Isolation and structural elucidation by 2D NMR of planteose, a major oligosaccharide in the mucilage of chia (Salvia hispanica L.) seeds

Xing, Xiaohui; Hsieh, Yves S. Y.; Yap, Kuok; Ang, Main Ern; Lahnstein, Jelle; Tucker, Matthew R.; Burton, Rachel A.; Bulone, Vincent

doi:10.1016/j.carbpol.2017.07.059

Cited by 42 publications

(29 citation statements)

References 58 publications

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“…Glucose, fructose, sucrose, raffinose, 1-kestose, maltose, nystose and stachyose analytical standards were purchased from Sigma-Aldrich, while 1,1,1-kestopentaose was obtained from Bio-Strategy. A standard of planteose was purified and prepared from Salvia hispanica seed mucilage as per Xing et al 56 . Schematic structures were prepared using the DrawGlycan-SNFG online tool ( http://www.virtualglycome.org/DrawGlycan/ ) 57 .…”

Section: Methodsmentioning

confidence: 99%

The composition of Australian Plantago seeds highlights their potential as nutritionally-rich functional food ingredients

Cowley

O’Donovan

Burton

2021

Sci Rep

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When wetted, Plantago seeds become covered with a polysaccharide-rich gel called mucilage that has value as a food additive and bulking dietary fibre. Industrially, the dry husk layer that becomes mucilage, called psyllium, is milled off Plantago ovata seeds, the only commercial-relevant Plantago species, while the residual inner seed tissues are either used for low value animal feed or discarded. We suggest that this practice is potentially wasting a highly nutritious resource and here describe the use of histological, physicochemical, and chromatographic analyses to compare whole seed composition/characteristics of P. ovata with 11 relatives already adapted to harsh Australian conditions that may represent novel commercial crop options. We show that substantial interspecific differences in mucilage yield and macromolecular properties are mainly a consequence of differences in heteroxylan and pectin composition and probably represent wide differences in hydrocolloid functionality that can be exploited in industry. We also show that non-mucilage producing inner seed tissues contain a substantial mannan-rich endosperm, high in fermentable sugars, protein, and fats. Whole seed Plantago flour, particularly from some species obtained from harsh Australian environments, may provide improved economic and health benefits compared to purified P. ovata psyllium husk, by retaining the functionality of the seed mucilage and providing additional essential nutrients.

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Section: Methodsmentioning

confidence: 99%

The composition of Australian Plantago seeds highlights their potential as nutritionally-rich functional food ingredients

Cowley

O’Donovan

Burton

2021

Sci Rep

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“…A benefit of HPAEC-PAD is that it does not require derivatization; it is more commonly used than the RP-HPLC-UV method for monosaccharide analysis of plant residues. In addition to monosaccharide analysis, HPAEC-PAD is an important method for detecting and quantifying oligosaccharides and evaluating the purity of purified oligosaccharide samples [67,68].…”

Section: High-performance Anion-exchange Chromatography With Pulsed Amentioning

confidence: 99%

“…Oligosaccharides are usually purified using graphitized carbon solid-phase extraction before structural characterization by LC-ESI-MS/MS [67]. NMR and other MS techniques (e.g., MALDI-tof-MS) are complimentary to LC-ESI-MS/MS for structural analysis of oligosaccharides released enzymatically or chemically from plant residues [67,68,80]. Recently, there has been interest in the development of LC-MS-based methods for glyosidic linkage analysis [81][82][83][84][85], and LC-ESI-MS/MS methods have been developed for fast monosaccharide analysis with high sensitivity [86][87][88].…”

Section: Liquid Chromatography Electrospray Ionization Tandem Mass Spmentioning

confidence: 99%

Combined whole cell wall analysis and streamlined in silico carbohydrate-active enzyme discovery to improve biocatalytic conversion of agricultural crop residues

