УДК 547.913: 615.28
DOI: https://doi.org/10.52540/2074-9457.2024.4.65
Скачать статью

 

Е. В. Феськова, Д. А. Палишкина, О. С. Игнатовец, В. Н. Леонтьев

КОМПОНЕНТНЫЙ СОСТАВ И АНТИМИКРОБНАЯ АКТИВНОСТЬ ЭФИРНОГО МАСЛА РАСТЕНИЙ РОДА SATUREJA, КУЛЬТИВИРУЕМЫХ В РЕСПУБЛИКЕ БЕЛАРУСЬ

Белорусский государственный технологический университет, г. Минск, Республика Беларусь

Satureja – род ароматических растений семейства Яснотковые, отличающийся разнообразным химическим составом, благодаря которому определяются его фармакологические и фитохимические свойства. В настоящей работе представлены результаты определения компонентного состава эфирного масла, выделенного из надземной части Satureja montana L. (чабер горный) и Satureja hortensis L. (чабер садовый) из коллекции Центрального ботанического сада НАН Беларуси. В изученных образцах идентифицированы 22 компонента эфирного масла, основными из которых для Satureja montana L. являются карвакрол (57,56%), п-цимен (18,68%), для Satureja hortensis L. – карвакрол (44,41%), γ-терпинен (27,82%), п-цимен (14,64%). Около 3% β-пинена обнаружено в эфирном масле Satureja montana L. Также в работе проведен сравнительный анализ компонентного состава эфирного масла растений рода Satureja, культивируемых в Центральном ботаническом саду НАН Беларуси и других агроклиматических зонах. Установлена антимикробная активность эфирного масла изучаемых видов в отношении таких санитарно-показательных микроорганизмов, как Salmonella alony, Bacillus subtilis, Clostridium sp., Escherichia coli Hfr H2, Candida albicans. Результаты исследований подтверждают перспективность использования растений рода Satureja для разработки фитопрепаратов с противомикробными свойствами.

Ключевые слова: чабер горный, чабер садовый, эфирное масло, карвакрол, п-цимен, γ-терпинен, антимикробная активность.

SUMMARY

V. Feskova, D. A. Palishkina, V. N. Leontiev, O. S. Ignatovets

ESSENTIAL OIL COMPOSITION AND ITS ANTIMICROBIAL ACTIVITY OF THE SATUREA GENUS PLANTS CULTIVATED IN THE REPUBLIC OF BELARUS

Satureja is the genus of aromatic plants of the Lamiaceae family characterized by diverse chemical composition due to which its pharmacological and phytochemical properties are determined. This paper presents the results of determination of essential oil composition released from the overground parts of Satureja montana L. (winter savory) and Satureja hortensis L. (garden savory) from the collection of the Central Botanical Garden of the National Academy of Sciences of Belarus. 22 essential oil components the main of which for Satureja montana L. are carvacrol (57.56%) and p-cymene (18.68%), for Satureja hortensis L. – carvacrol (44.41%), γ-terpinene (27.82%), p-cymene (14.64%) were identified in the samples studied. About 3% of β-pinene was found in essential oil of Satureja montana L. Сomparative analysis of the essential oil component composition in the Satureja genus plants cultivated in the Central Botanical Garden of the National Academy of Sciences of Belarus and in other agroclimatic zones was also carried out. Antimicrobial activity of essential oil in the studied species in relation to such sanitary indicating microorganisms such as Salmonella alony, Bacillus subtilis, Clostridium sp., Escherichia coli Hfr H2, Candida albicans was specified. The research results confirm the prospects of using plants of the genus Satureja for the development of phytopreparations with antimicrobial properties.

Keywords: winter savory, garden savory, essential oil, carvacrol, p-cymene, γ-terpinene, antimicrobial activity.

