Cyanopeptolin 963A, a chymotrypsin inhibitor of Microcystis PCC 7806

J Nat Prod. 2004 Oct;67(10):1755-7. doi: 10.1021/np049828f.

Abstract

A new depsipeptide, cyanopeptolin 963 A (1), was isolated from an axenic strain of the toxic freshwater cyanobacterium Microcystis PCC 7806. The structure of this compound was elucidated by chemical and spectroscopic analyses, including high-resolution ESI-FTICR-MS, 2-D NMR, and GC-MS of the hydrolysate. The major structural difference compared to previously characterized cyanopeptolins of this strain is the replacement of the basic amino acid in position 3 by L-tyrosine. Compound 1 displayed inhibitory activity against chymotrypsin with an IC50 value of 0.9 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chymotrypsin / antagonists & inhibitors*
  • Depsipeptides / chemistry
  • Depsipeptides / isolation & purification*
  • Depsipeptides / pharmacology
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology
  • Inhibitory Concentration 50
  • Microcystis / chemistry*
  • Molecular Structure
  • Spectrometry, Mass, Electrospray Ionization
  • Structure-Activity Relationship
  • Tyrosine / chemistry

Substances

  • Depsipeptides
  • Enzyme Inhibitors
  • cyanopeptolin 963A
  • Tyrosine
  • Chymotrypsin