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Colonic metabolites of berry polyphenols: the missing link to biological activity?

  • Gary Williamson (a1) and Michael N. Clifford (a2)
Abstract

The absorption of dietary phenols, polyphenols and tannins (PPT) is an essential step for biological activity and effects on health. Although a proportion of these dietary bioactive compounds are absorbed intact, depending on their chemical structure and the nature of any attached moiety (e.g. sugar, organic acid), substantial amounts of lower molecular weight catabolites are absorbed after biotransformation by the colon microflora. The main products in the colon are (a) benzoic acids (C6–C1), especially benzoic acid and protocatechuic acid; (b) phenylacetic acids (C6–C2), especially phenylacetic acid per se; (c) phenylpropionic acids (C6–C3), where the latter are almost entirely in the dihydro form, notably dihydrocaffeic acid, dihydroferulic acid, phenylpropionic acid and 3-(3′-hydroxyphenyl)-propionic acid. As a result of this biotransformation, some of these compounds can each reach mm concentrations in faecal water. Many of these catabolites are efficiently absorbed in the colon, appear in the blood and are ultimately excreted in the urine. In the case of certain polyphenols, such as anthocyanins, these catabolites are major products in vivo; protocatechuic acid is reported to represent a substantial amount of the ingested dose of cyanidin-3-O-glucoside. The major catabolites of berries, and especially blackcurrants, are predicted based on compositional data for polyphenols from berries and other sources. Since microbial catabolites may be present at many sites of the body in higher concentration than the parent compound, it is proposed that at least a part of the biological activities ascribed to berry polyphenols and other PPT are due to their colonic catabolites.

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*Corresponding author: G. Williamson, fax +44 113 343 2982, email g.williamson@leeds.ac.uk
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6GS Jensen , X Wu , KM Patterson , (2008) In vitro and in vivo antioxidant and anti-inflammatory capacities of an antioxidant-rich fruit and berry juice blend. Results of a pilot and randomized, double-blinded, placebo-controlled, crossover study. J Agric Food Chem 56, 83268333.

7A Crozier , IB Jaganath & MN Clifford (2009) Dietary phenolics: chemistry, bioavailability and effects on health. Nat Prod Rep 26, 10011043.

10 DC Savage (1977) Microbial ecology of the gastrointestinal tract. Ann Rev Microbiol 31, 107133.

12K Tuohy & GR Gibson (2006) Functions of the human intestinal flora: the use of probiotics and prebiotics. In Plant Secondary Metabolites. Occurrence, Structure and Role in the Human Diet, pp. 174207 [A Crozier , MN Clifford and H Ashihara , editors]. Oxford: Blackwell.

13SR Gill , M Pop , RT Deboy , (2006) Metagenomic analysis of the human distal gut microbiome. Science 312, 13551359.

14MM Gronlund , OP Lehtonen , E Eerola , (1999) Fecal microflora in healthy infants born by different methods of delivery: permanent changes in intestinal flora after cesarean delivery. J Pediatr Gastroenterol Nutr 28, 1925.

17PB Eckburg , EM Bik , CN Bernstein , (2005) Diversity of the human intestinal microbial flora. Science 308, 16351638.

18S Mueller , K Saunier , C Hanisch , (2006) Differences in fecal microbiota in different European study populations in relation to age, gender, and country: a cross-sectional study. Appl Environ Microbiol 72, 10271033.

19AN Phipps , J Stewart , B Wright , (1998) Effect of diet on the urinary excretion of hippuric acid and other dietary-derived aromatics in rat. A complex interaction between diet, gut microflora and substrate specificity. Xenobiotica 28, 527537.

21S Raimondi , L Roncaglia , M De Lucia , (2009) Bioconversion of soy isoflavones daidzin and daidzein by Bifidobacterium strains. Appl Microbiol Biotechnol 81, 943950.

23AM Aura , P Martin-Lopez , KA O'Leary , (2005) In vitro metabolism of anthocyanins by human gut microflora. Eur J Nutr 44, 133142.

24K Keppler & HU Humpf (2005) Metabolism of anthocyanins and their phenolic degradation products by the intestinal microflora. Bioorg Med Chem 13, 51955205.

26A Braune , W Engst & M Blaut (2005) Degradation of neohesperidin dihydrochalcone by human intestinal bacteria. J Agric Food Chem 53, 17821790.

