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Colonic Metabolites of Berry Polyphenols: the Missing Link to Biological Activity?

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Colonic Metabolites of Berry Polyphenols: the Missing Link to Biological Activity? Downloaded from British Journal of Nutrition (2010), 104, S48–S66 doi:10.1017/S0007114510003946 q The Authors 2010 https://www.cambridge.org/core Colonic metabolites of berry polyphenols: the missing link to biological activity? Gary Williamson1* and Michael N. Clifford2 . IP address: 1School of Food Science and Nutrition, University of Leeds, Leeds LS2 9JT, UK 2Division of Nutritional Sciences, Faculty of Health and Medical Sciences, University of Surrey, Guildford, Surrey GU2 7XH, UK 170.106.202.8 (Received 26 January 2010 – Accepted 16 March 2010) , on The absorption of dietary phenols, polyphenols and tannins (PPT) is an essential step for biological activity and effects on health. Although a 28 Sep 2021 at 22:35:02 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-(30-hydroxyphenyl)-propionic acid. As a result of this biotrans- formation, some of these compounds can each reach mM concentrations in faecal water. Many of these catabolites are efficiently absorbed in the , subject to the Cambridge Core terms of use, available at 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. Anthocyanins: Berry: Blackcurrant: Chlorogenic acids: Flavonoids: Gut microflora: Phenylacetic acid: Phenylpropionic acid: Protocatechuic acid Dietary polyphenols are found in fruits and vegetables, and in In excess of 8000 phenolic compounds have been products derived from plants such as fruit beverages, tea, reported, and they are widely dispersed throughout the British Journal ofcoffee Nutrition and dark chocolate. Epidemiological evidence shows plant kingdom. The nature of those occurring in foods and (7,8) that consumption of polyphenol-rich foods reduces the risk beverages has been reviewed . Briefly, they can be subdi- https://www.cambridge.org/core/terms of CVD and associated conditions(1), and human intervention vided into flavonoids (anthocyanins, chalcones and dihydro- studies have supported this association(2). The absorption and chalcones, flavanols or catechins, flavanones, flavones, metabolism of flavonoids is quite well described for some flavonols, isoflavones and proanthocyanidins or condensed compounds, such as quercetin and (–)-epicatechin(3). How- tannins) and non-flavonoids (benzoic acids, cinnamic acids ever, although the absorption of certain other phenols, poly- and cinnamic acid conjugates, such as the chlorogenic phenols and tannins (PPT) such as procyanidins, chlorogenic acids, and gallic acid esters or hydrolysable tannins). To acids and anthocyanins has been described in the literature, these must be added the ‘derived polyphenols’, substances the levels of the parent compounds in blood after a high that are characteristic of many traditionally processed dose, or a large amount of PPT-rich food, are very low com- foods and beverages (coffee, black tea, matured red wine, pared with other flavonoids(4,5). In contrast, intervention etc.) but which do not occur in healthy intact plant tissue. studies show that procyanidin-rich, chlorogenic acid-rich or Collectively, these three major groups will in this review https://doi.org/10.1017/S0007114510003946 anthocyanin-rich foods affect certain biomarkers, but because be referred to as PPT. In addition, this review will discuss the concentration of parent compounds to be expected in blood the aromatic and phenolic acids produced from these PPT after consumption is too low to affect these biomarkers(6), by the gut microflora, many of which do not occur pre- other bioactive substances such as metabolites may be respon- formed in the diet. These acids can be classified by the sible and must be identified. It is proposed that these ‘missing’ number of carbons in the side chain (one to five), and components are the colonic catabolites, and that they are whether the side chain is saturated or unsaturated, and potentially important compounds mediating some of the bio- whether it carries an aliphatic hydroxyl. Specimen structures logical activities and health benefits of polyphenol-rich foods. are shown in Fig. 1. Abbreviations: GIT, gastro-intestinal tract; PPT, phenols, polyphenols and tannins. * Corresponding author: G. Williamson, fax þ44 113 343 2982, email [email protected] Downloaded from Colonic metabolites of polyphenols S49 OH OH OH https://www.cambridge.org/core OH OH OH OH B HO O HO O