 

ЛИТЕРАТУРА

  1. Государственная фармакопея Республики Беларусь (ГФ РБ II) : разраб. на основе Европ. Фармакопеи : в 2 т. : введ. в действие с 1 июля 2016 г. приказом М-ва здравоохранения Респ. Беларусь от 31.03.2016 г. № 270. – Т. 2: Контроль качества субстанций для фармацевтического использования и лекарственного растительного сырья / М-во здравоохранения Респ. Беларусь, Центр экспертиз и испытаний в здравоохранении ; [под общ. ред. С. И. Марченко]. – Молодечно: Победа, 2016. – 1368 с.
  2. Phytochemical constituents of Lamiaceae family / H. Bendif, Y. B. Miri, N. Souilah [et al.] // Rhazes: Green and Applied Chemistry. – 2021. – Vol. 11, N 2. – P. 71–88. – DOI: 10.48419/IMIST.PRSM/rhazes-v11.25070. – URL: https://revues.imist.ma/index.php/RHAZES/article/view/25070 (date of access: 23.03.2024).
  3. Lamiaceae Martinov // Plants of the Wold Online: [website]. – URL: https://powo.science.kew.org/taxon/urn:lsid:ipni.org:names:30000097-2 (date of access: 23.03.2024).
  4. Bioactive Compounds and Aroma Profile of Some Lamiaceae Edible Flowers / I. Marchioni, B. Najar, B. Ruffoni [et al.] // Plants. – 2020. – Vol. 9, N 6. – DOI: 10.3390/plants9060691.
  5. Use of the Genus Satureja as Food Supplement: Possible Modulation of the Immune System via Intestinal Microbiota During SARS-CoV-2 Infection / A. Ezaouine, B. Nouadi, Y. Sbaoui [et al.] // Anti-infective agents. – 2021. – Vol. 20, N 3. – Р. 55–65. – DOI: 10.2174/2211352520666211222101244.
  6. Antiphytoviral Activity of Satureja montana L. ssp. variegata (Host) P. W. Ball Essential Oil and Phenol Compounds on CMV and TMV / V. Dunkiс, N. Bezic, E. Vuko, D. Cukrov // Molecules (Basel, Switzerland). – 2010. – Vol. 15, N 10. – Р. 6713–6721. – DOI:10.3390/molecules15106713.
  7. Phytochemical profile, comparative evaluation of Satureja montana alcoholic extract for antioxidants, anti-inflammatory and molecular docking studies / K. A. Abdelshafeek, A. F. Osman, S. M. Mouneir [et al.] // BMC complementary medicine and therapies. – 2023. – Vol. 23, N 1. – P. 108. – DOI: 10.1186/s12906-023-03913-0.
  8. Variability in Biological Activities of Satureja montana Subsp. montana and Subsp. variegata Based on Different Extraction Methods / M.Aсimoviс, O. Šovljanski, L. Pezo [et al.] // Antibiotics (Basel, Switzerland). – 2022. – Vol. 11, N 9. – P. 1235. – DOI: 10.3390/antibiotics11091235.
  9. Chemical composition, antimicrobial, antioxidative and anticholinesterase activity of Satureja Montana L. ssp montana essential oil / T. Mihajilov-Krstev, D. Radnovic, D. Kitic [et al.] // Central European journal of biology. – 2014. – Vol. 9, N 7. – Р. 668–677. – DOI: 10.2478/s11535-014-0298-x.
  10. A comparative study on the biological activity of essential oil and total hydro-alcoholic extract of Satureja hortensis L. / R. A. Popovici, D. Vaduva, I. Pinzaru [et al.] // Experimental and therapeutic medicine. – 2019. – Vol. 18, N 2. – Р. 932–942. – DOI: 10.3892/etm.2019.7635.