27MP Gonthier , C Remesy , A Scalbert , (2006) Microbial metabolism of caffeic acid and its esters chlorogenic and caftaric acids by human faecal microbiota in vitro. Biomed Pharmacother 60, 536540.

28S Labib , S Hummel , E Richling , (2006) Use of the pig caecum model to mimic the human intestinal metabolism of hispidulin and related compounds. Mol Nutr Food Res 50, 7886.

30SC Forester & AL Waterhouse (2008) Identification of Cabernet Sauvignon anthocyanin gut microflora metabolites. J Agric Food Chem 56, 92999304.

31HC Lee , AM Jenner , CS Low , (2006) Effect of tea phenolics and their aromatic fecal bacterial metabolites on intestinal microbiota. Res Microbiol 157, 876884.

40CJ Rumney & IR Rowland (1992) In vivo and in vitro models of the human colonic flora. CRC Crit Rev Food Sci Nutr 31, 299331.

44U Knust , G Erben , B Spiegelhalder , (2006) Identification and quantitation of phenolic compounds in faecal matrix by capillary gas chromatography and nano-electrospray mass spectrometry. Rapid Commun Mass Spectrom 20, 31193129.

46M Hattori , YZ Shu , AI El Sedawy , (1988) Metabolism of homoorientin by human intestinal bacteria. J Nat Prod 51, 874878.

47EM Daniel , S Ratnayake , T Kinstle , (1991) The effects of pH and rat intestinal contents on the liberation of ellagic acid from purified and crude ellagitannins. J Nat Prod 54, 946952.

48DH Kim , HJ Kang , SH Park , (1994) Characterization of β-glucosidase and β-glucuronidase of alkalotolerant intestinal bacteria. Biol Pharm Bull 17, 423426.

49PA Kroon , CB Faulds , P Ryden , (1996) Release of covalently bound ferulic acid from fiber in the human colon. J Agric Food Chem 45, 661667.

50BL Goodwin , CRJ Ruthven & M Sandler (1994) Gut flora and the origin of some urinary aromatic phenolic compounds. Biochem Pharmacol 47, 22942297.

51RH Adamson , JW Bridges , ME Evans , (1970) Species differences in the aromatization of quinic acid in vivo and the role of gut bacteria. Biochem J 116, 437443.

54 LA Griffiths & GE Smith (1972) Metabolism of myricetin and related compounds in the rat. Metabolite formation in vivo and by the intestinal microflora in vitro. Biochem J 130, 141151.

55GE Smith & LA Griffiths (1970) Metabolism of myricitrin and 3,4,5-trihydroxyphenylacetic acid. Biochem J 118, 53P54P.

57HC Curtius , M Mettler & L Ettlinger (1976) Study of the intestinal tyrosine metabolism using stable isotopes and gas chromatography-mass spectrometry. J Chromatogr 126, 569580.

58M Fuchs-Mettler , HC Curtius , K Baerlocher , (1980) A new rearrangement reaction in tyrosine metabolism. Eur J Biochem 108, 527534.

60M Blaut , L Schoefer & A Braune (2003) Transformation of flavonoids by intestinal microorganisms. Int J Vitam Nutr Res 73, 7987.

67AM Jeffrey , DM Jerina , R Self , (1972) The bacterial degradation of flavonoids. Oxidative fission of the A-ring of dihydrogossypetin by a Pseudomonas sp. Biochem J 130, 383390.

71H Schneider & M Blaut (2000) Anaerobic degradation of flavonoids by Eubacterium ramulus. Arch Microbiol 173, 7175.

74L Schoefer , R Mohan , A Braune , (2002) Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus. FEMS Microbiol Lett 208, 197202.

76C Herles , A Braune & M Blaut (2004) First bacterial chalcone isomerase isolated from Eubacterium ramulus. Arch Microbiol 181, 428434.

77MN Clifford (2000) Anthocyanins – nature, occurrence and dietary burden. J Sci Food Agric 80, 10631072.

80LQ Wang , MR Meselhy , Y Li , (2000) Human intestinal bacteria capable of transforming secoisolariciresinol diglucoside to mammalian lignans, enterodiol and enterolactone. Chem Pharm Bull 48, 16061610.

81LQ Wang , MR Meselhy , Y Li , (2001) The heterocyclic ring fission and dehydroxylation of catechins and related compounds by Eubacterium sp. strain SDG-2, a human intestinal bacterium. Chem Pharm Bull 49, 16401643.

