Lipopeptides from the tropical marine cyanobacterium Symploca sp

J Nat Prod. 2014 Apr 25;77(4):969-75. doi: 10.1021/np401051z. Epub 2014 Mar 3.

Abstract

A collection of the tropical marine cyanobacterium Symploca sp., collected near Kimbe Bay, Papua New Guinea, previously yielded several new metabolites including kimbeamides A-C, kimbelactone A, and tasihalide C. Investigations into a more polar cytotoxic fraction yielded three new lipopeptides, tasiamides C-E (1-3). The planar structures were deduced by 2D NMR spectroscopy and tandem mass spectrometry, and their absolute configurations were determined by a combination of Marfey's and chiral-phase GC-MS analysis. These new metabolites are similar to several previously isolated compounds, including tasiamide (4), grassystatins (5, 6), and symplocin A, all of which were isolated from similar filamentous marine cyanobacteria.

Publication types

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

MeSH terms

  • Cyanobacteria / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Lipopeptides / chemistry
  • Lipopeptides / isolation & purification*
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligopeptides
  • Papua New Guinea

Substances

  • Lipopeptides
  • Oligopeptides
  • tasiamide