  11. Involvement of Cholinergic and Opioid System in γ-Terpinene-Mediated Antinociception / F. F. Passos, E. M. Lopes, J. M. de Araújo [et al.] // Evidence-based complementary and alternative medicine. – 2015. – Vol. 2015. – P. 1–9. – DOI: 10.1155/2015/829414.
  12. Żukowska, G. Properties and Applications of Essential Oils: A Review / G. Żukowska, Z. Durczyńska // Journal of ecological engineering. – 2024. – Vol. 25, N 2. – P. 333–340. – DOI: 10.12911/22998993/177404.
  13. Antiviral activity of some plant oils against herpes simplex virus type 1 in Vero cell culture / S. Gavanji, S. S. Sayedipour, B. Larki, A. Bakhtari // Journal of acute medicine. – 2015. – Vol. 5, N 3. – Р. 62–68. – DOI: 10.1016/j.jacme.2015.07.001.
  14. Khajeh, M. Optimization of process variables for essential oil components from Satureja hortensis by supercritical fluid extraction using Box-Behnken experimental design / M. Khajeh // The Journal of supercritical fluids. – 2011. – Vol. 55, N 3. – Р. 944–948. – DOI: 10.1016/j.supflu.2010.10.017.
  15. Mahboubi, M. Chemical composition and antimicrobial activity of Satureja hortensis and Trachyspermum copticum essential oil / M. Mahboubi, N. Kazempour // Iranian journal of microbiology. – 2011. – Vol. 3, N 4. – Р. 194–200.
  16. Effects of fertilizer on yield, essential oil composition, total phenolic content and antioxidant activity in Satureja hortensis L. (Lamiaceae) cultivated in Iran / A. Alizadeh, M. Khoshkhui, K. Javidnia [et al.] // Journal of medicinal plant research. – 2010. – Vol. 4, N 1. – P. 33–40. – DOI: 10.5897/JMPR09.361.
  17. Antispasmodic and anti-diarrhoeal effect of Satureja hortensis L. essential oil / V. Hajhashemi, H. Sadraei, A. R. Ghannadi, M. Mohseni // Journal of ethnopharmacology. – 2000. – Vol. 71, N 1/2. – P. 187–192. – DOI: 10.1016/s0378-8741(99)00209-3.
  18. Binary and Tertiary Mixtures of Satureja hortensis and Origanum vulgare Essential Oils as Potent Antimicrobial Agents Against Helicobacter pylori / M. Lesjak, N. Simin, D. Orcic [et al.] // Phytotherapy research. – 2015. – Vol. 30, N 3. – P. 476–484. – DOI: 10.1002/ptr.5552.
  19. Abou Baker, D. H. The invitro cytotoxicity, antioxidant and antibacterial potential of Satureja hortensis L. essential oil cultivated in Egypt / D. H. Abou Baker, M. Al-Moghazy, A. A. ElSayed // Bioorganic chemistry. – 2020. – Vol. 95. – DOI: 10.1016/j.bioorg.2019.103559.
  20. Screening of antimicrobial activity of essential oil and methanol extract of Satureja hortensis on foodborne bacteria and fungi / A. Adiguzel, H. Ozer, H. Kilic, B. Cetin // Czech journal of food sciences. – 2007. – Vol. 25, N 2. – P. 81–89. – DOI: 10.17221/753-CJFS.
  21. Antimicrobial activity of Pistacia lentiscus and Satureja montana essential oils against Listeria monocytogenes CECT 935 using laboratory media: Efficacy and synergistic potential in minced beef / D. Djenane, J.Yangüela, L.Montañés [et al.] // Food control. – 2011. – Vol. 22, N 7. – Р. 1046–1053. – DOI: 10.1016/j.foodcont.2010.12.015.
