The microbial metabolism of (+)-catechin to two novel diarylpropan-2-ol metabolites<i>in vitro</i>

Groenewoud, G.; Hundt, H. K. L.

doi:10.3109/00498258409151469

Cited by 33 publications

(20 citation statements)

References 15 publications

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“…It has been proposed previously that the cleavage of the C4-C8 link is a major route for procyanidin B3 catabolism, generating free (1)-catechin [8], which then could degrade in the same way as the monomer [7][8][9]32]. Production of (1)-catechin was not observed in that study but that may have been due to the lack of sampling at the early time points such as used in the current study.…”

Section: Low Molecular Mass Catabolites Derived From Both (-)-Epicatecontrasting

confidence: 47%

A comparison of the in vitro biotransformation of (–)‐epicatechin and procyanidin B2 by human faecal microbiota

Stoupi¹,

Williamson²,

Drynan³

et al. 2010

Molecular Nutrition Food Res

155

138

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The catabolism by human faecal microbiota of (-)-epicatechin (1) (2, 3-cis stereochemistry) and its dimer pure procyanidin B2 (2), has been compared using a static in vitro culture model. The catabolites were characterised by LC-MS(n), UV absorption and relative retention time, and quantified relative to standards. No more than approximately 10% of procyanidin B2 (2) was converted to epicatechin (1) by scission of the interflavan bond. Five phenolic acid catabolites (M(r)<290) were unique to 2, and ten phenolic acid catabolites (M(r)<290) were common to both substrates. The dominant catabolites (> or =24 h incubation) were 5-(3'-hydroxy phenyl) valeric acid (9), 3-(3'-hydroxyphenyl) propionic acid (10) and phenyl acetic acid (12) (maximum yields 27.4+/-4.2, 38.2+/-4.2, 22.7+/-2.9%, respectively, from 1 and 9.4+/-1.2, 52.8+/-2.1, 28.8+/-1.6%, respectively, from 2). Substrate 2 was degraded twice as rapidly as 1. Evidence is presented for the production of previously unreported catabolites of 2 that retain the flavanol A-ring and the C4-->C8 interflavan bond. It was confirmed that catabolism favoured removal of the 4'-hydroxyl rather than the 3'-hydroxyl group and that both beta-oxidation and alpha-oxidation occurred.

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Section: Low Molecular Mass Catabolites Derived From Both (-)-Epicatecontrasting

confidence: 47%

A comparison of the in vitro biotransformation of (–)‐epicatechin and procyanidin B2 by human faecal microbiota

Stoupi¹,

Williamson²,

Drynan³

et al. 2010

Molecular Nutrition Food Res

155

138

View full text Add to dashboard Cite

show abstract

“…Transformations may be extensive, and include the removal of sugars, removal of phenolic hydroxyl groups, fission of aromatic rings, and metabolism to carbon dioxide, possibly via oxaloacetate [88]. A substantial range of microbial metabolites has been identified, including phenols and aromatic/phenolic acids/lactones possessing 0, 1 or 2 phenolic hydroxyl groups and up to five carbons in the side chain [89], [90], [91], [92], [93], [94], [95], [96], [97], [98], [99], [100], [101], [102], [103], [104], [105], [106], [107], [108], [109], [110], [111].…”

Section: Absorption and Metabolism Of Pptmentioning

confidence: 99%

Diet-Derived Phenols in Plasma and Tissues and their Implications for Health

2004

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This paper seeks to catalyse a reappraisal of the nature, fate and biological significance in humans of phenols, polyphenols and tannins (PPT) consumed in normal diets, and in particular questions the primacy of PPT radical-scavenging mechanisms for the supposed health benefits of diets rich in fruits and vegetables. PPT are classified by structure and function. Arguments are presented to show that cinnamates and derived polyphenols make significantly larger contributions to the total PPT intake than the flavonols and flavones upon which the vast majority of attention has been focussed previously. Daily intakes of total PPT may range from less than 100 mg to in excess of 2 g, and the critical importance of coffee and black tea as the major dietary sources is shown. Only some 5 % of the dietary PPT is absorbed in the duodenum, and of this only some 5 %, mainly flavanols, reaches the plasma unchanged, the balance being mammalian conjugates. Over 95 % of the intake passes to the colon and is fermented by the gut microflora. A fraction of the resulting microbial metabolites is absorbed and appears in the plasma primarily as mammalian conjugates. Even following high intakes of PPT, the plasma metabolites collectively make a very small (less than 5 %) and transient contribution to the total concentration of redox active substances in plasma. This explains the failure of most studies that sought to detect an increase in plasma antioxidant power after consuming a PPT-rich meal or supplement. The powerfully antioxidant PPT aglycones, much used in in vitro studies, do not reach the plasma. The redox potential of those unchanged PPT and PPT metabolites that reach the plasma enables them to scavenge damaging radicals, but the endogenous plasma antioxidants, especially ascorbate, are required for disposal of the resultant phenoxyl radicals. Black tea and coffee, the major sources of PPT, are poor sources of ascorbate. It is suggested that if diets rich in fruits and vegetables are health-promoting, and if these effects are due to PPT, then alternatives to radical-scavenging mechanisms must be sought. Evidence is presented to show that some mammalian metabolites of PPT may indeed be able to protect the vascular endothelium and that diets rich in PPT may in humans at normal dietary levels have the ability to protect against Type II diabetes and the metabolic syndrome through effects on glucose absorption and associated hormones. Such effects are recommended for further investigation.

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“…Benzoic acid may also be formed endogenously from β‐oxidation of 3‐phenylpropionic acid,58 a gut flora metabolite of tyrosine in man and of some flavonoids, at least in animals 58–61. Another source is from the aromatisation of dietary quinic acid in the liver 62…”

Section: Absorption and Metabolismmentioning

confidence: 99%

Dietary hydroxybenzoic acid derivatives - nature, occurrence and dietary burden

Tomás‐Barberán

Clifford

2000

J. Sci. Food Agric.

239

110

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Quantitative data for hydroxybenzoic acids (naturally occurring and permitted additives) and their conjugates in foods and beverages are summarised. Tea, rosaceous fruits, red wines and potatoes are important sources for which more comprehensive compositional data are required. Their absorption, metabolism, toxicological evaluation and possible biological significance are discussed. There are insufficient data to properly define the dietary burdens, but it would seem that ellagic acid and gallic acid from natural sources may dominate in many cases, although the intake of added benzoic acid may be of a similar magnitude. It is pointed out that an additional, previously overlooked and possibly significant burden, particularly of benzoic acid itself, might arise as a result of the gut flora metabolism of larger‐mass dietary phenols. © 2000 Society of Chemical Industry

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The microbial metabolism of (+)-catechin to two novel diarylpropan-2-ol metabolitesin vitro

Cited by 33 publications

References 15 publications

A comparison of the in vitro biotransformation of (–)‐epicatechin and procyanidin B2 by human faecal microbiota

A comparison of the in vitro biotransformation of (–)‐epicatechin and procyanidin B2 by human faecal microbiota

Diet-Derived Phenols in Plasma and Tissues and their Implications for Health

Dietary hydroxybenzoic acid derivatives - nature, occurrence and dietary burden

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