Anti-inflammatory activity of phenylpropyl triterpenoids from Osmanthus fragrans var. aurantiacus leaves

Int Immunopharmacol. 2020 Sep:86:106576. doi: 10.1016/j.intimp.2020.106576. Epub 2020 Jun 20.

Abstract

Osmanthus fragrans var. aurantiacus has been used for the treatment of menopausal pain, foul breath, and intestinal bleeding. Four phenylpropyl triterpenoids, 3-O-trans-p-coumaroyltormentic acid (1), 3β-trans-p-coumaroyloxy-2α-hydroxyl-urs-12-en-28-oic acid (2), 3β-cis-p-coumaroyloxy-2α-hydroxyl-urs-12-en-28-oic acid (3), 3-O-cis-coumaroylmaslinic acid (4), were isolated from the leaves of O. fragrans var. aurantiacus and the inhibitory effect on nitric oxide (NO) production in lipopolysaccharide (LPS)-induced macrophages were evaluated. Among them, compounds 2-4 concentration dependently showed NO production inhibitory effects. To determine the signaling factors involved in the inhibition of NO production by compounds 2-4, we assessed anti-inflammatory activity. Western blot analysis revealed compounds 2-4 significantly decreased the expression of LPS-stimulated protein, inducible nitric oxide synthase (iNOS), cyclooxygenase (COX)-2, nuclear factor-kappa B (NF-κB) and phosphorylated extracellular regulated kinase (pERK)1/2. Also, compounds 2-4 downregulated tumor necrosis factor (TNF)-α, interleukin (IL)-1β, IL-6 and IL-8 levels in LPS-induced macrophages and colonic epithelial cells. This study demonstrated that phenylpropyl triterpenoids 2-4 isolated from O. fragrans var. aurantiacus leaves can be used as potential candidates for the prevention and treatment of inflammatory bowel disease.

Keywords: HT-29; Inflammatory bowel disease; Osmanthus fragrans var. aurantiacus; Phenylpropyl triterpenoids; RAW 264.7.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Cell Survival / drug effects
  • Cyclooxygenase 2 / drug effects
  • Cytokines / drug effects
  • HT29 Cells
  • Humans
  • Lipopolysaccharides / toxicity
  • Mice
  • Mitogen-Activated Protein Kinase 1 / drug effects
  • Mitogen-Activated Protein Kinase 3 / drug effects
  • NF-kappa B p50 Subunit / drug effects
  • Nitric Oxide / metabolism
  • Nitric Oxide Synthase Type II / drug effects
  • Oleaceae / chemistry*
  • Plant Leaves / chemistry
  • RAW 264.7 Cells
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*

Substances

  • Anti-Inflammatory Agents
  • Cytokines
  • Lipopolysaccharides
  • NF-kappa B p50 Subunit
  • Triterpenes
  • Nfkb1 protein, mouse
  • Nitric Oxide
  • Nitric Oxide Synthase Type II
  • Nos2 protein, mouse
  • Ptgs2 protein, mouse
  • Cyclooxygenase 2
  • Mapk1 protein, mouse
  • Mapk3 protein, mouse
  • Mitogen-Activated Protein Kinase 1
  • Mitogen-Activated Protein Kinase 3