Bioactive diterpene derivatives from the marine sponge Spongionella sp

J Nat Prod. 2009 Aug;72(8):1471-6. doi: 10.1021/np900233c.

Abstract

Three new compounds of the rare classes trisnorditerpenes, bisnorditerpenes, and norditerpenes, gracilins J-L (1, 2, 6), and a new diterpene, 3'-norspongiolactone (8), were isolated from the extract of the marine sponge Spongionella sp. using NMR- and bioassay-guided fractionation, in addition to three known gracilins (3-5) as well as the known diterpenoid tetrahydroaplysulphurin-1 (7). The structures were elucidated using NMR spectroscopic techniques and mass spectrometric analysis. The structure of gracilin H (3) was confirmed by single-crystal X-ray analysis. All compounds were tested for their cytotoxicity and for their potential to inhibit EGF-R tyrosine kinase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / blood
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Crystallography, X-Ray
  • Diterpenes / blood
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology*
  • Drug Screening Assays, Antitumor
  • Humans
  • K562 Cells
  • Marine Biology
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*
  • Protein-Tyrosine Kinases / antagonists & inhibitors*

Substances

  • 3'-norspongiolactone
  • Antineoplastic Agents
  • Diterpenes
  • gracilin J
  • gracilin K
  • gracilin L
  • Protein-Tyrosine Kinases