Stabilizing effect of ascorbic acid on flavan-3-ols and dimeric procyanidins from cocoa

Qin Yan Zhu, John F. Hammerstone, Sheryl A. Lazarus, Harold H. Schmitz, Carl L Keen

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Cocoa flavanols and procyanidins have numerous biological activities. It is known that (-)-epicatechin, (+)-catechin, epicatechin-(4β-8)-epicatechin (dimer B2), and epicatechin-(4β-6)-epicatechin (dimer B5) are unstable at physiologic pH, degrading almost completely within several hours, whereas they are relatively stable at pH 5.0. The present study investigated the effects of ascorbic and citric acid on the stability of monomers and dimers in simulated intestinal juice (pH 8.5) and in sodium phosphate buffer (pH 7.4). The addition of ascorbic acid to the incubation mixture significantly increased the stability of the monomers and dimers, whereas the addition of citric acid provided no protective effects. LC-MS showed that with the degradation of dimer B2 and dimer B5, doubly linked A-type dimers were formed. The present results, although not directly transferable to in vivo conditions, suggest that ascorbic acid may stabilize cocoa flavanols and procyanidins in the intestine where the pH is neutral, or alkaline, before absorption.

Original languageEnglish (US)
Pages (from-to)828-833
Number of pages6
JournalJournal of Agricultural and Food Chemistry
Volume51
Issue number3
DOIs
StatePublished - Jan 29 2003

Fingerprint

Cocoa
Proanthocyanidins
procyanidins
Catechin
epicatechin
flavanols
Dimers
Ascorbic Acid
ascorbic acid
Citric Acid
citric acid
Monomers
sodium phosphate
catechin
Intestines
protective effect
bioactive properties
Bioactivity
Buffers
intestines

Keywords

  • (+)-catechin
  • (-)-epicatechin
  • (-)-epicatechin- (4β-8)-epicatechin
  • (-)-epicatechin-(4β-6)-epicatechin
  • Cocoa
  • Flavanol
  • Flavonoid
  • Procyanidin

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Food Science
  • Chemistry (miscellaneous)

Cite this

Stabilizing effect of ascorbic acid on flavan-3-ols and dimeric procyanidins from cocoa. / Zhu, Qin Yan; Hammerstone, John F.; Lazarus, Sheryl A.; Schmitz, Harold H.; Keen, Carl L.

In: Journal of Agricultural and Food Chemistry, Vol. 51, No. 3, 29.01.2003, p. 828-833.

Research output: Contribution to journalArticle

Zhu, Qin Yan ; Hammerstone, John F. ; Lazarus, Sheryl A. ; Schmitz, Harold H. ; Keen, Carl L. / Stabilizing effect of ascorbic acid on flavan-3-ols and dimeric procyanidins from cocoa. In: Journal of Agricultural and Food Chemistry. 2003 ; Vol. 51, No. 3. pp. 828-833.
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