Largamides A-C, tiglic acid-containing cyclodepsipeptides with elastase-inhibitory activity from the marine cyanobacterium Lyngbya confervoides

Planta Med. 2009 Apr;75(5):528-33. doi: 10.1055/s-0029-1185332. Epub 2009 Feb 12.

Abstract

Three unusual tiglic acid-containing cyclodepsipeptides, possessing the revised regioisomeric structures for largamides A-C (1-3), have been isolated from the marine cyanobacterium Lyngbya confervoides collected from southeastern Florida. The two-dimensional structures were determined by NMR spectroscopy and the absolute configurations by chiral HPLC analysis of degradation products. Compounds 1-3 are moderate inhibitors of mammalian elastase activity in vitro with IC(50) values ranging from 0.53 to 1.41 microM.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Cattle
  • Crotonates / analysis
  • Cyanobacteria / chemistry*
  • Depsipeptides / chemistry
  • Depsipeptides / isolation & purification*
  • Depsipeptides / pharmacology
  • Hemiterpenes
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification*
  • Plant Extracts / pharmacology
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / isolation & purification*
  • Protease Inhibitors / pharmacology
  • Swine

Substances

  • Crotonates
  • Depsipeptides
  • Hemiterpenes
  • Plant Extracts
  • Protease Inhibitors
  • largamide A
  • largamide C
  • tiglic acid