In vitro transformation of chlorogenic acid by human gut microbiota.

SCOPE Chlorogenic acid (3-O-caffeoyl-quinic acid, C-QA), the caffeic ester of quinic acid, is one of the most abundant phenolic acids in Western diet. The majority of C-QA escapes absorption in the small intestine and reaches the colon, where the resident microbiota transforms it into several metabolites. C-QA conversion by the gut microbiota from nine subjects was compared to evaluate the variability of bacterial metabolism. It was investigated whether a potentially probiotic Bifidobacterium strain, capable of C-QA hydrolysis, could affect C-QA fate. METHODS AND RESULTS Bioconversion experiments exploiting the microbiota from diverse subjects revealed that C-QA was metabolized through a succession of hydrogenation, dexydroxylation and ester hydrolysis, occurring in different order among the subjects. Transformation may proceed also through quinic acid residue breakdown, since caffeoyl-glycerol intermediates were identified (HPLC-MS/MS, Q-TOF). All the pathways converged on 3-(3-hydroxyphenyl)-propanoic acid, which was transformed to hydroxyphenyl-ethanol and/or phenylacetic acid in few subjects. A strain of Bifidobacterium animalis able to hydrolyze C-QA was added to microbiota cultures. It affected microbial composition but not to such an extent that C-QA metabolism was modified. CONCLUSION A picture of the variability of microbiota C-QA transformations among subjects is provided. The transformation route through caffeoyl-glycerol intermediates is described for the first time.

[1]  P. O’Toole,et al.  Diet-Microbiota Interactions and Their Implications for Healthy Living , 2013, Nutrients.

[2]  Jian-guo Xu,et al.  Antioxidant and DNA-protective activities of chlorogenic acid isomers. , 2012, Journal of agricultural and food chemistry.

[3]  D. Barron,et al.  Dose-dependent absorption of chlorogenic acids in the small intestine assessed by coffee consumption in ileostomists. , 2012, Molecular nutrition & food research.

[4]  Sun-Mee Lee,et al.  Protective effects of chlorogenic acid against ischemia/reperfusion injury in rat liver: molecular evidence of its antioxidant and anti-inflammatory properties. , 2012, The Journal of nutritional biochemistry.

[5]  J. Parkhill,et al.  Dominant and diet-responsive groups of bacteria within the human colonic microbiota , 2011, The ISME Journal.

[6]  Mitsuru Sugawara,et al.  In vitro and in vivo antioxidant properties of chlorogenic acid and caffeic acid. , 2011, International journal of pharmaceutics.

[7]  G. Williamson,et al.  Bioavailability of chlorogenic acids following acute ingestion of coffee by humans with an ileostomy. , 2010, Archives of biochemistry and biophysics.

[8]  K. Setchell,et al.  Equol: history, chemistry, and formation. , 2010, The Journal of nutrition.

[9]  D. Barron,et al.  Measurement of caffeic and ferulic acid equivalents in plasma after coffee consumption: small intestine and colon are key sites for coffee metabolism. , 2010, Molecular nutrition & food research.

[10]  Gordon van't Slot,et al.  Degradation and metabolism of catechin, epigallocatechin-3-gallate (EGCG), and related compounds by the intestinal microbiota in the pig cecum model. , 2009, Journal of agricultural and food chemistry.

[11]  D. Barron,et al.  Metabolite Profiling of Hydroxycinnamate Derivatives in Plasma and Urine after the Ingestion of Coffee by Humans: Identification of Biomarkers of Coffee Consumption , 2009, Drug Metabolism and Disposition.

[12]  J. Espín,et al.  Interaction between phenolics and gut microbiota: role in human health. , 2009, Journal of agricultural and food chemistry.

[13]  D. Perrone,et al.  Chlorogenic acid compounds from coffee are differentially absorbed and metabolized in humans. , 2007, The Journal of nutrition.

[14]  J. Doré,et al.  Bioavailability of lignans in human subjects , 2006, Nutrition Research Reviews.

[15]  Daniel Tomé,et al.  Chlorogenic acid is poorly absorbed, independently of the food matrix: A Caco-2 cells and rat chronic absorption study. , 2006, Molecular nutrition & food research.

