Specific modification of xyloglucan from Hymenaea courbaril seeds

Lucyszyn, Neoli; Lubambo, Adriana F.; Matos, K.F.; Marvilla, I.; Souza, Camilla Mariane Menezes; Sierakowski, Maria Rita

doi:10.1016/j.msec.2008.10.001

Cited by 20 publications

(14 citation statements)

References 30 publications

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“…[15] Therefore, in alkaline conditions C-6-oxidised pyranosides are susceptible to b-elimination reactions and subsequent depolymerisation of polysaccharides. [17] This phenomenon has been observed previously by Nooy et al, [7] Sierakowski et al, [8] Lucyszyn et al [11] and Cunha et al [12] The effects of the charges incorporated into the GM structure by the syntheses were studied by surface tension measurements. As the concentration of polymers increases in a solution, the physical properties of water are changed and the surface tension (ST) decreases.…”

Section: Resultssupporting

confidence: 65%

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Oxidation and N‐Alkylation at the C‐6 Position of Galactomannan Extracted from Caesalpinia ferrea var. ferrea Seeds

Souza

Lucyszyn

Ferraz

et al. 2011

Macromolecular Symposia

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Summary: Carboxyl (GMOX) and carboxyl-aminoalkylated derivatives (GMOXD) of galactomannan (GM), extracted from the seeds of Caesalpinia ferrea (Pau-ferro; Brazilian Ironwood), were synthesised by selective modification of the polysaccharide at the C-6 position in the presence of TEMPO reagent (2,2,6,6-tetramethylpiperidine-1-oxyl) and dodecylamine, with high yields (77 and 94% for GMOX and GMOXD, respectively). The chemical modifications were confirmed by Fourier-transform infrared (FTIR) and nuclear magnetic resonance ( 13 C-NMR) spectroscopy. Analysis by gel permeation chromatography (GPC) coupled to refractive index (RI), lightscattering (LS) and viscometer detectors revealed a decrease in molar-mass values and the intrinsic viscosity and an increase in polydispersity. Modification of galactomannan with a primary amine led to an interesting anionic water-soluble polymeric surfactant, as determined by interfacial tension values at 24 o C. The critical aggregation and micellar concentration values of amphiphilic GMOXD were determined to be 0.48 and 0.89% (w/v), respectively. The development of polyelectrolyte and amphiphilic derivatives of GM and their physicochemical characterisation can contribute to numerous product applications such as nano-structured films, cosmetics and pharmaceuticals.

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Section: Resultssupporting

confidence: 65%

“…Using the same process, a similar derivatisation efficiency has been obtained for galactomannan from Leucaena leucocephala, [8] xyloglucan from Hymenaea courbaril [11] and gum exudates of Anarcadium occidentale.…”

Section: Resultsmentioning

confidence: 58%

Oxidation and N‐Alkylation at the C‐6 Position of Galactomannan Extracted from Caesalpinia ferrea var. ferrea Seeds

Souza

Lucyszyn

Ferraz

et al. 2011

Macromolecular Symposia

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“…The crude extract obtained was subsequently centrifuged to remove the residue, in agreement with the literature [5]. Washing with ethanol removed contaminant, while washing with acetone permitted further removal of proteins.…”

Section: Extraction and Yieldmentioning

confidence: 67%

“…We believe that our methodology allowed us to achieve a high yield which is far above those of previous works, such as 15.5% [23] and 38% [5]. Different extraction times for xyloglucan were compared and demonstrated a variation of yield from 5.4 to 40.8% [25].…”

Section: Extraction and Yieldmentioning

confidence: 80%

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Structure and rheological properties of a xyloglucan extracted from Hymenaea courbaril var. courbaril seeds

Arruda

Albuquerque

Santos

et al. 2015

International Journal of Biological Macromolecules

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Hymenaea courbaril var courbaril seed xyloglucan was efficiently extracted with 0.1M NaCl, followed by ethanol precipitation (yield=72±5% w/w). Its amorphous structure was identified by the pattern of X-ray diffraction. The monosaccharide composition was determined by GC/MS analysis of the alditol acetates and showed the occurrence of glucose:xylose:galactose:arabinose (40:34:20:6). One-(1D) and two-dimensional-(2D) NMR spectra confirmed a central backbone composed by 4-linked β-glucose units partially branched at position 6 with non-reducing terminal units of α-xylose or β-galactose-(1→2)-α-xylose disaccharides. The xyloglucan solution was evaluated by dynamic light scattering and presents a polydisperse and practically neutral profile, and at 0.5 and 1.0% (w/v) the solutions behave as a viscoelastic fluid. The polysaccharide did not show significant antibacterial or hemolytic activities. Overall our results indicate that xyloglucan from H. courbaril is a promising polysaccharide for food and pharmaceutical industries.

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