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Structure, 1H and 13C NMR spectra of the minor component from the antimicrobial complex produced by actinomycete Streptomyces roseoflavus (INA-Ac-5812)

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Abstract

The antibiotics INA-5812, produced by the strain INA-Ac-5812 of Streptomyces roseoflavus have pronounced antibacterial and chemotherapeutic activity and low value of acute toxicity. The minor component of the complex was isolated from the culture liquid by extraction with organic solvents and purified by chromatographic methods. Its structure was established by mass spectrometry and 1H and 13C NMR spectroscopy.

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References

  1. A. Luther, C. Bisang, D. Obrecht, Bioorg. Med. Chem., 2018, 26, 2850–2858; DOI: https://doi.org/10.1016/j.bmc.2017.08.006.

    Article  CAS  PubMed  Google Scholar 

  2. M. A. T. Blaskovich, K. A. Hansford, M. S. Butler, Z. Jia, A. E. Mark, M. A. Cooper, ACS Infect. Dis., 2018, 4, 715–735; DOI: https://doi.org/10.1021/acsinfecdis.7b00258.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. S. V. Bukharov, R. G. Tagasheva, I. A. Litvinov, E. V. Nikitina, E. C. Bulatova, A. R. Burilov, E. M. Gibadullina, Russ. Chem. Bull., 2022, 71, 508; DOI:https://doi.org/10.1007/s11172-022-3441-2.

    Article  CAS  Google Scholar 

  4. D. J. Newman, G. M. Cragg, J. Nat. Prod., 2016, 79, 629–661; DOI: https://doi.org/10.1021/acs.jnatprod.5b01055.

    Article  CAS  PubMed  Google Scholar 

  5. A. S. Shashkov, D. E. Tsvetkov, A. A. Grachev, O. A. Lapchinskaia, M. F. Lavrova-Balashova, V. I. Ponomarenko, G. S. Katrukha, N. E. Nifantiev, Nat. Prod. Commun., 2008, 3, 1631; DOI:https://doi.org/10.1177/1934578X0800301010.

    CAS  Google Scholar 

  6. A. S. Shashkov, D. E. Tsvetkov, O. A. Lapchinskaya, V. V. Kulyaeva, G. B. Fedorova, A. S. Trenin, E. G. Gladkikh, V. V. Pogozheva, M. O. Makarova, G. I. Orlova, G. S. Katrukha, N. E. Nifantiev, Russ. Chem. Bull., 2011, 60, 2412; DOI: https://doi.org/10.1007/s11172-011-0371-9.

    Article  CAS  Google Scholar 

  7. S. Somma, L. Gastaldo, A. Corti, Antimicrob. Agents Chemother., 1984, 26, 917–923; DOI: https://doi.org/10.1128/aac.26.6.917.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. R. Ciabatti, J. K. Kettenring, G. Winters, G. Tuan, L. Zerilli, B. Cavalleri, J. Antibiot., 1989, 42, 254–267; DOI: https://doi.org/10.7164/antibiotics.42.254.

    Article  CAS  Google Scholar 

  9. T. Neuhof, P. Schmieder, K. Preussel, R. Dieckmann, H. Pham, F. Bartl, H. von Döhren, J. Nat. Prod., 2005, 68, 695–700; DOI: https://doi.org/10.1021/np049671r.

    Article  CAS  PubMed  Google Scholar 

  10. S.-E. Lu, J. Novak, F. W. Austin, G. Gu, D. Ellis, M. Kirk, S. Wilson-Stanford, M. Tonelli, L. Smith, Biochemistry, 2009, 48, 8312–8321; DOI: https://doi.org/10.1021/BI900814C.

    Article  CAS  PubMed  Google Scholar 

  11. O. A. Lapchinskaya, G. S. Katrukha, L. P. Terekhova, V. V. Kulyaeva, E. G. Gladkikh, V. V. Pogozheva, G. B. Fedorova, E. P. Mirchik, M. O. Makarova, I. D. Treshchalin, E. B. Isakova, V. I. Ponomarenko, E. R. Pereverzeva, E. A. Abramova, N. L. Tokareva, Patent RF 2572341, 10.01.2016; Byul. Izobret. [Invention Bull.], 2016, No. 1 (in Russian).

