Bioavailability of flavan-3-ols and procyanidins: gastrointestinal tract influences and their relevance to bioactive forms in vivo.
There is considerable interest in the bioavailability of flavan-3-ols such as tea catechins and cocoa-derived procyanidin components of the diet and their bioactivity in vivo. Their hydrogen-donating abilities and their propensity for nitration make these compounds powerful scavengers of reactive oxygen and nitrogen species. In addition, recent evidence has suggested that these compounds may interact with redox-sensitive cell signaling pathways. However, their bioactivity in vivo will be dependent on the absorption and metabolism of these compounds after ingestion and the reducing properties of resulting metabolites. Many cell, animal, and human studies have shown that flavanol monomers, such as epicatechin, are extensively metabolised to O-methylated forms and/or conjugated to glucuronides and sulphates during absorption into the circulation. The cleavage of higher procyanidin oligomers to mixtures of monomer and dimer in the stomach may act to enhance the potential for their absorption in the small intestine as higher oligomers have very limited absorption. Studies suggest that the major bioactive forms of flavanol monomers and procyanidins in vivo are likely to be metabolites and/or conjugates of epicatechin. One such metabolite, 3'-O-methylepicatechin, has been shown to exert protective effects against oxidative stress-induced cell death. Future studies will continue to concentrate on the exact mechanism of action of the bioactive forms of flavan-3-ols in vivo.
Spencer
J P
JP
Antioxidant Research Group, Wolfson Centre for Age-Related Diseases, GKT School of Biomedical Sciences, King's College London, UK.
Schroeter
H
H
Rechner
A R
AR
Rice-Evans
C
C
D000818:Animals; D000975:Antioxidants / Q000494:pharmacology; D044946:Biflavonoids; D002392:Catechin / Q000031:analogs & derivatives* / Q000493:pharmacokinetics* / Q000494:pharmacology; D004064:Digestive System / Q000187:drug effects*; D005419:Flavonoids / Q000493:pharmacokinetics*; D006801:Humans; D008954:Models, Biological; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry; D010084:Oxidation-Reduction; D018384:Oxidative Stress; D010636:Phenols / Q000737:chemistry; D011108:Polymers / Q000737:chemistry; D044945:Proanthocyanidins; D051381:Rats; D017382:Reactive Oxygen Species; D013997:Time Factors
C424450:3'-O-methylepicatechin; D000975:Antioxidants; D044946:Biflavonoids; D005419:Flavonoids; D010636:Phenols; D011108:Polymers; D044945:Proanthocyanidins; D017382:Reactive Oxygen Species; C404987:flavan-3-ol; C017674:procyanidin; D002392:Catechin; D009584:Nitrogen