New Biscembranoids Sardigitolides A-D and Known Cembranoid-Related Compounds from Sarcophyton digitatum: Isolation, Structure Elucidation, and Bioactivities

Mar Drugs. 2020 Aug 29;18(9):452. doi: 10.3390/md18090452.

Abstract

Chemical examination from the cultured soft coral Sarcophyton digitatum resulted in the isolation and structural identification of four new biscembranoidal metabolites, sardigitolides A-D (1-4), along with three previously isolated biscembranoids, sarcophytolide L (5), glaucumolide A (6), glaucumolide B (7), and two known cembranoids (8 and 9). The chemical structures of all isolates were elucidated on the basis of 1D and 2D NMR spectroscopic analyses. Additionally, in order to discover bioactivity of marine natural products, 1-8 were examined in terms of their inhibitory potential against the upregulation of inflammatory factor production in lipopolysaccharide (LPS)-stimulated murine macrophage J774A.1 cells and their cytotoxicities against a limited panel of cancer cells. The anti-inflammatory results showed that at a concentration of 10 µg/mL, 6 and 8 inhibited the production of IL-1β to 68 ± 1 and 56 ± 1%, respectively, in LPS-stimulated murine macrophages J774A.1. Furthermore, sardigitolide B (2) displayed cytotoxicities toward MCF-7 and MDA-MB-231 cancer cell lines with the IC50 values of 9.6 ± 3.0 and 14.8 ± 4.0 µg/mL, respectively.

Keywords: LPS-stimulated murine macrophage; Sarcophyton digitatum; biscembranoid-type metabolites; cytotoxicity; inflammatory factor production.

Publication types

  • Comparative Study

MeSH terms

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

Substances

  • Anti-Inflammatory Agents
  • Antineoplastic Agents
  • IL1B protein, mouse
  • Inflammation Mediators
  • Interleukin-1beta
  • Lipopolysaccharides