Complex Flavonoids in Cocoa: Synthesis and Degradation by Intestinal Microbiota
- 8 July 2010
- journal article
- Published by American Chemical Society (ACS) in Journal of Agricultural and Food Chemistry
- Vol. 58 (15), 8879-8886
- https://doi.org/10.1021/jf1012242
Abstract
Rarely occurring flavan-3-ol derivatives such as C-glycosides can be generated during food processing, for example, by cocoa production. These astringent taste compounds may also exert interesting behavior toward microbial metabolism, as other C-glycosides have been shown to be quite stable. Oligomeric flavan-3-ols, the procyanidins, bear also a C−C bond between the main moieties and are suspected to resist microbial metabolism for a prolonged time compared to other flavonoids. This paper describes a semisynthetic approach for the generation of flavan-3-ol C-glycosides. Results of incubation experiments studying five flavan-3-ol C-glycosides bearing different sugars, linkage positions, and stereochemistries are presented as well as the behavior of di- and trimeric B-type procyanidins toward intestinal microbiota. Low molecular weight degradation products are considered as well as concentration−time courses of degraded and liberated compounds. All metabolic studies were performed with the well-proven pig cecum model.This publication has 45 references indexed in Scilit:
- Application of a Molecular Sensory Science Approach to Alkalized Cocoa (Theobroma cacao): Structure Determination and Sensory Activity of Nonenzymatically C-Glycosylated Flavan-3-olsJournal of Agricultural and Food Chemistry, 2006
- On‐line identification of further flavone C‐ and O‐glycosides from sugarcane (Saccharum officinarum L., Gramineae) by HPLC‐UV‐MSPhytochemical Analysis, 2006
- The Flavonoid Glycosides and Procyanidin Composition of Deglet Noor Dates (Phoenix dactylifera)Journal of Agricultural and Food Chemistry, 2006
- Puerins A and B, Two New 8-C Substituted Flavan-3-ols from Pu-er TeaJournal of Agricultural and Food Chemistry, 2005
- Dietary proanthocyanidins: Occurrence, dietary intake, bioavailability, and protection against cardiovascular diseaseMolecular Nutrition & Food Research, 2005
- Cocoa procyanidins are stable during gastric transit in humans,,The American Journal of Clinical Nutrition, 2002
- Quantitative Characterization of Flavonoid Compounds in Rooibos Tea (Aspalathus linearis) by LC−UV/DADJournal of Agricultural and Food Chemistry, 2002
- Decomposition of Cocoa Procyanidins in the Gastric MilieuBiochemical and Biophysical Research Communications, 2000
- Structure-antioxidant activity relationships of flavonoids and phenolic acidsFree Radical Biology & Medicine, 1996
- Tannins and related compounds. XLV Rhubarb. 5 Isolation and characterization of flavan-3-ol and procyanidin glucosides.CHEMICAL & PHARMACEUTICAL BULLETIN, 1986