Structural assignment of poecillastrins B and C, macrolide lactams from the deep-water Caribbean sponge Poecillastra species

J Nat Prod. 2007 Mar;70(3):428-31. doi: 10.1021/np0604984.

Abstract

Two new chondropsin-type macrolide lactams, poecillastrins B (1) and C (2), were isolated from aqueous extracts of the marine sponge Poecillastra sp. These trace metabolites were isolated in low yield (400-600 microg), and their structures were determined primarily by analysis of NMR data acquired using a cyrogenically cooled probe. High-quality 1D and 2D NMR data sets allowed complete assignment of the spectroscopic data and defined the new structures as 35-membered ring analogues of poecillastrin A (3). Compounds 1 and 2 showed potent cytotoxic activity against a human melanoma tumor cell line (LOX) with an IC50 value of less than 1 microg/mL.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, N.I.H., Intramural

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Bahamas
  • Drug Screening Assays, Antitumor
  • Humans
  • Lactams / chemistry
  • Lactams / isolation & purification*
  • Lactams / pharmacology
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology
  • Melanoma
  • Molecular Structure
  • Porifera / chemistry*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Lactams
  • Macrolides
  • poecillastrin B
  • poecillastrin C