NF-κB inhibitory activity of sucrose fatty acid esters and related constituents from Astragalus membranaceus

J Agric Food Chem. 2013 Jul 24;61(29):7081-8. doi: 10.1021/jf4017509. Epub 2013 Jul 11.

Abstract

Twelve compounds, including six sucrose fatty acid esters (1-6), four galactosyl acylglycerols (7-10), and two sphingolipids (11 and 12), were isolated from the roots of Astragalus membranaceus . Their structures were identified on the basis of spectroscopic analysis. Among the isolated sucrose fatty acid esters, 6'-O-linoleyl sucrose (1) was identified as a new compound, and 6'-O-palmitoyl sucrose (2) and 6-O-palmitoyl sucrose (3) were isolated from nature for the first time. This is the first report on sucrose fatty acid ester components from A. membranaceus. The nuclear factor-κB (NF-κB) inhibitory activity of isolated compounds was measured in HepG2 cells stimulated with TNF-α using a luciferase reporter system. Among them, compounds 1-6 exhibited significant inhibition of NF-κB activation in a dose-dependent manner, with IC50 values ranging from 4.4 to 24.7 μM. Compounds 1-6 also exhibited inhibition of TNF-α-induced expression of iNOS and ICAM-1 mRNA and dose-dependent inhibition of iNOS promoter activity, with IC50 values ranging from 3.3 to 5.0 μM. These data demonstrate the potential of sucrose fatty acid esters from A. membranaceus to prevent and treat inflammatory diseases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Astragalus propinquus / chemistry*
  • Dose-Response Relationship, Drug
  • Drug Evaluation, Preclinical
  • Esters / chemistry
  • Esters / pharmacology*
  • Hep G2 Cells / drug effects
  • Humans
  • Inhibitory Concentration 50
  • Intercellular Adhesion Molecule-1 / genetics
  • Linoleic Acids / chemistry
  • Linoleic Acids / pharmacology*
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors*
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Nitric Oxide Synthase Type II / genetics
  • Sucrose / chemistry
  • Sucrose / pharmacology*
  • Tumor Necrosis Factor-alpha / pharmacology

Substances

  • 6'-O-linoleyl sucrose
  • Anti-Inflammatory Agents, Non-Steroidal
  • Esters
  • Linoleic Acids
  • NF-kappa B
  • Tumor Necrosis Factor-alpha
  • Intercellular Adhesion Molecule-1
  • Sucrose
  • NOS2 protein, human
  • Nitric Oxide Synthase Type II