title: Complex flavonoids in cocoa: synthesis and degradation by intestinal microbiota.
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.
authors.affiliation: Institute of Food Chemistry, University of Münster, Germany.
authors.forename: Gordon
authors.initials: G
authors.lastname: Van't Slot
authors.forename: Wera
authors.initials: W
authors.lastname: Mattern
authors.forename: Sebastian
authors.initials: S
authors.lastname: Rzeppa
authors.forename: Dagmar
authors.initials: D
authors.lastname: Grewe
authors.forename: Hans-Ulrich
authors.initials: HU
authors.lastname: Humpf
mesh_terms: D000818:Animals; D001419:Bacteria / Q000378:metabolism*; D002099:Cacao / Q000737:chemistry*; D005419:Flavonoids / Q000138:chemical synthesis / Q000378:metabolism*; D007413:Intestinal Mucosa / Q000378:metabolism; D007422:Intestines / Q000382:microbiology*; D010936:Plant Extracts / Q000138:chemical synthesis / Q000378:metabolism*; D013552:Swine
chemical_list: D005419:Flavonoids; D010936:Plant Extracts