HO O HO OH A OH OH I OH O II OH O III OH O IV COOH OH HO OH HO O . IP address: OH HO O HO O OH XI OH OH O HO OH 170.106.202.8 V VI HO O OH VII OOH OH OH , on OH 28 Sep 2021 at 22:35:02 OH HO OH OH OH HO HO HO HO XII , subject to the Cambridge Core terms of use, available at VIII X IX O OOH OH OOH OOH XIII XV XIV OOH O OOH OH Fig. 1. Structures of selected phenols, polyphenols and tannins, and selected gut microflora catabolites. A and B indicate the A- and B-ring, respectively, of a typi- cal flavonoid. Typical structures are shown for flavanols (catechins) (I); flavanones (II); flavones (III); dihydrochalcones (IV); chlorogenic acids (cinnamate conju- gates) (V); cinnamic acids (C6 –C3) (VI); anthocyanidins (VII); phenylvaleric acids (C6 –C5-g-OH) (VII); phenylpropionic acids (C6 –C3) (IX. XIII); phenylacetic acids (C6 –C2) (X, XIV); flavonols (XI); benzoic acids (C6 –C1) (XII, XV). Note: it is not possible to show all possible substrates, intermediates and pathways but those shown are representative. British Journal of Nutrition (11,12) Polyphenol breakdown in the colon Peptostreptococcus spp. and Bifidobacterium spp. https://www.cambridge.org/core/terms These bacteria are accompanied by a single methanogenic Bacterial composition of the human gut archaeon, Methanobrevibacter smithii (9,13). The eukarya The first part of this review is concerned primarily with the include protozoa, but those found in the GIT seem never to capability of the microflora in the distal gastro-intestinal have been studied with reference to PPT catabolism. tract (GIT) to transform PPT provided by the diet. A detailed It is generally accepted that colonisation of the GIT of discussion of the complex nature and composition of this neonates starts immediately after birth. The type of delivery microflora is beyond the scope of this review, but some (passage through the birth canal v. caesarean section), type of basic statistics are instructive. The GIT is home to between diet (breast v. formula feeding) and environment affect the some 10 and 100 trillion microbes(9), approximately colonisation pattern(14,15). The composition of the gut flora of (10) 10-times as many cells as found in the human body . a 2-year-old child is essentially the same as that of an . https://doi.org/10.1017/S0007114510003946 The corresponding microbiome is said to contain more than adult(16), but the variations in microflora composition associated 100-times as many genes as the human genome(9). Each with age, diet and health status are still not fully determined(17). portion of the GIT (mouth, oesophagus, stomach, small A study of faecal samples from 230 volunteers, aged 20–50 intestine and large intestine) has a distinctive flora, but the years, from four European countries has demonstrated marked majority of the organisms are located in the distal GIT, country–age interactions. The proportions of bifidobacteria where the concentration of some 500 bacterial species may were 2- to 3-fold higher in the Italian study population than in reach 1011 –1012 colony forming units/g, and account for any other study group, and this effect was independent of age. some 35–50 % of the contents(11). The flora contains bacteria, Higher proportions of enterobacteria were found in all elderly archaea and eukarya, and the bacterial component has been volunteers independent of the location(18). There is good studied the most extensively. Three genera, Bacteroides evidence that comparatively minor changes in the diet of rats spp., Clostridium spp. and Eubacterium spp., each account can produce significant changes in the catabolites eventually for approximately 30 % of the organisms present(9), but the produced from dietary PPT(19), but the extent to which the colon also has a significant content of Fusobacterium spp., human microflora can be modulated by diet is unknown. Downloaded from S50 G. Williamson and M. N. Clifford Models used to study colonic catabolism proper analysis of the transformations. Studies in the authors’ https://www.cambridge.org/core laboratories suggest that the catabolism of PPT that are not The distal GIT is conveniently viewed as an anaerobic fermen- strongly bound to protein is not significantly different from tation vessel in which polysaccharides, proteins, lipids and xeno- their catabolism in protein-free media, and protein-free biotics such as PPT can be transformed. Several strategies have media have been used to investigate the catabolism of procya- been used to investigate these transformations.
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