Protease inhibitors from Microcystis aeruginosa bloom material collected from the Dalton Reservoir, Israel

J Nat Prod. 2013 Dec 27;76(12):2307-15. doi: 10.1021/np4006844. Epub 2013 Nov 21.

Abstract

Nine new metabolites, aeruginosins DA495A (1), DA511 (2), DA642A (3), DA642B (4), DA688 (5), DA722 (6), and DA495B (7), microguanidine DA368 (8), and anabaenopeptin DA850 (9), were isolated along with the known micropeptins MZ924, MZ939A, and MZ1019, cyanopeptolins S and SS, microcin SF608, and aeruginazoles DA1497, DA1304, and DA1274 from bloom material of the cyanobacterium Microcystis aeruginosa collected from the Dalton reservoir, Israel, in October 2007. Their structures were elucidated by a combination of various spectroscopic techniques, primarily NMR and MS, while the absolute configurations of the asymmetric centers were determined by Marfey's and chiral-phase HPLC methods. Two of the new aeruginosins, DA511 (1) and DA495A (2), contain a new Choi isomer, (2S,3aS,6S,7aS)-Choi. The structure elucidation and biological activities of the new metabolites are described.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Depsipeptides
  • Israel
  • Microcystis / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligopeptides / chemistry
  • Oligopeptides / isolation & purification*
  • Oligopeptides / pharmacology*
  • Peptides / chemistry
  • Peptides / isolation & purification
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / isolation & purification*
  • Protease Inhibitors / pharmacology*
  • Trypsin Inhibitors / chemistry
  • Trypsin Inhibitors / isolation & purification*
  • Trypsin Inhibitors / pharmacology*

Substances

  • Depsipeptides
  • Oligopeptides
  • Peptides
  • Peptides, Cyclic
  • Protease Inhibitors
  • Trypsin Inhibitors
  • cyanopeptolin S
  • microcin SF608