Skip to main content
SpringerLink
Log in

Synthesis and Antitubercular, Antimicrobial, and Hemolytic Activity of Methyl D-Glucopyranuronate and Its Simplest Derivatives

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Methyl glucuronate and some of its simplest derivatives have been synthesized, and their antitubercular, antimicrobial, and hemolytic activities have been studied. The simplest derivatives of glucuronic acid have been shown for the first time to exhibit a high antitubercular activity which is comparable with the activity of isoniazid.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Ünak, T., Curr. Pharm. Des., 2000, vol. 6, no. 11, p. 1127. doi 10.2174/1381612003399798

    Article  Google Scholar 

  2. Stachulski, A.V. and Meng, X., Nat. Prod. Rep., 2013, vol. 30, no. 6, p. 806. doi 10.1039/c3np70003h

    Article  CAS  Google Scholar 

  3. Kawabata, K., Mukai, R., and Ishisaka, A., Food Funct., 2015, vol. 6, no. 5, p. 1399. doi 10.1039/C4FO01178C

    Article  CAS  Google Scholar 

  4. D’Andrea, G., Fitoterapia, 2015, vol. 106, p. 256. doi 10.1016/j.fitote.2015.09.018

    Article  Google Scholar 

  5. Paiva-Martins, F., Silva, A., Almeida, V., Carvalheira, M., Serra, C., Rodrígues-Borges, J.E., Fernandes, J., Belo, L., and Santos-Silva, A., J. Agric. Food Chem., 2013, vol. 61, no. 27, p. 6636. doi 10.1021/jf4016202

    Article  CAS  Google Scholar 

  6. Goh, D., Lee, Y.H., and Ong, E.S., J. Agric. Food Chem., 2005, vol. 53, no. 21, p. 8197. doi 10.1021/jf051506+

    Article  CAS  Google Scholar 

  7. Li, H., Huang, D., Gao, Z., Lv, Y., Zhang, L., Cui, H., and Zheng, J., Oncol. Rep., 2010, vol. 24, no. 5, p. 1153. doi 10.3892/or_00000967

    CAS  Google Scholar 

  8. Pan, Z.W., Feng, T.M., Shan, L.C., Cai, B.Z., Chu, W.F., Niu, H.L., Lu, Y.J., and Yang, B.F., Phytother. Res., 2008, vol. 22, no. 11, p. 1428. doi 10.1002/ptr.2364

    Article  CAS  Google Scholar 

  9. Haggag, E.G., Kamal, A.M., Abdelhady, M.I.S., El-Sayed, M.M., El-Wakil, E.A., and Abd-El-hamed, S.S., Pharm. Biol., 2011, vol. 49, no. 11, p. 1103. doi 10.3109/13880209.2011.568623

    Article  CAS  Google Scholar 

  10. Ryu, B., Kim, H.M., Lee, J.S., Lee, C.K., Sezirahiga, J., Woo, J.-H., Choi, J.-H., and Jang, D.S., J. Agric. Food Chem., 2016, vol. 64, no. 15, p. 3048. doi 10.1021/acs.jafc.6b00337

    Article  CAS  Google Scholar 

  11. Cuong, T.D., Hung, T.M., Lee, J.-S., Weon, K.-Y., Woo, M.H., and Min, B.S., Bioorg. Med. Chem. Lett., 2015, vol. 25, no. 5, p. 1129. doi 10.1016/j.bmcl.2014.12.055

    Article  CAS  Google Scholar 

  12. Sato, H., Goto, W., Yamamura, J., Kurokawa, M., Kageyama, S., Takahara, T., Watanabe, A., and Shiraki, K., Antiviral Res., 1996, vol. 30, nos. 2–3, p. 171. doi 10.1016/0166-3542(96)00942-4

    Article  CAS  Google Scholar 

  13. Baltina, L.A., Kondratenko, R.M., Mustafina, S.R., Flekhter, O.B., Murinov, Yu.I., Davydova, V.A., Zarudii, F.S., Ismagilova, A.F., and Tolstikov, G.A., Pharm. Chem. J., 2001, vol. 35, no. 1, p. 40. doi 10.1023/A:1010454810888

