Comparative biokinetics and metabolism of pure monomeric, dimeric, and polymeric flavan-3-ols: A randomized cross-over study in humans

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Authors

  • S. Wiese
  • T. Esatbeyoglu
  • P. Winterhalter
  • H.-P. Kruse
  • S. Winkler
  • A. Bub
  • S.E. Kulling
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Details

Original languageEnglish
Pages (from-to)610-621
Number of pages12
JournalMolecular Nutrition and Food Research
Volume59
Issue number4
Publication statusPublished - 1 Apr 2015

Abstract

Scope: Flavan-3-ols are abundant polyphenols in human nutrition and are associated with beneficial health effects. The aim of this study was to comparatively investigate the metabolic fate of (-)-epicatechin, procyanidin B1, and polymeric procyanidins in a randomized cross-over study in humans. Methods and results: Parent compounds, conjugates, and microbial metabolites were determined in plasma, urine, and faeces by HPLC-MS and GC-MS/MS. Glucuronidated, sulfated, and methylated (-)-epicatechin and 5-(3′,4′-dihydroxyphenyl)-valerolactone were the dominant metabolites in blood and urine. In addition, minor amounts of procyanidin B1 and 4-hydroxy-5-(3′,4′-dihydroxyphenyl)valeric acid and their conjugated metabolites were detected. The formation of 5-(3′,4′-dihydroxyphenyl)-valerolactone and 4-hydroxy-5-(3′,4′-dihydroxyphenyl)valeric acid varied largely between individuals as well as with the degree of polymerization of flavan-3-ols. Monomer units were not detectable in plasma or urine after procyanidin B1 and polymeric procyanidin intake. No correlation was found between the intake of flavan-3-ols and the occurrence of phenolic acids in blood and urine or the phenolic compound profiles in faeces. Conclusion: In addition to conjugated metabolites derived from the absorption of monomeric flavan-3-ols, 5-(3′,4′-dihydroxyphenyl)-valerolactone represents an important in vivo metabolite of (-)-epicatechin and procyanidin B1 produced by the gut microbiota.

Keywords

    Bioavailability, Catechins, Drug metabolism, Microbial degradation, Procyanidins

ASJC Scopus subject areas

Sustainable Development Goals

Cite this

Comparative biokinetics and metabolism of pure monomeric, dimeric, and polymeric flavan-3-ols: A randomized cross-over study in humans. / Wiese, S.; Esatbeyoglu, T.; Winterhalter, P. et al.
In: Molecular Nutrition and Food Research, Vol. 59, No. 4, 01.04.2015, p. 610-621.

Research output: Contribution to journalArticleResearchpeer review

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title = "Comparative biokinetics and metabolism of pure monomeric, dimeric, and polymeric flavan-3-ols: A randomized cross-over study in humans",
abstract = "Scope: Flavan-3-ols are abundant polyphenols in human nutrition and are associated with beneficial health effects. The aim of this study was to comparatively investigate the metabolic fate of (-)-epicatechin, procyanidin B1, and polymeric procyanidins in a randomized cross-over study in humans. Methods and results: Parent compounds, conjugates, and microbial metabolites were determined in plasma, urine, and faeces by HPLC-MS and GC-MS/MS. Glucuronidated, sulfated, and methylated (-)-epicatechin and 5-(3′,4′-dihydroxyphenyl)-valerolactone were the dominant metabolites in blood and urine. In addition, minor amounts of procyanidin B1 and 4-hydroxy-5-(3′,4′-dihydroxyphenyl)valeric acid and their conjugated metabolites were detected. The formation of 5-(3′,4′-dihydroxyphenyl)-valerolactone and 4-hydroxy-5-(3′,4′-dihydroxyphenyl)valeric acid varied largely between individuals as well as with the degree of polymerization of flavan-3-ols. Monomer units were not detectable in plasma or urine after procyanidin B1 and polymeric procyanidin intake. No correlation was found between the intake of flavan-3-ols and the occurrence of phenolic acids in blood and urine or the phenolic compound profiles in faeces. Conclusion: In addition to conjugated metabolites derived from the absorption of monomeric flavan-3-ols, 5-(3′,4′-dihydroxyphenyl)-valerolactone represents an important in vivo metabolite of (-)-epicatechin and procyanidin B1 produced by the gut microbiota.",
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T1 - Comparative biokinetics and metabolism of pure monomeric, dimeric, and polymeric flavan-3-ols: A randomized cross-over study in humans

AU - Wiese, S.

