Anthraquinone and Butenolide Constituents from the Crinoid Capillaster multiradiatus

Chem Pharm Bull (Tokyo). 2018 Nov 1;66(11):1023-1026. doi: 10.1248/cpb.c18-00472. Epub 2018 Aug 21.

Abstract

Seven anthraquinones including two new compounds namely capillasterquinones A and B (1 and 2) and one new butenolide namely capillasterolide (8) were isolated and structurally elucidated from the crinoid Capillaster multiradiatus. The inhibitory effect of compounds 1-8 on lipopolysaccharide (LPS)-induced nitric oxide (NO) production as well as inhibition of 1 on expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2) proteins in RAW264.7 cells were also evaluated. As the obtained results, capillasterquinone A (1) showed strong NO production inhibitory activity with an IC50 of 5.89±0.11 µM. In addition, compound 1 reduced the LPS-induced iNOS and COX-2 expressions in a dose-dependent manner.

Keywords: Capillaster multiradiatus; anthraquinone; crinoid; cyclooxygenase 2 (COX-2); inducible nitric oxide synthase (iNOS); nitric oxide (NO) production.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification
  • 4-Butyrolactone / pharmacology
  • Animals
  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification
  • Anthraquinones / pharmacology*
  • Cyclooxygenase 2 / metabolism
  • Dose-Response Relationship, Drug
  • Echinodermata / chemistry*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / metabolism
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Nitric Oxide Synthase Type II / metabolism
  • RAW 264.7 Cells
  • Structure-Activity Relationship

Substances

  • Anthraquinones
  • Enzyme Inhibitors
  • Lipopolysaccharides
  • Nitric Oxide
  • butenolide
  • Nitric Oxide Synthase Type II
  • Cyclooxygenase 2
  • 4-Butyrolactone