    Article  CAS  Google Scholar 

  14. Kondratenko, R.M., Baltina, L.A., Mustafina, S.R., Makarova, N.V., Nasyrov, Kh.M., and Tolstikov, G.A., Pharm. Chem. J., 2001, vol. 35, no. 2, p. 101. doi 10.1023/A:1010481123359

    Article  CAS  Google Scholar 

  15. Kim, K.H., Lee, I.K., Choi, S.U., Lee, J.H., Moon, E., Kim, S.Y., and Lee, K.R., Planta Med., 2011, vol. 77, no. 13, p. 1555. doi 10.1055/s-0030-1270781

    Article  CAS  Google Scholar 

  16. Li, S., Zhao, J., Liu, Y., Chen, Z., Xu, Q., Khan, I.A., and Yang, S., J. Agric. Food Chem., 2014, vol. 62, no. 2, p. 488. doi 10.1021/jf4046667

    Article  CAS  Google Scholar 

  17. Shan, Y., Li, H., Guan, F., Chen, Y., Yin, M., Wang, M., Feng, X., and Wang, Q., Molecules, 2015, vol. 20, no. 11, p. 20334. doi 10.3390/molecules201119695

    Article  CAS  Google Scholar 

  18. Miao, H., Suna, Y., Yuan, Y., Zhao, H., Wu, J., Zhang, W., and Zhou, L., Chem. Biodiversity, 2016, vol. 13, no. 4, p. 437. doi 10.1002/cbdv.201500130

    Article  CAS  Google Scholar 

  19. Andreeva, O.V., Sharipova, R.R., Strobykina, I.Yu., Kravchenko, M.A., Strobykina, A.S., Voloshina, A.D., Musin, R.Z., and Kataev, V.E., Russ. J. Org. Chem., 2015, vol. 51, no. 9, p. 1324. doi 10.1134/S1070428015090201

    Article  CAS  Google Scholar 

  20. Garifullin, B.F., Strobykina, I.Yu., Sharipova, R.R., Kravchenko, M.A., Andreeva, O.V., Bazanova, O.B., and Kataev, V.E., Carbohydr. Res., 2016, vol. 431, p. 15. doi 10.1016/j.carres.2016. 05.007

    Article  CAS  Google Scholar 

  21. Izmest’ev, E.S., Andreeva, O.V., Sharipova, R.R., Kravchenko, M.A., Garifullin, B.F., Strobykina, I.Yu., Kataev, V.E., and Mironov, V.F., Russ. J. Org. Chem., 2017, vol. 53, no. 1, p. 51. doi 10.1134/S1070428017010092

    Article  Google Scholar 

  22. Batrakov, S.G., Nikitin, D.I., and Pitryuk, I.A., Biochim. Biophys. Acta, 1996, vol. 1302, no. 2, p. 167. doi 10.1016/0005-2760(96)00060-4

    Article  Google Scholar 

  23. Toukach, F.V., Perepelov, A.V., Bartodziejska, B., Shashkov, A.S., Blaszczyk, A., Arbatsky, N.P., Rozalski, A., and Knirel, Y.A., Carbohydr. Res., 2003, vol. 338, p. 1431. doi 10.1016/S0008-6215(03)00096-X

    Article  CAS  Google Scholar 

  24. Sidorczyk, Z., Kondakova, A.N., Zych, K., Senchenkova, S.N., Shashkov, A.S., Drzewiecka, D., and Knirel, Y.A., Eur. J. Biochem., 2003, vol. 270, no. 15, p. 3182. doi 10.1046/j.1432-1033.2003.03698.x

    Article  CAS  Google Scholar 

  25. Katzenellenbogen, E., Kocharova, N.A., Shashkov, A.S., Gorska-Fraczek, S., Bogulska, M., Gamian, A., and Knirel, Y.A., Carbohydr. Res., 2013, vol. 368, p. 84. doi 10.1016/j.carres.2012.12.016

