A modified data filtering strategy for targeted characterization of polymers in complex matrixes using drift tube ion mobility-mass spectrometry: Application to analysis of procyanidins in the grape seed extracts

Li, Meng-Ning; Wang, Huiying; Rui, Wen; Li, Chaoran; Shen, Bingqing; Gao, Wen; Li, Ping; Yang, Hua

doi:10.1016/j.foodchem.2020.126693

Cited by 15 publications

(7 citation statements)

References 38 publications

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“…The (+)-catechin/(−)-epicatechin model produced, as expected, additional chromatographic peaks (peaks [25][26][27][28][29][30][31][32][33][34][35] and spots in the heat map (Figures 6 and 7) likely derived from both (+)-catechin and (−)-epicatechin. S2.…”

Section: Oxidation Dimers Of a Mixture Of (+)-Catechin And (−)-Epicat...supporting

confidence: 71%

“…These last two compounds are often (partly) coeluted in chromatography [19] and could not be distinguished on the basis of LC-MS/MS data alone in the present study. Li and co-workers [28] reported a slight mobility separation of these compounds with Rt of 12.3 min and drift time of 26.05 milliseconds for procyanidin B1, and 13 min and 25.79 milliseconds for procyanidin B3. Guyot and co-workers and Sun and co-workers [10,19] also described a chromatographic coelution of procyanidin B3 with a dehydrodicatechin B derived from (+)-catechin.…”

Section: Analysis Of Grape Seed Extractsmentioning

confidence: 95%

“…Trapped ion mobility spectrometry (TIMS), that separates ions by holding them using an electric field against a moving gas [22], has shown in many cases a greater resolving power compared with other IMS approaches [23]. IMS has been applied to polyphenols of different matrices such as herbal liqueurs, berries, and several natural products [20,[24][25][26] including the separation of black tea isomeric theasinensins which are oxidation products from pyrogallol-type flavan-3-ols, with structures similar to dehydrodicatechins [27] and to grape seed extract procyanidins [28]. However, to the best of our knowledge, no study has been published on the application of IMS to dehydrodicatechins.…”

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: Oxidation Dimers Of a Mixture Of (+)-Catechin And (−)-Epicat...supporting

confidence: 71%

Section: Analysis Of Grape Seed Extractsmentioning

confidence: 95%

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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“…Incorporating CCS values into the traditional MS-based compound identification workflow helps increase metabolite identification confidence. Many studies have created in-house CCS databases to increase the metabolite identification accuracy as well as coverage in biological samples. ,, Currently, publicly available CCS databases cover a wide range of compound classes, such as plant metabolites, , pesticides, , polymers, and pharmaceuticals . To facilitate the integration of CCS measurement into the conventional MS-based metabolomics workflows, metabolomics communities have made efforts to create open-access experimental CCS databases, such as the Unified CCS Compendium, AllCCS, CCSbase, and Pacific Northwest National Laboratory, and to develop CCS prediction models. ,,, Similar to the role of public MS databases, the growing CCS databases will lend support to large-scale metabolite identification.…”

Section: Introductionmentioning

confidence: 99%

Traveling Wave Ion Mobility-Derived Collision Cross Section Database for Plant Specialized Metabolites: An Application to Ventilago harmandiana Pierre

