Previously unknown conjugates of the diterpenoid isosteviol 1 and 1-O-methyl-2,3-di-O-acetyl-β-Darabinofuranoside in which the terpenoid and carbohydrate molecules were linked through polymethylene spacers of various lengths were synthesized. Isosteviol 1 and its conjugate 10 exhibited high bacteriostatic activity selectively against Staphylococcus aureus ATCC 209p. Conjugates 9–11 inhibited growth of Mycobacterium tuberculosis H37Rv at the level of the antituberculosis drug pyrazinamide. Removal of the acetyl protection from conjugate 9 increased the antituberculosis activity by eight times.
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E. Mosettig and W. R. Nes, J. Org. Chem., 20, 884 (1955).
V. S. P. Chaturvedula, J. Klucik, M. Upretti, and I. Prakash, Molecules, 16, 8402 (2011).
M. Zou, S.-S. Yu, K. Wang, D.-Y. Zhang, X.-M. Wu, and W.-Y. Hua, Chin. J. Nat. Med., 11, 289 (2013).
B. F. Garifullin, R. R. Sharipova, I. Yu. Strobykina, V. M. Babaev, and V. E. Kataev, Zh. Org. Khim., 50, 498 (2014).
C.-J. Liu, Y.-P. Liu, S.-L. Yu, X.-J. Dai, T. Zhang, and J.-C. Tao, Bioorg. Med. Chem. Lett., 26, 5455 (2016).
T. Ikeda, T. Kajimoto, H. Kondo, and C.-H. Wong, Bioorg. Med. Chem. Lett., 7, 2485 (1997).
O. V. Andreeva, R. R. Sharipova, I. Yu. Strobykina, and V. E. Kataev, Chem. Nat. Compd., 50, 465 (2014).
O. V. Andreeva, R. R. Sharipova, I. Yu. Strobykina, M. A. Kravchenko, A. S. Strobykina, A. D. Voloshina, R. Z. Musin, and V. E. Kataev, Zh. Org. Khim., 51, 1349 (2015).
B. F. Garifullin, I. Yu. Strobykina, R. R. Sharipova, M. A. Kravchenko, O. V. Andreeva, O. B. Bazanova, and V. E. Kataev, Carbohydr. Res., 431, 15 (2016).
B. F. Garifullin, R. R. Sharipova, O. V. Andreeva, I. Yu. Strobykina, M. A. Kravchenko, and V. E. Kataev, Zh. Org. Khim., 51, 1517 (2015).
B. C. Holland and N. W. Gilman, Synth. Commun., 4, 203 (1974).
A. K. Sanki, J. Boucau, P. Srivastava, S. S. Adams, D. R. Ronning, and S. J. Sucheck, Bioorg. Med. Chem., 16, 5672 (2008).
D. A. Ibrahim, J. Boucau, D. H. Lajiness, S. K. Veleti, K. R. Trabbic, S. S. Adams, D. R. Ronning, and S. J. Sucheck, Bioconjugate Chem., 23, 2403 (2012).
N. A. Hughes, K.-M. Kuhajda, and D. A. Miljkovic, Carbohydr. Res., 257, 299 (1994).
O. B. Andreeva, V. M. Babev, I. Kh. Rizvanov, I. Yu. Strobykina, and V. E. Kataev, Zh. Obshch. Khim., 84, 315 (2014).
P. R. Donald, Tuberculosis, 90, 279 (2010).
M. Korochkina, M. Fontanella, A. Casnati, A. Arduini, F. Sansone, R. Ungaro, Sh. Latypov, V. Kataev, and V. Alfonsov, Tetrahedron, 61, 5457 (2005).
L. Schmidt, E. B. Pedersen, and C. Nielsen, Acta Chem. Scand., 48, 215 (1994).
R. N. Khaibullin, I. Yu. Strobykina, V. E. Kataev, O. A. Lodochnikova, A. T. Gubaidullin, and R. Z. Musin, Zh. Obshch. Khim., 79, 795 (2009).
National Committee for Clinical Laboratory Standards, Methods for Dilution Antimicrobial Susceptibility. Tests for Bacteria that Grow Aerobically, 6th Ed.: Approved standard, M7-A5, NCCLS, Wayne, Pa., USA, 2000.
National Committee for Clinical Laboratory Standards, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Conidium-Forming Filamentous Fungi: Proposed Standard, M38-P, NCCLS, Wayne, Pa., USA, 1998.
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The work was supported financially by the Russian Science Foundation (Grant No. 14-50-00014).
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Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2018, pp. 81–85.
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Sharipova, R.R., Andreeva, O.V., Garifullin, B.F. et al. Synthesis and Antimicrobial and Antituberculosis Activity of the First Conjugates of the Diterpenoid Isosteviol and D-Arabinofuranose. Chem Nat Compd 54, 92–97 (2018). https://doi.org/10.1007/s10600-018-2267-5
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DOI: https://doi.org/10.1007/s10600-018-2267-5