Dysideaprolines A-F and barbaleucamides A-B, novel polychlorinated compounds from a Dysidea species

J Nat Prod. 2001 Sep;64(9):1133-8. doi: 10.1021/np0101999.

Abstract

Chemical investigation of a marine sponge, Dysidea sp., collected at Bararin Island, Philippines, has afforded the novel metabolites 1-6, proline-derived analogues of dysidenin (7). We have termed compounds 1-6 dysideaprolines A-F, respectively. Also isolated were compounds 8 and 9, structural analogues of barbamide (10), a metabolite originally isolated from the cyanobacterium Lyngbya majuscula. We have termed these novel compounds barbaleucamides A (8) and B (9). It is most probable that the compounds presented here are actually derived from a symbiotic cyanobacterium found in close association with the Dysidea sp. Structure elucidation of the isolated metabolites involved high-field 2D NMR spectroscopy including (1)H-(1)H COSY, HSQC, and HMBC.

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Cyanobacteria / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Conformation
  • Molecular Structure
  • Philippines
  • Porifera / chemistry*
  • Proline / analogs & derivatives*
  • Proline / chemistry
  • Proline / isolation & purification*
  • Spectrometry, Mass, Electrospray Ionization
  • Thiazoles* / chemistry
  • Thiazoles* / isolation & purification*
  • Thiazoles* / pharmacology

Substances

  • Thiazoles
  • barbaleucamide A
  • barbaleucamide B
  • dysidenin
  • Proline