The chemistry of gut microbial metabolism of polyphenols

Stevens, Jan F.; Maier, Christoph

doi:10.1007/s11101-016-9459-z

Cited by 180 publications

(133 citation statements)

References 124 publications

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“…In colon, there was nearly no absorption of quercetin. With regard to the large microbial system present in colon [36], there is the possibility that quercetin underwent microbial metabolism in a faster way than absorption processes took place. Metabolites were assumed to be small unspecific molecules such as phloroglucinol and acid derivatives [37] or carbon dioxide [38].…”

Section: Discussionmentioning

confidence: 99%

Sustained Release for St. John?s Wort: A Rational Idea?

Disch¹,

Forsch²,

Siewert³

et al. 2017

J Bioequiv Availab

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Section: Discussionmentioning

confidence: 99%

Sustained Release for St. John?s Wort: A Rational Idea?

Disch¹,

Forsch²,

Siewert³

et al. 2017

J Bioequiv Availab

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“…The chemistry of many transformations has been reviewed [152], but some transformations are still poorly understood. Several mandelic acids have sometimes been considered as gut microbiota catabolites, but it is now recognised that 4-hydroxymandelic acid is a metabolite of p-sympatol (p-synephrine) and / or p-octopamine, which in dietary terms are known only from citrus fruit [65,153].…”

Section: Controls Used In Model Fermentations Have Clearly Demonstratmentioning

confidence: 99%

Role of the small intestine, colon and microbiota in determining the metabolic fate of polyphenols

Williamson

Clifford

2017

Biochemical Pharmacology

272

172

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Please cite this article as: G. Williamson, M.N. Clifford, Role of the small intestine, colon and microbiota in determining the metabolic fate of polyphenols, Biochemical Pharmacology (2017), doi: http://dx.doi.org/10.1016/ j. bcp.2017.03.012 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. 1Role of the small intestine, colon and microbiota in determining the metabolic fate of in the small intestine, or reaches the colon and is subject to extensive catabolism by colonic microbiota. Untransformed substrates may be absorbed, appearing in plasma primarily as methylated, sulfated and glucuronidated derivatives, with in some cases the unchanged substrate. Many of the catabolites are well absorbed from the colon and appear in the plasma either similarly conjugated, or as glycine conjugates, or in some cases unchanged.Although many (poly)phenol catabolites have been identified in human plasma and / or urine, the pathways from substrate to final catabolite, and the species of bacteria and enzymes involved, are still scarcely reported. While it is clear that the composition of the human gut microbiota can be modulated in vivo by supplementation with some (poly)phenol-rich commodities, such modulation is definitely not an inevitable consequence of supplementation, it depends on the treatment, length of time and on the individual metabotype, and it is not clear whether the modulation is sustained when supplementation ceases. Some catabolites have been recorded in plasma of volunteers at concentrations similar to those shown to be effective in in vitro studies suggesting that some benefit may be achieved in vivo by diets yielding such catabolites. and are also present at high levels in supplements [4], and form essential components of many Chinese medicines [5]. A study within the European Prospective Investigation intoCancer and Nutrition (EPIC) using the Phenol Explorer database reported that the cohort studied consumed 427 different polyphenols including 94 that were consumed at a rate of >1 g/day. The estimated total polyphenol consumption ranged from 584 mg/day by Greek women to 1786 mg/day for men in Aarhus-Denmark. The corresponding data for Greek men and for Aarhus women were 744 mg/day and 1626 mg/ day, respectively, with all data adjusted for age and weighted by season and weekday of dietary recall [6]. This study defined the major contributors to be the phenolic acids (predominantly the caffeoylquinic acids (27-53%), also called chlorogenic acids) and flavonoids (predominantly flavanols (16-29%), proanthocyanidins (5-9%) and theaflavins (14-25%)) [6]. Hydroxybenzoic acids (3.3-7.4%), alkyl-phenols (1.6...

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“…Microbial metabolism frequently leads to a variety of smaller fragments, including simple phenolic acids, phloroglucinol derivatives, etc. Detailed reviews on this subject have recently been published by others . The following sub‐sections attempt to provide an overview on the known Phase I and Phase II metabolic transformations of curcuminoids ( 1 ‐ 3 ), resveratrol ( 4 ), a set of methyl‐hydroxycinnamates ( 5 ‐ 7 ), secoisolariciresinol ( 8 ), and luteolin ( 9 ), and on related pharmacological consequences.…”

Section: Metabolism Of Antioxidants In View Of Their Bioactivitymentioning

confidence: 99%

The mechanism(s) of action of antioxidants: From scavenging reactive oxygen/nitrogen species to redox signaling and the generation of bioactive secondary metabolites

Hunyadi

2019

Medicinal Research Reviews

166

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Small molecule, dietary antioxidants exert a remarkably broad range of bioactivities, and many of these can be explained by the influence of antioxidants on the redox homeostasis. Such compounds help to modulate the levels of harmful reactive oxygen/nitrogen species, and therefore participate in the regulation of various redox signaling pathways. However, upon ingestion, antioxidants usually undergo extensive metabolism that can generate a wide range of bioactive metabolites. This makes it difficult, but otherwise a need, to identify the ones responsible for the different activities of antioxidants. By better understanding their ways of action, the use of antioxidants in therapy can be improved. This review provides a summary on the role of the in vivo metabolic changes and the oxidized metabolites on the mechanisms behind the bioactivity of antioxidants. A special attention is given to metabolites described as products of biomimetic oxidative chemical reactions, which can be considered as models of free radical scavenging. During such reactions a wide variety of metabolites are formed, and they can exert completely different specific bioactivities as compared to their parent antioxidants. This implies that exploring the free radical scavenging‐related metabolite fingerprint of each antioxidant molecule, collectively defined here as the scavengome, will lead to a deeper understanding of the bioactivity of these compounds. Furthermore, this paper aims to be a working tool for systematic studies on oxidized metabolic fingerprints of antioxidants, which will certainly reveal an often‐neglected segment of chemical space that is a treasury of bioactive compounds.

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The chemistry of gut microbial metabolism of polyphenols

Cited by 180 publications

References 124 publications

Sustained Release for St. John?s Wort: A Rational Idea?

Sustained Release for St. John?s Wort: A Rational Idea?

Role of the small intestine, colon and microbiota in determining the metabolic fate of polyphenols

The mechanism(s) of action of antioxidants: From scavenging reactive oxygen/nitrogen species to redox signaling and the generation of bioactive secondary metabolites

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