    Article  CAS  Google Scholar 

  26. Wadouachi, A. and Kovensky, J., Molecules, 2011, vol. 16, no. 5, p. 3933. doi 10.3390/molecules16053933

    Article  CAS  Google Scholar 

  27. Baba, T., Kidera, Y., Kimura, N.T., Aoki, K., Kamura, T., Taniguchu, S., and Nishikawa, K., Jpn. J. Cancer Res., 1978, vol. 69, no. 2, p. 283. doi 10.20772/cancersci1959.69.2_283

    CAS  Google Scholar 

  28. Florent, J.-C., Dong, X., Gaudel, G., Mitaku, S., Monneret, C., Gesson, J.-P., Jacquesy, J.-C., Mondon, M., Renoux, B., Andrianomenjanahary, S., Michel, S., Koch, M., Tillequin, F., Gerken, M., Czech, J., Straub, R., and Bosslet, K., J. Med. Chem., 1998, vol. 41, no. 19, p. 3572. doi 10.1021/jm970589l

    Article  CAS  Google Scholar 

  29. De Graaf, M., Nevalainen, T.J., Scheeren, H.W., Pinedo, H.M., Haisma, H.J., and Boven, E., Biochem. Pharmacol., 2004, vol. 68, no. 11, p. 2273. doi 10.1016/j.bcp.2004.08.004

    Article  Google Scholar 

  30. Tietze, L.F., Schuster, H.J., Schmuck, K., Schuberth, I., and Alves, F., Bioorg. Med. Chem., 2008, vol. 16, no. 12, p. 6312. doi 10.1016/j.bmc.2008.05.009

    Article  CAS  Google Scholar 

  31. Thomas, M., Clarhaut, J., Tranoy-Opalinski, I., Gesson, J.-P., Roche, J., and Papot, S., Bioorg. Med. Chem., 2008, vol. 16, no. 17, p. 8109. doi 10.1016/j.bmc.2008.07.048

    Article  CAS  Google Scholar 

  32. Kolakowski, R.V., Haelsig, K.T., Emmerton, K.K., Leiske, C.I., Miyamoto, J.B., Cochran, J.H., Lyon, R.P., Senter, P.D., and Jeffrey, S.C., Angew. Chem., Int. Ed., 2016, vol. 55, no. 28, p. 7948. doi 10.1002/anie.201601506

    Article  CAS  Google Scholar 

  33. Grinda, M., Clarhaut, J., Tranoy-Opalinski, I., Renoux, B., Monvoisin, A., Cronier, L., and Papot, S., Chem. Med. Chem., 2011, vol. 6, no. 12, p. 2137. doi 10.1002/cmdc.201100355

    Article  CAS  Google Scholar 

  34. Ranganathan, A., Gee, S.J., and Hammock, B.D., Anal. Bioanal. Chem., 2015, vol. 407, no. 24, p. 7263. doi 10.1007/s00216-015-8918-5

    Article  CAS  Google Scholar 

  35. Albin, N., Massaad, L., Toussaint, C., Mathieu, M.-C., Morizet, J., Parise, O., Gouyette, A., and Chabot, G.G., Cancer Res., 1993, vol. 53, no. 15, p. 3541.

    CAS  Google Scholar 

  36. Wang, Y., Yuan, H., Wright, S.C., Wang, H., and Larrick, J.W., Bioorg. Med. Chem., 2003, vol. 11, no. 7, p. 1569. doi 10.1016/S0968-0896(02)00603-X

    Article  CAS  Google Scholar 

  37. Liu, Y.-H., Liang, W.-L., Lee, C.-C., Tsai, Y.-F., and Hou, W.-C., Food Chem., 2011, vol. 129, no. 2, p. 423. doi 10.1016/j.foodchem.2011.04.094

