Investigation of proanthocyanidins by HPLC with electrospray ionization mass spectrometry

Friedrich, Wolfgang; Eberhardt, A.; Galensa, Rudolf

doi:10.1007/s002170050589

Cited by 195 publications

(195 citation statements)

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“…Peaks St1 Friedrich, Eberhardt, and Galensa (2000) for the fragmentation of proanthocyanidin dimers and also observed by Salas et al (2004) for F-A + adducts found in red wines, the loss of a C 6 H 6 O 3 fragment is characteristic of the upper flavanol unit. Furthermore, the loss of 288 amu is expected when (epi)catechin constitutes the upper unit (but À290 amu when it is the terminal one).…”

Section: Resultsmentioning

confidence: 64%

Flavanol–anthocyanin condensed pigments in plant extracts

et al. 2006

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Pigments resulting from the direct condensation of anthocyanins and flavanols are usually associated with reactions taking place during processing and storage of plant-derived foods and beverages and have been particularly studied in aged red wines. In this paper, small amounts of flavanol-anthocyanin condensed pigments are found in different plant extracts. Structures are suggested for 10 such condensed pigments detected in extracts of strawberry, runner beans, purple corn and grape skins, based on their MS n fragmentation patterns, following analyses by electrospray tandem mass spectrometry. All of them correspond to dimers containing a flavan-3-ol [either (epi)afzelechin, (epi)catechin or (epi)gallocatechin] as the upper unit carbon-carbon linked to a lower anthocyanin unit consisting of different delphinidin, cyanidin, pelargonidin, peonidin or malvidin derivatives. The detection of these pigments in plant extracts may suggest that they are natural pigments and not products exclusively formed during storage and ageing of processed foods and beverages, as was previously assumed.

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Section: Resultsmentioning

confidence: 64%

Flavanol–anthocyanin condensed pigments in plant extracts

et al. 2006

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“…Additional structural information was obtained by CID-MS-MS experiments. For identification and characterization of PAs, four main fragmentation mechanisms were observed: the retro-Diels-Alder (RDA), quinone methide (QM), heterocyclic ring fission (HFR) and the benzofuranforming (BFF) mechanisms [22,37,38].…”

Section: Fia-esi-it-ms N Analysismentioning

confidence: 99%

“…Precursor ions at m/z 577, 593 and 609, corresponding to catechin dimers, were attributed to (epi)catechin-(epi)catechin (8)(9)(10)(11) [19], (epi)catechin-(epi)gallocatechin (12)(13)(14) and (epi)gallocatechin-(epi)gallocatechin (15)(16) [37], respectively.…”

Section: Fia-esi-it-ms N Analysismentioning

confidence: 99%

Characterization of Proanthocyanidins from Parkia biglobosa (Jacq.) G. Don. (Fabaceae) by Flow Injection Analysis — Electrospray Ionization Ion Trap Tandem Mass Spectrometry and Liquid Chromatography/Electrospray Ionization Mass Spectrometry

et al. 2013

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Abstract:The present study investigates the chemical composition of the African plant Parkia biglobosa (Fabaceae) roots and barks by Liquid Chromatography -Electrospray Ionization and Direct Injection Tandem Mass Spectrometry analysis. Mass spectral data indicated that B-type oligomers are present, namely procyanidins and prodelphinidins, with their gallate and glucuronide derivatives, some of them in different isomeric forms. The analysis evidenced the presence of up to 40 proanthocyanidins, some of which are reported for the first time. In this study, the antiradical activity of extracts of roots and barks from Parkia biglobosa was evaluated using DPPH method and they showed satisfactory activities.

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“…The phenolic compounds were detected in their deprotonated form as the quasimolecular ion [M-H] -one mass unit below their molecular mass. Identification of individual compounds was conducted by comparison of their UV-spectra and ion trap fragmentation patterns with a self prepared library from standard substances and known compounds as described in detail previously [33][34][35].…”

Section: Hplc-ms Analysismentioning

confidence: 99%

(-)-Catechin in Cocoa and Chocolate: Occurence and Analysis of an Atypical Flavan-3-ol Enantiomer

2007

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Cocoa contains high levels of different flavonoids. In the present study, the enantioseparation of catechin and epicatechin in cocoa and cocoa products by chiral capillary electrophoresis (CCE) was performed. A baseline separation of the catechin and epicatechin enantiomers was achieved by using 0.1 mol·L −1 borate buffer (pH 8.5) with 12 mmol·L -1 (2-hydroxypropyl)-γ-cyclodextrin as chiral selector, a fused-silica capillary with 50 cm effective length (75 μm I.D.), +18 kV applied voltage, a temperature of 20 °C and direct UV detection at 280 nm. To avoid comigration or coelution of other similar substances, the flavan-3-ols were isolated and purified using polyamide-solid-phaseextraction and LC-MS analysis. As expected, we found (-)-epicatechin and (+)-catechin in unfermented, dried, unroasted cocoa beans. In contrast, roasted cocoa beans and cocoa products additionally contained the atypical flavan-3-ol (-)-catechin. This is generally formed during the manufacturing process by an epimerization which converts (-)-epicatechin to its epimer (-)-catechin. High temperatures during the cocoa bean roasting process and particularly the alkalization of the cocoa powder are the main factors inducing the epimerization reaction. In addition to the analysis of cocoa and cocoa products, peak ratios were calculated for a better differentiation of the cocoa products.

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Investigation of proanthocyanidins by HPLC with electrospray ionization mass spectrometry

Cited by 195 publications

References 0 publications

Flavanol–anthocyanin condensed pigments in plant extracts

Flavanol–anthocyanin condensed pigments in plant extracts

Characterization of Proanthocyanidins from Parkia biglobosa (Jacq.) G. Don. (Fabaceae) by Flow Injection Analysis — Electrospray Ionization Ion Trap Tandem Mass Spectrometry and Liquid Chromatography/Electrospray Ionization Mass Spectrometry

(-)-Catechin in Cocoa and Chocolate: Occurence and Analysis of an Atypical Flavan-3-ol Enantiomer

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