Monanchoramides A–D, ceramides from the marine sponge Monanchora clathrata with cytotoxic activity. (February 2018)

• Record Type: Journal Article
• Authors: 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.
• Is Part Of: Phytochemistry letters. Volume 23(2018)
• Page Start: 83
• Page End: 89
• Publication Date: 2018-02
• Subjects: Marine sponge -- Monanchora clathrata -- Ceramides -- Monanchoramides -- Cytotoxic activity; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2017.11.015
• Languages: English
• ISSNs: 1874-3900

Abstract

Graphical abstract: Highlights: Four new ceramides were isolated from sponge the Monanchora clathrata . Their chemical structures were elucidated using a combination of Chemical spectroscopic methods. Compound1 showed cytotoxicity against MES-SA, MCF-7, and HK-2 cell lines with IC50 values of 2.37, 12.9 and 3.2 μg/mL, respectively. Abstract: 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 compounds5–8, 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 known17, 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 compounds1–4 were assigned as 2 S, 3 S, 4 R, 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. Compound1 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.