83J Winter , MR Popoff , P Grimont , (1991) Clostridium orbiscindens sp. nova., human intestinal bacterium capable of cleaving the flavonoid C-ring. Int J Syst Bacteriol 41, 355357.

84IS Jang & DH Kim (1996) Purification and characterization of alpha-L-rhamnosidase from Bacteroides JY-6, a human intestinal bacterium. Biol Pharm Bull 19, 15461549.

85VD Bokkenheuser , CH Shackleton & J Winter (1987) Hydrolysis of dietary flavonoid glycosides by strains of intestinal Bacteroides from humans. Biochem J 248, 953956.

86D-H Kim , IS Sohng , K Kobashi , (1996) Purification and characterization of β-glucosidase from Bacteroides JY-6, a human intestinal bacterium. Biol Pharm Bull 19, 11211125.

87DH Kim , SY Kim , SY Park , (1999) Metabolism of quercitrin by human intestinal bacteria and its relation to some biological activities. Biol Pharm Bull 22, 749751.

88CK Sung , GH Kang , SS Yoon , (1996) Glycosidases that convert natural glycosides to bioactive compounds. Adv Exp Med Biol 404, 2336.

89 U Justesen , E Arrigoni , BR Larsen , (2000) Degradation of flavonoid glycosides and aglycones during in vitro fermentation with human faecal flora. Lebensmittel Wissenschaft Technol 33, 424430.

90DH Kim , EA Jung , IS Sohng , (1998) Intestinal bacterial metabolism of flavonoids and its relation to some biological activities. Arch Pharm Res 21, 1723.

94G Groenewoud & HKL Hundt (1984) The microbial metabolism of (+)-catechins to two novel diarylpropan-2-ol metabolites in vitro. Xenobiotica 14, 711717.

95MR Meselhy , N Nakamura & M Hattori (1997) Biotransformation of ( − )-epicatechin 3-O-gallate by human intestinal bacteria. Chem Pharm Bull 45, 888893.

96B Doyle & LA Griffiths (1980) The metabolism of ellagic acid in the rat. Xenobiotica 10, 247256.

98M Larrosa , A Gonzalez-Sarrias , MT Garcia-Conesa , (2006) Urolithins, ellagic acid-derived metabolites produced by human colonic microflora, exhibit estrogenic and antiestrogenic activities. J Agric Food Chem 54, 16111620.

99NP Seeram , WJ Aronson , Y Zhang , (2007) Pomegranate ellagitannin-derived metabolites inhibit prostate cancer growth and localize to the mouse prostate gland. J Agric Food Chem 55, 77327737.

106K Kahle , M Kraus , W Scheppach , (2005) Colonic availability of apple polyphenols – a study in ileostomy subjects. Mol Nutr Food Res 49, 11431150.

108SC Marks , W Mullen , G Borges , (2009) Absorption, metabolism, and excretion of cider dihydrochalcones in healthy humans and subjects with an ileostomy. J Agric Food Chem 57, 20092015.

109 L Poquet , MN Clifford & G Williamson (2008) Transport and metabolism of ferulic acid through the colonic epithelium. Drug Metab Dispos 36, 190197.

110R Hayeshi , C Hilgendorf , P Artursson , (2008) Comparison of drug transporter gene expression and functionality in Caco-2 cells from 10 different laboratories. Eur J Pharm Sci 35, 383396.

111H Gutmann , G Fricker , M Torok , (1999) Evidence for different ABC-transporters in Caco-2 cells modulating drug uptake. Pharm Res 16, 402407.

112Y Sambuy , I De Angelis , G Ranaldi , (2005) The Caco-2 cell line as a model of the intestinal barrier: influence of cell and culture-related factors on Caco-2 cell functional characteristics. Cell Biol Toxicol 21, 126.

113DG Lindsay & MN Clifford (2000) Special issue devoted to critical reviews produced within the EU Concerted Action ‘Nutritional Enhancement of Plant-based Food in European Trade’ (NEODIET). J Sci Food Agric 80, 7931137.

114A Crozier , IB Jaganath & MN Clifford (2006) Phenols, polyphenols and tannins: an overview. In Plant Secondary Metabolites. Occurrence, Structure and Role in the Human Diet, pp. 124 [A Crozier , MN Clifford and H Ashihara , editors]. Oxford: Blackwell.

