Antiangiogenic tocotrienol derivatives from Garcinia amplexicaulis

J Nat Prod. 2013 Dec 27;76(12):2246-52. doi: 10.1021/np400598y. Epub 2013 Nov 18.

Abstract

Phytochemical investigation of a dichloromethane extract from Garcinia amplexicaulis stem bark led to the isolation of four new tocotrienols (1-4); two known tocotrienols, two triterpenes, and a xanthone were also isolated. Their structures were mainly established using NMR and MS methods. The main compounds isolated, δ-amplexichromanol (1) and γ-amplexichromanol (2), were evaluated on VEGF-induced angiogenesis using a Matrigel assay. Compounds 1 and 2 inhibited in vitro angiogenesis of VEGF-induced human primary endothelial cells in the low nanomolar range. Their capacity to inhibit VEGF-induced proliferation of endothelial cells partially explained this activity, although δ-amplexichromanol (1) also prevented adhesion and migration processes.

MeSH terms

  • Angiogenesis Inhibitors / chemistry
  • Angiogenesis Inhibitors / isolation & purification*
  • Angiogenesis Inhibitors / pharmacology*
  • Chromans / chemistry
  • Chromans / isolation & purification*
  • Chromans / pharmacology*
  • Garcinia / chemistry*
  • Humans
  • Molecular Structure
  • Neovascularization, Pathologic / drug therapy
  • New Caledonia
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Bark / chemistry
  • Plant Stems / chemistry
  • Tocotrienols / chemistry
  • Tocotrienols / isolation & purification*
  • Tocotrienols / pharmacology*
  • Vascular Endothelial Growth Factor A / pharmacology

Substances

  • Angiogenesis Inhibitors
  • Chromans
  • Tocotrienols
  • Vascular Endothelial Growth Factor A