Analysis of Oligomeric and Polymeric Tannins of Grape Berries by Liquid Chromatography/Electrospray Ionization Multiple-Stage Tandem Mass Spectrometry

Perret, Camille; Tabacchi, Raffaele; Pezet, R.

doi:10.1255/ejms.452

Cited by 10 publications

(4 citation statements)

References 32 publications

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“…Results are in good agreement with that reported by Pezet et al. ( 2001 ). All three compounds were also confirmed by 1 H and 13 C NMR (Lobô et al.…”

Section: Resultssupporting

confidence: 93%

Gastroprotective activity of the resin from Virola oleifera

Pereira

Lenz

Nogueira

et al. 2016

Pharmaceutical Biology

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Context: The resin from the trunk wood of Virola oleifera (Schott) A. C. Smith (Myristicaceae) is used in folk medicine to hasten wound repair and to treat pain and inflammatory conditions, and our previous report indicated the anti-oxidative properties in other oxidative stress model.Objective: To investigate the protective effects of resin from V. oleifera in two experimental models of gastric ulcer oxidative-stress dependent.Materials and methods: Plant material was collected and the resin was subjected to partitioning with organic solvents. The buthanol fraction was subjected to chromatographic and spectrometric methods for isolation and structural elucidation. The resin was quantified for polyphenols and flavonoids by colorimetric methods. Furthermore, the antioxidant activity of resin was determined by three different methods. The ulcers were induced acutely in Swiss male mice with ethanol/HCl and indomethacin using single-doses of 10 and 100 mg/kg. The gastroprotection of the experimental groups was comparable to reference control lansoprazole (3 mg/kg).Results: The high content of polyphenols (∼82%) and the presence of epicatechin and eriodictyol were determined. The LD50 was estimated at 2500 mg/kg. At minimum (10 mg/kg) and maximum (100 mg/kg) dosage of resin, both in ethanol/HCl as indomethacin ulcer induction models demonstrate reduction of lesions (minimum: ∼97% and ∼66%; maximum: ∼95% and ∼59%).Discussion: The gastroprotection might be related to tannins, phenolic acids and flavonoids present in the resin by antioxidant properties.Conclusions: The results indicate that this resin has gastroprotective activity probably associated with the presence of phenolic antioxidant substances.

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“…Results are in good agreement with that reported by Pezet et al. ( 2001 ). All three compounds were also confirmed by 1 H and 13 C NMR (Lobô et al.…”

Section: Resultssupporting

confidence: 93%

Gastroprotective activity of the resin from Virola oleifera

Pereira

Lenz

Nogueira

et al. 2016

Pharmaceutical Biology

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“…The MS2 experiment yields predominant ions at m/z 577 (DP2) and m/z 575, (quinone methide, QM) and other less abundant ions at m/z 821 (C‐ring (HO)C3 = C4 elimination, ACE), at m/z 739 (heterocyclic ring fission, HRF), and at m/z 713 (retro Diels–Alder fission, RDA). This agrees with the well‐known fragmentation pattern of the C 15 unit reported for related polyphenols …”

Section: Resultssupporting

confidence: 92%

Substitution pattern elucidation of hydroxypropyl Pinus pinaster (Ait.) bark polyflavonoid derivatives by ESI(−)‐MS/MS

et al. 2014

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The structure of condensed tannins (CTs) from Pinus pinaster bark extract and their hydroxypropylated derivatives with four degrees of substitution (DS 1, 2, 3 and 4) has been characterized for the first time using negative-ion mode electrospray ionization tandem mass spectrometry (ESI(-)-MS/MS). The results showed that P. pinaster bark CTs possess structural homogeneity in terms of monomeric units (C(15), catechin). The oligomer sizes were detected to be dimers to heptamers. The derivatives showed typical phenyl-propyl ether mass fragmentation by substituent elimination (58 amu) and inherent C(15) flavonoid fissions. The relative abundance of the product ions revealed a preferential triple, tetra-/penta- and octa- hydroxypropylation substitution pattern in the monomer, dimer and trimer derivatives, respectively. A defined order of -OH reactivity towards propylene oxide was established by means of multistage experiments (A-ring ≥ B-ring > C-ring). A high structural heterogeneity of the modified oligomers was detected.

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“…The structures of procyanidin oligomers (B-type) and their gallates with C4–C8 or C4–C6 linkages varied depending on the C-2 and C-3 configurations of their composing units, catechin or epicatechin. The MS n data were useful for their structural determination. − A procyanidin dimer monogallate (DP2G) loses its galloyl group first, to form the corresponding nongalloyl procyanidin dimers (DP2), or loses a catechin or epicatechin unit to form the lower procyanidin unit. Usually, it has two main fragmentation paths for procyanidins: dehydration and retro-Diels–Alder (RDA) reaction (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Antioxidative Flavan-3-ol Dimers from the Leaves of Camellia fangchengensis

Meng

Liu²,

Fan

et al. 2017

J. Agric. Food Chem.

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Camellia fangchengensis Liang et Zhong, belonging to the genus Camellia sect. Thea (Theaceae), is an endemic tea species to the south and southwest areas of Guangxi province, People's Republic of China. Known as a wild tea plant, the leaves have been used for producing green tea or black tea by the local people of its growing area. HPLC and LC-MS analysis showed the leaves contain oligomeric catechins as major phenolic components. Further detailed phytochemical study led to the identification of five flavan-3-ol dimers (1-5) including two new ones, fangchengbisflavans A (1) and B (2) from the leaves of C. fangchengensis, together with six known monomers (6-11) and one glucoside (12), in addition to gallic acid (13). Their structures were determined by extensive spectroscopic analysis. Most of the isolates displayed significant antioxidant activities in 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging assays. The results suggested that the leaves of C. fangchengensis, rich in flavan-3-ol oligomers and monomers as potent antioxidants, could be a valuable plant resource for the production of tea and natural beverages.

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Analysis of Oligomeric and Polymeric Tannins of Grape Berries by Liquid Chromatography/Electrospray Ionization Multiple-Stage Tandem Mass Spectrometry

Cited by 10 publications

References 32 publications

Gastroprotective activity of the resin from Virola oleifera

Gastroprotective activity of the resin from Virola oleifera

Substitution pattern elucidation of hydroxypropyl Pinus pinaster (Ait.) bark polyflavonoid derivatives by ESI(−)‐MS/MS

Antioxidative Flavan-3-ol Dimers from the Leaves of Camellia fangchengensis

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