Analysis of commercial proanthocyanidins. Part 2: An electrospray mass spectrometry investigation into the chemical composition of sulfited quebracho (Schinopsis lorentzii and Schinopsis balansae) heartwood extract

Venter, Pieter; Senekal, Nadine D.; Amra-Jordaan, Maryam; Bonnet, Susan L.; Westhuizen, Jan H. van der

doi:10.1016/j.phytochem.2012.01.027

Cited by 23 publications

(17 citation statements)

References 32 publications

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“…As published before [38] for proanthocyanidin A5′ isolated from a commercial Ephedra plant, the upper unit has to be (+)-epigallocatechin, because the optical rotation is negative. The NMR data were compared with the literature [38][39][40][41][42] The three isolated extension units were confirmed with the LC-MS/MS experiments and are in accordance with the literature [17,21,46,47]. The purity of the compounds was determined by HPLC-DAD at UV 280 nm and found to be 96.0 % in the case of (−)-epigallocatechin-4β-benzylthioether (4b) and the mixture of (+)-epigallocatechin-(4 → 6″; 2 → O → 7″) -(epi)gallocatechin-4benzylthioether stereoisomers (5a, 5b, and 5c), and 94.4 % in the case of (−)-epicatechin-4β-benzylthioether (6b).…”

Section: Preparation and Purification Of Reference Compounds For Quantificationsupporting

confidence: 76%

Characterization of the XIAP-Inhibiting Proanthocyanidin Fraction of the Aerial Parts of Ephedra sinica

et al. 2016

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The X-linked inhibitor of apoptosis protein is a cellular protein that inhibits the activity of mammalian caspases and promotes resistance to apoptosis. The ethanol extract of the aerial parts of Ephedra sinica has been identified to possess inhibitory activity of the X-linked inhibitor of apoptosis protein by an in vitro fluorescence polarization assay using the BIR3 domain of the X-linked inhibitor of apoptosis protein. Bioactivity-guided fractionation identified proanthocyanidin-enriched fractions as the active principles. The most active fraction showed an IC50 value of 27.3??g/mL (CI95: 25.9?28.9??g/mL) corresponding to 9.6??M (CI95: 9.1?10.1??M) calculated by the use of the determined average molecular weight of 2853.5. Samples were analyzed by a thiolytic degradation/HPLC-MS assay, UHPLC-HRMS, and 1D NMR. The thiolytic degradation/HPLC-MS assay revealed a mean degree of polymerization of 9.5???0.2 units (calculated average MW 2853.5) for the active fraction and 11.4???0.6 units (calculated average MW 3437.0) for the most related inactive fraction. Chemical characterization identified (epi)gallocatechin (76.6???1.0?% active; 80.7???2.7?% inactive sample) and (epi)catechin units as building blocks. Interestingly, the investigated proanthocyanidins turned out to be a complex mixture of double linked A-type (binding 2-O-7?, 4?6?) and single linked B-type units. This study identified oligomeric proanthocyanidins as active principles of E. sinica in vitro by a fluorescence polarization assay and via protein fragment complementation analysis.

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Section: Preparation and Purification Of Reference Compounds For Quantificationsupporting

confidence: 76%

Characterization of the XIAP-Inhibiting Proanthocyanidin Fraction of the Aerial Parts of Ephedra sinica

et al. 2016

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“…A poor chromatographic separation on a silica-bonded stationary phase is a common feature of proanthocyanidins, due to the similarity in their structures and to the large number of phenolic groups giving similar interactions with the stationary phase [ 30 , 31 ]. Thus, it is not surprising that largely overlapped peaks are observed between 28 and 36 min.…”

Section: Resultsmentioning

confidence: 99%

“…The corresponding polyphenols generated [M − H] − signals at m / z 643 and 915, which were tentatively assigned to two sulfited oligomers, namely a dimer ( 8 ) and a trimer ( 10 ). The presence of sulfited oligomers in commercial tannins is due to industrial treatment, with sodium hydrogen sulfite applied to reduce viscosity and increase tannins solubility in water; the sulfites are formed via cleavage of the pyran ring and the introduction of a C-2 sulfonic acid moiety [ 31 ]. The fragmentation patterns ( Figure S5 of Supplementary Material ) of 8 and 10 encompass signals at M-H-82 ( m / z 561 and 833, respectively), corresponding to the loss of HSO 3 - occurring at C-2 position; signals at m/z 409 and 681 originated from rDA fragmentation of the m / z 561 and 833, respectively; signals at M-H-354 ( m / z 289 and 561, respectively), corresponding to the loss of a unit of monosulfited fisetinidol.…”

