1466
SHARIPOVA et al.
10. Gianfagna, T., Zeevaart, J.A.D., and Lusk, W.J.,
Phytochemistry, 1983, vol. 22, no. 2, p. 427. DOI:
10.1016/0031-9422(83)83017- 9.
glucopyranosyl-1''-oxy]-2,3,14,15-tetraaza-18,27-
dioxa-1,16(16,4α)-di(19-nor-ent-kaurana)cycloocta-
cosaphane-116(2),1616(15)-diene-4,13,17,28-tetraone
(XVIIIc) and 113,1613,2913,4413-tetra[2',3',4',6'-tetra-
О-acetyl-β-D-glucopyranosyl-(1→2)-3'',4'',6''-tri-О-
acetyl-β-D-glucopyranosyl-1''-oxy]-2,3,14,15,30,31,-
42,43-octaaza-18,27,46,55-tetraoxa-1,16,29,44(16,4α)-
tetra-(19-nor-ent-kaurana)-cyclopentacosaphane-116(2),
1616(15),2916(30),4416(43)-tetraen-4,13,17,28,32,41,45,56-
octaone (XIXc). Yield 90%. Mass spectrum, m/z:
2204.6 [M + Na]+ (calculated for C108H156N4NaO42:
2205.01) (XVIIIc), 4364.9 [M]+ (calculated for
C216H312N8O84: 4365.05 (XIXc).
11. Upreti, M., DuBois, G., and Prakash, I., Molecules,
2012, vol. 17, no. 4, p. 4186. DOI: 10.3390/
molecules17044186.
12. Chaturvedula, V.S.P. and Prakash, I., J. Appl. Pharm.
Sci., 2011, vol. 1, no. 8, p. 104.
13. Sharipova, R.R., Garifullin, B.F., Andreeva, O.V.,
Strobykina, I.Yu., Bazanova, O.B., and Kataev, V.E.,
Russ. J. Org. Chem., 2015, vol. 51, no. 3, p. 424. DOI:
10.1134/S1070428015030239.
14. Bindu, P.J., Mahadevan, K.M., Satyanarayan, N.D., and
Naik, T.R.R., Bioorg. Med. Chem. Lett., 2012, vol. 22,
no. 2, p. 898. DOI: 10.1016/j.bmcl.2011.12.037.
ACKNOWLEDGMENTS
15. Harini, S.T., Kumar, H.V., Rangaswamy, J., and Naik, N.,
Bioorg. Med. Chem. Lett., 2012, vol. 22, no. 24,
p. 7588. DOI: 10.1016/j.bmcl.2012.10.019.
The work was financially supported by the
President of the Russian Federation (project no. MK-
1052.2014.3).
16. Zaware, P., Shah, S.R., Pingali, H., Makadia, P., Thube, B.,
Pola, S., Patel, D., Priyadarshini, P., Suthar, D., Shah, M.,
Jamili, J., Sairam, K.V.V.M., Giri, S., Patel, L., Patel, H.,
Sudani, H., Patel, H., Jain, M., Patel, P., and Bahekar, R.,
Bioorg. Med. Chem. Lett., 2011, vol. 21, no. 2, p. 628.
DOI: 10.1016/j.bmcl. 2010.12.032.
REFERENCES
1. Stevia: The genus Stevia, Kinghorn, A.D., Ed., London:
Taylor & Francis, 2002.
2. Brahmachari, G., Mandal, L.C., Roy, R., Mondal, S.,
and Brahmachari, A.K., Arch. Pharm. Chem. Life Sci.,
2011, vol. 1, p. 5. DOI:10.1002/ardp.201000181.
3. Kataev, V.E., Khaibullin, R.N., Sharipova, R.R., and
Strobykina, I.Yu., Rev. J. Chem., 2011, vol. 1, no. 2,
p. 93. DOI: 10.1134/S2079978011010043.
4. Wood, H.B., Allerton, R., Diehl, H.W., and Fletcher, H.G.,
J. Org. Chem., 1955, vol. 20, no. 8, p. 875. DOI:
10.1021/jo01125a012.
5. DuBois, G.E., Bunes, L.A., Dietrich, P.S., and
Stephenson, R.A., Agric. Food Chem., 1984, vol. 32,
no. 6, p. 1321. DOI: 10.1021/jf00126a026.
17. Akritopoulou-Zanze, I., Phelan, K.M., Marron, T.G.,
Yong, H., Ma, Zh., Stone, G.G., Daly, M.M., Hensey, D.M.,
Nilius, A.M., and Djuric, S.W., Bioorg. Med. Chem.
Lett., 2004, vol. 14, no. 14, p. 3809. DOI: 10.1016/
j.bmcl.2004.04.077.
18. Csuk, R., Schwarz, S., Siewert, B., Kluge, R., and
Strohl, D., Eur. J. Med. Chem., 2011, vol. 46, no. 11,
p. 5356. DOI: 10.1016/j.ejmech.2011.08.038.
19. Bednarczyk-Cwynar, B., Zaprutko, L., Marciniak, J.,
Lewandowski, G., Szulc, M., Kaminska, E., Wacho-
wiak, N., and Mikolajczak, P.R., Eur. J. Pharm. Sci.,
2012, vol. 47, no. 3, p. 549. DOI: 10.1016/
j.ejps.2012.07.017.
6. DuBois, G.E. and Stephenson, R.A., J. Med. Chem.,
1985, vol. 28, no. 1, p. 93. DOI: 10.1021/jm00379a017.
20. Singhal, N., Johar, M., Lown, J.W., and Sondhi, S.M.,
Phosphorus, Sulfur, Silicon, Relat. Elem., 2001, vol. 174,
no. 1, p. 81. DOI: 10.1080/10426500108040234.
7. Lin, L.-H., Lee, L.-W., Lin, Sh.-Y., and Lin, P.-Y.,
Chem. Pharm. Bull., 2004, vol. 52, no. 9, p. 1117. DOI:
10.1248/cpb.52.1117.
8. Sharipova, R.R., Strobykina, I.Yu., Kataev, V.E., Lodo-
chnikova, O.A., Gubaidullin, A.T., and Stomakhin, A.A.,
Russ. J. Gen. Chem., 2009, vol. 79, no. 12, p. 2668.
DOI: 10.1134/S1070363209120196.
9. Sharipova, R.R., Strobykina, I.Yu., Mordovskoi, G.G.,
Chestnova, R.V., Mironov, V.F., and Kataev, V.E.,
Chem. Nat. Compd., 2011, vol. 46, no. 6, p. 902. DOI:
10.1007/s10600-011-9779-6.
21. Schwarz, S., Lucas, S.D., Sommerwerk, S., and Csuk, R.,
Bioorg. Med. Chem., 2014, vol. 22, no. 13, p. 3370.
DOI: 10.1016/j.bmc.2014.04.046.
22. Paschke, R.F. and Wheeler, D.H., J. Am. Oil Chem.
Soc., 1949, vol. 26, no. 11, p. 637. DOI: 10.1007/
BF02651500.
23. Vis E., Fletcher H.G., J. Am. Chem. Soc., 1956, vol. 78,
no. 18, p. 4709. DOI: 10.1021/ja01599a047.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 6 2015