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Article: Synthetic and analytical strategies for the quantification of phenyl-γ-valerolactone conjugated metabolites in human urine

TitleSynthetic and analytical strategies for the quantification of phenyl-γ-valerolactone conjugated metabolites in human urine
Authors
KeywordsColonic metabolites
Flavan-3-ol
Green tea
Phenolic compounds
Stereoselective synthesis
Issue Date2017
PublisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1613-4133
Citation
Molecular Nutrition & Food Research, 2017, v. 61 n. 9, article no. 1700077 How to Cite?
AbstractScope: The contribution of the gut microbiota to the metabolism of catechins and proanthocyanidins remains unclear. Phenyl‐γ‐valerolactones have been identified as the most representative metabolites of these dietary flavan‐3‐ols, but their accurate quantification has posed problems because of a lack of appropriate bioanalytical standards. This work aimed at synthesizing a novel set of sulphate‐ and glucuronide‐conjugated phenyl‐γ‐valerolactones and at developing an analytical platform using UHPLC‐ESI‐MS/MS for their quantification in urine. Methods and results: Eight glucuronide and sulphate conjugates of hydroxyphenyl‐γ‐valerolactones were synthesized and used as analytical standards, together with five phenyl‐γ‐valerolactone aglycones, for the development of a high‐throughput, validated analytical method. Chromatographic and MS conditions were optimized. The method validation showed acceptable linearity, intra‐day and inter‐day repeatability, and accuracy, with the analytical range, limit of detection (LOD), and lower limit of quantification (LLOQ) varying notably among compounds. The method was used to calculate the excretion of phenyl‐γ‐valerolactones in healthy subject consuming green tea, providing novel information on the real concentrations of phenyl‐γ‐valerolactones in urine. Conclusion: This work opens the door to better studying the bioavailability of flavan‐3‐ols and the real exposition to flavan‐3‐ol sources, as well as to define the bioactivity of these colonic metabolites in cell assays.
Persistent Identifierhttp://hdl.handle.net/10722/263953
ISSN
2020 Impact Factor: 5.914
2015 SCImago Journal Rankings: 1.679
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorBrindani, N-
dc.contributor.authorMena, P-
dc.contributor.authorCalani, L-
dc.contributor.authorBenzie, I-
dc.contributor.authorChoi, SW-
dc.contributor.authorBrighenti, F-
dc.contributor.authorZanardi, F-
dc.contributor.authorCurti, C-
dc.contributor.authorDel Rio, D-
dc.date.accessioned2018-10-22T07:47:08Z-
dc.date.available2018-10-22T07:47:08Z-
dc.date.issued2017-
dc.identifier.citationMolecular Nutrition & Food Research, 2017, v. 61 n. 9, article no. 1700077-
dc.identifier.issn1613-4125-
dc.identifier.urihttp://hdl.handle.net/10722/263953-
dc.description.abstractScope: The contribution of the gut microbiota to the metabolism of catechins and proanthocyanidins remains unclear. Phenyl‐γ‐valerolactones have been identified as the most representative metabolites of these dietary flavan‐3‐ols, but their accurate quantification has posed problems because of a lack of appropriate bioanalytical standards. This work aimed at synthesizing a novel set of sulphate‐ and glucuronide‐conjugated phenyl‐γ‐valerolactones and at developing an analytical platform using UHPLC‐ESI‐MS/MS for their quantification in urine. Methods and results: Eight glucuronide and sulphate conjugates of hydroxyphenyl‐γ‐valerolactones were synthesized and used as analytical standards, together with five phenyl‐γ‐valerolactone aglycones, for the development of a high‐throughput, validated analytical method. Chromatographic and MS conditions were optimized. The method validation showed acceptable linearity, intra‐day and inter‐day repeatability, and accuracy, with the analytical range, limit of detection (LOD), and lower limit of quantification (LLOQ) varying notably among compounds. The method was used to calculate the excretion of phenyl‐γ‐valerolactones in healthy subject consuming green tea, providing novel information on the real concentrations of phenyl‐γ‐valerolactones in urine. Conclusion: This work opens the door to better studying the bioavailability of flavan‐3‐ols and the real exposition to flavan‐3‐ol sources, as well as to define the bioactivity of these colonic metabolites in cell assays.-
dc.languageeng-
dc.publisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1613-4133-
dc.relation.ispartofMolecular Nutrition & Food Research-
dc.rightsThis is the peer reviewed version of the following article: Molecular Nutrition & Food Research, 2017, v. 61 n. 9, article no. 1700077, which has been published in final form at https://doi.org/10.1002/mnfr.201700077. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.-
dc.subjectColonic metabolites-
dc.subjectFlavan-3-ol-
dc.subjectGreen tea-
dc.subjectPhenolic compounds-
dc.subjectStereoselective synthesis-
dc.titleSynthetic and analytical strategies for the quantification of phenyl-γ-valerolactone conjugated metabolites in human urine-
dc.typeArticle-
dc.identifier.emailChoi, SW: htswchoi@hku.hk-
dc.identifier.authorityChoi, SW=rp02552-
dc.description.naturepostprint-
dc.identifier.doi10.1002/mnfr.201700077-
dc.identifier.pmid28440064-
dc.identifier.scopuseid_2-s2.0-85020472587-
dc.identifier.hkuros294129-
dc.identifier.volume61-
dc.identifier.issue9-
dc.identifier.spagearticle no. 1700077-
dc.identifier.epagearticle no. 1700077-
dc.identifier.isiWOS:000408981500035-
dc.publisher.placeGermany-
dc.identifier.issnl1613-4125-

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