Flavonoids were extracted from cranberry powder with acetone and ethyl acetate and subsequentlyfractionated with Sephadex LH-20 column chromatography. The fraction eluted with a 60% methanolsolution was composed primarily of phenolic constituents with maximum absorbance at
340 nm. Ahigh-performance liquid chromatography procedure was developed, which resolved 22 distinct peakswith UV/vis and mass spectra corresponding to flavonol glycoside conjugates. Six new constituentsnot previously reported in cranberry or in cranberry products were determined through NMRspectroscopy to be
myricetin-
3-
-xylopyranoside, quercetin-
3-
-glucoside, quercetin-
3-
-arabinopyranoside,
3'-methoxyquercetin-
3-
-xylopyranoside, quercetin-
3-
O-(6' '-
p-coumaroyl)-
-
galactoside,and quercetin-
3-
O-(6' '-benzoyl)-
-
galactoside. Quercetin-
3-
O-(6' '-
p-coumaroyl)-
-
galactoside andquercetin-
3-
O-(6' '-benzoyl)-
-
galactoside represent a new class of cranberry flavonol compoundswith three conjugated components consisting of a flavonol, sugar, and carboxylic acid (benzoic orhydroxycinnamic acids). This is also the first report identifying quercetin-
3-arabinoside in both furanoseand pyranose forms in cranberry. Elucidation of specific flavonol glycosides in cranberry is significantsince the specificity of the sugar moiety may play a role in the bioavailability of the flavonol glycosidesin vivo.Keywords:
Vaccinium macrocarpon Ait.; cranberry; flavonol glycosides; quercetin;
myricetin; arabinopyranoside; acylated quercetin-
3-glycosides