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

Ali E. Raslan, Mohamed M. Radwan, Safwat A. Ahmed, Alaa M. Nafady, Mohamed A. Zaki, Amira S. Wanas, Mohamed Abou-Karam, Thomas W. Shier, Hashim A. Hassanean, Mahmoud A. ElSohly

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

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 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.

Original languageEnglish (US)
Pages (from-to)83-89
Number of pages7
JournalPhytochemistry Letters
Volume23
DOIs
StatePublished - Feb 2018

Bibliographical note

Funding Information:
We are grateful to Dr. Bharathi Avula and Dr. Babu Tekwani, National Center for Natural Products Research for assistance with the HRESIMS, and antiprotozoal assays. Financial support was partially provided by the Egyptian government .

Publisher Copyright:
© 2017

Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.

Keywords

  • Ceramides
  • Cytotoxic activity
  • Marine sponge
  • Monanchora clathrata
  • Monanchoramides

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