Anti-Inflammatory Activity of 3, 5-Diprenyl-4-hydroxyacetophenone Isolated from Ageratina pazcuarensis

Int J Mol Sci. 2022 Nov 30;23(23):15012. doi: 10.3390/ijms232315012.

Abstract

Inflammation is implicated in a wide variety of physiological and pathological processes. Plants are an important source of active anti-inflammatory compounds. The compound 3, 5-diprenyl-4-hydroxyacetophenone (DHAP) was isolated from the dichloromethane extract of the aerial parts of Ageratina pazcuarensis by chromatography and identified by spectroscopic (IR, NMR) and spectrometric (GC-MS) methods. Anti-inflammatory activity was evaluated on ear edema mouse induced with 12-O-tetradecanoylphorbol 13-acetate (TPA) at 2 mg/ear. The antioxidant activity of DHAP was determined using DPPH assay. Cell viability was tested in J774A.1 macrophages, the levels of NO, TNF-α, IL-1β, IL-6, and IL-10 production in macrophages stimulated with lipopolysaccharide (LPS), and membrane lysis induced by hypotonic solution in erythrocytes were evaluated. DHAP diminished the ear edema mouse in 70.10%, and it had scavenger effect against the radical with IC50 of 26.00 ± 0.37 µg/mL. Likewise, 91.78 µM of this compound inhibited the production of NO (38.96%), IL-1β (55.56%), IL-6 (51.62%), and TNF-α (59.14%) in macrophages and increased the levels of IL-10 (61.20%). Finally, 25 and 50 µg/mL DHAP provided the greatest protection against erythrocyte membrane lysis. These results demonstrate that DHAP has anti-inflammatory activity.

Keywords: 12-O-tetradecanoylphorbol 13-acetate; 3, 5-diprenyl-4-hydroxyacetophenone; Ageratina pazcuarensis; DPPH assay; J774A.1 macrophages; anti-inflammatory activity; cytokines.

MeSH terms

  • Ageratina* / chemistry
  • Animals
  • Anti-Inflammatory Agents* / pharmacology
  • Edema / chemically induced
  • Interleukin-10
  • Interleukin-6
  • Lipopolysaccharides
  • Mice
  • Plant Extracts* / pharmacology
  • Tumor Necrosis Factor-alpha

Substances

  • Anti-Inflammatory Agents
  • Interleukin-10
  • Interleukin-6
  • Lipopolysaccharides
  • Plant Extracts
  • Tumor Necrosis Factor-alpha