Preparative isolation of sargachromanol E from Sargassum siliquastrum by centrifugal partition chromatography and its anti-inflammatory activity

Food Chem Toxicol. 2013 Dec:62:54-60. doi: 10.1016/j.fct.2013.08.010. Epub 2013 Aug 20.

Abstract

Centrifugal partition chromatography (CPC) can be used to isolate various bioactive compounds from natural materials by one-step. We confirmed antioxidative compounds existed in chloroform (CHCl3) fraction of Sargassum siliquastrum using online-HPLC. Fractions (A, B, C, D and E) were separated from the CHCl3 fraction by preparative CPC (n-hexane:ethyl acetate:methanol:water, 5:5:7:3, v/v). In this study, we proved that the isolated compounds exhibit anti-inflammatory activities using lipopolysaccharide (LPS) stimulated RAW 264.7 macrophages. The fraction A which exhibited the strongest inhibitory effect on nitric oxide (NO) production level, was confirmed as sargachromanol E by LC-MS-ESI, (1)H NMR and (13)C NMR data. The sargachromanol E significantly reduced the inflammatory response in LPS induced macrophages, decreasing LPS-induced transcription factor of pro-inflammatory cyclooxygenase-2, NO synthase, phosphate P38, phosphate ERK1/2, LPS-stimulated tumor-necrosis factor alpha, interleukin-1 beta and prostaglandin E2 release. In conclusion, it was suggested that sargachromanol E inhibited inflammation in LPS induced RAW 264.7 cells via MAPK pathway.

Keywords: Antiinflammatory activity; Centrifugal partition chromatography; MAPK pathway; Sargachromanol E; Sargassum siliquastrum.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / pharmacology*
  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification*
  • Benzopyrans / pharmacology*
  • Cells, Cultured / drug effects
  • Centrifugation / methods
  • Chromatography, High Pressure Liquid / methods
  • Chromatography, Liquid / methods
  • Cyclooxygenase 2 / metabolism
  • Dinoprostone / metabolism
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects*
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Mice
  • Mitogen-Activated Protein Kinases / metabolism
  • Molecular Structure
  • Nitric Oxide / metabolism
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Nitric Oxide Synthase Type II / metabolism
  • Sargassum / chemistry*
  • Solvents / chemistry

Substances

  • Anti-Inflammatory Agents
  • Benzopyrans
  • Lipopolysaccharides
  • Solvents
  • Nitric Oxide
  • Nitric Oxide Synthase Type II
  • Nos2 protein, mouse
  • Ptgs2 protein, mouse
  • Cyclooxygenase 2
  • Mitogen-Activated Protein Kinases
  • sargachromanol E
  • Dinoprostone