PHYTOREGULATING ACTION OF BACTERIAL PARACETAMOL DEGRADATION PRODUCTS

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Михаил/Mikhail Юрьевич/Yur'evich Коротаев/Korotaev
Елена/Elena Владимировна/Vladimirovna Вихарева/Vikhareva
Валентина/Valentina Дмитриевна/Dmitrievna Белоногова/Belonogova
Ирина/Irina Борисовна/Borisovna Ившина/Ivshina

Abstract

Products of bacterial paracetamol degradation by Rhodococcus ruber IEGM 77 cells were shown to be humic-like substances. According to our data, the molecules of the products of bacterial paracetamol deg-radation comprise “symmetric” and “asymmetric” sites, including aminophenol, phenoxazine, indole and benzofuran fragments. The chemical structures of these fragments are based on aromatic and quinoid rings with equivalent substituents, i.e. phenol hydroxyl and nitrogen-containing functional groups, in para- (“symmetric”) and meta- (“asymmetric”) positions. The products of bacterial paracetamol degrada-tion were found to produce a phytoregulating action on seed germination of soft wheat Triticum aestivum L. due to the influence of “symmetric” and “asymmetric” molecular sites on the functional peroxidase ac-tivity. It was experimentally proved that the phytostimulating effect depends on the plant growth phase and concentrations of substances contained in water extracts from products of bacterial paracetamol deg-radation.

Article Details

How to Cite
Коротаев/Korotaev М. Ю., Вихарева/Vikhareva Е. В., Белоногова/Belonogova В. Д., & Ившина/Ivshina И. Б. (2018). PHYTOREGULATING ACTION OF BACTERIAL PARACETAMOL DEGRADATION PRODUCTS. Bulletin of Perm University. Biology, (1), 60–69. Retrieved from https://press.psu.ru/index.php/bio/article/view/1837
Section
Микробиология
Author Biographies

Михаил/Mikhail Юрьевич/Yur'evich Коротаев/Korotaev, Perm State Pharmaceutical Academy

Analytical Chemistry department

Елена/Elena Владимировна/Vladimirovna Вихарева/Vikhareva, Perm State Pharmaceutical Academy

Doctor of pharmacy, Professor, Head of Analytical Chemistry department

Валентина/Valentina Дмитриевна/Dmitrievna Белоногова/Belonogova, Perm State Pharmaceutical Academy

Doctor of pharmacy, Professor, Head of Pharmacognosy with botany course department

Ирина/Irina Борисовна/Borisovna Ившина/Ivshina, Institute of Ecology and Genetics of Microorganism UB RAS; Perm State University

Doctor of Microbiology, Academician of the Russian Academy of Sciences, Head of Alkanotrophic Microorganism Laboratory;Professor of the department Microbiology and Immunology

References

Бондарчук С.С. Основы практический биостатистики. Томск: Изд-во ТГПУ, 2010. 72 с.

Воскресенская О.Л. и др. Большой практикум по биоэкологии. Ч. 1: учеб. пособие. Йошкар-Ола, 2006. 107 с.

Газарян И.Г. и др. Особенности структуры и механизма действия пероксидаз растений // Успехи биологической химии. 2006. Т. 46. С. 303-322.

Гладков О.А. и др. Способ получения солей гуминовых кислот: Евраз. пат. № 006824. Бюл. № 2. 2006. 6 с.

Давидянц Э.С. Влияние обработки семян тритерпеновыми гликозидами на активность пероксидазы, ИУК-оксидазы и полифенолоксидазы в проростках пшеницы // Химия растительного сырья. 2013. № 4. С. 225-231.

Ившина И.Б. и др. Алканотрофные родококки как катализаторы процесса биодеструкции не пригодных к использованию лекарственных средств // Прикладная биохимия и микробиология. 2006 . Т. 42, № 4. С. 443-447.

Коротаев М.Ю., Вихарева Е.В., Ившина И.Б. Меланизация полиаминофенолов в процессе биотрансформации парацетамола клетками Rhodococcus ruber ИЭГМ 77 // Вестник Пермского университета. Сер. Биология, 2016. Вып. 2. С. 166-170.

