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Glycobiology
2019 Oct 21;2911:755-764. doi: 10.1093/glycob/cwz057.
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Bottom-up analysis using liquid chromatography-Fourier transform mass spectrometry to characterize fucosylated chondroitin sulfates from sea cucumbers.
Yan L
,
Li L
,
Li J
,
Yu Y
,
Liu X
,
Ye X
,
Linhardt RJ
,
Chen S
.
Abstract
Fucosylated chondroitin sulfates (FCSs) from sea cucumbers have repetitive structures that exhibit minor structural differences based on the organism from which they are recovered. A detailed characterization of FCSs and their derivatives is important to establish their structure-activity relationship in the development of new anticoagulant drugs. In the current study, online hydrophilic interaction chromatography-Fourier transform mass spectrometry (FTMS) was applied to analyze the FCS oligosaccharides generated by selective degradation from four species of sea cucumbers, Isostichopus badionotus, Pearsonothuria graeffei, Holothuria mexicana and Acaudina molpadioides. These depolymerized FCS fragments were quantified and compared using the glycomics software package, GlycReSoft. The quantified fragments mainly had trisaccharide-repeating compositions and showed significant differences in fucosylation (including its sulfation) among different species of sea cucumbers. Detailed analysis of FTMS ion peaks and top-down nuclear magnetic resonance spectroscopy of native FCS polysaccharides verified the accuracy of this method. Thus, a new structural model for FCS chains from these different sea cucumbers was defined. This bottom-up approach provides rich detailed structural analysis and provides quantitative information with high accuracy and reproducibility and should be suitable for the quality control in FCSs as well as their oligosaccharides.
Fig. 1. HPGPC profiles of depolymerized FCS from sea cucumber Ib obtained by different N-deacetylation time.
Fig. 2. TICs of depolymerized FCS by partial N-deacetylation–deaminative cleavage from four species of sea cucumbers profiled by HILIC-FTMS.
Fig. 3. Typical oligosaccharide composition quantification of depolymerized FCS from four species of sea cucumbers calculated by GlycResoft. Oligomer composition plotted on the x-axis was given as [GlcA, Fuc/anTal-ol, GalNAc, Ac (acetyl), SO3 (sulfation)] (e.g. [1,2,0,0,4] means 1 GlcA, 2 Fuc/anTal-ol, 0 GalNAc, 0 Ac, 4 SO3).
Fig. 4. High-resolution FTMS spectrograms of the 6-mer group (hexasaccharide with nearby saccharides) with matched structures of depolymerized FCS by partial N-deacetylation–deaminative cleavage from four species of sea cucumbers. The patterns of sulfation in the fucose residues are based on literature (Chen et al. 2011; Dong et al. 2014; Mou et al. 2017; Agyekum et al. 2018) and combined with 1H NMR spectra analysis of native FCS in Figure 5.
Fig. 5.
1H NMR spectra analysis of native FCS from four species of sea cucumbers.
Fig. 6. New model structure definition of FCS polysaccharide chains from four species of sea cucumbers.
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