Synthesis and anti-inflammatory activity of aromatic glucosinolates

Bioorg Med Chem. 2013 Oct 1;21(19):5945-54. doi: 10.1016/j.bmc.2013.07.049. Epub 2013 Aug 9.

Abstract

Aromatic GLs are important members of the glucosinolate family of compounds because of their potential biological activity and medicinal properties. This study has shown success in the high yielding synthesis of some important aromatic GLs as well as the results of testing for anti-inflammatory properties of the synthetic GLs. 3,4-Dimethoxyphenylglucosinolate was found to be the most active anti-inflammatory of the seven glucosinolates assayed.

Keywords: 1,2-dimethoxyethane; 3,4-Dimethoxyphenylglucosinolate; Anti-inflammatory; Aromatic glucosinolate; Brassica; DCM; DME; DMF; ELISA; ESI; FTMS; GLs; HESI; HRMS; IR; LPS; MS; N,N-dimethylformamide; N-chlorosuccinimide; NCS; NMR; PMA; THF; TLC; TNF-α; TNFalpha; UV; Z; benzyloxycarbonyl; dichloromethane; electrospray ionization; enzyme-linked immunosorbent assay; fourier transform mass spectrometry; glucosinolates; heated electrospray ionization; high resolution mass spectrometry; infra-red; lipopolysaccharides; mass spectrometry; nuclear magnetic resonance; phorbol-12-myristate-13-acetate; tetrahydrofuran; thin layer chromatography; tumor necrosis factor alpha; ultra-violet.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology
  • Carbohydrate Sequence
  • Cell Line
  • Glucosinolates / chemical synthesis*
  • Glucosinolates / chemistry
  • Glucosinolates / pharmacology
  • Humans
  • Molecular Structure

Substances

  • 3,4-dimethoxyphenylglucosinolate
  • Anti-Inflammatory Agents
  • Glucosinolates