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

Authors
  • Canals, Daniel1
  • Mormeneo, David
  • Fabriàs, Gemma
  • Llebaria, Amadeu
  • Casas, Josefina
  • Delgado, Antonio
  • 1 Research Unit on BioActive Molecules (RUBAM), Departament de Química Biomèdica, Institut de Química Avançada de Catalunya (IQAC-C.S.I.C), Jordi Girona 18-26, 08034 Barcelona, Spain. , (Spain)
Type
Published Article
Journal
Bioorganic & medicinal chemistry
Publication Date
Jan 01, 2009
Volume
17
Issue
1
Pages
235–241
Identifiers
DOI: 10.1016/j.bmc.2008.11.026
PMID: 19056278
Source
Medline
Language
English
License
Unknown

Abstract

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 in autophagy.

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