Complex flavonoids in cocoa: synthesis and degradation by intestinal microbiota.
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.
Van't Slot
Gordon
G
Institute of Food Chemistry, University of Münster, Germany.
Mattern
Wera
W
Rzeppa
Sebastian
S
Grewe
Dagmar
D
Humpf
Hans-Ulrich
HU
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
D005419:Flavonoids; D010936:Plant Extracts