115A Crozier , T Yokota , IB Jaganath , (2006) Secondary metabolites in fruits, vegetables, beverages and other plant-based dietary components. In Plant Secondary Metabolites. Occurrence, Structure and Role in the Human Diet, pp. 208302 [A Crozier , MN Clifford and H Ashihara , editors]. Oxford: Blackwell.

119S Shahrzad & I Bitsch (1998) Determination of gallic acid and its metabolites in human plasma and urine by high-performance liquid chromatography. J Chrom B Biomed Sci Appl 705, 8795.

120 H Matsumoto , H Inaba , M Kishi , (2001) Orally administered delphinidin 3-rutinoside and cyanidin 3-rutinoside are directly absorbed in rats and humans and appear in the blood as the intact forms. J Agric Food Chem 49, 15461551.

121H Matsumoto , K Ito , K Yonekura , (2007) Enhanced absorption of anthocyanins after oral administration of phytic acid in rats and humans. J Agric Food Chem 55, 24892496.

123W Mullen , CA Edwards , M Serafini , (2008) Bioavailability of pelargonidin-3-O-glucoside and its metabolites in humans following the ingestion of strawberries with and without cream. J Agric Food Chem 56, 713719.

124T Tsuda , F Horio & T Osawa (1999) Absorption and metabolism of cyanidin 3-O-β-d-glucoside in rats. FEBS Lett 449, 179182.

126WR Russell , L Scobbie , A Labat , (2009) Selective bio-availability of phenolic acids from Scottish strawberries. Mol Nutr Food Res 53, Suppl. 1, S85S91.

129T Ichiyanagi , Y Kashiwada , Y Ikeshiro , (2004) Complete assignment of bilberry (Vaccinium myrtillus L.) anthocyanins separated by capillary zone electrophoresis. Chem Pharm Bull (Tokyo) 52, 226229.

130N Katsube , K Iwashita , T Tsushida , (2003) Induction of apoptosis in cancer cells by bilberry (Vaccinium myrtillus) and the anthocyanins. J Agric Food Chem 51, 6875.

131T Ichiyanagi , Y Hatano , S Matsugo , (2004) Structural dependence of HPLC separation pattern of anthocyanins from Bilberry (Vaccinium myrtillus L.). Chem Pharm Bull (Tokyo) 52, 628630.

133 MP Gonthier , JL Donovan , O Texier , (2003) Metabolism of dietary procyanidins in rats. Free Radic Biol Med 35, 837844.

139DS Goldstein , R Stull , SP Markey , (1984) Dihydrocaffeic acid: a common contaminant in the liquid chromatographic-electrochemical measurement of plasma catecholamines in man. J Chromatogr 311, 148153.

140SM Wittemer , M Ploch , T Windeck , (2005) Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of artichoke leaf extracts in humans. Phytomed 12, 2838.

144BP Nutley , P Farmer & J Caldwell (1994) Metabolism of trans-cinnamic acid in the rat and the mouse and its variation with dose. Food Chem Toxicol 32, 877886.

145E Haughton , MN Clifford & P Sharp (2007) Monocarboxylate transporter expression is associated with the absorption of benzoic acid in human intestinal epithelial cells. J Sci Food Agric 87, 239244.

146S Mori , H Takanaga , S Ohtsuki , (2003) Rat organic anion transporter 3 (rOAT3) is responsible for brain-to-blood efflux of homovanillic acid at the abluminal membrane of brain capillary endothelial cells. J Cereb Blood Flow Metab 23, 432440.

148HX Liu , Y Liu , JW Zhang , (2008) UDP-glucuronosyltransferase 1A6 is the major isozyme responsible for protocatechuic aldehyde glucuronidation in human liver microsomes. Drug Metab Dispos 36, 15621569.

151T Tanaka , T Kojima , T Kawamori , (1995) Chemoprevention of digestive organs carcinogenesis by natural product protocatechuic acid. Cancer 75, 14331439.

153EC Yip , AS Chan , H Pang , (2006) Protocatechuic acid induces cell death in HepG2 hepatocellular carcinoma cells through a c-Jun N-terminal kinase-dependent mechanism. Cell Biol Toxicol 22, 293302.

154H Wang , TQ Liu , S Guan , (2008) Protocatechuic acid from Alpinia oxyphylla promotes migration of human adipose tissue-derived stromal cells in vitro. Eur J Pharmacol 599, 2431.