AU - Esatbeyoglu, T.

AU - Winterhalter, P.

AU - Kruse, H.-P.

AU - Winkler, S.

AU - Bub, A.

AU - Kulling, S.E.

N1 - Publisher Copyright: © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Copyright: Copyright 2015 Elsevier B.V., All rights reserved.

PY - 2015/4/1

Y1 - 2015/4/1

N2 - Scope: Flavan-3-ols are abundant polyphenols in human nutrition and are associated with beneficial health effects. The aim of this study was to comparatively investigate the metabolic fate of (-)-epicatechin, procyanidin B1, and polymeric procyanidins in a randomized cross-over study in humans. Methods and results: Parent compounds, conjugates, and microbial metabolites were determined in plasma, urine, and faeces by HPLC-MS and GC-MS/MS. Glucuronidated, sulfated, and methylated (-)-epicatechin and 5-(3′,4′-dihydroxyphenyl)-valerolactone were the dominant metabolites in blood and urine. In addition, minor amounts of procyanidin B1 and 4-hydroxy-5-(3′,4′-dihydroxyphenyl)valeric acid and their conjugated metabolites were detected. The formation of 5-(3′,4′-dihydroxyphenyl)-valerolactone and 4-hydroxy-5-(3′,4′-dihydroxyphenyl)valeric acid varied largely between individuals as well as with the degree of polymerization of flavan-3-ols. Monomer units were not detectable in plasma or urine after procyanidin B1 and polymeric procyanidin intake. No correlation was found between the intake of flavan-3-ols and the occurrence of phenolic acids in blood and urine or the phenolic compound profiles in faeces. Conclusion: In addition to conjugated metabolites derived from the absorption of monomeric flavan-3-ols, 5-(3′,4′-dihydroxyphenyl)-valerolactone represents an important in vivo metabolite of (-)-epicatechin and procyanidin B1 produced by the gut microbiota.

AB - Scope: Flavan-3-ols are abundant polyphenols in human nutrition and are associated with beneficial health effects. The aim of this study was to comparatively investigate the metabolic fate of (-)-epicatechin, procyanidin B1, and polymeric procyanidins in a randomized cross-over study in humans. Methods and results: Parent compounds, conjugates, and microbial metabolites were determined in plasma, urine, and faeces by HPLC-MS and GC-MS/MS. Glucuronidated, sulfated, and methylated (-)-epicatechin and 5-(3′,4′-dihydroxyphenyl)-valerolactone were the dominant metabolites in blood and urine. In addition, minor amounts of procyanidin B1 and 4-hydroxy-5-(3′,4′-dihydroxyphenyl)valeric acid and their conjugated metabolites were detected. The formation of 5-(3′,4′-dihydroxyphenyl)-valerolactone and 4-hydroxy-5-(3′,4′-dihydroxyphenyl)valeric acid varied largely between individuals as well as with the degree of polymerization of flavan-3-ols. Monomer units were not detectable in plasma or urine after procyanidin B1 and polymeric procyanidin intake. No correlation was found between the intake of flavan-3-ols and the occurrence of phenolic acids in blood and urine or the phenolic compound profiles in faeces. Conclusion: In addition to conjugated metabolites derived from the absorption of monomeric flavan-3-ols, 5-(3′,4′-dihydroxyphenyl)-valerolactone represents an important in vivo metabolite of (-)-epicatechin and procyanidin B1 produced by the gut microbiota.

KW - Bioavailability

KW - Catechins

KW - Drug metabolism

KW - Microbial degradation

KW - Procyanidins

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U2 - 10.1002/mnfr.201400422

DO - 10.1002/mnfr.201400422

M3 - Article

VL - 59

SP - 610

EP - 621

JO - Molecular Nutrition and Food Research

JF - Molecular Nutrition and Food Research

SN - 1613-4125

IS - 4

ER -

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