Коротаев М.Ю. и др. Определение средней молекулярной массы нерастворимых продуктов биодеструкции парацетамола клетками Rhodococ-cus ruber ИЭГМ 77 // Фундаментальные исследования. 2015. № 2, Ч. 26. С. 5850-5854.

Коротаев М.Ю. и др. Химическая структура осадка, образующегося в процессе биотрансформации парацетамола клетками Rhodococcus ruber ИЭГМ 77 // Биофармацевтический журнал. 2016. Т. 8, № 1. С. 13-19.

Коротаев М.Ю., Солодянкина Е.С., Шибанова Е.Н. Определение удельного показателя поглощения водорастворимых продуктов бактериальной деструкции парацетамола // Научный альманах. 2015. № 12-2(14). С. 372-375.

Орлов Д.С. Гумусовые кислоты почв и общая теория гумификации. М.: Изд-во МГУ, 1990. 325 с.

Орлов Д.С. Гуминовые вещества в биосфере // Со-росовский образовательный журнал. 1997. № 2. С. 56-63.

Рогожин В.В. Пероксидаза как компонент антиоксидантной системы живых организмов. СПб.: ГИОРД, 2004. 240 с.

Рогожин В.В., Рогожина Т.В. Роль индолил-3-уксусной кислоты в реакциях окисления быстро и медленно окисляемых субстратов пероксидаз // Вестник Московского университета. Сер. 2. Химия. 2004. Т. 45. № 6. С. 423-428.

Рогожин В.В., Рогожина Т.В. Физиолого-биохимические механизмы прорастания зерновок пшеницы // Вестник Алтайского государственного аграрного университета. 2011. № 8 (82). С. 17-21.

Сильверстейн Р., Басслер Г., Моррил Т. Спектрометрическая идентификация органических соединений / под ред. А.А. Мальцева. М.: Мир, 1977. 592 с.

Христин М.С., Ковальченко Ю.М., Алкацева Н.И. Препарат для стимуляции проращивания семян и повышения устойчивости проростков к дефициту влаги и способ его получения: Пат. РФ 2337543. Бюл. № 31. 2008. 13 с.

Arora P.K. Bacterial degradation of monocyclic aromatic amines // Frontiers in Microbiology. 2015. Vol. 6, № 820. URL: http://dx.doi.org/10.3389/ fmicb.2015.00820

Buffle J.A.E. The humic substances in water and their interactions with mineral ions ("Les substances humiques et leurs interactions avec les ions mineraux"). Conference proceedings de la commission d' hydrologie appliquee de A.G.H.T.M. L' Universite d' Orsay, 1977. P. 3-10.

Catalogue of Strains of Regional Specialized Collection of Alkanotrophic Microorganisms. 2016. URL: http://www.iegm.ru/iegmcol/strains/index.html (дата обращения: 26.12.2016).

de Gusseme B. et al. Degradation of acetaminophen by Delftia tsuruhatensis and Pseudomonas aeruginosa in a membrane bioreactor // Water Research. 2011. Vol. 45. P. 1829-1837.

Gopalasamy T. et al. Poly Meta-Aminophenol: chemical synthesis, characterization and AC impedance study // Journal of Polymers. 2014. Vol. 2014. The mode of access: http://dx.doi.org/10.1155/2014/827043

Kawano T. Roles of the reactive oxygen species-generating peroxidase reactions in plant defense and growth induction // Plant Cell Reports. 2003. Vol. 21, № 9. P. 829-837.

Nardi S. et al. Physiological effects of humic substances on higher plants // Soil Biology and Biochemistry. 2002. Vol. 34. P. 1527-1536.

Savitsky P.A. et al. Oxidation of indole-3-acetic acid by dioxygen catalysed by plant peroxidases: specificity for the enzyme structure // Biochemical Journal. 1999. Vol. 340, № 3. P. 579-583.

Stevenson F.J. Humus Chemistry: Genesis, Composition, Reactions. N. Y.: John Wiley & Sons, 1994. 512 p.

Takenaka S. et al. The metabolic pathway of 4-aminophenol in Burkholderia sp. strain AK-5 differs from that of aniline and aniline with C-4 sub-stituents // Applied and Environmental Microbiology. 2003. Vol. 69, № 9. P. 5410-5413.