155S Guan , D Ge , TQ Liu , (2009) Protocatechuic acid promotes cell proliferation and reduces basal apoptosis in cultured neural stem cells. Toxicol In Vitro 23, 201208.

157P Thompson , F Balis , BM Serabe , (2003) Pharmacokinetics of phenylacetate administered as a 30-min infusion in children with refractory cancer. Cancer Chemother Pharmacol 52, 417423.

158A Wajngot , V Chandramouli , WC Schumann , (2000) A probing dose of phenylacetate does not affect glucose production and gluconeogenesis in humans. Metabolism 49, 12111214.

159O Inoue , R Hosoi , S Momosaki , (2006) Evaluation of [14C]phenylacetate as a prototype tracer for the measurement of glial metabolism in the rat brain. Nucl Med Biol 33, 985989.

160A Thibault , D Samid , MR Cooper , (1995) Phase I study of phenylacetate administered twice daily to patients with cancer. Cancer 75, 29322938.

163 RB MacArthur , A Altincatal & M Tuchman (2004) Pharmacokinetics of sodium phenylacetate and sodium benzoate following intravenous administration as both a bolus and continuous infusion to healthy adult volunteers. Mol Genet Metab 81, Suppl. 1, S67S73.

164HL Kang , S Benzer & KT Min (2002) Life extension in Drosophila by feeding a drug. Proc Natl Acad Sci U S A 99, 838843.

165 T Kasumov , LL Brunengraber , B Comte , (2004) New secondary metabolites of phenylbutyrate in humans and rats. Drug Metab Dispos 32, 1019.

166XN Li , S Parikh , Q Shu , (2004) Phenylbutyrate and phenylacetate induce differentiation and inhibit proliferation of human medulloblastoma cells. Clin Cancer Res 10, 11501159.

169MN Clifford (2000) Chlorogenic acids and other cinnamates – nature, occurrence, dietary burden, absorption and metabolism. J Sci Food Agric 80, 10331042.

170MN Clifford (1999) Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden. J Sci Food Agric 79, 362372.

173L Poquet , MN Clifford & G Williamson (2008) Investigation of the metabolic fate of dihydrocaffeic acid. Biochem Pharmacol 75, 12181229.

175Y Konishi & S Kobayashi (2004) Transepithelial transport of chlorogenic acid, caffeic acid, and their colonic metabolites in intestinal caco-2 cell monolayers. J Agric Food Chem 52, 25182526.

176CC Wong , W Meinl , H-R Glatt , (2010) In vitro and in vivo conjugation of dietary hydroxycinnamic acids by UDP-glucuronosyltransferases and sulfotransferases in humans. J Nutr Biochem, (Epublication ahead of print version).

177L Poquet , MN Clifford & G Williamson (2008) Effect of dihydrocaffeic acid on UV irradiation of human keratinocyte HaCaT cells. Arch Biochem Biophys 476, 196204.

178M Larrosa , M Lodovici , L Morbidelli , (2008) Hydrocaffeic and p-coumaric acids, natural phenolic compounds, inhibit UV-B damage in WKD human conjunctival cells in vitro and rabbit eye in vivo. Free Radic Res 42, 903910.

180M Larrosa , C Luceri , E Vivoli , (2009) Polyphenol metabolites from colonic microbiota exert anti-inflammatory activity on different inflammation models. Mol Nutr Food Res 53, 10441054.

181CS Bhat & T Ramasarma (1979) Effect of phenyl and phenolic acids on mevalonate-5-phosphate kinase and mevalonate-5-pyrophosphate decarboxylase of the rat brain. J Neurochem 32, 15311537.

182JS Lee , MS Choi , SM Jeon , (2001) Lipid-lowering and antioxidative activities of 3,4-di(OH)-cinnamate and 3,4-di(OH)-hydrocinnamate in cholesterol-fed rats. Clin Chim Acta 314, 221229.

183T Yasuda , A Takasawa , T Nakazawa , (2003) Inhibitory effects of urinary metabolites on platelet aggregation after orally administering Shimotsu-To, a traditional Chinese medicine, to rats. J Pharm Pharmacol 55, 239244.

185HK Kim , TS Jeong , MK Lee , (2003) Lipid-lowering efficacy of hesperetin metabolites in high-cholesterol fed rats. Clin Chim Acta 327, 129137.

