Epicatechin B-Ring Conjugates: First Enantioselective Synthesis and Evidence for Their Occurrence in Human Biological Fluids

Romanov‐Michailidis, Fedor; Viton, Florian; Fumeaux, René; Lévêques, Antoine; Actis‐Goretta, Lucas; Rein, Maarit J.; Williamson, Gary; Barron, Denís

doi:10.1021/ol3016463

Cited by 27 publications

(20 citation statements)

References 14 publications

(10 reference statements)

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“…These metabolites are present in blood and tissues. Major conjugates of (À)-epicatechin in human plasma, bile, and urine were (À)-epicatechin 3 0 -O-sulfonate and (À)-epicatechin 3 0 -O-b-glucuronide after ingestion of 50 mg of (À)-epicatechin by volunteers (Romanov-Michailidis et al, 2012).…”

Section: Absorption Of Proanthocyanidin Oligomersmentioning

confidence: 98%

Absorption and metabolism of proanthocyanidins

2014

Journal of Functional Foods

336

249

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Section: Absorption Of Proanthocyanidin Oligomersmentioning

confidence: 98%

Absorption and metabolism of proanthocyanidins

2014

Journal of Functional Foods

336

249

View full text Add to dashboard Cite

“…Major conjugates of (−)-epicatechin in human plasma, bile, and urine were (−)-epicatechin 3′- O -sulfonate and (−)-epicatechin 3′- O -β-glucuronide after ingestion of 50 mg of (−)-epicatechin by volunteers [ 61 ]. Conjugation of (−)-epicatechin with glucuronic acid had already been observed in human blood brain barrier cell line model [ 62 ].…”

Section: Bioavailability Of Red Wine Phenolicsmentioning

confidence: 99%

Wine Flavonoids in Health and Disease Prevention

et al. 2017

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Wine, and particularly red wine, is a beverage with a great chemical complexity that is in continuous evolution. Chemically, wine is a hydroalcoholic solution (~78% water) that comprises a wide variety of chemical components, including aldehydes, esters, ketones, lipids, minerals, organic acids, phenolics, soluble proteins, sugars and vitamins. Flavonoids constitute a major group of polyphenolic compounds which are directly associated with the organoleptic and health-promoting properties of red wine. However, due to the insufficient epidemiological and in vivo evidences on this subject, the presence of a high number of variables such as human age, metabolism, the presence of alcohol, the complex wine chemistry, and the wide array of in vivo biological effects of these compounds suggest that only cautious conclusions may be drawn from studies focusing on the direct effect of wine and any specific health issue. Nevertheless, there are several reports on the health protective properties of wine phenolics for several diseases such as cardiovascular diseases, some cancers, obesity, neurodegenerative diseases, diabetes, allergies and osteoporosis. The different interactions that wine flavonoids may have with key biological targets are crucial for some of these health-promoting effects. The interaction between some wine flavonoids and some specific enzymes are one example. The way wine flavonoids may be absorbed and metabolized could interfere with their bioavailability and therefore in their health-promoting effect. Hence, some reports have focused on flavonoids absorption, metabolism, microbiota effect and overall on flavonoids bioavailability. This review summarizes some of these major issues which are directly related to the potential health-promoting effects of wine flavonoids. Reports related to flavonoids and health highlight some relevant scientific information. However, there is still a gap between the knowledge of wine flavonoids bioavailability and their health-promoting effects. More in vivo results as well as studies focused on flavonoid metabolites are still required. Moreover, it is also necessary to better understand how biological interactions (with microbiota and cells, enzymes or general biological systems) could interfere with flavonoid bioavailability.

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“…Romanov-Michailidis et al synthesized the conjugated sulfate and detected it in human biological uids. 22) e product ion spectra of the synthetic sulfate conjugate showed that m/z 231 corresponds to the 3′-or 4′-O-sulfate, and the product ion at m/z 247 corresponds to the 5-or 7-O-sulfate. 23) Compared to previous results, the assignment results for O-methyl-gallocatechin also suggest that a sulfate conjugated to the B-ring is produced.…”

Section: Analysis Of Conjugates Of Green Tea Components In Mouse Urinementioning

confidence: 99%

Method for the Compound Annotation of Conjugates in Nontargeted Metabolomics Using Accurate Mass Spectrometry, Multistage Product Ion Spectra and Compound Database Searching

et al. 2015

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Owing to biotransformation, xenobiotics are o en found in conjugated form in biological samples such as urine and plasma. Liquid chromatography coupled with accurate mass spectrometry with multistage collision-induced dissociation provides spectral information concerning these metabolites in complex materials. Unfortunately, compound databases typically do not contain a su cient number of records for such conjugates. We report here on the development of a novel protocol, referred to as ChemProphet, to annotate compounds, including conjugates, using compound databases such as PubChem and ChemSpider.e annotation of conjugates involves three steps: 1. Recognition of the type and number of conjugates in the sample; 2. Compound search and annotation of the deconjugated form; and 3. In silico evaluation of the candidate conjugate. ChemProphet assigns a spectrum to each candidate by automatically exploring the substructures corresponding to the observed product ion spectrum. When nished, it annotates the candidates assigning a rank for each candidate based on the calculated score that ranks its relative likelihood. We assessed our protocol by annotating a benchmark dataset by including the product ion spectra for 102 compounds, annotating the commercially available standard for quercetin 3-glucuronide, and by conducting a model experiment using urine from mice that had been administered a green tea extract. e results show that by using the ChemProphet approach, it is possible to annotate not only the deconjugated molecules but also the conjugated molecules using an automatic interpretation method based on deconjugation that involves multistage collision-induced dissociation and in silico calculated conjugation.Please cite this article as: Mass Spectrom (Tokyo) 2015; 4(1): A0036

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Epicatechin B-Ring Conjugates: First Enantioselective Synthesis and Evidence for Their Occurrence in Human Biological Fluids

Cited by 27 publications

References 14 publications

Absorption and metabolism of proanthocyanidins

Absorption and metabolism of proanthocyanidins

Wine Flavonoids in Health and Disease Prevention

Method for the Compound Annotation of Conjugates in Nontargeted Metabolomics Using Accurate Mass Spectrometry, Multistage Product Ion Spectra and Compound Database Searching

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