Anti-inflammatory and antitumor phenylpropanoid sucrosides from the seeds of Raphanus sativus

Bioorg Med Chem Lett. 2015 Jan 1;25(1):96-9. doi: 10.1016/j.bmcl.2014.11.001. Epub 2014 Nov 7.

Abstract

A bioassay-guided fractionation and chemical investigation of the MeOH extract of Raphanus sativus seeds resulted in the isolation and identification of eight phenylpropanoid sucrosides (1-8) including two new compounds, named raphasativuside A and B (1-2) from the most active CHCl₃-soluble fraction. The structures of these new compounds were elucidated through spectral analysis, including extensive 2D-NMR data, and chemical reaction experiments. We evaluated the anti-inflammatory effects of 1-8 in lipopolysaccharide (LPS)-stimulated murine microglia BV2 cells. Compounds 2 and 5 exhibited significant inhibitory effect on nitric oxide production in LPS-activated BV-2 cells with IC₅₀ values of 21.63 and 26.96 μM, respectively. All isolates were also evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15). Compounds 1-7 showed consistent cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines with IC50 values of 6.71-27.92 μM. Additionally, the free-radical scavenging activity of 1-8 was assessed using the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay where compounds 1, 3, and 4 scavenged DPPH radical strongly with IC₅₀ values of 23.05, 27.10, and 29.63 μg/mL, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / isolation & purification*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Line, Tumor
  • Humans
  • Mice
  • Oxidative Stress / drug effects
  • Oxidative Stress / physiology
  • Phenylpropionates / chemistry
  • Phenylpropionates / isolation & purification*
  • Phenylpropionates / pharmacology
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification*
  • Plant Extracts / pharmacology
  • Raphanus*
  • Seeds*

Substances

  • Anti-Inflammatory Agents
  • Antineoplastic Agents, Phytogenic
  • Phenylpropionates
  • Plant Extracts