Warhurst A.M., Fewson C.A. Biotransformations catalyzed by the genus Rhodococcus // Critical Reviews in Biotechnology. 1994. Vol. 14, № 1. P. 29-73.

Wu S., Zhang L., Chen J. Paracetamol in the environment and its degradation by microorganisms // Applied Microbiology Biotechnology. 2012. Vol. 96. P. 875-884.

Zhang L. et al. Degradation of paracetamol by pure bacterial cultures and their microbial consortium // Applied Microbiology and Biotechnology. 2013. Vol. 97, № 8. P. 3687-3698.

References

Bondarchuk S.S. Osnovy prakticheskoy biostatistiki [Fundamentals of practical biostatistics]. Tomsk: TGPU Publ., 2010. 72 p. (In Russ.).

Voskresenskaya O.L., Alyabysheva E.A., Polovnikova M.G. (2006) Bol'shoi praktikum po bioekologii [Large Manual on bioecology]. Ch. 1. Ioshkar-Ola: Mariisk. Gos. Univ. Publ. 107 p. (In Russ.).

Gazaryan I. G., Khushpul'yan D. M., Tishkov V. I. [Features of the structure and mode of action of peroxidases in plants]. Uspekhi biologicheskoy khimii. V. 46 (2006): pp. 303-322. (In Russ.).

Gkadkov O.A., Poloskin R.B., Polyakov Yu.Yu., Sokolova I.V., Sorokin N.I., Glebov A.V. Sposob polucheniya soley guminovykh kislot [Method for producing humic acid salts]. Eurasian patent N. 006824. Bull., 2006, N. 2. 6 p. (In Russ.).

Davidyants E.S. [Effect of the treatment of seeds of triterpenoid glycosides on peroxidase, IAA-oxidase, polyphenoloxidase activities in wheat seedlings]. Khimiya rastitel'nogo syr'ya (Barnaul). N. 4 (2013): pp. 225-231. (In Russ.).

Korotaev M.Yu., Rychkova M.I., Vikhareva E.V., Ivshina I.B. [Polyaminophenol melanization in the process of paracetamol biotransformation by Rhodococcus ruber H3rM 77]. Vestnik Perm-skogo universiteta. Ser. Biologiya (Perm). V. 2 (2016): pp. 166-170. (In Russ.).

Korotaev M.Yu., Polyakova E.B., Vikhareva E.V., Rychkova M.I. [Chemical structure and biological activity of precipitate formed in the process of paracetamol biotransformation with Rhodococcus ruber IEGM 77]. Biofarmatsevticheskiy zhurnal (Moscow). V. 8, N. 1 (2016): pp. 13-19. (In Russ.).

Korotaev M.Yu., Rychkova M.I., Vikhareva E.V., Ivshina I.B. [Determination of the mean molecular weights of insoluble products formed during paracetamol biodegradation by Rhodococcus ru-ber IEGM 77]. Fundamental'nye issledovaniya (Moscow). N. 2 (2015): pp. 5850-5854. (In Russ.).

Korotaev M.Yu., Solodyankina E.S., Shibanova E.N. [Determination of paracetamol bacterial degradation water-soluble products mass extinction coefficient]. Nauchnyy al'manakh (Tambov). V. 12-2, N. 14 (2015): pp. 372-375. (In Russ.).

Orlov D.S. Humusovye kisloty pochv i obshchaya te-oriya gumifikatsii [Humic substances of soils and general theory of humification]. Moscow, MSU Publ., 1990. 325 p. (In Russ.).

Orlov D.S. [Humic substances in the biosphere] Sorosovskiy obrazovatel'nyy zhurnal (Moscow). N. 2 (1997): pp. 56-63. (In Russ.).

Khristin M.S., Koval'chenko Yu.M., Alkatseva N.I. Preparat dlya stimulyatsii prorashchivaniya semyan i povysheniya ustoychivosti prorostkov k defitsitu vlagi I sposob ego polucheniya [Agent for seed greensprouting stimulation and increasing sprout resistance to moisture deficiency, and method for its obtaining]. Russian patent N. 2337543. Bull., 2008, N. 31. 13 p. (In Russ.).

Rogozhin V.V. Peroksidaza kak komponent antioksi-dantnoy sistemy zhivykh organizmov [Peroxidase as a component of the antioxidant system of living organisms]. St. Petersburg: GIORD, 2004. 240 p. (In Russ.).