  12. A. P. Tyurin, V. A. Alferova, A. S. Paramonov, M. V. Shuvalov, G. K. Kudryakova, E. A. Rogozhin, A. Y. Zherebker, V. A. Brylev, A. A. Chistov, A. A. Baranova, M. V. Biryukov, I. A. Ivanov, I. A. Prokhorenko, N. E. Grammatikova, T. V. Kravchenko, E. B. Isakova, E. P. Mirchink, E. G. Gladkikh, E. V. Svirshchevskaya, A. V. Mardanov, A. V. Beletsky, M.V. Kocharovskaya, V. V. Kulyaeva, A. S. Shashkov, D. E. Tsvetkov, N. E. Nifantiev, A. S. Apt, K. B. Majorov, S. S. Efimova, N. V. Ravin, E. N. Nikolaev, O. S. Ostroumova, G. S. Katrukha, O. A. Lapchinskaya, O. A. Dontsova, S. S. Terekhov, I. A. Osterman, Z. O. Shenkarev, V. A. Korshun, Angew. Chem., Int. Ed., 2021, 60, 18694–18703; DOI: https://doi.org/10.1002/anie.202104528.

    Article  CAS  Google Scholar 

  13. O. A. Lapchinskaya, G. S. Katrukha, E. G. Gladkikh, V. V. Kulyaeva, P. V. Coodan, A. P. Topolyan, V. A. Alferova, V. V. Pogozheva, M. A. Sukonnikov, E. A. Rogozhin, I. A. Prokhorenko, V. A. Brylev, A. M. Korolev, M. S. Slyundina, R. S. Borisov, M. V. Serebryakova, M. V. Shuvalov, A. L. Ksenofontov, L. G. Stoyanova, I. A. Osterman, A. A. Formanovsky, V. N. Tashlitsky, L. A. Baratova, A. V. Timofeeva, A. P. Tyurin, Russ. J. Bioorg. Chem., 2016, 42, 664–671; DOI: https://doi.org/10.1134/S1068162016060078.

    Article  CAS  Google Scholar 

  14. T. V. Kravchenko, A. A. Baranova, V. A. Alferova, A. P. Tyurin, V. A. Korshun, G. Kh. Kudryakova, I. A. Prokhorenko, N. E. Grammatikova, O. A. Lapchinskaya, E. G. Gladkikh, M. Yu. Lapchinskaya, V. V. Pogozheva, V. A. Filicheva, L. A. Kharitonova, G. I. Orlova, Z. O. Shenkarev, A. S. Paramonov, RF Patent 2762182, 16.12.2021; Byul. Izobret. [Invention Bull.], 2021, No. 35 (in Russian).

  15. D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, V. M. Menshov, D. V. Yashunsky, A. Ya. Yashin, Ya. I. Yashin, R. Kumar, V. K. Varshney, N. E. Nifantiev, J. Biol. Act. Prod. Nat., 2016, 6, 272; DOI: https://doi.org/10.1080/22311866.2016.1253502.

    CAS  Google Scholar 

  16. D. E. Tsvetkov, R. Kumar, A. S. Dmitrenok, Yu. E. Tsvetkov, A. O. Chizhov, A. Ya. Yashin, Ya. I. Yashin, V. K. Varshney, N. E. Nifantiev, Russ. Chem. Bull., 2019, 68, 1756; DOI: https://doi.org/10.1007/s11172-019-2621-1.

    Article  CAS  Google Scholar 

  17. D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, R. Kumar, V. K. Varshney, N. E. Nifantiev, Russ. J. Bioorg. Chem., 2021, 47, 103; DOI: https://doi.org/10.1134/S1068162021010271.

    Article  Google Scholar 

  18. D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, A. O. Chizhov, N. E. Nifantiev, Russ. Chem. Bull., 2019, 69, 2390; DOI: https://doi.org/10.1007/s11172-020-3050-x.

    Article  Google Scholar 

  19. D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, Yu. V. Tomilov, V. A. Dokichev, N. E. Nifantiev, Russ. Chem. Bull., 2015, 64, 1413–1418; DOI: https://doi.org/10.1007/s11172-015-1025-0.

    Article  CAS  Google Scholar 

  20. D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, V. M. Men’shov, N. E. Nifantiev, Russ. Chem. Bull., 2021, 70, 1356–1362; DOI: https://doi.org/10.1007/s11172-021-3223-2.

    Article  CAS  Google Scholar 

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Correspondence to N. E. Nifantiev.

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No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 9, pp. 2197–2205, September, 2023.

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Tsvetkov, D.E., Chizhov, A.O., Dmitrenok, A.S. et al. Structure, 1H and 13C NMR spectra of the minor component from the antimicrobial complex produced by actinomycete Streptomyces roseoflavus (INA-Ac-5812). Russ Chem Bull 72, 2197–2205 (2023). https://doi.org/10.1007/s11172-023-4016-6

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  • DOI: https://doi.org/10.1007/s11172-023-4016-6

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