Abstract
Three new cembrene diterpenoids, sarcoehrenbergilid A–C (1–3), along with four known diterpenoids, sarcophine (4), (+)-7α,8β-dihydroxydeepoxysarcophine (5), sinulolide A (6), and sinulolide B (7), and one steroid, sardisterol (8), were isolated and characterized from a solvent extract of the Red Sea soft coral Sarcophyton ehrenbergi. Chemical structures were elucidated by NMR and MS analyses with absolute stereochemistry determined by X-ray analysis. Since these isolated cembrene diterpenes contained 10 or more carbons in a large flexible ring, conformer stabilities were examined based on density functional theory calculations. Anti-proliferative activities for 1–8 were evaluated against three human tumor cell lines of different origins including the: lung (A549), colon (Caco-2), and liver (HepG2). Sardisterol (8) was the most potent of the metabolites isolated with an IC50 of 27.3 µM against the A549 cell line. Since an elevated human-cancer occurrence is associated with an aberrant receptor function for the epidermal growth factor receptor (EGFR), molecular docking studies were used to examine preferential metabolite interactions/binding and probe the mode-of-action for metabolite-anti tumor activity.
Highlights
Cembrane diterpenoids are a large and structurally diverse group of natural products isolated from both terrestrial and marine organisms [1]
All optimized conformers were subjected to a vibrational frequency calculation to confirm the minimum energy states and the corresponding free energies were obtained
Molecular docking studies are consistent with the binding of 8 to the epidermal growth factor receptor (EGFR) kinase domain and the inhibition of cell growth
Summary
Cembrane diterpenoids are a large and structurally diverse group of natural products isolated from both terrestrial and marine organisms [1]. Sarcophyton soft coral species are characterized by the production of cembrene-type diterpenoids [4,5,6,7,8,9,10] and these cyclic diterpenes usually exhibit cyclic ether, lactone, or furane moieties around the cembrane framework [11,12]. Cembranoid diterpenes exhibit a diverse range of biological protection. Cembranoid diterpenes exhibit a diverse range of biological protection against tumors, inflammation, and fish toxins (ichthyotoxic), as well as microbial and/or viral infections [4,5,13]. With cancer occurrence and mortality associated with cancer increasing in the U.S and around the world, the exploration of cytotoxic agents for improved
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