Stability of the flavan-3-ols epicatechin and catechin and related dimeric procyanidins derived from cocoa

Qin Yan Zhu, Roberta R. Holt, Sheryl A. Lazarus, Jodi L. Ensunsa, John F. Hammerstone, Harold H. Schmitz, Carl L Keen

Research output: Contribution to journalArticle

139 Scopus citations

Abstract

Cocoa flavanols and procyanidins possess wide-ranging biological activities. The present study investigated the stability of the cocoa monomers, (-)-epicatechin and (+)-catechin, and the dimers, epicatechin-(4,β-8)-epicatechin (Dimer B2) and epicatechin-(4,β-6)-epicatechin (Dimer B5), in simulated gastric and intestinal juice and at different pH values. The dimers were less stable than the monomers at both acidic and alkaline pH. Incubation of Dimer B2 and Dimer B5 in simulated gastric juice (pH 1.8) or acidic pH resulted in degradation to epicatechin and isomerization to Dimer B5 and Dimer B2, respectively. When incubated in simulated intestinal juice or at alkaline pH, all four compounds degraded almost completely within several hours. These results suggest that the amount, and type, of flavanols and procyanidins in the gastrointestinal tract following the consumption of cocoa can be influenced by the stability of these compounds in both acidic and alkaline environments.

Original languageEnglish (US)
Pages (from-to)1700-1705
Number of pages6
JournalJournal of Agricultural and Food Chemistry
Volume50
Issue number6
DOIs
StatePublished - Mar 13 2002

Keywords

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

ASJC Scopus subject areas

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

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    Zhu, Q. Y., Holt, R. R., Lazarus, S. A., Ensunsa, J. L., Hammerstone, J. F., Schmitz, H. H., & Keen, C. L. (2002). Stability of the flavan-3-ols epicatechin and catechin and related dimeric procyanidins derived from cocoa. Journal of Agricultural and Food Chemistry, 50(6), 1700-1705. https://doi.org/10.1021/jf011228o