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Monanchoramides A–D, ceramides from the marine sponge Monanchora clathrata with cytotoxic activity

Raslan, Ali E., Radwan, Mohamed M., Ahmed, Safwat A., Nafady, Alaa M., Zaki, Mohamed A., Wanas, Amira S., Abou-Karam, Mohamed, Shier, Thomas W., Hassanean, Hashim A., ElSohly, Mahmoud A.
Phytochemistry letters 2018 v.23 pp. 83-89
Porifera, acetylation, antimalarials, cell lines, ceramides, cytotoxicity, inhibitory concentration 50, moieties, nuclear magnetic resonance spectroscopy, spectral analysis, sterols, triacylglycerols, uracil
Four new ceramides (1–4) were isolated from the sponge Monanchora clathrata, along with four epidioxysterols (5–8), two sterols (9, 10), uracil (11), and three triglycerides (12–14). All compounds were isolated for the first time from the genus Monanchora, also this is the first time for isolation and identification of compounds 5–8, and the ceramide moieties from the family Crambeidae. Acetylation of compounds (5–8) yielded two new chemically modified compounds (15, 16), in addition to the known 17, 18. Their chemical structures were elucidated using a combination of spectroscopic methods, including extensive 1D and 2D NMR, IR, HRESIMS, and GC/MS. The configuration of compounds 1–4 were assigned as 2S,3S,4R,2′R based on the modified Mosher’s reaction, optical rotation measurements and spectroscopic data comparison. The compounds were evaluated for their, cytotoxic, antiprotozoal, antimicrobial, and antimalarial potentials. Compound 1 showed remarkable cytotoxicity against MES-SA, MCF-7, and HK-2 cell lines with IC50 values of 3.29, 17.95 and 4.45 μM, respectively.