Homophymine A, an anti-HIV cyclodepsipeptide from the sponge Homophymia sp

J Org Chem. 2008 Jul 18;73(14):5319-27. doi: 10.1021/jo800583b. Epub 2008 Jun 19.

Abstract

A new anti-HIV cyclodepsipeptide, homophymine A, was isolated from a New Caledonian collection of the marine sponge Homophymia sp. The structure of homophymine A was determined by interpretation of spectroscopic data, acid hydrolysis, and LC-MS analysis. Homophymine A contains 11 amino acid residues and an amide-linked 3-hydroxy-2,4,6-trimethyloctanoic acid moiety. Along with four D-, two L-, and one N-methyl amino acids, it also contains four unusual amino acid residues: (2S,3S,4R)-3,4-diMe-Gln, (2R,3R,4S)-4-amino-2,3-dihydroxy-1,7-heptandioic acid, L-ThrOMe, and (2R,3R,4R)-2-amino-3-hydroxy-4,5-dimethylhexanoic acid. In a cell-based XTT assay, homophymine A exhibited cytoprotective activity against HIV-1 infection with a IC50 of 75 nM.

MeSH terms

  • Animals
  • Anti-HIV Agents / chemistry*
  • Depsipeptides / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Porifera / chemistry*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Anti-HIV Agents
  • Depsipeptides
  • homophymine A