Characterization of Flavonols in Cranberry (Vaccinium macrocarpon) Powder

Irina O. Vvedenskaya, Robert T. Rosen, Jane E. Guido, David J. Russell, Kent A. Mills, Nicholi Vorsa

Research output: Contribution to journalArticlepeer-review

158 Scopus citations

Abstract

Flavonoids were extracted from cranberry powder with acetone and ethyl acetate and subsequently fractionated with Sephadex LH-20 column chromatography. The fraction eluted with a 60% methanol solution was composed primarily of phenolic constituents with maximum absorbance at 340 nm. A high-performance liquid chromatography procedure was developed, which resolved 22 distinct peaks with UV/vis and mass spectra corresponding to flavonol glycoside conjugates. Six new constituents not previously reported in cranberry or in cranberry products were determined through NMR spectroscopy to be myricetin-3-β -xylopyranoside, quercetin-3-β-glucoside, quercetin-3-α -arabinopyranoside, 3′-methoxyquercetin-3-α-xylopyranoside, quercetin-3-O-(6″-p-coumaroyl)-β-galactoside, and quercetin-3-O-(6″-benzoyl)-β-galactoside. Quercetin-3-O-(6″ -p-coumaroyl)-β-galactoside and quercetin-3-O-(6″-benzoyl)-β -galactoside represent a new class of cranberry flavonol compounds with three conjugated components consisting of a flavonol, sugar, and carboxylic acid (benzoic or hydroxycinnamic acids). This is also the first report identifying quercetin-3-arabinoside in both furanose and pyranose forms in cranberry. Elucidation of specific flavonol glycosides in cranberry is significant since the specificity of the sugar moiety may play a role in the bioavailability of the flavonol glycosides in vivo.

Original languageEnglish (US)
Pages (from-to)188-195
Number of pages8
JournalJournal of agricultural and food chemistry
Volume52
Issue number2
DOIs
StatePublished - Jan 28 2004

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

Keywords

  • Acylated quercetin-3-glycosides
  • Arabinopyranoside
  • Cranberry
  • Flavonol glycosides
  • Myricetin
  • Quercetin
  • Vaccinium macrocarpon Ait.

Fingerprint

Dive into the research topics of 'Characterization of Flavonols in Cranberry (Vaccinium macrocarpon) Powder'. Together they form a unique fingerprint.

Cite this