Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products.
The metabolism of chlorogenic acid, naringin, and rutin, representative members of three common families of dietary polyphenols, the hydroxycinnamates, the flavanones, and the flavonols, respectively, was studied in an in vitro mixed culture model of the human colonic microflora. Time- and concentration-dependent degradation of all three compounds was observed, which was associated with the following metabolic events after cleavage of the ester or glycosidic bond: reduction of the aliphatic double bond of the resulting hydroxycinnamate caffeic acid residue; dehydroxylation and ring fission of the heterocyclic C-ring of the resulting deglycosylated flavanone, naringenin, and of the deglycosylated flavonol, quercetin (which differed depending on the substitution). The metabolic events, their sequences, and major phenolic end products, as identified by GC-MS or LC-MS/MS, were elucidated from the structural characteristics of the investigated compounds. The major phenolic end products identified were 3-(3-hydroxyphenyl)-propionic acid for chlorogenic acid, 3-(4-hydroxyphenyl)-propionic acid and 3-phenylpropionic acid for naringin, and 3-hydroxyphenylacetic acid and 3-(3-hydroxyphenyl)-propionic acid for rutin. The degree of degradation of the compounds studied was significantly influenced by the substrate concentration as well as individual variations in the composition of the fecal flora. The results support extensive metabolism of dietary polyphenols in the colon, depending on substrate concentration and residence time, with resultant formation of simple phenolics, which can be considered biomarkers of colonic metabolism if subsequently absorbed. It is also apparent that a relatively small number of phenolic degradation products are formed in the colon from the diverse group of natural polyphenols.
Rechner
Andreas R
AR
Antioxidant Research Group, Wolfson Centre for Age-Related Diseases, School of Biomedical Sciences, King's College London, SE1 9RT, London, UK.
Smith
Martin A
MA
Kuhnle
Gunter
G
Gibson
Glenn R
GR
Debnam
Edward S
ES
Srai
S Kaila S
SK
Moore
Kevin P
KP
Rice-Evans
Catherine A
CA
D002851:Chromatography, High Pressure Liquid; D003106:Colon / Q000378:metabolism* / Q000382:microbiology*; D003373:Coumaric Acids / Q000737:chemistry / Q000378:metabolism; D004032:Diet; D005243:Feces / Q000737:chemistry / Q000382:microbiology; D005285:Fermentation / Q000502:physiology*; D044950:Flavanones / Q000737:chemistry / Q000378:metabolism; D005419:Flavonoids / Q000008:administration & dosage / Q000737:chemistry* / Q000378:metabolism*; D044948:Flavonols / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D010636:Phenols / Q000008:administration & dosage / Q000737:chemistry* / Q000378:metabolism*; D059808:Polyphenols; D013997:Time Factors
D003373:Coumaric Acids; D044950:Flavanones; D005419:Flavonoids; D044948:Flavonols; D010636:Phenols; D059808:Polyphenols