MALDI‐TOF‐CID for the microstructure elucidation of polymeric hydrolysable tannins

Radebe, Nonhlanhla; Rode, Karsten; Pizzi, A.; Giovando, Samuele; Pasch, Harald

doi:10.1002/app.38156

Cited by 54 publications

(50 citation statements)

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“…Generally, tannins can be classified as condensed or hydrolysable tannins (Nakano et al 2000;Schofield et al 2001). Condensed tannins have been identified as oligomers with varying degrees of polymerization, formed by condensation and polymerization reactions of flavonoid repeating units (Nicollin et al 2013;Radebe et al 2013). Hydrolysable tannins are classified into gallotannins and ellagitannins according to their differing structural characters (Khanbabaee and van Ree 2001).…”

Section: Introductionmentioning

confidence: 99%

Reactivity of Larch and Valonia Tannins in Synthesis of Tannin-Formaldehyde Resins

Wang

et al. 2016

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Tannin-formaldehyde resins (TFR) were prepared by copolycondensation of tannins (larch tannin or valonia tannin) and formaldehyde. The performances of TFR and the free formaldehyde residue in the system during the course of reaction were tested. Chemical and structural changes of TFR during the reaction process were detected by Fourier transform infrared spectroscopy (FTIR) and 13 C nuclear magnetic resonance spectroscopy ( 13 C NMR). The results indicated that larch tannin-formaldehyde (LTF) resins demonstrated higher viscosity, higher solids content, shorter gel time, and lower free formaldehyde content than valonia tannin-formaldehyde (VTF) resins. The FTIR and 13 C NMR tests demonstrated that larch tannin had higher reactivity than valonia tannin with formaldehyde, which was confirmed by the results of the free formaldehyde content measurement and the characteristics of TFR.

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Section: Introductionmentioning

confidence: 99%

Reactivity of Larch and Valonia Tannins in Synthesis of Tannin-Formaldehyde Resins

Wang

et al. 2016

BioResources

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“…These diagnostic fragment ions were also observed by the LIFT system, which assisted in the structural identification of saponins from the sea cucumber Holothuria forskali [150,151]. Hydrolysable and condensed tannins are another group of secondary metabolites analyzed by MALDI due to its advantages, such as sensitivity, the formation of singly charged molecular ions, and lower ion suppression for complex mixture analysis [66,128,137,152]. Several articles have reported the potential to identify such compounds by MALDI-MS, which contains different combinations and connectivity between the monomers and produces tannins of the same molecular weight.…”

Section: Maldi-ms/ms To Identify Natural Productsmentioning

confidence: 98%

“…Initially, PSD was applied in peptides [131,132] and carbohydrate sequencing [133], and currently, there are some applications in natural products studies. It was used to identify saponins [134], flavonoids [122], isoflavones [135], carotenoids [136], and hydrolysable and condensed tannins [66,137] as well as to examine triacylglycerols and phosphatidylethanolamines from plants, algae, and animal tissue [138][139][140]. Different carotenes (polyenes without oxygen) and xanthophylls (polyenes with oxygen) were analyzed by MALDI and produced radical ions (molecular ions) through the removal (M •+ ) of one electron (l " Fig.…”

Section: Maldi-ms/ms To Identify Natural Productsmentioning

confidence: 99%

“…MS/MS data obtained by MALDI QIT-TOF, PSD, and CID have been applied to determine the chemical structure of hydrolysable tannins from Rosa chinensis Jacq. (Rosaceae) [159], Chinese galls [59], tara, Turkey gall, chestnut woods [137], Mangifera indica L. (Anacardiaceae) [160], and others, which are preferentially acquired in the positive ion mode due to the visualization of fewer signal peaks in the negative ion mode for gallotannins [59]. However, an extensive application of different matrices must be evaluated to confirm this statement.…”

