UHPLC-Q-Orbitrap /MS2 identification of (+)-Catechin oxidation reaction dimeric products in red wines and grape seed extracts

Deshaies, Stacy; Sommerer, Nicolas; Garcia, François; Mouls, Laetitia; Saucier, Cédric

doi:10.1016/j.foodchem.2022.132505

Cited by 9 publications

(15 citation statements)

References 37 publications

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“…In the same way, the single spot from the peak of the N6 compound also had HRMS data and MS/MS fragmentation pattern consistent with a dehydrodicatechin of ε-configuration, but additionally another fragment ion at m/z 439.1037 was detected, corresponding to an RDA fragment (Table S1 and Figure S7). These dehydrodicatechins of ε-configuration formed by (+)-catechin units exhibited higher Rts in relation to the Rt of the N2 standard, as reported earlier [11,15]. Finally, the N3 and N6 compound showed similar mobility values indicating that they have similar molecular shapes.…”

Section: Analysis Of Dehydrodicatechin Reference Compoundssupporting

confidence: 78%

“…However, the spots of greater and lower mobility may not be detected in a less concentrated sample. In addition, the N1a peak showed a Rt close to procyanidin B3 (Rt = 5.3 min), as already reported for a dehydrodicatechin B [10,15]. Guyot and coworkers suggested that their dehydrodicatechin fraction coeluted with procyanidin B3 corresponded to a mixture of dehydrodicatechin of β-configuration based on (+)-catechin from the NMR, MS, and MS/MS spectra.…”

Section: Analysis Of Dehydrodicatechin Reference Compoundssupporting

confidence: 75%

“…Moreover, the [M − H] − ions of these spots may correspond to isomers or protomers as discussed for N1a and N1b peaks. Deshaies and co-workers [15] observed two peaks for the N1 fraction. They used a different column and chromatographic method which may explain why in the present work we found three peaks for this fraction.…”

Section: Analysis Of Dehydrodicatechin Reference Compoundsmentioning

confidence: 93%

“…(a-c,e,f) correspond to N2, N4, N8, N3, and N6 standards, respectively, that were used in the present work. Adapted from Deshaies and co-workers [15] and Verloop and co-workers [14].…”

Section: Introductionmentioning

confidence: 99%

“…Dehydrodicatechins have been analyzed by LC-MS/MS in different matrices such as black tea [14], green tea [4], beer [16], processed cocoa powders [17], and in wines and grape seed extracts [15]. This last work identified one dehydrodicatechin B and two dehydrodicatechins A, all derived from (+)-catechin and at low concentrations.…”

Section: Introductionmentioning

confidence: 99%

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Improved Analysis of Isomeric Polyphenol Dimers Using the 4th Dimension of Trapped Ion Mobility Spectrometry—Mass Spectrometry

et al. 2022

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Dehydrodicatechins resulting from (epi)catechin oxidation have been investigated in different foods and natural products, but they still offer some analytical challenges. The purpose of this research is to develop a method using ultra-high performance liquid chromatography coupled with trapped ion mobility spectrometry and tandem mass spectrometry (UHPLC−ESI−TIMS−QTOF−MS/MS) to improve the characterization of dehydrodicatechins from model solutions (oxidation dimers of (+)-catechin and/or (−)-epicatechin). Approximately 30 dehydrodicatechins were detected in the model solutions, including dehydrodicatechins B with β and ε-interflavanic configurations and dehydrodicatechins A with γ-configuration. A total of 11 dehydrodicatechins B, based on (−)-epicatechin, (+)-catechin, or both, were tentatively identified in a grape seed extract. All of them were of β-configuration, except for one compound that was of ε-configuration. TIMS allowed the mobility separation of chromatographically coeluted isomers including dehydrodicatechins and procyanidins with similar MS/MS fragmentation patterns that would hardly be distinguished by LC-MS/MS alone, which demonstrates the superiority of TIMS added to LC-MS/MS for these kinds of compounds. To the best of our knowledge, this is the first time that ion mobility spectrometry (IMS) was applied to the analysis of dehydrodicatechins. This method can be adapted for other natural products.

