theonella swinhoei

Org Lett. 2011 Mar 18;13(6):1532-5. doi: 10.1021/ol200221n. Epub 2011 Feb 22.

Abstract

Two unprecedented cyclic peptides, solomonamides A and B, were isolated from the marine sponge Theonella swinhoei. The structures were elucidated on the basis of comprehensive 1D and 2D NMR analysis and high-resolution mass spectrometry. A combined approach, involving Marfey's method, QM J based analysis, and DFT J/(13)C calculations, was used for establishing the absolute configuration of the entire molecule. Solomonamide A showed in vivo anti-inflammatory activity.

MeSH terms

  • Alanine / chemistry
  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Dose-Response Relationship, Drug
  • Edema / drug therapy
  • Marine Biology
  • Mice
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology*
  • Serine / chemistry
  • Theonella / chemistry*

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Peptides, Cyclic
  • solomonamide A
  • solomonamide B
  • Serine
  • Alanine