  22. Essential oil Composition and Internal Transcribed Spacer (ITS) Sequence Variability of Four South-Croatian Satureja Species (Lamiaceae) / N. Beziс, I. Samanic, V. Dunkic [et al.] // Molecules (Basel, Switzerland). – 2009. – Vol. 14, N 3. – Р. 925–938. – DOI: 10.3390/molecules14030925.
  23. Influence of pre-treatments on yield, chemical composition and antioxidant activity of Satureja montana extracts obtained by supercritical carbon dioxide / S. Vidoviс, Z. Zekovic, B. Marosanovic [et al.] // The Journal of supercritical fluids. – 2014. – Vol. 95. – Р. 468–473. – DOI: 10.1016/j.supflu.2014.10.019.
  24. Chemical composition and antioxidant and antimicrobial activity of two Satureja essential oils / S. Сavar, M. Maksimovic,
    M. E. Solic [et al.] // Food chemistry. – 2008. – Vol. 111, N 3. – Р. 648–653. – DOI: 10.1016/j.foodchem.2008.04.033.
  25. Satureja montana L. essential oil and its antimicrobial activity alone or in combination with gentamicin / L. Vitanza, A. Maccelli, M. Marazzato [et al.] // Microbial pathogenesis. – 2019. – Vol. 126. – Р. 323–331. – DOI: 10.1016/j.micpath.2018.11.025.
  26. Chemical composition and antimicrobial activity of Satureja montana byproducts essential oils / J. D. C. Santos, E. Coelho, R. Silva [et al.] // Industrial crops and products. – 2019. – Vol. 137. – Р. 541–548. – DOI: 10.1016/j.indcrop.2019.05.058.
  27. Composition and biocidal properties of essential oil from pre-domesticated Spanish Satureja Montana / J. Navarro-Rocha, M. F. Andres, C. E. Diaz [et al.] // Industrial crops and products. – 2019. – Vol. 145, N 3. – DOI: 10.1016/j.indcrop.2019.111958.
  28. Агроклиматическое зонирование территории Беларуси с учетом изменения климата. – URL: https://minpriroda.gov.by/uploads/files/Agroklimaticheskoe-zonirovanie-Respubliki-Belarus.pdf (дата обращения: 10.06.2024).
  29. Update on monoterpenes as antimicrobial agents: A particular focus on p-cymene / A. Marchese, C. R. Arciola, R. Barbieri [et al.] // Materials (Basel, Switzerland). – 2017. – Vol. 10, N 8. – Р. 947–962. – DOI: 10.3390/ma10080947.
  30. Carvacrol and human health: A comprehensive review / M. Sharifi-Rad, E. M. Varoni, M. Iriti [et al.] // Phytotherapy research. – 2018. – Vol. 32, N 9. – Р. 1675–1687. – DOI: 10.1002/ptr.6103.
  31. Baser, K. H. Biological and pharmacological activities of carvacrol and carvacrol bearing essential oils / K. H. Baser // Current pharmaceutical design. – 2008. – Vol. 14, N 29. – Р. 3106–3119. – DOI: 10.2174/138161208786404227.
  32. Gamma-Terpinene Modulation of LPS-Stimulated Macrophages is Dependent on the PGE2/IL-10 Axis / T. R. Ramalho, L. R. Filgueiras, M. T. Racheco de Oliveira [et al.] // Planta medica. – 2016. – Vol. 82, N 15. – P. 1341–1345. – DOI: 10.1055/s-0042-107799.
  33. Growth inhibitory, immunosuppressive, cytotoxic, and genotoxic effects of γ-terpinene on Zeugodacus cucurbitae (Coquillett) (Diptera: Tephritidae) / Diksha, S. Singh, E. Mahajan, S. K. Sohal // Scientific reports. – 2023. – Vol. 13, N 1. – P. 16472. – DOI: 10.1038/s41598-023-43499-8.

