Isolation of Lignan and Fatty Acid Derivatives from the Grains of Echinochloa utilis and Their Inhibition of Lipopolysaccharide-Induced Nitric Oxide Production in RAW 264.7 Cells

J Agric Food Chem. 2016 Jan 20;64(2):425-32. doi: 10.1021/acs.jafc.5b05638. Epub 2016 Jan 11.

Abstract

Two new fatty acid derivatives, echinochlorins A (8) and B (9) and a racemic lignan, (±)-anti-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-acetoxypropen-1-yl]-2-methoxyphenoxy}propan-1,3-diol 3-acetate (1), were isolated from Echinochloa utilis grains, along with six known lignans (2-7) and two fatty acid derivatives (10, 11). Their structures were established by spectroscopic data analyses (IR, UV, HR-FABMS, GC-MS, and 1D and 2D NMR). The configuration of 1 was determined by Mosher's method. Compound 5 displayed potential inhibitory activity on lipopolysaccharide-induced NO production in macrophage RAW 264.7 cells with an IC50 value of 4.8 ± 0.5 μM. These isolated compounds in crude EtOH extract were also quantitated by HPLC.

Keywords: Echinochloa utilis; NO inhibitory activity; echinochlorins A and B; lignans.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Echinochloa / chemistry*
  • Fatty Acids / chemistry
  • Fatty Acids / isolation & purification
  • Fatty Acids / pharmacology*
  • Lignans / chemistry
  • Lignans / isolation & purification
  • Lignans / pharmacology*
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects*
  • Macrophages / metabolism
  • Mice
  • Molecular Structure
  • Nitric Oxide / metabolism*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • RAW 264.7 Cells
  • Seeds / chemistry

Substances

  • Fatty Acids
  • Lignans
  • Lipopolysaccharides
  • Plant Extracts
  • Nitric Oxide