Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines.
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.
Canals
Daniel
D
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.
Mormeneo
David
D
Fabriàs
Gemma
G
Llebaria
Amadeu
A
Casas
Josefina
J
Delgado
Antonio
A
D001343:Autophagy; D016923:Cell Death / Q000187:drug effects; D002460:Cell Line; D002518:Ceramides / Q000378:metabolism; D003500:Cyclization; D004305:Dose-Response Relationship, Drug; D006801:Humans; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D002518:Ceramides; C468594:pachastrissamine; C012491:phytosphingosine; D013110:Sphingosine