Two undescribed benzopyran derivatives from Ranunculus sceleratus L. with their in vitro anti-inflammatory activity in lipopolysaccharide-activated RAW 264.7 cells

Nat Prod Res. 2024 Mar;38(6):933-940. doi: 10.1080/14786419.2023.2208257. Epub 2023 May 5.

Abstract

Previous studies on Ranunculus sceleratus L. have shown the existence of coumarins and their anti-inflammatory effect. Phytochemical work was conducted to investigate the bioactive compounds, leading to the isolation of two undescribed benzopyran derivatives, namely ranunsceleroside A (1) and B (3), together with two known coumarins (2, 4) from the whole plant of R. sceleratus L. All compounds were structurally identified by extensive spectroscopic analysis and then investigated for their inhibitory effect on nitric oxide (NO), tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β) and interleukin-6 (IL-6) production induced by lipopolysaccharide (LPS) in RAW 264.7 murine macrophages, repectively. As a result, compound 1-4 presented inhibitory effects on the production of NO, TNF-α, IL-1β, and IL-6 in a concentration-dependent manner, which provides a potential chemical basis for the traditional use of R. sceleratus L. as an anti-inflammatory plant.

Keywords: Ranunculus sceleratus; anti-inflammation; benzopyran derivatives; coumarin; nitric oxide.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / pharmacology
  • Benzopyrans* / pharmacology
  • Coumarins / pharmacology
  • Interleukin-1beta
  • Interleukin-6
  • Lipopolysaccharides / pharmacology
  • Mice
  • Nitric Oxide
  • RAW 264.7 Cells
  • Ranunculus*
  • Tumor Necrosis Factor-alpha

Substances

  • Benzopyrans
  • Lipopolysaccharides
  • Interleukin-6
  • Tumor Necrosis Factor-alpha
  • Coumarins
  • Anti-Inflammatory Agents
  • Interleukin-1beta
  • Nitric Oxide