Section: Maldi-ms/ms To Identify Natural Productsmentioning

confidence: 99%

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2016

Planta Med

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“…Vegetable tannins are important renewable natural resources and have been used industrially in a wide range of applications. On the basis of their chemical structural characteristics, tannins are divided into hydrolysable tannins and condensed tannins (Venter et al 2012;Radebe et al 2013;Ricci et al 2015). Condensed tannins obtained from natural resources have been used for the production of wood adhesives since the 1970s.…”

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confidence: 99%

Selective Biodegradation of Grape Pomace Tannins by Aspergillus niger and Application in Wood Adhesive

Lan¹,

Brosse²,

Cui³

et al. 2017

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The selective biodegradation of grape pomace tannins was studied using Aspergillus niger strains. The conditions were optimized in terms of monomeric catechin production. The optimal degradation conditions were: 10.0 g·L -1 of tannins in the induced medium, pH 6.5, and cultured on a shaking table at a rate of 120 r·min -1 at 28 °C for 36 h. The biodegraded tannins were used to partially substitute for phenol-formaldehyde in adhesive formulations. The biodegradation enabled the production of adhesives and wood panels with better properties (lower resin viscosity, higher internal bond strength, and lower thickness swelling). A particleboard in which the resin contained 60% biodegraded grape tannins displayed good performances (IBdry = 0.46 MPa, IBwet = 0.15 MPa) and passed the standard specifications for dry and wet conditions. Keywords INTRODUCTIONVegetable tannins are polyphenolic substances that are widely present in the plant kingdom (such as bark, wood, fruits, leaves, roots, and needles) as secondary metabolites for protective purposes, with molecular weights between 500 Da and 30,000 Da. Vegetable tannins are important renewable natural resources and have been used industrially in a wide range of applications. On the basis of their chemical structural characteristics, tannins are divided into hydrolysable tannins and condensed tannins (Venter et al. 2012;Radebe et al. 2013;Ricci et al. 2015). Condensed tannins obtained from natural resources have been used for the production of wood adhesives since the 1970s. They can be used to prepare tannin-based adhesives and/or to replace part of the phenol in phenol-formaldehyde adhesives (Pizzi 1994(Pizzi , 2006Lei et al. 2008;Tondi and Pizzi 2009;Kemppainen et al. 2014;Grasel et al. 2016).Grape pomace, consisting of skins, seeds, and stems, is a co-product generated by grape juice and wine-making processes and retains a high level of condensed tannins (20% to 30% of the initial weight) (Llobera and Canellas 2007;Zocca et al. 2007;Rondeau et al. 2013;Bosso et al. 2016). In previous works, the authors described the optimization of the extraction of crude condensed tannin extracts from grape pomace using water as a solvent, in the presence of a base (carbonate or sodium hydroxide) and sodium sulfite. The tannins extracted from grape pomace mainly consist of phloroglucinol A-ring procyanidin polymers with a minor amount of prodelphinidin linked through a C4-C8 linear bond, and a part of procyanidins that contain glucose and gallic acid substituents. It has been demonstrated that these extracts can be successfully employed in the formulation of tannin-PEER-REVIEWED ARTICLE bioresources.com Lan et al. (2018). "Grape tannins in wood adhesive," BioResources 13(1), 894-905. 895formaldehyde-based adhesives usable for the production of wood panels (Ping et al. 2011a(Ping et al. ,b, 2012. However, it was concluded that, compared with tannins extracted from barks, the performance of some of the pomace-based formulations was poor. This was probably due to the large variability...

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MALDI‐TOF‐CID for the microstructure elucidation of polymeric hydrolysable tannins

Cited by 54 publications

References 22 publications

Reactivity of Larch and Valonia Tannins in Synthesis of Tannin-Formaldehyde Resins

Reactivity of Larch and Valonia Tannins in Synthesis of Tannin-Formaldehyde Resins

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Selective Biodegradation of Grape Pomace Tannins by Aspergillus niger and Application in Wood Adhesive

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