title: Stability of the flavan-3-ols epicatechin and catechin and related dimeric procyanidins derived from cocoa.
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-(4beta-8)-epicatechin (Dimer B2) and epicatechin-(4beta- 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.
authors.affiliation: Department of Nutrition, University of California, Davis, California, USA.
authors.forename: Qin Yan
authors.initials: QY
authors.lastname: Zhu
authors.forename: Roberta R
authors.initials: RR
authors.lastname: Holt
authors.forename: Sheryl A
authors.initials: SA
authors.lastname: Lazarus
authors.forename: Jodi L
authors.initials: JL
authors.lastname: Ensunsa
authors.forename: John F
authors.initials: JF
authors.lastname: Hammerstone
authors.forename: Harold H
authors.initials: HH
authors.lastname: Schmitz
authors.forename: Carl L
authors.initials: CL
authors.lastname: Keen
mesh_terms: D001826:Body Fluids / Q000378:metabolism; D002099:Cacao / Q000737:chemistry*; D002392:Catechin / Q000737:chemistry / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D019281:Dimerization; D004355:Drug Stability; D005750:Gastric Juice / Q000378:metabolism; D006801:Humans; D006863:Hydrogen-Ion Concentration; D007413:Intestinal Mucosa / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
chemical_list: D002392:Catechin