Tetramethylammonium hydroxide (TMAH) thermochemolysis of the aliphatic biopolymer cutan: insights into the chemical structure

McKinney, Daniel; Bortiatynski, Jacqueline M.; Carson, Daniel M.; Clifford, David; Leeuw, J.W. de; Hatcher, Patrick G.

doi:10.1016/0146-6380(96)00055-1

Cited by 126 publications

(48 citation statements)

References 37 publications

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“…Isolation of cutan from plant cuticular material is performed in much the same way as classical algaenan isolation, namely, through solvent extraction and the application of strong reducing/oxidizing reagents to remove carbohydrates, proteins, and free and ester-bound lipids (45,(116)(117)(118)(119). As with the characterization of algaenan, structural determi-nations of cutan are uncertain because of study-to-study variation in isolation procedures and the potential for artifact generation introduced by aggressive isolation approaches (45,118,120). However, it appears that this material comprises long-chain (ϳC 30 ) alkanes and alkenes joined by ether linkages and is, thus, at least an analogue of Nannochloropsis algaenan (45,121).…”

Section: Discussionmentioning

confidence: 99%

Ultrastructure and Composition of the Nannochloropsis gaditana Cell Wall

et al. 2014

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e Marine algae of the genus Nannochloropsis are promising producers of biofuel precursors and nutraceuticals and are also harvested commercially for aquaculture feed. We have used quick-freeze, deep-etch electron microscopy, Fourier transform infrared spectroscopy, and carbohydrate analyses to characterize the architecture of the Nannochloropsis gaditana (strain CCMP 526) cell wall, whose recalcitrance presents a significant barrier to biocommodity extraction. The data indicate a bilayer structure consisting of a cellulosic inner wall (ϳ75% of the mass balance) protected by an outer hydrophobic algaenan layer. Cellulase treatment of walls purified after cell lysis generates highly enriched algaenan preparations without using the harsh chemical treatments typically used in algaenan isolation and characterization. Nannochloropsis algaenan was determined to comprise long, straight-chain, saturated aliphatics with ether cross-links, which closely resembles the cutan of vascular plants. Chemical identification of >85% of the isolated cell wall mass is detailed, and genome analysis is used to identify candidate biosynthetic enzymes.

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Section: Discussionmentioning

confidence: 99%

Ultrastructure and Composition of the Nannochloropsis gaditana Cell Wall

et al. 2014

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“…This latter biopolymer is non-saponifiable and non-hydrolyzable and has been found in fossilized cuticles (Gupta et al 2006). The cutan biopolymer is constructed from longchain alcohols and n-alkanes linked to the aromatic backbone (McKinney et al 1996;Villena et al 1999).…”

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confidence: 99%

Decomposition and sorption characterization of plant cuticles in soil

Chefetz¹

2007

Plant Soil

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The sorption of organic compounds by plant cuticular matter has been extensively investigated; however, little has been studied regarding the effect of plant cuticle degradation on their role in the sorption of organic compounds in soils. The sorption of phenanthrene was studied in soil samples which had been incubated for up to 9 months with three different types of plant cuticle isolated from tomato fruits, pepper fruits and citrus leaves. The main change in the diffuse reflectance Fourier-transform infrared (DRIFT) spectra during incubation of the cuticles was related to cutin decomposition. The peaks assigned to methyl and ethyl vibration and C=O vibration in ester links decreased with decomposition. In general, with all samples, the phenanthrene sorption coefficients calculated for the whole incubated soils (K d ) decreased with incubation time. In contrast, the carbon-normalized K d values (K oc ) did not exhibit a similar trend for the different cuticles during incubation. The origin of the cuticle also affected the linearity of the sorption isotherms. With the tomato and citrus cuticle samples, the Freundlich N values were close to unity and were stable throughout incubation. However with the green pepper cuticle, the N values exhibited a significant decrease (from 0.98 to 0.70). This study demonstrates that the structural composition of the plant cuticle affects its biodegradability and therefore its ability to sorb organic compounds in soils. Of the residues originating from plant cuticular matter in soils, the cutan biopolymer and lignin-derived structures appear to play a dominant role in sorption as decomposition progresses.

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“…Deshmukh et al 1964;Kolattukudy 1981;Holloway 1982;McKinney et al 1996;Collinson and van Bergen 2004;van Bergen et al 2004). These aromatic components may be derived from the cell wall of the epidermis directly underlying the cuticle.…”

Section: Cutin and Cutanmentioning

confidence: 93%

Biomacromolecules of Algae and Plants and their Fossil Analogues

2006

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A review of our current understanding of resistant biomacromolecules derived from present and past algae and higher plants is presented. Insight in the nature of recent and fossil macromolecules is strongly hampered by the difficulties in obtaining the material in pure and unaltered form. For the extant material, avoiding artificial condensation and structural alteration as a result of chemical isolation and purification of biomacromolecules requires constant attention. To date, several types of sporopollenin seem to occur. One type is characterised by oxygenated aromatic building blocks, in particular p-coumaric acid and ferrulic acid. The other type is thought to consist predominantly of an aliphatic biopolymer. In this review it is concluded that extant sporopollenin consists of the aromatic type, whereas the aliphatic component of fossil sporopollenin is due to early-diagenetic oxidative polymerization of unsaturated lipids. The cuticles of most higher plants contain the aliphatic biopolyester cutin. Additionally, cuticles of drought-adapted, mostly CAM plants, seem to contain the non-hydrolysable aliphatic biopolymer cutan. Only a very few algae are able to biosynthesize resistant, (fossilisable) cell walls: some Chlorophyta, Eustigmatophyta and Prasinophyta produce the aliphatic biopolymer algaenan. Some Dinophyta are also capable of producing algaenan cell walls. Additionally, some taxa produce highly resistant cyst-walls with a high proportion of aromatic moieties. For the morphologically well-preserved fossil material, contamination by organic particles other than the target taxon is hard to eliminate and can contribute to either the aliphatic or aromatic signal. Furthermore, post-mortem migration of aliphatic moieties into, and their condensation onto the macromolecule might occur, e.g. by oxidative polymerization. These phenomena hamper the evaluation of the aliphatic signature of fossil plant material and may for example explain the preservation of initially cutin-based cuticles or non-algaenan containing algae. The extent to which migration and in situ formation of aromatic moieties plays a role in modifying resistant algal macromolecules, notably under elevated temperature and/or pressure conditions, still remains an open question.

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Tetramethylammonium hydroxide (TMAH) thermochemolysis of the aliphatic biopolymer cutan: insights into the chemical structure

Cited by 126 publications

References 37 publications

Ultrastructure and Composition of the Nannochloropsis gaditana Cell Wall

Ultrastructure and Composition of the Nannochloropsis gaditana Cell Wall

Decomposition and sorption characterization of plant cuticles in soil

Biomacromolecules of Algae and Plants and their Fossil Analogues

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