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. 2023 Feb 22;28(5):2062.
doi: 10.3390/molecules28052062.

Relationships between Molecular Characteristics of Novel Organic Selenium Compounds and the Formation of Sulfur Compounds in Selenium Biofortified Kale Sprouts

Paweł Zagrodzki  1 , Agnieszka Wiesner  1 , Monika Marcinkowska  2 , Marek Jamrozik  2 , Enrique Domínguez-Álvarez  3 , Katarzyna Bierła  4 , Ryszard Łobiński  4   5 , Joanna Szpunar  4 , Jadwiga Handzlik  6 , Agnieszka Galanty  7 , Shela Gorinstein  8 , Paweł Paśko  1
Affiliations

Relationships between Molecular Characteristics of Novel Organic Selenium Compounds and the Formation of Sulfur Compounds in Selenium Biofortified Kale Sprouts

Paweł Zagrodzki et al. Molecules. .

Abstract

Due to problems with selenium deficiency in humans, the search for new organic molecules containing this element in plant biofortification process is highly required. Selenium organic esters evaluated in this study (E-NS-4, E-NS-17, E-NS-71, EDA-11, and EDA-117) are based mostly on benzoselenoate scaffolds, with some additional halogen atoms and various functional groups in the aliphatic side chain of different length, while one compound contains a phenylpiperazine moiety (WA-4b). In our previous study, the biofortification of kale sprouts with organoselenium compounds (at the concentrations of 15 mg/L in the culture fluid) strongly enhanced the synthesis of glucosinolates and isothiocyanates. Thus, the study aimed to discover the relationships between molecular characteristics of the organoselenium compounds used and the amount of sulfur phytochemicals in kale sprouts. The statistical partial least square model with eigenvalues equaled 3.98 and 1.03 for the first and second latent components, respectively, which explained 83.5% of variance in the predictive parameters, and 78.6% of response parameter variance was applied to reveal the existence of the correlation structure between molecular descriptors of selenium compounds as predictive parameters and biochemical features of studied sprouts as response parameters (correlation coefficients for parameters in PLS model in the range-0.521 ÷ 1.000). This study supported the conclusion that future biofortifiers composed of organic compounds should simultaneously contain nitryl groups, which may facilitate the production of plant-based sulfur compounds, as well as organoselenium moieties, which may influence the production of low molecular weight selenium metabolites. In the case of the new chemical compounds, environmental aspects should also be evaluated.

Keywords: biofortification; brassica sprouts; chemometric analysis; selenium; sulfur compounds.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Loadings of first and second latent components in the PLS model. The model correlated the predictive parameters (MlogP, MolVol, N_Atoms, N_Carbon, N_Hydrgn, N_Oxygen, N_Bonds, F_SgleB, F_DbleB, F_TpleB, Carbonyl_C=O, HBAo, HBAch, BAoch, HBAnch) and response ones (allyl isothiocyanate (ALLYL ITC), butyl isothiocyanate (BUTYL ITC), glucoerucin, glucoiberin, indol-3-carbinol (I3C), phenyl isothiocyanate (PHENYL ITC), phenethyl isothiocyanate (PHENYLETHYL ITC), progoitrin, and sinigrin).
Figure 2
Figure 2
Score scatterplot of PLS model.
Figure 3
Figure 3
Possible implications of organic selenium compounds biofortification on the synthesis of active compounds in kale sprouts. * Selenosulfides, Selenoethers.
Figure 4
Figure 4
Chemical structures of selenium compounds used in the kale sprouts biofortification.
Figure 5
Figure 5
Summary of the main relationship regarding structure of organic selenium compounds and synthesis of different sulfur compounds.
See this image and copyright information in PMC

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