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Section: Analysis Of Dehydrodicatechin Reference Compoundssupporting

confidence: 78%

Section: Analysis Of Dehydrodicatechin Reference Compoundssupporting

confidence: 75%

Section: Analysis Of Dehydrodicatechin Reference Compoundsmentioning

confidence: 93%

“…(a-c,e,f) correspond to N2, N4, N8, N3, and N6 standards, respectively, that were used in the present work. Adapted from Deshaies and co-workers [15] and Verloop and co-workers [14].…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Improved Analysis of Isomeric Polyphenol Dimers Using the 4th Dimension of Trapped Ion Mobility Spectrometry—Mass Spectrometry

et al. 2022

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Comprehensive profiling of chemical composition of Gleditsiae spina using ultra‐high‐performance liquid chromatography coupled with electrospray ionization quadrupole time‐of‐flight mass spectrometry

Bai

Jing

Yang

et al. 2023

Rapid Comm Mass Spectrometry

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RationaleGleditsiae spina (GS) is an important herb used in traditional and folk medicinal systems of East Asian countries for its various medicinal properties. In China, it has been traditionally used through the centuries for its anticancer, detoxication, detumescence, apocenosis, and antiparasitic effects. Although some of its ingredients have been isolated and identified, most active constituents remain unknown. Past research mostly exploited nuclear magnetic resonance for the identification of compounds, which is suitable for monomers only. Moreover, the extraction and isolation procedures for obtaining purified molecules are time consuming. Therefore, establishing an efficient approach will assist in rapid discovery of the potential active ingredients of GS. The present study aimed to identify the chemical constituents in GS by a data analysis strategy using ultra‐high‐performance liquid chromatography combined with quadrupole time‐of‐flight tandem mass spectrometry.MethodsFirst, the theoretical formula of the candidate compound was calculated using the accurate mass of the precursor/adduct ions. Second, the compounds were classified by the diagnostic ions from the MS/MS data. Third, characteristic ion filtering was used to identify the structures. Finally, the diverse skeletons and substitutions were further identified through the neutral loss in the GS.ResultsA total of 277 compounds were identified in GS, comprising 169 flavonoids, 70 lignans, and 38 other compounds. At least 43 potential new compounds were represented.ConclusionsThis experiment devised an efficient and systematic method for detecting complex compounds and provided a foundation for future research into bioactive ingredients and quality control of GS.

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Oxidative Assemblies of Flavonoids Dimers – Synthesis of Dehydrodicatechin A

2023

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Catechin and quercetin were subjected to different oxidative conditions. Reagents such as silver oxide, potassium ferricyanide or PIDA (phenyliodine diacetate), as well as electrochemical and photocatalytic conditions were evaluated. From quercetin, the formation of a dimer resulting from an oxa‐Diels‐Alder has been systematically observed. From catechin, dehydrodicatechin A was obtained by the action of silver oxide in a toluene/acetone mixture. Complementary experiments in the presence of catechol gave information on the mechanisms of formation. Products resulting from these reactions have already been identified in plants and beverages made from plants and are supposed to result from the oxidation of flavonoids. This reactivity exploration provides a better understanding of the role of catechols in the formation of natural compounds arising from the dimerization of flavonoids during oxidative process. These results shed some light on the intrinsic reactivity of catechin and quercetin.

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UHPLC-Q-Orbitrap /MS2 identification of (+)-Catechin oxidation reaction dimeric products in red wines and grape seed extracts

Cited by 9 publications

References 37 publications

Improved Analysis of Isomeric Polyphenol Dimers Using the 4th Dimension of Trapped Ion Mobility Spectrometry—Mass Spectrometry

Improved Analysis of Isomeric Polyphenol Dimers Using the 4th Dimension of Trapped Ion Mobility Spectrometry—Mass Spectrometry

Comprehensive profiling of chemical composition of Gleditsiae spina using ultra‐high‐performance liquid chromatography coupled with electrospray ionization quadrupole time‐of‐flight mass spectrometry

Oxidative Assemblies of Flavonoids Dimers – Synthesis of Dehydrodicatechin A

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