REFERENCES

  1. Ministerstvo zdravookhraneniia Respubliki Belarus’, Tsentr ekspertiz i ispytanii v zdravookhranenii. State Pharmacopoeia of the Republic of Belarus: v 2 t. Т. 2, Quality control of substances for pharmaceutical use and medicinal herbal raw materials. Marchenko SI, redactor. Molodechno, RB: Pobeda; 2016. 1368 s. (In Russ.)
  2. Bendif H, Miri YB, Souilah N, Benabdallah A, Miara MD. Phytochemical constituents of Lamiaceae family. Rhazes: Green and Applied Chemistry. 2021;11(2):71–88. doi: 10.48419/IMIST.PRSM/rhazes-v11.25070. URL: https://revues.imist.ma/index.php/RHAZES/article/view/25070 (date of access 2024 March 23)
  3. Lamiaceae Martinov. Plants of the Wold Online: [website]. URL: https://powo.science.kew.org/taxon/urn:lsid:ipni.org:names:30000097-2 (date of access 2024 March 23)
  4. Marchioni I, Najar B, Ruffoni B, Copetta A, Pistelli L, Pistelli L. Bioactive Compounds and Aroma Profile of Some Lamiaceae Edible Flowers. Plants. 2020;9(6). doi: 10.3390/plants9060691
  5. Ezaouine A, Nouadi B, Sbaoui Y, El Messal M, Chegdani F, Bennis F. Use of the Genus Satureja as Food Supplement: Possible Modulation of the Immune System via Intestinal Microbiota During SARS-CoV-2 Infection. Antiinfect Agents. 2021;20(3):55–65. doi: 10.2174/2211352520666211222101244
  6. Dunkiс V, Bezic N, Vuko E, Cukrov E. Antiphytoviral Activity of Satureja montana L. ssp. variegata (Host) P. W. Ball Essential Oil and Phenol Compounds on CMV and TMV. Molecules. 2010;15(10):6713–21. doi:10.3390/molecules15106713
  7. Abdelshafeek KA, Osman AF, Mouneir SM, Elhenawy AA, Abdallah WE. Phytochemical profile, comparative evaluation of Satureja montana alcoholic extract for antioxidants, anti-inflammatory and molecular docking studies. BMC Complement Med Ther. 2023;23(1):108. doi: 10.1186/s12906-023-03913-0
  8. Aсimoviс M, Šovljanski O, Pezo L, Travičić V, Tomić A, Zheljazkov VD, et al. Variability in Biological Activities of Satureja montana Subsp. montana and Subsp. variegata Based on Different Extraction Methods. Antibiotics (Basel). 2022;11(9):1235. doi: 10.3390/antibiotics11091235
  9. Mihajilov-Krstev T, Radnovic D, Kitic D, Stankov-Jovanovic V, Mitic V, Stojanovic-Radic Z, et al. Chemical composition, antimicrobial, antioxidative and anticholinesterase activity of Satureja Montana L. ssp montana essential oil. Cent Eur J Biol. 2014;9(7):668–77. doi: 10.2478/s11535-014-0298-x
  10. Popovici RA, Vaduva D, Pinzaru I, Dehelean CA, Farcas CG, Coricovac D, et al. A comparative study on the biological activity of essential oil and total hydro-alcoholic extract of Satureja hortensis L. Exp Ther Med. 2019;18(2):932–42. doi: 10.3892/etm.2019.7635
  11. Passos FF, Lopes EM, de Araújo JM, de Sousa DP, Veras LM, Leite JR, et al. Involvement of Cholinergic and Opioid System in γ-Terpinene-Mediated Antinociception. Evid Based Complement Alternat Med. 2015;2015:1–9. doi: 10.1155/2015/829414
  12. Żukowska G, Durczyńska Z. Properties and Applications of Essential Oils: A Review. J of Ecological Engineering. 2024;25(2):333–40. doi: 10.12911/22998993/177404
  13. Gavanji S, Sayedipour SS, Larki B, Bakhtari A. Antiviral activity of some plant oils against herpes simplex virus type 1 in Vero cell culture. J Acute Med. 2015;5(3):62–8. doi: 10.1016/j.jacme.2015.07.001
  14. Khajeh M. Optimization of process variables for essential oil components from Satureja hortensis by supercritical fluid extraction using Box-Behnken experimental design. J Supercrit Fluids. 2011;55(3):944–8. doi: 10.1016/j.supflu.2010.10.017
  15. Mahboubi M, Kazempour N. Chemical composition and antimicrobial activity of Satureja hortensis and Trachyspermum copticum essential oil. Iran J Microbiol. 2011;3(4):194–200
  16. Alizadeh A, Khoshkhui M, Javidnia K, Firuzi O, Tafazoli E, Khalighi A. Effects of fertilizer on yield, essential oil composition, total phenolic content and antioxidant activity in Satureja hortensis L. (Lamiaceae) cultivated in Iran. J Med Plant Res. 2010;4(1):33–40. doi: 10.5897/JMPR09.361
  17. Hajhashemi V, Sadraei H, Ghannadi AR, Mohseni M. Antispasmodic and anti-diarrhoeal effect of Satureja hortensis L. essential oil. J Ethnopharmacol. 2000;71(1-2):187–92. doi: 10.1016/s0378-8741(99)00209-3
