Three Novel Alkaloids from Portulaca oleracea L. and Their Anti-inflammatory Effects

J Agric Food Chem. 2016 Jul 27;64(29):5837-44. doi: 10.1021/acs.jafc.6b02673. Epub 2016 Jul 20.

Abstract

Three novel carbon skeleton alkaloids, named oleracimine (1), oleracimine A (2), and oleracone A (3), with one novel azulene carbon skeleton compound, oleracone B (4), and one known compound, β-carboline (5), were first isolated from Portulaca oleracea L. The structures were determined using spectroscopic methods, including one- and two-dimensional nuclear magnetic resonance and high-resolution electrospray ionization time-of-flight mass spectrometry techniques. In addition, oleracimine (1) was used to investigate the anti-inflammatory effects on lipopolysaccharide-stimulated macrophages. The results of enzyme-linked immunosorbent assay, western blot, and real-time polymerase chain reaction showed that oleracimine (1) remarkably inhibited nitric oxide production and could dose-dependently decrease the secretions of interleukin 6, tumor necrosis factor α, nitric oxide, and prostaglandin E2 in cell culture supernatants as well as the mRNA of cyclooxygenase-2 and inducible nitric oxide synthase.

Keywords: Portulaca oleracea L.; alkaloids; anti-inflammatory effects.

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Animals
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Cyclooxygenase 2 / immunology
  • Macrophages / drug effects
  • Macrophages / immunology
  • Mice
  • Molecular Structure
  • Nitric Oxide / immunology
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Portulaca / chemistry*
  • RAW 264.7 Cells

Substances

  • Alkaloids
  • Anti-Inflammatory Agents
  • Plant Extracts
  • Nitric Oxide
  • Cyclooxygenase 2