Comparison of different extraction methods and HPLC quantification of prenylated and unprenylated phenylpropanoids in raw Italian propolis

J Pharm Biomed Anal. 2016 Sep 10;129:219-223. doi: 10.1016/j.jpba.2016.07.006. Epub 2016 Jul 6.


In this paper the presence of selected prenylated and unprenylated phenylpropanoids, namely ferulic acid 1, boropinic acid 2, 4'-geranyloxyferulic acid 3, umbelliferone 4, 7-isopentenyloxycoumarin 5, and auraptene 6, have been determined in Italian raw propolis after having been extracted with different methodologies. An aqueous solution of β-cyclodextrin was the best extraction method for ferulic acid 1, treatment with indifferently EtOH or aqueous β-cyclodextrin were the most effective one for umbelliferone 4, boropinic acid 2 gave the best yields either with H2O/β-cyclodextrin or olive oil treatment or in biphasic systems, maceration with biphasic mixtures of aqueous β-cyclodextrin and olive oil was seen to be the most effective procedure for 7-isopentenyloxycoumarin 5, the only method providing significant quantities of 4'-geranyloxyferulic acid 3 was the maceration of raw propolis with olive oil, and finally auraptene 4 was best extracted with absolute EtOH. "Classic" maceration in general performed better than ultrasound-assisted one.

Keywords: 4′-Geranyloxyferulic acid; Auraptene; Boropinic acid; Ferulic acid; Propolis; Umbelliferone.

MeSH terms

  • Chromatography, High Pressure Liquid / methods
  • Coumaric Acids / chemistry
  • Coumarins / chemistry
  • Italy
  • Propanols / chemistry*
  • Propolis / chemistry*
  • Umbelliferones / chemistry
  • beta-Cyclodextrins / chemistry


  • 4'-geranyloxyferulic acid
  • 7-isopentenyloxycoumarin
  • Coumaric Acids
  • Coumarins
  • Propanols
  • Umbelliferones
  • beta-Cyclodextrins
  • 1-phenylpropanol
  • 7-hydroxycoumarin
  • Propolis
  • ferulic acid
  • aurapten