et al. 2022

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The combination of ion mobility mass spectrometry (IM-MS) and chromatography is a valuable tool for identifying compounds in natural products. In this study, using an ultra-performance liquid chromatography system coupled to a high-resolution quadrupole/traveling wave ion mobility spectrometry/time-of-flight MS (UPLC-TWIMS-QTOF), we have established and validated a comprehensive TWCCSN2 and MS database for 112 plant specialized metabolites. The database included 15 compounds that were isolated and purified in-house and are not commercially available. We obtained accurate m/z, retention times, fragment ions, and TWIMS-derived CCS (TWCCSN2) values for 207 adducts (ESI+ and ESI–). The database included novel 158 TWCCSN2 values from 79 specialized metabolites. In the presence of plant matrix, the CCS measurement was reproducible and robust. Finally, we demonstrated the application of the database to extend the metabolite coverage of Ventilago harmandiana Pierre. In addition to pyranonaphthoquinones, a group of known specialized metabolites in V. harmandiana, we identified flavonoids, xanthone, naphthofuran, and protocatechuic acid for the first time through targeted analysis. Interestingly, further investigation using IM-MS of unknown features suggested the presence of organonitrogen compounds and lipid and lipid-like molecules, which is also reported for the first time. Data are available on the MassIVE (, data set identifier MSV000090213).

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“…In general, procyanidins are analyzed by reverse (RP) and/or normal phase high pressure liquid chromatography (HPLC) or ultra-high pressure chromatography (UPLC), or two-dimensional HPLC, coupled to photodiode array (PAD) and different kinds of mass spectrometry (MS) detectors, but only some procyanidins have been separated (up to heptamers) and quantified (up to tetramers) in this way [ 25 , 26 , 27 ]. It is only recently when the development of some multi-model regression tools for computational analysis of wide range of analytical parameters acquired by UPLC coupled to adrift tube ion mobility MS detector were capable to discriminate among co-eluting procyanidin ions and allowed Li et al [ 28 ] to do an important leapfrogging by the simultaneous characterization of up to 686 procyanidins with degree of polymerization of up to 15. Nevertheless, it should be highlighted that these results should be taken with precaution, as their identification is only tentative.…”

Section: Introductionmentioning

confidence: 99%

Procyanidin-Rich Extract from Grape Seeds as a Putative Tool against Helicobacter pylori

Silván

Gutiérrez-Docio

Moreno-Fernández

et al. 2020

Foods

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Strains of Helicobacter pylori (H. pylori) resistant to various antibiotics have increased in recent years. In this context, the search for new therapeutic approaches is crucial. The aim of the present study was to demonstrate the antibacterial activity of a procyanidin-rich extract obtained from food-grade winery grape seeds against 14 H. pylori strains and elucidate its phenolic composition. Ten strains (71.4%) showed resistance to at least some of the tested antibiotics, while four isolates (28.6%) were susceptible to all antibiotics. Resistance to more than one class of antibiotics was observed in six strains (42.9%). The extract was able to inhibit the growth of all H. pylori strains in a range of a minimum inhibitory concentration (MIC) from 0.015 mg/mL to 0.125 mg/mL, confirming also the existence of a strain-dependent effect. The phenolic composition determined by reverse phase high pressure liquid chromatography, photodiode array, and mass spectrometry detection (RP-HPLC-PAD-MS) analysis revealed the presence of 43 individual compounds and allowed the quantification of 41 of them, including seven procyanidin tetramers, seven procyanidin pentamers, and six galloylated procyanidin dimers, trimers, and tetramers. The extract was composed mainly by catechin and procyanidin oligomers with a total amount of 5,801 mg/100 g, which represent 92% of the total individual phenolic content. Among them, the most abundant were catechins (2,047 mg/100 g), followed by procyanidin dimers (1,550 mg/100 g), trimers (1,176 mg/100 g), tetramers (436 mg/100 g), and pentamers (296 mg/100 g) that represent 35, 27, 20, 8, and 5%, respectively of the total flavanol constituents. The composition profile information may help to improve the production process of useful antibacterial extracts against H. pylori.

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A modified data filtering strategy for targeted characterization of polymers in complex matrixes using drift tube ion mobility-mass spectrometry: Application to analysis of procyanidins in the grape seed extracts

Cited by 15 publications

References 38 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

Traveling Wave Ion Mobility-Derived Collision Cross Section Database for Plant Specialized Metabolites: An Application to Ventilago harmandiana Pierre

Procyanidin-Rich Extract from Grape Seeds as a Putative Tool against Helicobacter pylori

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