New Hydroquinone Monoterpenoid and Cembranoid-Related Metabolites from the Soft Coral Sarcophyton tenuispiculatum

Mar Drugs. 2020 Dec 27;19(1):8. doi: 10.3390/md19010008.

Abstract

Chemical investigation of the marine soft coral Sarcophyton tenuispiculatum resulted in the isolation of a 1,4-dihydrobenzoquinone, sarcotenuhydroquinone (1), three new cembranoids, sarcotenusenes A‒C (24), and ten previously reported metabolites 5-14. The chemical structures of all isolated metabolites were determined by detailed spectroscopic analyses. In biological assays, anti-inflammatory, cytotoxic, and peroxisome proliferator-activated receptor γ (PPAR-γ) transcription factor assays of all compounds were performed. None of the isolated compounds were found to exhibit activity in the PPAR-γ transcription factor assay. The anti-inflammatory assays showed that (+)-7α,8β-dihydroxydeepoxysarcophine (13) inhibited the production of IL-1β to 56 ± 1% at a concentration of 30 µM in lipopolysaccharide (LPS)-stimulated J774A.1 macrophage cells. In addition, 1 and 2 were found to exhibit cytotoxicity towards a panel of cancer cell lines.

Keywords: LPS-stimulated J774A.1 macrophage cells; PPAR-γ transcription factor; Sarcophyton tenuispiculatum; anti-inflammatory; cembranoid; cytotoxicity; hydroquinone.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Anthozoa / metabolism*
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Cell Survival / drug effects
  • Diterpenes / metabolism*
  • HeLa Cells
  • Hep G2 Cells
  • Humans
  • Hydroquinones / metabolism*
  • Inflammation Mediators / metabolism
  • Interleukin-1beta / metabolism
  • MCF-7 Cells
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Molecular Structure
  • Monoterpenes / metabolism*
  • Neoplasms / drug therapy
  • Neoplasms / pathology
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents
  • Antineoplastic Agents
  • Diterpenes
  • Hydroquinones
  • IL1B protein, mouse
  • Inflammation Mediators
  • Interleukin-1beta
  • Monoterpenes
  • hydroquinone