Tingley

Low

Xing

et al. 2021

Biotechnol Biofuels

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The production of biofuels as an efficient source of renewable energy has received considerable attention due to increasing energy demands and regulatory incentives to reduce greenhouse gas emissions. Second-generation biofuel feedstocks, including agricultural crop residues generated on-farm during annual harvests, are abundant, inexpensive, and sustainable. Unlike first-generation feedstocks, which are enriched in easily fermentable carbohydrates, crop residue cell walls are highly resistant to saccharification, fermentation, and valorization. Crop residues contain recalcitrant polysaccharides, including cellulose, hemicelluloses, pectins, and lignin and lignin-carbohydrate complexes. In addition, their cell walls can vary in linkage structure and monosaccharide composition between plant sources. Characterization of total cell wall structure, including high-resolution analyses of saccharide composition, linkage, and complex structures using chromatography-based methods, nuclear magnetic resonance, -omics, and antibody glycome profiling, provides critical insight into the fine chemistry of feedstock cell walls. Furthermore, improving both the catalytic potential of microbial communities that populate biodigester reactors and the efficiency of pre-treatments used in bioethanol production may improve bioconversion rates and yields. Toward this end, knowledge and characterization of carbohydrate-active enzymes (CAZymes) involved in dynamic biomass deconstruction is pivotal. Here we overview the use of common “-omics”-based methods for the study of lignocellulose-metabolizing communities and microorganisms, as well as methods for annotation and discovery of CAZymes, and accurate prediction of CAZyme function. Emerging approaches for analysis of large datasets, including metagenome-assembled genomes, are also discussed. Using complementary glycomic and meta-omic methods to characterize agricultural residues and the microbial communities that digest them provides promising streams of research to maximize value and energy extraction from crop waste streams.

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“…Uronic acids in the sample wall material (~2 mg) were converted to their 6,6‐dideuterio neutral sugar counterparts using carbodi‐imide activation at pH 4.75 followed by sodium borodeuteride (NaBD4) reduction at pH 7.0 (Kim & Carpita, 1992). Glycosidic linkage analysis by methylation was performed as described in Xing et al () to produce permethylated alditol acetates. These derivatives were analysed using an Agilent 7890B/5977B GC‐MS fitted with an Agilent J&W VF‐23 ms GC (30 m × 0.25 mm, film thickness 0.25 μm) capillary column.…”

Section: Methodsmentioning

confidence: 99%

“…Glycosidic linkage analysis by methylation was performed as described in Xing et al (2017) to produce permethylated alditol acetates. These derivatives were analysed using an Agilent 7890B/5977B GC-MS fitted with an Agilent J&W VF-23 ms GC (30 m × 0.25 mm, film thickness 0.25 μm) capillary column.…”

Section: Glycosidic Linkage Analysismentioning

confidence: 99%

Genetic and environmental factors contribute to variation in cell wall composition in mature desi chickpea (Cicer arietinumL.) cotyledons

et al. 2018

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Chickpea (Cicer arietinum L.) is an important nutritionally rich legume crop that is consumed worldwide. Prior to cooking, desi chickpea seeds are most often dehulled and cleaved to release the split cotyledons, referred to as dhal. Compositional variation between desi genotypes has a significant impact on nutritional quality and downstream processing, and this has been investigated mainly in terms of starch and protein content. Studies in pulses such as bean and lupin have also implicated cell wall polysaccharides in cooking time variation, but the underlying relationship between desi chickpea cotyledon composition and cooking performance remains unclear. Here, we utilized a variety of chemical and immunohistological assays to examine details of polysaccharide composition, structure, abundance, and location within the desi chickpea cotyledon. Pectic polysaccharides were the most abundant cell wall components, and differences in monosaccharide and glycosidic linkage content suggest both environmental and genetic factors contribute to cotyledon composition. Genotype-specific differences were identified in arabinan structure, pectin methylesterification, and calcium-mediated pectin dimerization. These differences were replicated in distinct field sites and suggest a potentially important role for cell wall polysaccharides and their underlying regulatory machinery in the control of cooking time in chickpea.

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Isolation and structural elucidation by 2D NMR of planteose, a major oligosaccharide in the mucilage of chia (Salvia hispanica L.) seeds

Cited by 42 publications

References 58 publications

The composition of Australian Plantago seeds highlights their potential as nutritionally-rich functional food ingredients

The composition of Australian Plantago seeds highlights their potential as nutritionally-rich functional food ingredients

Combined whole cell wall analysis and streamlined in silico carbohydrate-active enzyme discovery to improve biocatalytic conversion of agricultural crop residues

Genetic and environmental factors contribute to variation in cell wall composition in mature desi chickpea (Cicer arietinumL.) cotyledons

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