186CH Lee , TS Jeong , YK Choi , (2001) Anti-atherogenic effect of citrus flavonoids, naringin and naringenin, associated with hepatic ACAT and aortic VCAM-1 and MCP-1 in high cholesterol-fed rabbits. Biochem Biophys Res Commun 284, 681688.

187N Matsumoto , K Okushio & Y Hara (1998) Effect of black tea polyphenols on plasma lipids in cholesterol-fed rats. J Nutr Sci Vitaminol 44, 337342.

188J Yamakoshi , S Kataoka , T Koga , (1999) Proanthocyanidin-rich extract from grape seeds attenuates the development of aortic atherosclerosis in cholesterol-fed rabbits. Atherosclerosis 142, 139149.

196T Okubo , N Ishihara , A Oura , (1992) In vivo effect of tea polyphenol intake on human intestinal microflora and metabolism. Biosci Biotechnol Biochem 56, 588591.

197BR Min , GT Attwood , K Reilly , (2002) Lotus corniculatus condensed tannins decrease in vivo populations of proteolytic bacteria and affect nitrogen metabolism in the rumen of sheep. Can J Microbiol 48, 911921.

198ME Ramos-Niño , CA Ramìrez-Rodriguez , MN Clifford , (1997) A comparison of quantitative structure-activity relationships for the effect of benzoic and cinnamic acids on Listeria monocytogenes using multiple linear regression, artificial neural networks and fuzzy systems. J Appl Microbiol 82, 168176.

199G Gargala , A Baishanbo , L Favennec , (2005) Inhibitory activities of epidermal growth factor receptor tyrosine kinase-targeted dihydroxyisoflavone and trihydroxydeoxybenzoin derivatives on Sarcocystis neurona,Neospora caninum, and Cryptosporidium parvum development. Antimicrob Agents Chemother 49, 46284634.

201C Li , M-J Lee , S Sheng , (2000) Stuctural identification of two metabolites of catechins and their kinetics in human urine and blood after tea ingestion. Chem Res Toxicol 13, 177184.

202MN Clifford , EL Copeland , JP Bloxsidge , (2000) Hippuric acid is a major excretion product associated with black tea consumption. Xenobiotica 30, 317326.

204AN Booth & RT Williams (1963) Dehydroxylation of caffeic acid by rat and rabbit caecal contents and sheep rumen liquor. Nature 684685.

205J Dayman & JB Jepson (1969) The metabolism of caffeic acid in humans: the dehydroxylating action of intestinal bacteria. Biochem J 113, 11P.

206GW Plumb , MT García-Conesa , PA Kroon , (1999) Metabolism of chlorogenic acid by human plasma, liver, intestine and gut microflora. J Sci Food Agric 79, 390392.

207D Couteau , AL McCartney , GR Gibson , (2001) Isolation and characterization of human colonic bacteria able to hydrolyse chlorogenic acid. J Appl Microbiol 90, 873881.

208AR Rechner , MA Smith , G Kuhnle , (2004) Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products. Free Radic Biol Med 36, 212225.

209CL Gavaghan , JK Nicholson , SC Connor , (2001) Directly coupled high-performance liquid chromatography and nuclear magnetic resonance spectroscopic with chemometric studies on metabolic variation in Sprague–Dawley rats. Anal Biochem 291, 245252.

136A Stalmach , W Mullen , D Barron , (2009) Metabolite profiling of methyl, glucuronyl and sulfate conjugates in plasma and urine derived from chlorogenic acids following the ingestion of coffee by humans: identification of biomarkers of coffee consumption. Drug Metab Dispos 37, 17491758.

212NP Das (1969) Studies on flavonoid metabolism. Degradation of (+)-catechin by rat intestinal contents. Biochim Biophys Acta 177, 668670.

213RR Scheline (1970) The metabolism of (+)-catechin to hydroxyphenylvaleric acids by the intestinal microflora. Biochim Biophys Acta 222, 228230.

215NP Das & LA Griffiths (1968) Studies on flavonoid metabolism. Metabolism of (+)-catechin in the guinea pig. Biochem J 110, 449456.

219KJ Cheng , GA Jones , FJ Simpson , (1969) Isolation and identification of rumen bacteria capable of anaerobic rutin degradation. Can J Microbiol 15, 13651371.

220HG Krishnamurty , KJ Cheng , GA Jones , (1970) Identification of products produced by the anaerobic degradation of rutin and related flavonoids by Butyrivibrio sp. C3. Can J Microbiol 16, 759767.

