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Antioxidant Properties and Effects of Aporphine Alkaloids and Their Phenanthrene Seco-Isomers on Acetylcholinesterase Activity

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Abstract—

Model phenanthrene seco-alkaloids (seco-glaucine and seco-boldine) obtained in the medium of subcritical water (SBW) from plant aporphine alkaloids have been studied for the first time as antioxidants and inhibitors of acetylcholinesterase (AChE). Antioxidant activities (in vitro) of model aporphine and phenanthrene alkaloids: boldine, seco-boldine, glaucine and seco-glaucine (BD, s-BD, GL and s-GL) were studied in the reaction with a stable free radical DPPH (1,1-diphenyl-2-picrylhydrazyl). In vivo, antioxidant activity was determined in a bioluminescent test system using genetically modified E. coli strains. In the experiments in vitro (DPPH test) and in vivo (biotest), phenanthrene alkaloids s-GL and s-BD demonstrate the higher antioxidant activity than their aporphine precursors GL and BD. The anticholinesterase activity of alkaloids and their phenanthrene seco-isomers was studied (in vitro) using Ellman’s method with minor modifications. The data on the inhibitory activity of the AChE enzyme with aporphine and phenanthrene alkaloids expressed as IC50 values obtained from dose–response curves demonstrate that the inhibitory activity for seco-boldine (IC50 = 0.21 mM) and seco-glaucine (IC50 = 0.04 mM) is higher than for the initial aporphine alkaloids boldine (IC50 = 0.29 mM) and glaucine (IC50 = 0.44 mM), respectively. Thus, it has been shown that phenanthrene alkaloids obtained in SBW exhibit the higher antioxidant activity and the better inhibitory AChE activity than their aporphine precursors.

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Funding

The work was supported by the Ministry of Science and Higher Education of the Russian Federation (State assignment in the field of scientific activity, Southern Federal University, 2020, no. BAЗ0110/20-3-09IH) and by the Russian Foundation for Basic Research (project no. 19-33-90211-Aspiranty).

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Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry, Southern Federal University, 344090, Rostov-on-Don, Russia

    S. S. Khizrieva, S. N. Borisenko, E. V. Maksimenko, E. V. Vetrova, N. I. Borisenko & V. I. Minkin

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  1. S. S. Khizrieva
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  2. S. N. Borisenko
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Correspondence to N. I. Borisenko.

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The authors declare that they have no conflicts of interest. This article does not contain any studies involving animals or human participants performed by any of the authors.

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Translated by E. Makeeva

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Khizrieva, S.S., Borisenko, S.N., Maksimenko, E.V. et al. Antioxidant Properties and Effects of Aporphine Alkaloids and Their Phenanthrene Seco-Isomers on Acetylcholinesterase Activity. Russ J Bioorg Chem 48, 1433–1440 (2022). https://doi.org/10.1134/S106816202207010X

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