POLYAMINOPHENOL MELANIZATION IN THE PROCESS OF PARACETAMOL BIOTRANSFORMATION BY RHODOCOCCUSRUBER ИЭГМ 77

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Михаил/Mikhail Юрьевич/Yur'evich Коротаев/Korotaev
Елена/Elena Владимировна/Vladimirovna Вихарева/Vikhareva
Ирина/Irina Борисовна/Borisovna Ившина/Ivshina

Abstract

Precipitate formed in the process of paracetamol biotransformation by Rhodococcus ruber IEGM 77 was found to include indole and benzofuran ring fragments using 13C NMR spectroscopy and chromatography-mass-spectrometry methods. Mechanisms of the formation of conjugated indole and benzofuran cyclic systems resulting from the fermentative condensation of polyaminophenols contained in the precipitate chemical structure have been proposed. According to our data, polyaminophenol molecules and indole and benzofuran fragments in chemical structure of melanin-like compounds contain symmetric ("Sym") and asymmetric ("Asym") sites comprising aromatic and quinoid rings with equivalent substituents in para- and ortho- positions, respectively. Originally substantiated possibility of enzyme melanization of polyaminophenols by R. ruber IEGM 77 cells is viewed from the perspective of humification hypothesis.

Article Details

How to Cite
Коротаев/Korotaev М. Ю., Вихарева/Vikhareva Е. В., & Ившина/Ivshina И. Б. (2018). POLYAMINOPHENOL MELANIZATION IN THE PROCESS OF PARACETAMOL BIOTRANSFORMATION BY RHODOCOCCUSRUBER ИЭГМ 77. Bulletin of Perm University. Biology, (2), 166–170. Retrieved from https://press.psu.ru/index.php/bio/article/view/1804
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

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

Doctor of biology, Corresponding member of RAS, Head of Alkanotrophic Microorganism laboratory;Professor of the department Microbiology and Immunology

References

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References

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 biodégradation by Rhodococcus ruber IEGM 77]. Fundamental'nye issledovaniya (Moscow). N. 2 (2015): pp. 5850-5854. (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.).

Bosetto M., Arfaioli P., Pantani O.L., Ristori G.G. Study of the humic-like compounds formed from L-tyrosine on homoionic clays. Clays Minerals. V. 32 (1997): pp. 341-349.

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

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

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

Subianto S. Electrochemical Synthesis of Melanin-Like Polyindolequinone. Thesis of dissertation. Brisbane St Lucia: The University of Queensland, 2006. 197 p.

Thorn K.A., Mikita M.A. Ammonia fixation by humic substances: a nitrogen-15 and carbon-13 NMR study. The Science of the Total Environment. V. 113 (1992): pp. 67-87.

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 3687-3698.

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