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. 2020 Jul 24;21(15):5265.
doi: 10.3390/ijms21155265.

New Methodology for the Identification of Metabolites of Saccharides and Cyclitols by Off-Line EC-MALDI-TOF-MS

Gulyaim Sagandykova  1   2 , Justyna Walczak-Skierska  1 , Fernanda Monedeiro  1 , Paweł Pomastowski  1 , Bogusław Buszewski  1   2
Affiliations

New Methodology for the Identification of Metabolites of Saccharides and Cyclitols by Off-Line EC-MALDI-TOF-MS

Gulyaim Sagandykova et al. Int J Mol Sci. .

Abstract

A combination of electrochemistry (EC) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (off-line EC-MALDI-TOF-MS) was applied for determination of the studied biologically active compounds (D-glucose, D-fructose, D-galactose, D-pinitol, L-chiro-inositol, and myo-inositol) and their possible electrochemical metabolites. In this work, boron-doped diamond electrode (BDD) was used as a working electrode. MALDI-TOF-MS experiments were carried out (both in positive and negative ion modes and using two matrices) to identify the structures of electrochemical products. This was one of the first applications of the EC system for the generation of electrochemical products produced from saccharides and cyclitols. Moreover, exploratory data analysis approaches (correlation networks, hierarchical cluster analysis, weighted plots) were used in order to present differences/similarities between the obtained spectra, regarding the class of analyzed compounds, ionization modes, and used matrices. This work presents the investigation and comparison of fragmentation patterns of sugars, cyclitols, and their respective products generated through the electrochemistry (EC) process.

Keywords: MALDI-TOF-MS; biologically active compounds; cyclitols; electrochemistry; saccharides.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
(a) Fragmentation pathways of D-pinitol; (b) MS spectrum before electrochemical process, (c) MS spectrum after electrochemical process.
Figure 2
Figure 2
(a) Fragmentation pathways of L-chiro-inositol; (b) MS spectrum before electrochemical process, (c) MS spectrum after electrochemical process.
Figure 3
Figure 3
(a) Fragmentation pathways of myo-inositol; (b) MS spectrum before electrochemical process, (c) MS spectrum after electrochemical process.
Figure 4
Figure 4
(a) Fragmentation pathways of D-glucose; (b) MS spectrum before electrochemical process, (c) MS spectrum after electrochemical process.
Figure 5
Figure 5
(a) Fragmentation pathways of D-fructose; (b) MS spectrum before electrochemical process, (c) MS spectrum after electrochemical process.
Figure 6
Figure 6
(a) Fragmentation pathways of D-galactose; (b) MS spectrum before electrochemical process, (c) MS spectrum after electrochemical process.
Figure 7
Figure 7
Networks built based on MS spectra obtained using (a) 2,5-dihydroxybenzoic acid (DHB) and (b) α-cyano-4-hydroxycinnamic acid (HCCA) matrices, in positive ionization mode; (c) DHB and (d) HCCA matrices, in negative ionization mode. Colored nodes: compounds, white rectangles: MS ions, e—compounds subjected to the electrochemical process, FRU: D-fructose, GAL: D-galactose, GLU: D-glucose, PI: D-pinitol, CI: L-chiro-inositol, and MI: myo-inositol.
Figure 8
Figure 8
Heatmaps associated to hierarchical cluster analysis (HCA), which were generated for analysis using (a) DHB and (b) HCCA matrix; (c) chart showing ions specifically incident in the spectrum of one of the analytes. P: positive mode, N: negative mode, e—compounds subject to electrochemical process, FRU: D-fructose, GAL: D-galactose, GLU: D-glucose, PI: D-pinitol, CI: L-chiro-inositol, MI: myo-inositol.
Figure 9
Figure 9
Scatter plots weighted according to the significance of ions (-log10 (p)), referring to a comparison between MS spectra obtained before and after the electrochemical process, using (a) DHB and (b) the HCCA matrix.
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