Thalassospiramide G, a new γ-amino-acid-bearing peptide from the marine bacterium Thalassospira sp

Mar Drugs. 2013 Feb 26;11(3):611-22. doi: 10.3390/md11030611.

Abstract

In the chemical investigation of marine unicellular bacteria, a new peptide, thalassospiramide G (1), along with thalassospiramides A and D (2-3), was discovered from a large culture of Thalassospira sp. The structure of thalassospiramide G, bearing γ-amino acids, such as 4-amino-5-hydroxy-penta-2-enoic acid (AHPEA), 4-amino-3,5-dihydroxy-pentanoic acid (ADPA), and unique 2-amino-1-(1H-indol-3-yl) ethanone (AIEN), was determined via extensive spectroscopic analysis. The absolute configuration of thalassospiramide D (3), including 4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA), was rigorously determined by 1H-1H coupling constant analysis and chemical derivatization. Thalassospiramides A and D (2-3) inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated mouse macrophage RAW 264.7 cells, with IC(50) values of 16.4 and 4.8 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Inhibitory Concentration 50
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects*
  • Macrophages / metabolism
  • Mice
  • Nitric Oxide / biosynthesis
  • Peptides / chemistry
  • Peptides / isolation & purification
  • Peptides / pharmacology*
  • Peptides, Cyclic / administration & dosage
  • Peptides, Cyclic / isolation & purification
  • Peptides, Cyclic / pharmacology*
  • Rhodospirillaceae / chemistry*
  • Spectrum Analysis

Substances

  • Lipopolysaccharides
  • Peptides
  • Peptides, Cyclic
  • thalassospiramide A
  • thalassospiramide B
  • Nitric Oxide