Section: Resultsmentioning

confidence: 99%

“…The corresponding polyphenols generated [M − H] − signals at m/z 643 and 915, which were tentatively assigned to two sulfited oligomers, namely a dimer (8) and a trimer (10). The presence of sulfited oligomers in commercial tannins is due to industrial treatment, with sodium hydrogen sulfite applied to reduce viscosity and increase tannins solubility in water; the sulfites are formed via cleavage of the pyran ring and the introduction of a C-2 sulfonic acid moiety [31]. The fragmentation patterns (Figure S5 The MS data interpretation of fraction A-2 highlighted the presence of 1, whose identification was also supported by the HPLC-UV profile (Figure S1 of Supplementary Material).…”

Section: Mass Spectrometric and 1 H-nmr Analysis Of A-1-a-9 Fractionsmentioning

confidence: 99%

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Mass Spectrometry and 1H-NMR Study of Schinopsis lorentzii (Quebracho) Tannins as a Source of Hypoglycemic and Antioxidant Principles

et al. 2020

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The ethyl acetate extract of the commercial tannin Tan’Activ QS-SOL (from Schinopsis lorentzii wood), employed for the production of red wine, was subjected to chromatography on Sephadex LH-20, providing nine fractions (A-1–A-9), which were estimated for total phenols content (GAE), antioxidant activity (DPPH, ORAC), and hypoglycemic activity (α-glucosidase and α-amylase inhibition). All the fractions were analyzed by means of HPLC/ESI-MS/MS and 1H-NMR to identify the principal active constituents. Fractions A-1 and A-3 showed the highest antioxidant activity and gallic acid (1), pyrogallol (3), eriodictyol (6), catechin (12), and taxifolin (30) were identified as the major constituents. The highest α-glucosidase and α-amylase inhibitory activity was observed in fractions A-7–A-9 containing condensed (9′, 15, 18, 19, 23, and 27) hydrolysable tannins (13 and 32) as well as esters of quinic acid with different units of gallic acid (5, 11, 11′, 14, and 22). This last class of gallic acid esters are here reported for the first time as α-glucosidase and α-amylase inhibitors.

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“…A research (Venter, Senekal, Amra-Jordaan, Bonnet, & Van Der Westhuizen, 2012) shows that (+) catechin derived has as ion fragment of 139 m/z which is fragmentation result of Retro Diels Alder (RDA). Enzyme modelling evaluation performed to know whether isomaltase α-glucosidase is good or not.…”

Section: Resultsmentioning

confidence: 99%

α-Glucosidase Inhibition Activity of Stem Bark Ceiba pentandra Linn. In Vitro and In Silico

Syihabudin

2018

Indonesian J. Pharm.

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Bark of Kapok (Ceiba pentandra (L.)) contains tannin, flavonoid, alkaloid, terpenoid, and saponin compounds. Flavonoid known to have inhibitory activity of α-glucosidase. The purpose of this study was to observe the n-hexane, ethyl acetate and water extract of bark of Ceiba pentandra (L.) to inhibitory activity of αglucosidase. The method used for the activity measurement of the fractions was spectrophotometry UV-Vis. Water fraction analyzed by LCMS/MS to identify the chemical compounds. The pure compound suspected analyzed using molecular docking to predict the complementarity related to the model of isomaltase αglucosidase using Autodock Vina, therefore the bond of the antidiabetic active compounds can be predicted. The results show the α-glucosidase inhibitory activity of the bark in n-hexane fraction is 4.60μg/mL, ethyl acetate fraction is 8.55μg/mL and water fraction is 5.61μg/mL. Water fraction analyzed by LCMS/MS eludated at retention time of 3.61min be fathomed as (+) catechin derivate and at retention time of 8.70min be fathomed as vavain derivate. The vavain derived compound, (+) catechin derived compound, acarbose and quercetin each shows docking score of -8.1; -8.8; -6.2 and -7.6 kkal/mol and have similarity to amino acid Glu276 bond which is a catalytic residue that plays role in hydrolysis process. The similarity of chemical bond of the active site be expected to have the same activity as α-glucosidase inhibitory agent.

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Analysis of commercial proanthocyanidins. Part 2: An electrospray mass spectrometry investigation into the chemical composition of sulfited quebracho (Schinopsis lorentzii and Schinopsis balansae) heartwood extract

Cited by 23 publications

References 32 publications

Characterization of the XIAP-Inhibiting Proanthocyanidin Fraction of the Aerial Parts of Ephedra sinica

Characterization of the XIAP-Inhibiting Proanthocyanidin Fraction of the Aerial Parts of Ephedra sinica

Mass Spectrometry and 1H-NMR Study of Schinopsis lorentzii (Quebracho) Tannins as a Source of Hypoglycemic and Antioxidant Principles

α-Glucosidase Inhibition Activity of Stem Bark Ceiba pentandra Linn. In Vitro and In Silico

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