In Vitro Gut Metabolism of [U-13C]-Quinic Acid, The Other Hydrolysis Product of Chlorogenic Acid

Martine Naranjo Pinta, Ivan Montoliu, Anna Marja Aura, Tuulikki Seppänen-Laakso, Denis Barron, Sofia Moco (Corresponding Author)

Research output: Contribution to journalArticleScientificpeer-review

2 Citations (Scopus)

Abstract

Scope: Quinic acid in its free form is broadly abundant in plants, and can accumulate in copious amounts in coffee, tea, and certain fruits. However, it has been mostly studied as chlorogenic acid, an ester of caffeic and quinic acids. When chlorogenic acid reaches the colon, it is hydrolyzed by microbial esterases releasing caffeic and quinic acids. While biotransformation of chlorogenic and caffeic acids have been elucidated by in vitro and in vivo studies, the gut metabolism of quinic acid has been so far overlooked. Methods and Results: [U-13C]-Quinic acid is submitted to a colonic model using human fecal microbiota for assessing its metabolic fate. The metabolite profiles formed along microbial biotransformation are monitored by a combined metabolomics approach, using both 2D GC– and ultra-HPLC–MS. Six metabolic intermediates are identified by incorporation of isotopic label. Conclusion: Two parallel degradation pathways could be proposed: (1) an oxidative route, leading to aromatization and accumulation of protocatechuic acid, and a (2) reductive route, including dehydroxylation to cyclohexane carboxylic acid. Elucidating the biotransformation of food bioactives by the gut microbiota is of relevance for understanding nutrition, interindividual variability and potential effects on human metabolism.

Original languageEnglish
Article number1800396
JournalMolecular Nutrition and Food Research
Volume62
Issue number22
DOIs
Publication statusPublished - 1 Nov 2018
MoE publication typeNot Eligible

Fingerprint

Caffeic Acids
Quinic Acid
Chlorogenic Acid
quinic acid
chlorogenic acid
Biotransformation
Hydrolysis
digestive system
hydrolysis
caffeic acid
biotransformation
metabolism
Metabolomics
Microbiota
Coffee
Tea
Esterases
Carboxylic Acids
Fruit
Colon

Keywords

  • colonic model
  • gut metabolism
  • metabolomics
  • quinate
  • quinic acid
  • stable isotopes

Cite this

@article{f53bc0c226c84ca1b6d23bcf5b63d492,
title = "In Vitro Gut Metabolism of [U-13C]-Quinic Acid, The Other Hydrolysis Product of Chlorogenic Acid",
abstract = "Scope: Quinic acid in its free form is broadly abundant in plants, and can accumulate in copious amounts in coffee, tea, and certain fruits. However, it has been mostly studied as chlorogenic acid, an ester of caffeic and quinic acids. When chlorogenic acid reaches the colon, it is hydrolyzed by microbial esterases releasing caffeic and quinic acids. While biotransformation of chlorogenic and caffeic acids have been elucidated by in vitro and in vivo studies, the gut metabolism of quinic acid has been so far overlooked. Methods and Results: [U-13C]-Quinic acid is submitted to a colonic model using human fecal microbiota for assessing its metabolic fate. The metabolite profiles formed along microbial biotransformation are monitored by a combined metabolomics approach, using both 2D GC– and ultra-HPLC–MS. Six metabolic intermediates are identified by incorporation of isotopic label. Conclusion: Two parallel degradation pathways could be proposed: (1) an oxidative route, leading to aromatization and accumulation of protocatechuic acid, and a (2) reductive route, including dehydroxylation to cyclohexane carboxylic acid. Elucidating the biotransformation of food bioactives by the gut microbiota is of relevance for understanding nutrition, interindividual variability and potential effects on human metabolism.",
keywords = "colonic model, gut metabolism, metabolomics, quinate, quinic acid, stable isotopes",
author = "{Naranjo Pinta}, Martine and Ivan Montoliu and Aura, {Anna Marja} and Tuulikki Sepp{\"a}nen-Laakso and Denis Barron and Sofia Moco",
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In Vitro Gut Metabolism of [U-13C]-Quinic Acid, The Other Hydrolysis Product of Chlorogenic Acid. / Naranjo Pinta, Martine; Montoliu, Ivan; Aura, Anna Marja; Seppänen-Laakso, Tuulikki; Barron, Denis; Moco, Sofia (Corresponding Author).

In: Molecular Nutrition and Food Research, Vol. 62, No. 22, 1800396, 01.11.2018.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - In Vitro Gut Metabolism of [U-13C]-Quinic Acid, The Other Hydrolysis Product of Chlorogenic Acid

AU - Naranjo Pinta, Martine

AU - Montoliu, Ivan

AU - Aura, Anna Marja

AU - Seppänen-Laakso, Tuulikki

AU - Barron, Denis

AU - Moco, Sofia

PY - 2018/11/1

Y1 - 2018/11/1

N2 - Scope: Quinic acid in its free form is broadly abundant in plants, and can accumulate in copious amounts in coffee, tea, and certain fruits. However, it has been mostly studied as chlorogenic acid, an ester of caffeic and quinic acids. When chlorogenic acid reaches the colon, it is hydrolyzed by microbial esterases releasing caffeic and quinic acids. While biotransformation of chlorogenic and caffeic acids have been elucidated by in vitro and in vivo studies, the gut metabolism of quinic acid has been so far overlooked. Methods and Results: [U-13C]-Quinic acid is submitted to a colonic model using human fecal microbiota for assessing its metabolic fate. The metabolite profiles formed along microbial biotransformation are monitored by a combined metabolomics approach, using both 2D GC– and ultra-HPLC–MS. Six metabolic intermediates are identified by incorporation of isotopic label. Conclusion: Two parallel degradation pathways could be proposed: (1) an oxidative route, leading to aromatization and accumulation of protocatechuic acid, and a (2) reductive route, including dehydroxylation to cyclohexane carboxylic acid. Elucidating the biotransformation of food bioactives by the gut microbiota is of relevance for understanding nutrition, interindividual variability and potential effects on human metabolism.

AB - Scope: Quinic acid in its free form is broadly abundant in plants, and can accumulate in copious amounts in coffee, tea, and certain fruits. However, it has been mostly studied as chlorogenic acid, an ester of caffeic and quinic acids. When chlorogenic acid reaches the colon, it is hydrolyzed by microbial esterases releasing caffeic and quinic acids. While biotransformation of chlorogenic and caffeic acids have been elucidated by in vitro and in vivo studies, the gut metabolism of quinic acid has been so far overlooked. Methods and Results: [U-13C]-Quinic acid is submitted to a colonic model using human fecal microbiota for assessing its metabolic fate. The metabolite profiles formed along microbial biotransformation are monitored by a combined metabolomics approach, using both 2D GC– and ultra-HPLC–MS. Six metabolic intermediates are identified by incorporation of isotopic label. Conclusion: Two parallel degradation pathways could be proposed: (1) an oxidative route, leading to aromatization and accumulation of protocatechuic acid, and a (2) reductive route, including dehydroxylation to cyclohexane carboxylic acid. Elucidating the biotransformation of food bioactives by the gut microbiota is of relevance for understanding nutrition, interindividual variability and potential effects on human metabolism.

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KW - gut metabolism

KW - metabolomics

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KW - quinic acid

KW - stable isotopes

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