Cembrene diterpenoids with ether linkages from sarcophyton ehrenbergi: An anti-proliferation and molecular-docking assessment

Mohamed Elamir F. Hegazy, Abdelsamed I. Elshamy, Tarik A. Mohamed, Ahmed R. Hamed, Mahmoud A.A. Ibrahim, Shinji Ohta, Paul W. Paré

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

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.

Original languageEnglish
Article number192
JournalMarine Drugs
Volume15
Issue number6
DOIs
StatePublished - Jun 2017

Keywords

  • Cembranoids
  • Cytotoxic activity
  • Molecular docking
  • Sarcophyton ehrenbergi
  • Soft coral
  • Terpenes

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