Evaluation of different detection modes for the analysis of procyanidins in leaves and flowers of Crataegus spp. Part II. Liquid chromatography-mass spectrometry

Rohr, Gabriela E.; Riggio, Gaetano; Meier, Beat H.; Sticher, Otto

doi:10.1002/(sici)1099-1565(200003/04)11:2<113::aid-pca495>3.0.co;2-z

Cited by 21 publications

(11 citation statements)

References 18 publications

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“…Two trimeric proanthocyanidins were characterized by mass spectrometry, 1 H, -152-138] Ð ) by the cleavage of a monomeric catechin/epi-catechin and the retroDiels-Alder reaction of this monomer to 4-(2-hydroxyethenyl)-1,2-benzenediol and 2,4,6-trihydroxybenzylium ion, respectively (Rohr et al, 2000;Hayasaka et al, 2003). By detailed NMR experiments via 1D-( 1 H, 13 C-ATP) und 2D-NMR (ge-DQF-COSY, ge-HSQC, ge-HMBC, NOESY) (see Table I) and comparison with published data aesculitannin B [epicatechin-(2 5O57, 4 58)-ent-chatechin-(4 58)-epichatechin] and cinnamtannin B-1 [epicatechin-(2 5O57, 4 58)-epichatechin-(4 58)-epichatechin] were identified (Kamiya et al, 2001) (see Fig.…”

Section: Resultsmentioning

confidence: 99%

Chemical and Pharmacological Investigations of Metaxya rostrata

Virtbauer

Krenn

Kählig

et al. 2008

Zeitschrift Für Naturforschung C

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In a bioassay-guided approach the chemical composition of rhizomes of Metaxya rostrata (Kunth C. Presl) was studied for the first time. Investigations of the cytotoxicity of extracts and fractions on SW480 colorectal carcinoma cells resulted in the isolation of two polyphenols Ð cinnamtannin B-1 and aesculitannin B. The structures of the compounds were elucidated by different NMR experiments. Additionally, sugars, common sterols, such as sitosterol, stigmasterol and campesterol, as well as chlorogenic acid and caffeic acid were identified in Metaxya rostrata.

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Section: Resultsmentioning

confidence: 99%

Chemical and Pharmacological Investigations of Metaxya rostrata

Virtbauer

Krenn

Kählig

et al. 2008

Zeitschrift Für Naturforschung C

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“…The B6 and B7 identification was supported in their elution characteristics. The fragmentation profile of these dimers shows an unusual ion at m/z 287, which might be the result of an oxidation reaction that produces another quinone structure (Rohr et al, 2000). Trimers and tetramers were also found in Agrimonia eupatoria L. ethyl acetate fraction, although the absence of standards and the lack of information relating to the order of elution only allowed the identity of compounds 5, 7 and 14 to be suggested as the procyanidin trimers catechin-(4→8)-catechin-(4→8)-catechin (C2), epicatechin-(4→8)-epicatechin-(4→8)-catechin (EEC) and epicatechin-(4→8)-epicatechin-(4→8)-epicatechin (C1), respectively.…”

Section: Phytochemical Characterizationmentioning

confidence: 99%

Polyphenolic profile characterization ofAgrimonia eupatoria L. by HPLC with different detection devices

Correia

González-Paramás

Amaral

et al. 2005

Biomed. Chromatogr.

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Liquid chromatography coupled to diode array and electrospray ionization mass spectrometry detection was used to establish the polyphenolic profile of an ethyl acetate fraction from Agrimonia eupatoria L. aqueous-alcoholic extract. Additionally, an HPLC technique with post-column derivatization by p-dimethylaminocinnamaldehyde was employed for the selective detection and quantification of flavan-3-ols. Important information was obtained by combining the data of these two HPLC techniques. Flavan-3-ols (catechin and procyanidins B1, B2, B3, B6, B7, C1, C2 and epicatechin-epicatechin-catechin), quercetin 3-O-glucoside, quercetin 3-O-galactoside, kaempferol 3-O-glucoside, kaempferol 3-O-(6''-O-p-coumaroyl)-glucoside, apigenin 6-C-glucoside and various phenolic acids were identified. Antioxidant activity of the Agrimonia eupatoria L. fraction containing these compounds was assessed through the 1,1-diphenyl-2-picrylhydrazyl, trolox equivalent antioxidant capacity and thiobarbituric acid reactive substances methods. Significant activity was observed for this fraction, where compounds with recognized antiinflammatory properties such as procyanidins, kaempferol 3-O-(6''-O-p-coumaroyl)-glucoside and quercetin glycosides were identified for the first time. These results are predictive of the beneficial effects of this fraction, or some of its compounds, in human health, as possible anti-inflammatory drug.

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“…This is different from the pattern observed for the cacao tannin; therefore, the structure of the two trimers must be significantly different. The same fragmentation pathway was observed in ESI‐MS and was shown to be to a Retro‐Diels Alder fission tending to remove the B ring from the oligomer chain 24, 25. The RDA fission of the m/z 857 ion forms the fragment at m/z 706, which then looses a water molecule from the C3/C4 of the heterocycle to form the fragment ion at m/z 688.…”

Section: Resultsmentioning

confidence: 57%

“…This fragment ion is the lowest mass ion formed and no smaller fragments are observed. There are various mechanisms that have been suggested to occur during CID 14, 25, 26. In a Retro‐Diels‐Alder (RDA) fission fragments with masses of 152 or 138 Da can be formed as has been documented for ESI with atmospheric pressure chemical ionization.…”

Section: Resultsmentioning

confidence: 99%

Microstructure elucidation of polyflavonoid tannins by MALDI‐TOF‐CID

Radebe

Rode

Pizzi

et al. 2012

J of Applied Polymer Sci

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High molar mass wood tannin extracts are complex mixtures that are distributed in both molar mass and chemical composition. Condensed tannins from quebracho and mimosa woods were analyzed and compared with cacao tannins using matrix-assisted laser desorption/ionization-time of flight (MALDI-TOF) mass spectrometry. Although MALDI-TOF MS reveals the oligomer structure of the tannins, this method cannot distinguish between isomers with isobaric masses, and therefore, ambiguous structural assignments were made in a number of cases. To determine the actual microstructures present, MALDI-TOF collision-induced dissociation (CID) experiments were conducted. MALDI-TOF-CID enables monomer sequence determination, and positive assignments of isobaric structures can be made

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Evaluation of different detection modes for the analysis of procyanidins in leaves and flowers of Crataegus spp. Part II. Liquid chromatography-mass spectrometry

Cited by 21 publications

References 18 publications

Chemical and Pharmacological Investigations of Metaxya rostrata

Chemical and Pharmacological Investigations of Metaxya rostrata

Polyphenolic profile characterization ofAgrimonia eupatoria L. by HPLC with different detection devices

Microstructure elucidation of polyflavonoid tannins by MALDI‐TOF‐CID

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