Cite this article as:
Pankratov A. N., Tsivileva O. M., Tsymbal O. A., Drevko Y. B., Tumskiy R. S., Marakaeva A. V. Exploration of Possibilities for Organic Selenides and Dihydroselenochromilium Salt Interaction with Diphenylpicrylhydrazyl. Izvestiya of Saratov University. Chemistry. Biology. Ecology, 2019, vol. 19, iss. 1, pp. 39-49. DOI: https://doi.org/10.18500/1816-9775-2019-19-1-39-49
Exploration of Possibilities for Organic Selenides and Dihydroselenochromilium Salt Interaction with Diphenylpicrylhydrazyl
Higher fungi – basidiomycetes play significant role as food and biological subjects for establishing the regularities of the living systems’ operation, development and response to the different-nature effectors impact. Insufficient activity of the living organisms’ antioxidant system interfering the ability of overcoming the negative consequences of oxidative stress (excessive level of free radicals in cells) is believed to be a reason for the organisms aging and death. For enhancing the sustainability of mushroom cultures to the oxidative stress, and for providing their adequate redox status in respect to cytodifferentiation and transition to the generative stage, antioxidants are utilized. Profound antioxidant properties are attributed to the compounds of selenium, which is also an essential microelement. One of the antioxidant action indicators is the antiradical activity determined by means of the reaction occurring with the participation of stable free radical diphenylpicrylhydrazyl (DPPH) (C6H5)2N–N•–C6H2(NO2)3-2,4,6. Another important antioxidant activity rate is the lipid peroxidation (LPO) level assessed by the reaction the reaction with thiobarbituric acid. In view of toxicity of inorganic selenium compounds, just the organoselenium ones are promising as the antioxidant and microelement supplementations at the basidiomycetes cultivation. With a view to future testing of the aforesaid compounds as a kind of supplement, their own possible interaction with DPPH and TBA must be explored to take that into account. That is why the implementation of reference reactions between the organoselenium compounds and DPPH should be provided. The present work is aimed to clarify the possibilities of interaction of three organic selenides and dihydroselenochromilium salt with DPPH. Conventional determination techniques for the antiradical activity and LPO level have been adjusted to the research goal. By means of spectrophotometric method involving quantum chemical computations at a B3LYP/6-311++G(d,p) level of theory, and NBO-analysis, we studied a number of organoselenium and model compounds interaction with DPPH and TBA. It has been shown that diacetophenonylselenide C6H5COCH2SeCH2COC6H5 barely inhibits DPPH. The inhibition level is rather high with 2-(4-bromophenyl)-4-phenyl-7,8-benzo-5,6-dihydro-4Н-selenochromene, and especially with 2,4-diphenyl-7,8-benzo-5,6-dihydroselenochromilium perchlorate. Considerable extent of inhibition of the latter salt could be related to the activation of methylene groups in organoelement cation on account of positive charge acquisition by heteroring. The mixture of organoselenium (diacetophenonylselenide, dihydroselenochromenes, dihydroselenochromilium salt) or model compound with TBA does not yield any products with the absorbance bands in the visible spectrum region.
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