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A Novel Jaspine BCeramide Hybrid Modulates Sphingolipid Metabolism
Author(s) -
Garcia Virginie,
Le Faouder Pauline,
Dupuy Aude,
Levade Thierry,
Ballereau Stéphanie,
Génisson Yves
Publication year - 2015
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201400357
Subject(s) - sphingolipid , ceramide , chemistry , sphingosine , sphingomyelin , moiety , pharmacophore , biochemistry , cytotoxicity , stereochemistry , lipid signaling , metabolism , sphingosine 1 phosphate , receptor , apoptosis , in vitro , cholesterol
Abstract A new sphingolipid hybrid molecule was designed to assemble, within a tail‐to‐tail double‐chain structure, the ceramide hydrophilic moiety and the tetrahydrofuran pharmacophore of jaspine B, a natural product known to interfere with sphingolipid metabolism. This compound was prepared through acylation of sphingosine with a jaspine B derivative bearing a COOH group in the terminal position of the aliphatic backbone. This new hybrid molecule was evaluated for its capacities to affect melanoma cell viability and sphingolipid metabolism. While retaining the cytotoxicity of ceramide itself, this compound was shown to lower the sphingomyelin cellular levels and significantly enhance the production of sphingosine‐1‐phosphate, thus representing a novel sphingolipid metabolism modulator.