New Cytotoxic Monoalkyl Glycerol Ether from the Red Sea Soft Coral Nephthea mollis

Chem Biodivers. 2023 Nov;20(11):e202301208. doi: 10.1002/cbdv.202301208. Epub 2023 Oct 23.

Abstract

A new monoalkyl glycerol ether, 3-(n-henicosyloxy)propane-1,2-diol (1), was isolated from the CH2 Cl2 /MeOH crude extract of the Red Sea soft coral Nephthea mollis. Additionally, three known related analogs were identified: chimyl alcohol (2), batyl alcohol (3), and 3-(icosyloxy)propane-1,2-diol (4). The chemical structure of 3-(n-henicosyloxy)propane-1,2-diol was determined using advanced spectroscopic analyses, including 1D, 2D Nuclear Magnetic Resonance (NMR), Electron Ionization mass spectra (EI-MS), and High-Resolution Electron Spray Ionization mass spectra (HR-ESI-MS) analyses. Furthermore, the identification of chimyl alcohol, batyl alcohol and 3-(icosyloxy)propane-1,2-diol was achieved by studying their EI mass fragmentation analyses and comparing their mass data with those previously reported in the literature. The cytotoxic activity of the Nephthea mollis crude extract and 3-(n-henicosyloxy)propane-1,2-diol was evaluated against five human cancer cell lines: HepG2 (hepatocellular carcinoma), MCF-7 (breast carcinoma), NCI-1299 (lung carcinoma), HeLa (cervical cancer cell), and HT-29 (colon adenocarcinoma). Moreover, 3-(n-henicosyloxy)propane-1,2-diol revealed moderate cytotoxicity against the HeLa cell lines with an IC50 value of 24.1 μM, while showing inactivity against the remaining cell lines (IC50 >100 μM).

Keywords: Nephthea mollis; Red Sea; cytotoxicity; monoalkyl glycerol ether; soft coral.

MeSH terms

  • Adenocarcinoma*
  • Animals
  • Anthozoa* / chemistry
  • Antineoplastic Agents* / chemistry
  • Cell Line, Tumor
  • Colonic Neoplasms*
  • Complex Mixtures / metabolism
  • Ether
  • Ethers
  • Ethyl Ethers / metabolism
  • Glycerol / metabolism
  • Glyceryl Ethers / metabolism
  • HeLa Cells
  • Humans
  • Indian Ocean
  • Propane

Substances

  • chimyl alcohol
  • batyl alcohol
  • Ether
  • Glycerol
  • Propane
  • Glyceryl Ethers
  • Antineoplastic Agents
  • Ethyl Ethers
  • Ethers
  • Complex Mixtures