Apramides A-G, novel lipopeptides from the marine cyanobacterium Lyngbya majuscula

J Nat Prod. 2000 Aug;63(8):1106-12. doi: 10.1021/np000078t.

Abstract

Six new metabolites have been isolated from a lyngbyastatin 2-producing strain of the marine cyanobacterium Lyngbya majuscula collected at Apra Harbor, Guam, and their structures elucidated. These linear lipopeptides have been assigned the trivial names apramides A-F (1-6). From a more recent collection of this cyanobacterium, a structurally related compound, apramide G (7), has been found instead of apramides A-F (1-6). Structure elucidation of the lipopeptides 1-7 is based on spectroscopic techniques and chiral chromatography of hydrolysis products. The apramides appear as NMR-spectroscopically distinguishable conformers in solution, and this has been ascribed to the presence of a thiazole-containing modified amino acid unit.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Chromatography, Gel
  • Chromatography, High Pressure Liquid
  • Cyanobacteria / chemistry*
  • Guam
  • Lipoproteins / chemistry
  • Lipoproteins / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Optical Rotation
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet

Substances

  • Lipoproteins