    Article  CAS  Google Scholar 

  38. Cheng, T.C., Roffler, S.R., Tzou, S.C., Chuang, K.H., Su, Y.C., Chuang, C.H., Kao, C.H., Chen, C.S., Harn, I.H., Liu, K.Y., Cheng, T.L., and Leu, Y.L., J. Am. Chem. Soc., 2012, vol. 134, no. 6, p. 3103. doi 10.1021/ja209335z

    Article  CAS  Google Scholar 

  39. Duranová, M., Hirsch, J., Kolenová, K., and Biely, P., Biosci. Biotechnol. Biochem., 2009, vol. 73, no. 11, p. 2483. doi 10.1271/bbb.90486

    Article  Google Scholar 

  40. Williams, J.M., Carbohydr. Res., 1983, vol. 117, p. 89. doi 10.1016/0008-6215(83)88077-X

    Article  CAS  Google Scholar 

  41. Khodair, A.I. and Bertrand, P., Tetrahedron, 1998, vol. 54, no. 19, p. 4859. doi 10.1016/S0040-4020(98)00170-7

    Article  CAS  Google Scholar 

  42. Johgkees, S.A.K. and Withers, S.G., J. Am. Chem. Soc., 2011, vol. 133, no. 48, p. 19334. doi 10.1021/ja209067v

    Article  Google Scholar 

  43. Pilgrim, W. and Murphy, P.V., J. Org. Chem., 2010, vol. 75, no. 20, p. 6747. doi 10.1021/jo101090f

    Article  CAS  Google Scholar 

  44. Mönch, B., Gebert, A., Emmerling, F., Becker, R., and Nehls, I., Carbohydr. Res., 2012, vol. 352, p. 186. doi 10.1016/j.carres. 2012.01.002

    Article  Google Scholar 

  45. Donald, P.R., Tuberculosis, 2010, vol. 90, no. 5, p. 279. doi 10.1016/j.tube.2010.07.002

    Article  CAS  Google Scholar 

  46. Bollenback, G.N., Long, J.W., Benjamin, D.G., and Lindquist, J.A., J. Am. Chem. Soc., 1955, vol. 77, no. 12, p. 3310. doi 10.1021/ja01617a047

    Article  CAS  Google Scholar 

  47. Methods for Dilution Antimicrobial Susceptibility. Tests for Bacteria that Grow Aerobically: Approved Standard. M7-A5, Wayne, PA, USA: National Committee for Clinical Laboratory Standards, 2000.

  48. Voloshina, A.D., Semenov, V.E., Strobykina, A.S., Kulik, N.V., Krylova, E.S., Zobov, V.V., and Reznik, V.S., Russ. J. Bioorg. Chem., 2017, vol. 43, no. 2, p. 170. doi 10.1134/S1068162017020170

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, Tatarstan, 420088, Russia

    M. G. Belenok, O. V. Andreeva, B. F. Garifullin, A. S. Strobykina, A. D. Voloshina & V. E. Kataev

  2. Ural Research Institute of Phthisiopulmonology, Ministry of Health Protection of the Russian Federation, ul. 22 Parts”ezda 50, Yekaterinburg, 620039, Russia

    M. A. Kravchenko

Authors
  1. M. G. Belenok
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. V. Andreeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. F. Garifullin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. S. Strobykina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. A. Kravchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. D. Voloshina
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. V. E. Kataev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. E. Kataev.

Additional information

Dedicated to B.I. Buzykin on His 80th Anniversary

Original Russian Text © M.G. Belenok, O.V. Andreeva, B.F. Garifullin, A.S. Strobykina, M.A. Kravchenko, A.D. Voloshina, V.E. Kataev, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 12, pp. 1999–2008.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Belenok, M.G., Andreeva, O.V., Garifullin, B.F. et al. Synthesis and Antitubercular, Antimicrobial, and Hemolytic Activity of Methyl D-Glucopyranuronate and Its Simplest Derivatives. Russ J Gen Chem 87, 2816–2825 (2017). https://doi.org/10.1134/S1070363217120106

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363217120106

Keywords

Search

Navigation