  18. Lesjak M, Simin N, Orcic D, Franciskovic M, Knezevic P, Beara I, et al. Binary and Tertiary Mixtures of Satureja hortensis and Origanum vulgare Essential Oils as Potent Antimicrobial Agents Against Helicobacter pylori. Phytother Res. 2016;30(3):476–84. doi: 10.1002/ptr.5552
  19. Abou Baker DH, Al-Moghazy M, ElSayed AA. The invitro cytotoxicity, antioxidant and anti-bacterial potential of Satureja hortensis L. essential oil cultivated in Egypt. Bioorg Chem. 2020;95. doi: 10.1016/j.bioorg.2019.103559
  20. Adiguzel A, Ozer H, Kilic H, Cetin B. Screening of antimicrobial activity of essential oil and methanol extract of Satureja hortensis on foodborne bacteria and fungi. Czech J Food Sci. 2007;25(2):81–9. doi: 10.17221/753-CJFS
  21. Djenane D, Yangüela J, Montañés L, Djerbal M, Roncales P. Antimicrobial activity of Pistacia lentiscus and Satureja montana essential oils against Listeria monocytogenes CECT 935 using laboratory media: Efficacy and synergistic potential in minced beef. Food Control. 2011;22(7):1046–53. doi: 10.1016/j.foodcont.2010.12.015
  22. Beziс N, Samanic I, Dunkic V, Besendorfer V, Puizina J. Essential oil Composition and Internal Transcribed Spacer (ITS) Sequence Variability of Four South-Croatian Satureja Species (Lamiaceae). Molecules. 2009;14(3):925–38. doi: 10.3390/molecules14030925
  23. Vidoviс S, Zekovic Z, Marosanovic B, Todorovic MP, Vladic J. Influence of pre-treatments on yield, chemical composition and antioxidant activity of Satureja montana extracts obtained by supercritical carbon dioxide. J Supercrit Fluids. 2014;95:468–73. doi: 10.1016/j.supflu.2014.10.019
  24. Сavar S, Maksimovic M, Solic ME, Jerkovic-Mujkic A, Besta R. Chemical composition and antioxidant and antimicrobial
    activity of two Satureja essential oils. Food Chem. 2008;111(3):648–53. doi: 10.1016/j.foodchem.2008.04.033
  25. Vitanza L, Maccelli A, Marazzato M, Scazzocchio F, Comanducci A, Fornarini S, et al. Satureja montana L. essential oil and its antimicrobial activity alone or in combination with gentamicin. Microb Pathog. 2019;126:323–31. doi: 10.1016/j.micpath.2018.11.025
  26. Santos JDC, Coelho E, Silva R, Rassos CP, Teixeira P, Henriques I, et al. Chemical composition and antimicrobial activity of Satureja montana byproducts essential oils. Ind Crops Prod. 2019;137:541–8. doi: 10.1016/j.indcrop.2019.05.058
  27. Navarro-Rocha J, Andres MF, Diaz CE, Burillo J, Gonzalez-Coloma A. Composition and biocidal properties of essential oil from pre-domesticated Spanish Satureja Montana. Ind Crops Prod. 2019;145(3). doi: 10.1016/j.indcrop.2019.111958
  28. Agroclimatic zoning of the territory of Belarus taking into account climate change. URL: https://minpriroda.gov.by/uploads/files/Agroklimaticheskoe-zonirovanie-Respubliki-Belarus.pdf (data obrashcheniia 2024 Iiun’ 10). (In Russ.)
  29. Marchese A, Arciola CR, Barbieri R, Silva AS, Nabavi SF, Tsetegho Sokeng AJ, et al. Update on monoterpenes as antimicrobial agents: A particular focus on p-cymene. Materials (Basel). 2017;10(8):947–62. doi: 10.3390/ma10080947
  30. Sharifi-Rad M, Varoni EM, Iriti M, Martorell M, Setzer WN, Del Mar Contreras M, et al. Carvacrol and human health: A comprehensive review. Phytother Res. 2018;32(9):1675–87. doi: 10.1002/ptr.6103
  31. Baser KH. Biological and pharmacological activities of carvacrol and carvacrol bearing essential oils. Currt Pharm Des. 2008;14(29):3106–19. doi: 10.2174/138161208786404227
  32. Ramalho TR, Filgueiras LR, Racheco de Oliveira MT, Lima AL, Bezerra-Santos CR, Jancar S, et al. Gamma-Terpinene Modulation of LPS-Stimulated Macrophages is Dependent on the PGE2/IL-10 Axis. Planta Med. 2016;82(15):1341–5. doi: 10.1055/s-0042-107799
  33. Diksha, Singh S, Mahajan E, Sohal SK. Growth inhibitory, immunosuppressive, cytotoxic, and genotoxic effects of γ-terpinene on Zeugodacus cucurbitae (Coquillett) (Diptera: Tephritidae). Sci Rep. 2023;13(1):16472. doi: 10.1038/s41598-023-43499-8

 

Адрес для корреспонденции:

220006, Республика Беларусь,

г. Минск, ул. Свердлова, 13а,

Учреждение образования «Белорусский государственный технологический университет»,

кафедра биотехнологии,

e-mail: Адрес электронной почты защищен от спам-ботов. Для просмотра адреса в вашем браузере должен быть включен Javascript.,

Феськова Е. В.

Поступила 19.07.2024 г.