Ferulone A and ferulone B: two new coumarin esters from Ferula orientalis L. roots

Nat Prod Res. 2016 Oct;30(19):2183-9. doi: 10.1080/14786419.2016.1155574. Epub 2016 Mar 18.

Abstract

Ferula orientalis (Apiaceae) is a well-known perennial herb growing wild in Iran used in traditional medicine. To perform phytochemical studies, dried ground roots of F. orientalis were sequentially Soxhlet-extracted using n-hexane, dichloromethane and methanol. A combination of vacuum liquid chromatography and preparative thin-layer chromatographic analyses were performed to isolate coumarin esters. The structures of the isolated compounds were elucidated by spectroscopic means, and in vitro free-radical-scavenging property was determined by the DPPH assay. Two new coumarin esters, 7-O-(4,8,12,16-tetrahydroxy-4,8,12,16-tetramethyl-heptadecanoyl)-coumarinand 7-O-(4-hydroxy-4,8,12-trimethyl-trideca-7,11-dienoyl)-coumarin, named ferulone A and ferulone B, respectively, were isolated from the n-hexane extract of the roots of F. orientalis. Both compounds showed a low level of free-radical-scavenging property with the RC50 values of 0.252 and 0.556 mg/mL for compounds 1 and 2, respectively, as opposed to that of the positive control (quercetin) 0.004 mg/mL. This is the first report on the purification of coumarin esters from the genus Ferula.

Keywords: DPPH; Ferula orientalis; ferulone; free-radical-scavenging; umbelliferone.

MeSH terms

  • Chemical Fractionation
  • Chromatography, Thin Layer
  • Coumarins / chemistry
  • Coumarins / isolation & purification*
  • Coumarins / pharmacology
  • Drug Evaluation, Preclinical / methods
  • Esters / chemistry
  • Esters / isolation & purification
  • Esters / pharmacology
  • Fatty Alcohols / isolation & purification*
  • Fatty Alcohols / pharmacology
  • Ferula / chemistry*
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology
  • Hexanes / chemistry
  • Iran
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Roots / chemistry
  • Plants, Medicinal / chemistry

Substances

  • Coumarins
  • Esters
  • Fatty Alcohols
  • Free Radical Scavengers
  • Hexanes
  • Plant Extracts
  • ferulone A
  • ferulone B
  • n-hexane