Abstract
A cooxidation of carbohydrate and terpene thiols gives mixtures of disulfides containing 51—90% of the unsymmetric product. Membranoprotective and antioxidant properties of obtained unsymmetric and symmetric disulfides were evaluated based on their ability to inhibit the H2O2-induced hemolysis of erythrocytes, as well as the accumulation of secondary products of the peroxy oxidation of lipids and the oxidation of hemoglobin.
Similar content being viewed by others
References
J. S. Bain, C. A. Shaw, Brain Res. Rev., 1997, 25, 335.
A. Pompella, A. Visvikis, A. Paolicchi, V. Tata, A. F. Casini, Biochem. Pharmacol., 2003, 66, 1499.
G. Atmaca, Yonsei Med. J., 2004, 45, 776.
L. Packer, E. Witt, H. J. Tritschler, Free Radical Biol. Med., 1995, 19, 227.
C. H. Lillig, C. Berndt, Antioxid. Red. Signal., 2013, 18, 1654.
R. L. Krawth-Siegel, Eur._J. Biochem., 1982, 121, 259.
D. P. Ilić, V. D. Nikolić, L. B. Nikolić, M. Z. Stanković, L. P. Stanojević, M. D. Cakić, Facta Universitatis. Ser. Phys., Chem., Technol., 2011, 9, 9.
P. L. Folkins, D. N. Harpp, J. Am. Chem. Soc., 1993, 115, 3066.
J. L. Kice, C. G. Venier, G. B. Large, L. Heasley, J. Am. Chem. Soc., 1969, 91, 2028.
E. S. Izmestév, D. V. Sudarikov, O. G. Shevchenko, C. A. Rubtsova, A. V. Kuchin, Bioorg. Khim., 2015, 41, 90 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2015, 41].
S. Andre, Z. Pei, H. C. Siebert, O. Ramstrom, H. J. Gabius, Bioorg. Med. Chem., 2006, 14, 6314.
T. Nkano, Y. Shikisai, Y. Okamoto, Polym. J., 1996, 28, 51.
M. Weiwer, X. Chaminde, J. C. Bayon, E. Dunch, Eur. J. Org. Chem., 2007, 15, 2464.
A. Gadras, J. Dungues, R. Calas, G. Deleris, J. Org. Chem., 1984, 49, 442.
I. A. Vakulenko, V. A. Startseva, L. E. Nikitin, N. P. Artemova, L. L. Frolova, A. V. Kuchin, Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 686 [Khim. Prirod. Soedin., 2005, 41, 585].
F. N. Ko, G. Hsiao, Y. H. Kuo, Free Radical Biol. Med., 1997, 22, 215.
A. López-Revuelta, J. I. Sánchez-Gallego, A. HernandezHernandez, J. Sánchez-Yague, M. Llanillo, Chem. Biol. Interact., 2006, 161, 79.
R. M. Costa, A. S. Magalhães, J. A. Pereira, P. B. Andrade, P. Valentão, M. Carvalho, B. M. Silva, Food Chem. Toxicol., 2009, 47, 860.
J. Takebayashi, J. Chen, A. Tai, in Advanced Protocols in Oxidative Stress II, Methods in Molecular Biology, Ed. D. Armstrong, Human Press, New York-Dordrecht-Heidelberg-London, 2010, 594, 287.
C. Wang, X. Qin, B. Huang, F. He, C. Zeng, Biochem. Biophys._R. Commun., 2010, 402, 773.
O. G. Shevchenko, L. N. Shishkina, Uspekhi Sovremennoi Biologii [Modern Biol. Rev.], 2014, 134, 133 (in Russian).
E. S. Izmestév, D. V. Sudarikov, S. A. Rubtsova, P. A. Slepukhin, A. V. Kuchin, Russ. J. Org. Chem. (Engl. