Pedein A and B: production, isolation, structure elucidation and biological properties of new antifungal cyclopeptides from Chondromyces pediculatus (Myxobacteria)

J Antibiot (Tokyo). 2008 Jan;61(1):18-26. doi: 10.1038/ja.2008.104.

Abstract

Two new secondary metabolites, named pedein A and B, were isolated from the cell mass of the myxobacterium Chondromyces pediculatus. Their planar structures were elucidated by spectroscopic methods, in particular 2D NMR as 24-membered cyclic hexapeptides composed of a variable tryptophan residue, glycine, sarcosine and three unusual hydroxy beta- and gamma-amino acids. The main component, pedein A, strongly inhibited the growth of yeasts and fungi, induced hemolysis of erythrocytes, and caused changes in membrane permeability of Rhodotorula glutinis. The structures of the pedeins are closely related to the large family of the microsclerodermins, which have been isolated from lithistid sponges of Microscleroderma and Theonella species.

MeSH terms

  • Animals
  • Antifungal Agents / chemistry*
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / metabolism
  • Antifungal Agents / pharmacology
  • Chemical Phenomena
  • Chemistry, Physical
  • Fermentation
  • Fungi / drug effects
  • Hemolysis / drug effects
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Myxococcales / metabolism*
  • Peptides, Cyclic / biosynthesis
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / metabolism
  • Peptides, Cyclic / pharmacology
  • Yeasts / drug effects

Substances

  • Antifungal Agents
  • Peptides, Cyclic
  • pedein A
  • pedein B