Analysis of Biologically Active Oxyprenylated Phenylpropanoids in Tea Tree Oil Using Selective Solid-Phase Extraction With UHPLC-PDA Detection

J Pharm Biomed Anal. 2018 May 30;154:174-179. doi: 10.1016/j.jpba.2018.03.004. Epub 2018 Mar 10.

Abstract

An efficient analytical strategy based on different extraction methods of biologically active naturally occurring oxyprenylated umbelliferone and ferulic acid derivatives 7-isopentenyloxycoumarin, auraptene, umbelliprenin, boropinic acid, and 4'-geranyloxyferulic acid and quantification by UHPLC with spectrophotometric (UV/Vis) detection from Tea tree oil is reported. Absorption of the pure oil on Al2O3 (Brockmann activity II) prior washing the resulting solid with MeOH and treatment of this latter with CH2Cl2 resulted the best extraction methodology in terms of yields of oxyprenylated secondary metabolites. Among the five O-prenylphenylpropanoids herein under investigation auraptene and umbelliprenin were never detected while 4'-geranyloxyferulic acid was the most abundant compound resulting from all the three extraction methods employed. The UHPLC analytical methodology set up in the present study resulted to be an effective and versatile technique for the simultaneous characterization and quantification of prenyloxyphenylpropanoids in Tea tree oil and applicable to other complex matrices from the plant kingdom.

Keywords: Melaleuca alternifolia; Prenyloxyphenylpropanoids; Tea tree oil; UHPLC.

MeSH terms

  • Chromatography, High Pressure Liquid / methods
  • Coumaric Acids / chemistry
  • Coumarins / chemistry
  • Solid Phase Extraction / methods
  • Tea Tree Oil / analysis*
  • Tea Tree Oil / chemistry*
  • Umbelliferones / chemistry

Substances

  • 4'-geranyloxyferulic acid
  • Coumaric Acids
  • Coumarins
  • Umbelliferones
  • 7-hydroxycoumarin
  • Tea Tree Oil
  • ferulic acid
  • aurapten
  • umbelliprenin