Isoflavones and anti-inflammatory constituents from the fruits of Psoralea corylifolia

Phytochemistry. 2017 Nov:143:186-193. doi: 10.1016/j.phytochem.2017.08.004. Epub 2017 Aug 18.

Abstract

The fruits of Psoralea corylifolia, known as Psoraleae Fructus (Buguzhi in Chinese), are traditionally used for the treatment of spermatorrhea, nephritis, asthma, pollakiuria, and various inflammatory diseases. Three previously undescribed isoflavone derivatives, 7-O-methylcorylifol A, 7-O-isoprenylcorylifol A, and 7-O-isoprenylneobavaisoflavone, have been isolated from the fruits of P. corylifolia, together with 9 known compounds. The structures of these compounds were determined through spectroscopic and MS analyses. Among the isolated compounds, 7-O-methylcorylifol A and psoralen exhibited potent inhibition (IC50 values ≤ 10.89 μM) of superoxide anion generation by human neutrophils in response to N-formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). 7-O-Isoprenylcorylifol A, 7-O-isoprenylneobavaisoflavone, and 12,13-dihydro-12,13-epoxybakuchiol inhibited fMLP/CB-induced elastase release with IC50 values ≤ 14.30 μM. In addition, 7-O-isoprenylcorylifol A, bakuchiol, 12,13-dihydro-12,13-epoxybakuchiol, and psoralidin showed potent inhibition with IC50 values ≤ 36.65 μM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation.

Keywords: Anti-inflammatory activity; Isoflavone; Leguminosae; Psoralea corylifolia; Structure elucidation.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Benzofurans
  • Coumarins
  • Fruit
  • Humans
  • Isoflavones / chemistry
  • Isoflavones / isolation & purification*
  • Isoflavones / pharmacology*
  • Lipopolysaccharides / pharmacology
  • Mice
  • N-Formylmethionine Leucyl-Phenylalanine
  • Neutrophils / drug effects
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Pancreatic Elastase / antagonists & inhibitors
  • Phenols
  • Phenylalanine
  • Psoralea / chemistry*
  • Superoxides

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Benzofurans
  • Coumarins
  • Isoflavones
  • Lipopolysaccharides
  • Phenols
  • Superoxides
  • Nitric Oxide
  • Phenylalanine
  • N-Formylmethionine Leucyl-Phenylalanine
  • Pancreatic Elastase
  • psoralidin
  • bakuchiol