Thermally assisted transmethylation gas chromatography-mass spectrometry of suberin components in cork fromQuercus suber L.

Bento, M. Filomena; Pereira, Helena; Cunha, M. A.; Moutinho, A.M.C.; Berg, Klaas Jan van den; Boon, Jaap J.

doi:10.1002/(sici)1099-1565(199803/04)9:2<75::aid-pca386>3.0.co;2-8

Cited by 23 publications

(29 citation statements)

References 26 publications

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“…TMAH/Py is a thermochemolysis procedure mixing hydrolytic, methylating and pyrolytic reactions [36,[46][47][48], where the strong alkaline character of TMAH causes dominant chemolytic reactions at the used temperatures which favors hydrolysis of labile bonds, as esters, in less extent ethers, and with high difficulty the C-C bonds. Therefore TMAH/Py-GC/MS is well suited to study suberinderived products from cork since they constitute the major peaks and areas while lignin or other cork-derived products were not identified [39,40]. The use of Py-GC/FID instead of TMAH/Py-GC/FID seems to be a more reliable choice regarding the scope of this work and previous works results.…”

Section: Introductionmentioning

confidence: 88%

“…Identification of these peaks was beyond the scope of this work but they can be attributed to the thermal degradation of suberin. Pyrolysis promotes the liberation of high quantities of suberin pyrolysates, which can be used for suberin studies when pyrolysis is performed under transmethylation conditions [39,40]. These peaks are clearly visible in retention times lower than 25 min and higher than 45 min.…”

Section: Analytical Pyrolysismentioning

confidence: 99%

“…It was preferred to other pyrolysis-based methods, namely pyrolysis with in situ methylation using tetramethylammonium hydroxyde (TMAH) that has been introduced as an improvement for the analysis of biopolymers [36] including lignins [37,38], cork suberin [39,40] and grapefruit suberin [41], but still is in study and improvement [42][43][44][45]. TMAH/Py is a thermochemolysis procedure mixing hydrolytic, methylating and pyrolytic reactions [36,[46][47][48], where the strong alkaline character of TMAH causes dominant chemolytic reactions at the used temperatures which favors hydrolysis of labile bonds, as esters, in less extent ethers, and with high difficulty the C-C bonds.…”

Section: Introductionmentioning

confidence: 96%

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Isolation and comparative characterization of a Björkman lignin from the saponified cork of Douglas-fir bark

Marques

Pereira

Rodrigues

et al. 2006

Journal of Analytical and Applied Pyrolysis

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Section: Introductionmentioning

confidence: 88%

Section: Analytical Pyrolysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

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Isolation and comparative characterization of a Björkman lignin from the saponified cork of Douglas-fir bark

Marques

Pereira

Rodrigues

et al. 2006

Journal of Analytical and Applied Pyrolysis

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“…Although the amounts of the different components can show significant variations (Pereira, 1988;Lopes et al, 2001), on average it contains 15% extractives (7.5% waxes and 7.5% tannins), 41% aliphatic suberin (referred to as suberin in cork tree literature), 22% aromatic suberin (referred to as lignin in cork tree literature), 20% polysaccharides, and 2% ashes (Pereira, 1988). The monomeric composition of the aliphatic (suberin) fraction has been analyzed by Holloway (1983) and by Bento et al (1998) and that of the aromatic (lignin) fraction by Marques et al (1999) and Lopes et al (2000), among others. Waxes have been analyzed by Castola et al (2005) and mainly consist of terpenes and sterols.…”

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confidence: 99%

A Genomic Approach to Suberin Biosynthesis and Cork Differentiation

Soler

Serra²,

Molinas³

et al. 2007

Plant Physiology

142

139

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Cork (phellem) is a multilayered dead tissue protecting plant mature stems and roots and plant healing tissues from water loss and injuries. Cork cells are made impervious by the deposition of suberin onto cell walls. Although suberin deposition and cork formation are essential for survival of land plants, molecular studies have rarely been conducted on this tissue. Here, we address this question by combining suppression subtractive hybridization together with cDNA microarrays, using as a model the external bark of the cork tree (Quercus suber), from which bottle cork is obtained. A suppression subtractive hybridization library from cork tree bark was prepared containing 236 independent sequences; 69% showed significant homology to database sequences and they corresponded to 135 unique genes. Out of these genes, 43.5% were classified as the main pathways needed for cork biosynthesis. Furthermore, 19% could be related to regulatory functions. To identify genes more specifically required for suberin biosynthesis, cork expressed sequence tags were printed on a microarray and subsequently used to compare cork (phellem) to a non-suberin-producing tissue such as wood (xylem). Based on the results, a list of candidate genes relevant for cork was obtained. This list includes genes for the synthesis, transport, and polymerization of suberin monomers such as components of the fatty acid elongase complexes, ATP-binding cassette transporters, and acyltransferases, among others. Moreover, a number of regulatory genes induced in cork have been identified, including MYB, No-Apical-Meristem, and WRKY transcription factors with putative functions in meristem identity and cork differentiation.

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“…Small amounts of glycerol (usually in the range from 2 to 5.2%) have been reported by different authors (Bento et al, 1998;Graça and Pereira, 1997;Parameswaran et al, 1981;Rosa and Pereira, 1994). In contrast, more recently other authors detected in the complete suberin extract by GC-FID analysis using the internal standard calibration procedure higher amounts of glycerol (up to 14%) in Q. suber cork (Graça and Pereira, 2000b).…”

Section: Suberin Composition As Observed By Thermally-assisted Methylmentioning

confidence: 99%

Binding interactions between suberin monomer components and pesticides

Olivella

Bazzicalupi

Bianchi

et al. 2015

Science of The Total Environment

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Understanding the role of biomacromolecules and their interactions with pollutants is a key for elucidating the sorption mechanisms and making an accurate assessment of the environmental fate of pollutants. The knowledge of the sorption properties of the different constituents of these biomacromolecules may furnish a significant contribution to this purpose. Suberin is a very abundant biopolymer in higher plants. In this study, suberin monomers isolated from cork were analyzed by thermally-assisted methylation with tetramethylammonium hydroxide (TMAH) in a pyrolysis unit coupled to gas chromatography-mass spectrometry (GC/MS). The isolated monomer mixture was used to study the sorption of three pesticides (isoproturon, methomyl and oxamyl). The modes of pesticide-sorbent interactions were analyzed by means of two modeling calculations, the first one representing only the mixture of suberin monomers used in the sorption study, and the second one including glycerol to the mixture of suberin monomers, as a building block of the suberin molecule. The results indicated that the highest sorption capacity exhibited by the sorbent was for isoproturon (33%) being methomyl and oxamyl sorbed by the main suberin components to a lesser extent (3% and<1%, respectively). In addition to van der Waals interactions with the apolar region of sorbent and isoproturon, modeling calculations evidenced the formation of a hydrogen bond between the isoproturon NH group and a carboxylic oxygen atom of a suberin monomer. In the case of methomyl and oxamyl only weak van der Waals interactions stabilize the pesticide-sorbent adducts. The presence of glycerol in the model provoked significant changes in the interactions with isoproturon and methomyl.

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Thermally assisted transmethylation gas chromatography-mass spectrometry of suberin components in cork fromQuercus suber L.

Cited by 23 publications

References 26 publications

Isolation and comparative characterization of a Björkman lignin from the saponified cork of Douglas-fir bark

Isolation and comparative characterization of a Björkman lignin from the saponified cork of Douglas-fir bark

A Genomic Approach to Suberin Biosynthesis and Cork Differentiation

Binding interactions between suberin monomer components and pesticides

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