ABSTRACT
An efficient column chromatography of the CH2Cl2/MeOH crude extract from the soft coral Litophyton mollis (Macfadyen, 1936) yielded seven steroids, including five 4α-methylated steroids (1-5) and two 19-oxygenated steroids (6-7). Notably, both compounds 3 and 7 are new, identified as (22E)-4α,24-dimethyl-5α-cholesta-22,24(28)-dien-3ß,8ß-diol (3) and (22E,24R)-7ß-acetoxy-24-methyl-cholesta-5,22-dien-3ß,19-diol (7). The chemical structures and relative configurations were elucidated through comprehensive spectroscopic analyses, including 1D and 2D NMR, as well as HRESIMS analysis. The cytotoxicity of metabolites 1-7 was evaluated against three cancer cell lines: MCF-7, HepG2, and NCI-1299. Remarkably, metabolites 6 and 7 exhibited strong cytotoxic activity against MCF-7, with IC50 values of 8.6 and 8.4 µM, respectively, while also showing moderate effects against NCI-1299, with IC50 values of 15.7 and 15.1 µM, respectively. Additionally, steroids 4 and 5 displayed weak cytotoxicity against all three cell lines, with IC50 values in the ranges of 34.7-37.5 and 30.8-46.3 µM, respectively.
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 24.1â µM, while showing inactivity against the remaining cell lines (IC50 >100â µM).
Subject(s)
Adenocarcinoma , Anthozoa , Antineoplastic Agents , Colonic Neoplasms , Animals , Humans , HeLa Cells , Ether , Glycerol/metabolism , Anthozoa/chemistry , Propane , Indian Ocean , Glyceryl Ethers/metabolism , Antineoplastic Agents/chemistry , Ethyl Ethers/metabolism , Ethers , Complex Mixtures/metabolism , Cell Line, TumorABSTRACT
A successful column chromatography of a CHCl3/MeOH crude extract of Dendronephthya spp. soft coral led to the isolation of two new aromatic A-ring steroids (1-2), together with three known compounds (3-5). Both 1 and 2 are 19-norsteroids. The chemical structures were elucidated based on extensive 1D, 2D NMR, and EIMS analyses. In cytotoxic bioassays, compounds 1-5 were tested against three cancer cell lines: MCF-7, NCI-1299, and HepG2, with IC50 in the ranges of 22.1-85.4, 26.9-88.7, and 25.9-93.7 µM, respectively. Compounds 1, 2, and 5 showed moderate degrees of inhibition against Escherichia coli and Pseudomonas sp. at 100 and 150 µg/mL, while exhibiting weak inhibition against Bacillus cereus and Staphylococcus aureus at 150 µg/mL.
