Cytotoxic and anti-inflammatory compounds from Red Sea grass Thalassodendron ciliatum

Abstract

Chemical investigation of the less polar fraction methylene dichloride–methanol extract of the Red Sea grass Thalassodendron ciliatum led to the isolation of a new phytoceramide molecular species TCC-1, along with four known compounds: 7β-hydroxy cholesterol (10), 7β-hydroxysitosterol (11), stigmasterol glucoside (12), and β-sitosterol glucoside (13). Phytosphingosines with 2-hydroxy fatty acid residues constituted the phytoceramide molecular species TCC-1. Further purification of TCC-1 afforded two new phytoceramides: TCC-1-5 (5) and TCC-1-7 (7) as well as the known ceramide TCC-1-6 (6). All compounds are reported for the first time from this genus. The chemical structures of the isolated compounds were clarified on the basis of spectroscopic techniques including IR, NMR experiments, mass spectrometry, and chemical methods, in addition to comparison with literature data. All isolated compounds exhibited significant cytotoxicity against two human cell lines (Hep G2 and MCF-7). Moreover, compounds (10–13) have been found to possess significant anti-inflammatory activity in which compound (13) is the most potent.