Rogozhin V.V., Rogozhina T.V. [Effect of indolyl-3-acetic acid in oxidation reaction of slowly and rapidly oxidizable peroxidaze substrates]. Vestnik Moskovskogo universiteta. Ser. 2. Khimiya (Moscow). V. 45, N. 6 (2004): pp. 423-428. (In Russ.).

Rogozhin V.V., Rogozhina T.V. [Physiological and biochemical mechanisms of germination of wheat grains]. Vestnik Altayskogo gosudarstvennogo agrarnogo universiteta (Barnaul). V. 8, N. 82 (2011): pp. 17-21. (In Russ.).

Silverstein R.M., Bassler G.C., Morrill T.C. Spektro-metricheskaya identifikatsiya organicheskih soedineniy [Spectrometric identification of organic compounds]. Edited by A.A. Mal'tsev. Moscow, Mir Publ., 1977. 592 p. (In Russ.).

Arora P.K. Bacterial degradation of monocyclic aromatic amines. Frontiers in Microbiology. V. 6, N. 820 (2015). The mode of access: http://dx.doi.org/10.3389/fmicb.2015.00820

Buffle J.A.E. The humic substances in water and their interactions with mineral ions ("Les substances humiques et leurs interactions avec les ions mineraux"). Conference proceedings de la commission d' hydrologie appliquee de A.G.H.T.M. L' Universite d' Orsay, 1977. p. 3-10.

de Gusseme B., Vanhaecke L., Verstraete W., Boon N. Degradation of acetaminophen by Delftia tsu-ruhatensis and Pseudomonas aeruginosa in a membrane bioreactor. Water Research. V. 45. (2011): pp. 1829-1837.

Gopalasamy T., Gopalswamy M., Gopichand M., Raj J. Poly Meta-Aminophenol: chemical synthesis, characterization and AC impedance study. Journal of Polymers. V. 2014 (2014). The mode of access: http://dx.doi.org/10.1155/2014/827043

Ivshina I.B., Rychkova M.I., Vikhareva E.V., Chek-ryshkina L.A., Mishenina I.I. Catalysis of the biodegradation of unusable medicines by alkanotro-phic rhodococci. Applied Biochemistry and Microbiology. V. 42, N. 4 (2006): pp. 392-395.

Kawano T. Roles of the reactive oxygen species-generating peroxidase reactions in plant defense and growth induction. Plant Cell Reports. V. 21, N. 9 (2003): pp. 829-837.

Nardi S., Pizzeghello D., Muscolo A., Vianello A. Physiological effects of humic substances on higher plants. Soil Biology and Biochemistry. V. 34 (2002): pp. 1527-1536.

Catalogue of Strains of Regional Specialized Collection of Alkanotrophic Microorganisms. 2010. The mode of access: http://www.iegm.ru/iegmcol/strains/index.html

Savitsky P.A., Gazaryan I.G., Tishkov V.I., La-grimini L.M. Oxidation of indole-3-acetic acid by dioxygen catalysed by plant peroxidases: specificity for the enzyme structure. Biochemical Journal. V. 340, N. 3 (1999): pp. 579-583.

Stevenson F.J. Humus Chemistry: Genesis, Composition, Reactions. New York: John Wiley & Sons, 1994. 512 p.

Takenaka S., Okugawa S., Kadowaki M., Murakami S., Aoki K. The metabolic pathway of 4-aminophenol in Burkholderia sp. strain AK-5 differs from that of aniline and aniline with C-4 substituents. Applied and Environmental Microbiology. V. 69, N. 9 (2003): pp. 5410-5413.

Warhurst A.M., Fewson C.A. Biotransformations catalyzed by the genus Rhodococcus. Critical Reviews in Biotechnology. V. 14, N. 1 (1994): pp. 29-73.

Wu S., Zhang L., Chen J. Paracetamol in the environment and its degradation by microorganisms Applied Microbiology Biotechnology. V. 96 (2012): pp. 875-884.

Zhang L., Hu J., Zhu R., Zhou Q., Chen J. Degradation of paracetamol by pure bacterial cultures and their microbial consortium. Applied Microbiology and Biotechnology. V. 97, N. 8 (2013): pp. 36873698

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