Cytotoxic tetraprenylated alkaloids from the South China Sea gorgonian Euplexaura robusta

Chem Biodivers. 2012 Oct;9(10):2218-24. doi: 10.1002/cbdv.201100374.

Abstract

Nine achiral tetraprenylated alkaloids, including three new compounds, named malonganenones I-K (1-3, resp.), together with six known analogs, 4-9, were isolated from the gorgonian Euplexaura robusta collected from Weizhou Island of Guangxi Province, China. The structures of compounds 1-3 were elucidated by extensive spectral analyses, especially of their 1D- and 2D-NMR data. Compounds 1, 4, 6, and 7 showed moderate cytotoxicities against K562 and HeLa tumor cell lines with IC(50) values ranging from 0.35 to 10.82 μM. Compound 6 also showed moderate inhibitory activity against c-Met kinase at a concentration of 10 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology
  • Alkaloids / toxicity
  • Animals
  • Anthozoa / chemistry*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • China
  • Drug Screening Assays, Antitumor
  • Formamides / chemistry*
  • Formamides / isolation & purification
  • Formamides / toxicity
  • HeLa Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Neoprene / chemistry*
  • Oceans and Seas
  • Proto-Oncogene Proteins c-met / antagonists & inhibitors
  • Proto-Oncogene Proteins c-met / metabolism
  • Purines / chemistry
  • Purines / isolation & purification
  • Purines / pharmacology
  • Purines / toxicity

Substances

  • 3,7-dihydro-3-methyl-7-((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)-6 H-purin-6-one
  • 3,7-dihydro-3-methyl-7-((2E,6E,10Z)-3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10-trien-1-yl)-6H-purin-6-one
  • Alkaloids
  • Formamides
  • N-((2E,6E,10E)-3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10-trien-1-yl)formamide
  • Purines
  • prenyl
  • Neoprene
  • Proto-Oncogene Proteins c-met