221S Baba , T Furuta , M Fujioka , (1983) Studies on drug metabolism by use of isotopes XXVII: urinary metabolites of rutin in rats and the role of intestinal microflora in the metabolism of rutin. J Pharm Sci 72, 11551158.

222W Mullen , JM Rouanet , C Auger , (2008) Bioavailability of [2-14C]quercetin-4′-glucoside in rats. J Agric Food Chem 56, 1212712137.

224NG Coldham , C Darby , M Hows , (2002) Comparative metabolism of genistin by human and rat gut microflora: detection and identification of the end-products of metabolism. Xenobiotica 32, 4562.

225D Tsangalis , JE Ashton , AEJ McGill , (2002) Enzymic transformation of isoflavone phytoestrogens in soymilk by β-glucosidase-producing Bifidobacteria. J Food Sci 67, 31043113.

228G Liang , T Zhang , J Wang , (2005) X-ray single-crystal analysis of ( − )-(S)-equol isolated from rat's feces. Chem Biodivers 2, 959963.

229AL Simons , M Renouf , S Hendrich , (2005) Metabolism of glycitein (7,4′-dihydroxy-6-methoxy-isoflavone) by human gut microflora. J Agric Food Chem 53, 85198525.

230DO Otieno , JF Ashton & NP Shah (2006) Evaluation of enzymic potential for biotransformation of isoflavone phytoestrogen in soymilk by Bifidobacterium animalis, Lactobacillus acidophilus and Lactobacillus casei. Food Res Int 39, 394407.

231M Tamura , T Tsushida & K Shinohara (2007) Isolation of an isoflavone-metabolizing, Clostridium-like bacterium, strain TM-40, from human faeces. Anaerobe 13, 3235.

233GE Kelly , C Nelson , MA Waring , (1993) Metabolites of dietary (soya) isoflavones in human urine. Clin Chim Acta 223, 922.

235S Heinonen , K Wahala & H Adlercreutz (1999) Identification of isoflavone metabolites dihydrodaidzein, dihydrogenistein, 6′-OH-O-DMA, and cis-4-OH-equol in human urine by gas chromatography–mass spectroscopy using authentic reference compounds. Anal Biochem 274, 211219.

241KU Yu , IS Jang , KH Kang , (1997) Metabolism of Saikosaponin C and naringin by human intestinal bacteria. Arch Pharmacal Res 20, 420424.

244 S Roowi , W Mullen , CA Edwards , (2009) Yoghurt impacts on the excretion of phenolic acids derived from colonic breakdown of orange juice flavanones in humans. Mol Nutr Food Res 53, Suppl. 1, S68S75.

245I Skjevrak , E Solheim & RR Scheline (1986) Dihydrochalcone metabolism in the rat: trihydroxylated derivatives related to phloretin. Xenobiotica 16, 3545.

246G Borges , S Roowi , JM Rouanet , (2007) The bioavailability of raspberry anthocyanins and ellagitannins in rats. Mol Nutr Food Res 51, 714725.

249MA Appeldoorn , JP Vincken , MA Aura , (2009) Procyanidin dimers are metabolized by human microbiota with 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-γ-valerolactone as the major metabolites. J Agric Food Chem 57, 10841092.

250 NC Ward , KD Croft , IB Puddey , (2004) Supplementation with grape seed polyphenols results in increased urinary excretion of 3-hydroxyphenylpropionic acid, an important metabolite of proanthocyanidins in humans. J Agric Food Chem 52, 55455549.

252S Heinonen , T Nurmi , K Liukkonen , (2001) In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol. J Agric Food Chem 49, 31783186.

253T Clavel , G Henderson , W Engst , (2006) Phylogeny of human intestinal bacteria that activate the dietary lignan secoisolariciresinol diglucoside. FEMS Microbiol Ecol 55, 471478.

260PA Kroon , CB Faulds , P Ryden , (1996) Solubilisation of ferulic acid from plant cell wall materials in a model human gut system. Biochem Soc Trans 24, 384S.

261NP Das & SP Sothy (1971) Studies on flavonoid metabolism. Biliary and urinary excretion of metabolites of (+)-(U-14C)catechin. Biochem J 125, 417423.

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British Journal of Nutrition
  • ISSN: 0007-1145
  • EISSN: 1475-2662
  • URL: /core/journals/british-journal-of-nutrition
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