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

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Autoren

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

OriginalspracheEnglisch
Seiten (von - bis)610-621
Seitenumfang12
FachzeitschriftMolecular Nutrition and Food Research
Jahrgang59
Ausgabenummer4
PublikationsstatusVeröffentlicht - 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.

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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, Jahrgang 59, Nr. 4, 01.04.2015, S. 610-621.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-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.",
keywords = "Bioavailability, Catechins, Drug metabolism, Microbial degradation, Procyanidins",
author = "S. Wiese and T. Esatbeyoglu and P. Winterhalter and H.-P. Kruse and S. Winkler and A. Bub and S.E. Kulling",
note = "Publisher Copyright: {\textcopyright} 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Copyright: Copyright 2015 Elsevier B.V., All rights reserved.",
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doi = "10.1002/mnfr.201400422",
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TY - JOUR

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 -