Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines.

@article{Canals2009SynthesisAB,
  title={Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines.},
  author={Daniel Canals and David Mormeneo and Gemma F{\'a}brias and Amadeu Llebaria and Josefina Casas and A {\'A}lvarez Delgado},
  journal={Bioorganic & medicinal chemistry},
  year={2009},
  volume={17 1},
  pages={235-41}
}
The synthesis of isomeric jaspines (anhydro phytosphingosines), arising from intramolecular cyclization of the corresponding phytosphingosines with different configurations at C3 and C4 positions of the sphingoid backbone, is reported. Natural jaspine B is the most cytotoxic isomer on A549 cells and it induces cell death in a dose-dependent manner. The cytotoxicity of jaspine B has been correlated with a significant increase of intracellular dihydroceramides, which seem to play an active role… CONTINUE READING