Cyclooxygenase Inhibitory and Antioxidant Cyanidin Glycosides in Cherries and Berries

Phytomedicine. 2001 Sep;8(5):362-9. doi: 10.1078/0944-7113-00053.

Abstract

Anthocyanins from tart cherries, Prunus cerasus L. (Rosaceae) cv. Balaton and Montmorency; sweet cherries, Prunus avium L. (Rosaceae); bilberries, Vaccinum myrtillus L. (Ericaceae); blackberries, Rubus sp. (Rosaceae); blueberries var. Jersey, Vaccinium corymbosum L. (Ericaceae); cranberries var. Early Black, Vaccinium macrocarpon Ait. (Ericaceae); elderberries, Sambucus canadensis (Caprifoliaceae); raspberries, Rubus idaeus (Rosaceae); and strawberries var. Honeoye, Fragaria x ananassa Duch. (Rosaceae), were investigated for cyclooxygenase inhibitory and antioxidant activities. The presence and levels of cyanidin-3-glucosylrutinoside 1 and cyanidin-3-rutinoside 2 were determined in the fruits using HPLC. The antioxidant activity of anthocyanins from cherries was comparable to the commercial antioxidants, tert-butylhydroquinone, butylated hydroxytoluene and butylated hydroxyanisole, and superior to vitamin E, at a test concentration of 125 microg/ml. Anthocyanins from raspberries and sweet cherries demonstrated 45% and 47% cyclooxygenase-I and cyclooxygenase-II inhibitory activities, respectively, when assayed at 125 microg/ml. The cyclooxygenase inhibitory activities of anthocyanins from these fruits were comparable to those of ibuprofen and naproxen at 10 microM concentrations. Anthocyanins 1 and 2 are present in both cherries and raspberry. The yields of pure anthocyanins 1 and 2 in 100 g Balaton and Montmorency tart cherries, sweet cherries and raspberries were 21, 16.5; 11, 5; 4.95, 21; and 4.65, 13.5 mg, respectively. Fresh blackberries and strawberries contained only anthocyanin 2 in yields of 24 and 22.5 mg/100 g, respectively. Anthocyanins 1 and 2 were not found in bilberries, blueberries, cranberries or elderberries.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Anthocyanins / chemistry*
  • Anthocyanins / isolation & purification
  • Anthocyanins / pharmacology
  • Antioxidants / metabolism*
  • Antioxidants / pharmacology
  • Biological Assay
  • Caprifoliaceae / chemistry
  • Chromatography, High Pressure Liquid
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors / metabolism*
  • Cyclooxygenase Inhibitors / pharmacology
  • Ericaceae / chemistry
  • Fruit / chemistry*
  • Glucosides / pharmacology
  • Isoenzymes / antagonists & inhibitors
  • Isoenzymes / metabolism
  • Liposomes
  • Molecular Structure
  • Oxidation-Reduction / drug effects
  • Oxygen Consumption / drug effects
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Prostaglandin-Endoperoxide Synthases / metabolism
  • Rosaceae / chemistry

Substances

  • Anthocyanins
  • Antioxidants
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors
  • Glucosides
  • Isoenzymes
  • Liposomes
  • Plant Extracts
  • cyanidin 3-O-glucoside
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Prostaglandin-Endoperoxide Synthases
  • cyanidin 3-rutinoside