Brazilian red propolis: unreported substances, antioxidant and antimicrobial activities

J Sci Food Agric. 2011 Oct;91(13):2363-70. doi: 10.1002/jsfa.4468. Epub 2011 May 17.


Background: Chloroform, ethyl acetate and methanol extracts of a sample of red propolis from the state of Alagoas (northeast Brazil) were analyzed by gas chromatography-mass spectrometry and high-performance liquid chromatography-diode array detection-electrospray ionization-mass spectrometry. Antimicrobial and antioxidant activities were also obtained.

Results: The propolis sample contained low content of narigenin-8-C-hexoside, this being the first report of a C-glycoside in propolis. The main constituent found was characterized as 3,4,2',3'-tetrahydroxychalcone. Other important constituents were the chalcone isoliquiritigenin, the isoflavans (3S)-vestitol, (3S)-7-O-methylvestitol, the pterocarpan medicarpin, the phenylpropenes trans-anethol, methyl eugenol, elimicin, methoxyeugenol and cis-asarone, and the triterpenic alcohols lupeol and α- and β- amyrins. The methanol extract exhibited high antioxidant activities by 2,2-diphenyl-1-picrylhydrazyl and β-carotene/linoleic acid assay methods, and antimicrobial activity toward Gram-positive and Gram-negative bacteria.

Conclusion: Structures are suggested for new substances never before seen in any kind of propolis. This is the first report of 3,4,2',3'-tetrahydroxychalcone and a flavone C-glycoside in a propolis sample.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / analysis*
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Antioxidants / analysis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Brazil
  • Candida albicans / drug effects
  • Chemical Fractionation
  • Chromatography, High Pressure Liquid
  • Drug Discovery*
  • Flavonoids / analysis
  • Flavonoids / chemistry
  • Gas Chromatography-Mass Spectrometry
  • Glycosides / analysis
  • Glycosides / chemistry
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Microbial Sensitivity Tests
  • Polyphenols / analysis
  • Polyphenols / chemistry
  • Propolis / chemistry*
  • Propolis / pharmacology*
  • Solvents / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Tandem Mass Spectrometry


  • Anti-Infective Agents
  • Antioxidants
  • Flavonoids
  • Glycosides
  • Polyphenols
  • Solvents
  • Propolis