Structural characterization of suberan isolated from river birch (Betula nigra) bark

Turner, John; Hartman, Blaine E.; Hatcher, Patrick G.

doi:10.1016/j.orggeochem.2013.01.004

Cited by 21 publications

(30 citation statements)

References 57 publications

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“…The carbons at d 33 ppm have been 31 This has been related to the presence of methylene groups near oxygen vicinities (suggestive of linkage to lignin and polysaccharides), 31 or to the presence of crystalline/recalcitrant domains. 50,51 Other resonances typical of suberin can be noticed in all spectra, namely signals at d 50-90 ppm, d 130 and 148 ppm, assigned to carbons linked to oxygen, vinylic and quaternary carbons, respectively. One cannot disregard the hypothesis that cholinium hexanoate contamination contributed to the resonance at d 54 ppm (more intense in the suberin samples extracted for one or two hours, see * in Fig.…”

Section: Suberin Depolymerisation Occurs Through Cleavage Of Ester Bomentioning

confidence: 80%

Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation

et al. 2014

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Disruption of the three-dimensional network of suberin in cork by cholinium hexanoate leads to its efficient and selective isolation. The reaction mechanism, which likely involves selective cleavage of some intermonomeric bonds in suberin, was still unanswered. To address this question, the role of the ionic liquid during suberin depolymerisation and during cleavage of standard compounds carrying key chemical functionalities was herein investigated. A clear demonstration that the ionic liquid catalyses the hydrolysis of acylglycerol ester bonds was attained herein, both experimentally and computationally (DFT calculations). This behaviour is related to cholinium hexanoate capacity to activate the nucleophilic attack of water. The data showed also that the most favourable reaction is the hydrolysis of acylglycerol ester bonds, with the C2 position reporting the faster kinetics, whilst most of the linear aliphatic esters remained intact. The study emphasises that the ionic liquid plays the dual role of solvent and catalyst and leads to suberin efficient extraction through a mild depolymerisation. It is also one of the few reports of ionic liquids as efficient catalysts in the hydrolysis of esters.

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Section: Suberin Depolymerisation Occurs Through Cleavage Of Ester Bomentioning

confidence: 80%

Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation

et al. 2014

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“…6A-C) all display strong signals in the aliphatic region, with a sharp peaks at 30 and 33 ppm. These peaks have been previously associated with aliphatic biopolymers, cutan, cutin, suberan, and suberin (Deshmukh et al, 2005;Turner et al, 2013); however, we believe that photoCCAM materials are also contributing to the signal in the aliphatic region.…”

Section: Nmr Datamentioning

confidence: 59%

A non-thermogenic source of black carbon in peat and coal

Hartman

Chen

Hatcher

2015

International Journal of Coal Geology

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“…Later, the same authors adopted a similar analytical approach to identify the structure of cutan and a cutin/cutan mixture from the Agave americana leaf cuticle [39]. The structure of suburban, a protective biopolymer associated with suberin and located in the periderm of above ground parts of plants or in the endoderm of roots, was also investigated by combining HRMAS NMR to other techniques, such as CPMAS NMR, Scanning Electron Microscopy (SEM), flash-pyrolysis Gas Chromatography coupled to Mass Spectrometry (GC-MS), and FT-IR (Fourier TransformInfraRed spectroscopy) [40]. The integration of results from these different techniques enabled the authors to propose a model structural unit for the specific suburban from Betula nigra bark under study.…”

Section: Plantsmentioning

confidence: 99%

HRMAS NMR spectroscopy applications in agriculture

Mazzei¹,

Piccolo²

2017

Chem. Biol. Technol. Agric.

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The relatively recent and advanced high-resolution magic angle spinning (HRMAS) NMR technique enables the direct application of NMR spectroscopy to semi-solid and gel-like samples. It combines the advantages of both solid-and liquid-state NMR by allowing to concomitantly measure intact and non-manipulated samples. Based on both 1D and 2D homo-and heteronuclear NMR spectra, HRMAS evaluates the composition of fresh semi-solid samples with a similar resolution as that of classical liquid-state NMR techniques. The enhanced spectral quality still obtained for semi-solid samples is mainly due to the MAS system, whose rapid spinning and sample orientation minimize the anisotropic processes that prevent the acquisition of meaningful NMR spectra for non-liquid materials. Moreover, HRMAS allows us to use edited pulse sequences which, especially in the case of biological tissues or agrofood products, may provide a simultaneous information on polar and non-polar components without the need of preliminary sample extraction. Additionally, this technique may differentiate molecular species according to their degree of mobility in hydrated matrices. The evident versatile potential of the HRMAS NMR makes this technique particularly useful for life science molecular studies. Despite the focus of HRMAS has been greatly devoted on clinical biomedicine, materials chemistry, and metabolomics, there are already enough studies that show useful applications on agricultural issues. This report reviews the latest representative studies that employ HRMAS NMR on systems related to agricultural chemistry, requiring the characterization and dynamics of soil components, plant tissues, agrofood products, and in vivo organisms.

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Structural characterization of suberan isolated from river birch (Betula nigra) bark

Cited by 21 publications

References 57 publications

Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation

Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation

A non-thermogenic source of black carbon in peat and coal

HRMAS NMR spectroscopy applications in agriculture

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