Procyanidin dimers are metabolized by human microbiota with 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-{gamma}-valerolactone as the major metabolites

Maaike M. Appeldoorn, Jean-Paul Vincken, Anna-Marja Aura, Peter C. H. Hollman, Harry Gruppen (Corresponding Author)

Research output: Contribution to journalArticleScientificpeer-review

175 Citations (Scopus)

Abstract

Procyanidins (PCs) are highly abundant phenolic compounds in the human diet and might be responsible for the health effects of chocolate and wine. Due to low absorption of intact PCs, microbial metabolism might play an important role. So far, only a few studies, with crude extracts rich in PCs but also containing a multitude of other phenolic compounds, have been performed to reveal human microbial PC metabolites. Therefore, the origin of the metabolites remains questionable. This study included in vitro fermentation of purified PC dimers with human microbiota. The main metabolites identified were 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-γ-valerolactone. Other metabolites detected were 3-hydroxyphenylacetic acid, 4-hydroxyphenylacetic acid, 3-hydroxyphenylpropionic acid, phenylvaleric acids, monohydroxylated phenylvalerolactone, and 1-(3′,4′-dihydroxyphenyl)-3-(2′′,4′′,6′′-trihydroxyphenyl)propan-2-ol. Metabolites that could be quantified accounted for at least 12 mol % of the dimers, assuming 1 mol of dimers is converted into 2 mol of metabolite. A degradation pathway, partly different from that of monomeric flavan-3-ols, is proposed.
Original languageEnglish
Pages (from-to)1084 - 1092
JournalJournal of Agricultural and Food Chemistry
Volume57
Issue number3
DOIs
Publication statusPublished - 2009
MoE publication typeA1 Journal article-refereed

Fingerprint

Microbiota
Metabolites
Acetic Acid
Dimers
acetic acid
metabolites
microorganisms
Proanthocyanidins
acids
Wine
Complex Mixtures
Fermentation
phenolic compounds
Diet
procyanidins
Health
chocolate
flavanols
Nutrition
Metabolism

Keywords

  • Degradation pathway
  • human microbial metabolites
  • hydroxyphenylacetic acids
  • proanthocyanidins
  • valerolactones

Cite this

@article{7023c6b752654fae8a0188378bd6d332,
title = "Procyanidin dimers are metabolized by human microbiota with 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-{gamma}-valerolactone as the major metabolites",
abstract = "Procyanidins (PCs) are highly abundant phenolic compounds in the human diet and might be responsible for the health effects of chocolate and wine. Due to low absorption of intact PCs, microbial metabolism might play an important role. So far, only a few studies, with crude extracts rich in PCs but also containing a multitude of other phenolic compounds, have been performed to reveal human microbial PC metabolites. Therefore, the origin of the metabolites remains questionable. This study included in vitro fermentation of purified PC dimers with human microbiota. The main metabolites identified were 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-γ-valerolactone. Other metabolites detected were 3-hydroxyphenylacetic acid, 4-hydroxyphenylacetic acid, 3-hydroxyphenylpropionic acid, phenylvaleric acids, monohydroxylated phenylvalerolactone, and 1-(3′,4′-dihydroxyphenyl)-3-(2′′,4′′,6′′-trihydroxyphenyl)propan-2-ol. Metabolites that could be quantified accounted for at least 12 mol {\%} of the dimers, assuming 1 mol of dimers is converted into 2 mol of metabolite. A degradation pathway, partly different from that of monomeric flavan-3-ols, is proposed.",
keywords = "Degradation pathway, human microbial metabolites, hydroxyphenylacetic acids, proanthocyanidins, valerolactones",
author = "Appeldoorn, {Maaike M.} and Jean-Paul Vincken and Anna-Marja Aura and Hollman, {Peter C. H.} and Harry Gruppen",
year = "2009",
doi = "10.1021/jf803059z",
language = "English",
volume = "57",
pages = "1084 -- 1092",
journal = "Journal of Agricultural and Food Chemistry",
issn = "0021-8561",
publisher = "American Chemical Society",
number = "3",

}

Procyanidin dimers are metabolized by human microbiota with 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-{gamma}-valerolactone as the major metabolites. / Appeldoorn, Maaike M.; Vincken, Jean-Paul; Aura, Anna-Marja; Hollman, Peter C. H.; Gruppen, Harry (Corresponding Author).

In: Journal of Agricultural and Food Chemistry, Vol. 57, No. 3, 2009, p. 1084 - 1092.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Procyanidin dimers are metabolized by human microbiota with 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-{gamma}-valerolactone as the major metabolites

AU - Appeldoorn, Maaike M.

AU - Vincken, Jean-Paul

AU - Aura, Anna-Marja

AU - Hollman, Peter C. H.

AU - Gruppen, Harry

PY - 2009

Y1 - 2009

N2 - Procyanidins (PCs) are highly abundant phenolic compounds in the human diet and might be responsible for the health effects of chocolate and wine. Due to low absorption of intact PCs, microbial metabolism might play an important role. So far, only a few studies, with crude extracts rich in PCs but also containing a multitude of other phenolic compounds, have been performed to reveal human microbial PC metabolites. Therefore, the origin of the metabolites remains questionable. This study included in vitro fermentation of purified PC dimers with human microbiota. The main metabolites identified were 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-γ-valerolactone. Other metabolites detected were 3-hydroxyphenylacetic acid, 4-hydroxyphenylacetic acid, 3-hydroxyphenylpropionic acid, phenylvaleric acids, monohydroxylated phenylvalerolactone, and 1-(3′,4′-dihydroxyphenyl)-3-(2′′,4′′,6′′-trihydroxyphenyl)propan-2-ol. Metabolites that could be quantified accounted for at least 12 mol % of the dimers, assuming 1 mol of dimers is converted into 2 mol of metabolite. A degradation pathway, partly different from that of monomeric flavan-3-ols, is proposed.

AB - Procyanidins (PCs) are highly abundant phenolic compounds in the human diet and might be responsible for the health effects of chocolate and wine. Due to low absorption of intact PCs, microbial metabolism might play an important role. So far, only a few studies, with crude extracts rich in PCs but also containing a multitude of other phenolic compounds, have been performed to reveal human microbial PC metabolites. Therefore, the origin of the metabolites remains questionable. This study included in vitro fermentation of purified PC dimers with human microbiota. The main metabolites identified were 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-γ-valerolactone. Other metabolites detected were 3-hydroxyphenylacetic acid, 4-hydroxyphenylacetic acid, 3-hydroxyphenylpropionic acid, phenylvaleric acids, monohydroxylated phenylvalerolactone, and 1-(3′,4′-dihydroxyphenyl)-3-(2′′,4′′,6′′-trihydroxyphenyl)propan-2-ol. Metabolites that could be quantified accounted for at least 12 mol % of the dimers, assuming 1 mol of dimers is converted into 2 mol of metabolite. A degradation pathway, partly different from that of monomeric flavan-3-ols, is proposed.

KW - Degradation pathway

KW - human microbial metabolites

KW - hydroxyphenylacetic acids

KW - proanthocyanidins

KW - valerolactones

U2 - 10.1021/jf803059z

DO - 10.1021/jf803059z

M3 - Article

VL - 57

SP - 1084

EP - 1092

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

SN - 0021-8561

IS - 3

ER -