[16]  N. Lopes,et al.  Evaluation of the anti-inflammatory, analgesic and antipyretic activities of the natural polyphenol chlorogenic acid. , 2006, Biological & pharmaceutical bulletin.

[17]  A. Scalbert,et al.  Microbial metabolism of caffeic acid and its esters chlorogenic and caftaric acids by human faecal microbiota in vitro. , 2006, Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.

[18]  E. Hein,et al.  Metabolism of quercetin and rutin by the pig caecal microflora prepared by freeze-preservation. , 2006, Molecular nutrition & food research.

[19]  A. Scalbert,et al.  Absorption and metabolism of caffeic acid and chlorogenic acid in the small intestine of rats. , 2006, The British journal of nutrition.

[20]  A. Scalbert,et al.  Chlorogenic acid is absorbed in its intact form in the stomach of rats. , 2006, The Journal of nutrition.

[21]  H. Flint,et al.  pH and Peptide Supply Can Radically Alter Bacterial Populations and Short-Chain Fatty Acid Ratios within Microbial Communities from the Human Colon , 2005, Applied and Environmental Microbiology.

[22]  H. Flint,et al.  Lactate-Utilizing Bacteria, Isolated from Human Feces, That Produce Butyrate as a Major Fermentation Product , 2004, Applied and Environmental Microbiology.

[23]  H. Flint,et al.  Contribution of acetate to butyrate formation by human faecal bacteria. , 2004, The British journal of nutrition.

[24]  Liliana Jiménez,et al.  Polyphenols: food sources and bioavailability. , 2004, The American journal of clinical nutrition.

[25]  C. Rice-Evans,et al.  Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products. , 2004, Free radical biology & medicine.

[26]  P. Kroon,et al.  Characterization of metabolites of hydroxycinnamates in the in vitro model of human small intestinal epithelium caco-2 cells. , 2003, Journal of agricultural and food chemistry.

[27]  A. Scalbert,et al.  Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. , 2003, The Journal of nutrition.

[28]  P. Hollman,et al.  Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. , 2003, The Journal of nutrition.

[29]  M. Meselhy,et al.  The heterocyclic ring fission and dehydroxylation of catechins and related compounds by Eubacterium sp. strain SDG-2, a human intestinal bacterium. , 2001, Chemical & pharmaceutical bulletin.

[30]  G. Williamson,et al.  Isolation and characterization of human colonic bacteria able to hydrolyse chlorogenic acid , 2001, Journal of applied microbiology.

[31]  P. Hollman,et al.  Consumption of high doses of chlorogenic acid, present in coffee, or of black tea increases plasma total homocysteine concentrations in humans. , 2001, The American journal of clinical nutrition.

[32]  J. Terao,et al.  Absorption of chlorogenic acid and caffeic acid in rats after oral administration. , 2000, Journal of agricultural and food chemistry.

[33]  G. Williamson,et al.  Dietary intake and bioavailability of polyphenols. , 2000, The Journal of nutrition.

[34]  Michael N. Clifford,et al.  Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden , 1999 .

[35]  Gerwin C. Raangs,et al.  Variations of Bacterial Populations in Human Feces Measured by Fluorescent In Situ Hybridization with Group-Specific 16S rRNA-Targeted Oligonucleotide Probes , 1998, Applied and Environmental Microbiology.

[36]  K. Hellingwerf,et al.  Specific detection and analysis of a probiotic Bifidobacterium strain in infant feces , 1996, Applied and environmental microbiology.

[37]  F. M. Rombouts,et al.  Raffinose-Bifidobacterium (RB) agar, a new selective medium for bifidobacteria. , 1996 .

[38]  G. Macfarlane,et al.  Influence of mucin on glycosidase, protease and arylamidase activities of human gut bacteria grown in a 3-stage continuous culture system. , 1989, The Journal of applied bacteriology.

[39]  T. Kawamoto,et al.  Influence of coffee intake on urinary hippuric acid concentration. , 2011, Industrial health.

[40]  R. Scheline,et al.  Quinic acid aromatization in the rat. Urinary hippuric acid and catechol excretion following the singular or repeated administration of quinic acid. , 1973, Xenobiotica; the fate of foreign compounds in biological systems.