Mechanism of action of antiepileptic ceramide from Red Sea soft coral Sarcophyton auritum

[Display omitted] Chemical investigation of the Red Sea soft coral Sarcophyton auritum led to the isolation and structure elucidation of a new ceramide N-((2S,3R,4E,6E)-1,3-dihydroxyhenicosa-4,6-dien-2-yl)tridecanamide (1). Structure elucidation was achieved using spectroscopic techniques, including...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2015-12, Vol.25 (24), p.5819-5824
Main Authors: Eltahawy, Nermeen A., Ibrahim, Amany K., Radwan, Mohamed M., Zaitone, Sawsan A., Gomaa, Mohamed, ElSohly, Mahmoud A., Hassanean, Hashim A., Ahmed, Safwat A.
Format: Article
Language:English
Subjects:
5HT3 receptors
Allosteric Regulation
Animals
Anthozoa - chemistry
Anthozoa - metabolism
Anticonvulsant
Anticonvulsants - chemistry
Anticonvulsants - isolation & purification
Anticonvulsants - therapeutic use
Anxiolytic
Binding Sites
Ceramide
Ceramides - chemistry
Ceramides - isolation & purification
Ceramides - therapeutic use
Disease Models, Animal
GABA receptors
Magnetic Resonance Spectroscopy
Mass Spectrometry
Maze Learning
Mice
Molecular Conformation
Molecular Docking Simulation
Pentylenetetrazole - toxicity
Protein Structure, Tertiary
Receptors, GABA-A - chemistry
Receptors, GABA-A - metabolism
Receptors, Serotonin - chemistry
Receptors, Serotonin - metabolism
Sarcophyton auritum
Seizures - chemically induced
Seizures - drug therapy
Static Electricity
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Summary:[Display omitted] Chemical investigation of the Red Sea soft coral Sarcophyton auritum led to the isolation and structure elucidation of a new ceramide N-((2S,3R,4E,6E)-1,3-dihydroxyhenicosa-4,6-dien-2-yl)tridecanamide (1). Structure elucidation was achieved using spectroscopic techniques, including 1D and 2D NMR and HRMS. The anticonvulsant activity of the isolated ceramide was measured in vivo using the pentylenetetrazole (PTZ)-induced seizure model, where it successfully antagonized the lethality of pentylenetetrazole in mice. In addition, the isolated ceramide showed good anxiolytic activity when used in the light–dark transition box and the elevated plus maze compared to diazepam. The molecular modeling studies for the antiepileptic and antianxiety mechanism of the isolated ceramide suggested a CNS depressing activity possibly through GABA and serotonin receptors modulation. The pharmacological activity of the ceramide involved agonistic activity on GABA-A receptors but not 5HT3 receptors.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2015.08.039