Identification and Quantification of Potential Anti-inflammatory Hydroxycinnamic Acid Amides from Wolfberry

J Agric Food Chem. 2017 Jan 18;65(2):364-372. doi: 10.1021/acs.jafc.6b05136. Epub 2017 Jan 6.

Abstract

Wolfberry or Goji berry, the fruit of Lycium barbarum, exhibits health-promoting properties that leads to an extensive study of their active components. We synthesized a set of hydroxycinnamic acid amide (HCCA) compounds, including trans-caffeic acid, trans-ferulic acid, and 3,4-dihydroxyhydrocinnamic acid, with extended phenolic amine components as standards to identify and quantify the corresponding compounds from wolfberry and to investigate anti-inflammatory properties of these compounds using in vitro model. With optimized LC-MS/MS and NMR analysis, nine amide compounds were identified from the fruits. Seven of these compounds were identified in this plant for the first time. The amide compounds with a tyramine moiety were the most abundant. In vitro studies indicated that five HCCA compounds showed inhibitory effect on NO production inuded by lipopolysaccharides with IC50 less than 15.08 μM (trans-N-feruloyl dopamine). These findings suggested that wolfberries demonstrated anti-inflammatory properties.

Keywords: Lycium barbarum; anti-inflammation; hydroxycinnamic acid amides; organic synthesis; wolfberries.

MeSH terms

  • Amides / chemistry
  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Caffeic Acids / chemical synthesis
  • Caffeic Acids / chemistry
  • Cell Line
  • Chemistry Techniques, Synthetic
  • Coumaric Acids / chemistry
  • Coumaric Acids / pharmacology*
  • Drug Evaluation, Preclinical / methods
  • Lipopolysaccharides / pharmacology
  • Lycium / chemistry*
  • Macrophages / drug effects
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Nitric Oxide / metabolism
  • Tandem Mass Spectrometry
  • Tyramine / chemistry

Substances

  • Amides
  • Anti-Inflammatory Agents, Non-Steroidal
  • Caffeic Acids
  • Coumaric Acids
  • Lipopolysaccharides
  • 3,4-dihydroxyphenylpropionic acid
  • Nitric Oxide
  • ferulic acid
  • Tyramine