A rare prenylated isoflavone-quinone from the roots of Flemingia philippinensis

J Asian Nat Prod Res. 2025 Jan;27(1):98-105. doi: 10.1080/10286020.2024.2421918. Epub 2024 Nov 1.

Abstract

In order to make more rational use of Flemingia Philippinensis, a systematic separation from the roots of F. philippinensis was performed in the current study. The investigation of chemical constituents resulted in the isolation of a rare prenylated isoflavone-quinone, fleminquinone A (1), together with four known analogues (2-5). Their structures were established by extensive physical and spectroscopic data analysis. Anti-inflammatory activities of the isolated compounds were evaluated in lipopolysaccharide induced mouse mononuclear macrophage leukemia cells RAW 264.7 model. Compound 1 exhibited significant inhibitory effects on LPS-induced NO production and COX-2. Compound 1 also significantly affected the levels of inflammatory cytokines.

Keywords: Flemingia Philippinensis; anti-inflammatory activity; inflammatory cytokines; isoflavone-quinone; structure elucidation.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology
  • Cyclooxygenase 2 / metabolism
  • Cytokines / metabolism
  • Fabaceae* / chemistry
  • Isoflavones* / chemistry
  • Isoflavones* / isolation & purification
  • Isoflavones* / pharmacology
  • Lipopolysaccharides* / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis
  • Plant Roots* / chemistry
  • Prenylation
  • Quinones / chemistry
  • Quinones / isolation & purification
  • Quinones / pharmacology
  • RAW 264.7 Cells

Substances

  • Isoflavones
  • Lipopolysaccharides
  • Nitric Oxide
  • Quinones
  • Anti-Inflammatory Agents
  • Cyclooxygenase 2
  • Cytokines