Hassallidin A, a glycosylated lipopeptide with antifungal activity from the cyanobacterium Hassallia sp

J Nat Prod. 2005 May;68(5):695-700. doi: 10.1021/np049671r.

Abstract

Hassallidin A (1), a new antifungal glycosylated lipopeptide, was isolated from an epilithic cyanobacterium collected in Bellano, Italy, identified as Tolypothrix (basionym Hassallia) species. Chemical, mass spectrometric, and spectroscopic analyses, including one- and two-dimensional NMR, were performed to determine an esterified eight-residue cyclic peptide linked with a carbohydrate and a fatty acid residue. Chiral GC-MS analysis revealed the occurrence of the nonproteinogenic amino acids D-allo-Thr, D-Thr, D-Tyr, D-Gln, and dehydroaminobutyric acid (Dhb) within the peptide moiety. The additional components of hassallidin A could be identified as alpha,beta-dihydroxytetradecanoic acid (Dht) and mannose. This is the first report on a cyclic peptide of cyanobacterial origin that contains both a fatty acid and a carbohydrate moiety. Compound 1 exhibits antifungal activity against Aspergillus fumigatus and Candida albicans with MIC values of 4.8 microg/mL for both test organisms.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Amino Acid Sequence
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Aspergillus fumigatus / drug effects
  • Candida albicans / drug effects
  • Cyanobacteria / chemistry*
  • Glycolipids / chemistry
  • Glycolipids / isolation & purification*
  • Glycolipids / pharmacology
  • Glycopeptides / chemistry
  • Glycopeptides / isolation & purification*
  • Glycopeptides / pharmacology
  • Italy
  • Lipopeptides
  • Lipoproteins / chemistry
  • Lipoproteins / isolation & purification*
  • Lipoproteins / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular

Substances

  • Alkaloids
  • Antifungal Agents
  • Glycolipids
  • Glycopeptides
  • Lipopeptides
  • Lipoproteins
  • hassallidin A