Anti-neuroinflammatory activities of indole alkaloids from kanjang (Korean fermented soy source) in lipopolysaccharide-induced BV2 microglial cells

Food Chem. 2016 Dec 15:213:69-75. doi: 10.1016/j.foodchem.2016.06.068. Epub 2016 Jun 21.

Abstract

Kanjang (Korean soy sauce) is a byproduct of the production of the Korean fermented soybean. In the present study, seven indole alkaloid derivatives were isolated from methanol extract of kanjang. Their structures were identified as 1-propyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1), 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2), 1-methyl-1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid (3), 3-indoleacetic acid (4), Nb-acetyltryptamine (5), 1-methyl-3,4-dihydro-β-carboline (6), and flazine (7) by NMR and MS analyses. Preliminary screening for anti-neuroinflammatory effects of isolated indole alkaloids in lipopolysaccharide (LPS)-stimulated BV2 cells revealed that these compounds inhibited the production of nitric oxide and prostaglandin E2. For the subsequent investigation of anti-neuroinflammatory action of these metabolites, compounds 4 and 7 were selected, and the results revealed that these inhibitory effects correlated with the suppressive effect of 4 and 7 on inducible nitric oxide synthase and cyclooxygenase-2 expression in LPS-stimulated BV2 cells. In regards to the mechanism of the anti-inflammatory effect, 4 and 7 significantly inhibited the nuclear factor-kappa B pathway.

Keywords: Anti-neuroinflammation; Indole alkaloids; Kanjang (Korean soy sauce); NF-κB.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry*
  • Carbolines / chemistry
  • Cell Nucleus / metabolism
  • Cell Survival
  • Cyclooxygenase 2 / metabolism
  • Cytosol / metabolism
  • Dinoprostone / metabolism
  • Dose-Response Relationship, Drug
  • Glycine max / chemistry*
  • Indole Alkaloids / chemistry
  • Indoleacetic Acids
  • Inflammation
  • Lipopolysaccharides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mice
  • Microglia / drug effects
  • Microglia / metabolism
  • NF-kappa B / metabolism
  • Nitric Oxide / chemistry
  • Nitric Oxide / metabolism
  • Nitric Oxide Synthase Type II / metabolism
  • Soy Foods / analysis*
  • p38 Mitogen-Activated Protein Kinases / metabolism

Substances

  • Anti-Inflammatory Agents
  • Carbolines
  • Indole Alkaloids
  • Indoleacetic Acids
  • Lipopolysaccharides
  • NF-kappa B
  • Nitric Oxide
  • 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid
  • 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid
  • indoleacetic acid
  • Nitric Oxide Synthase Type II
  • Nos2 protein, mouse
  • Ptgs2 protein, mouse
  • Cyclooxygenase 2
  • p38 Mitogen-Activated Protein Kinases
  • Dinoprostone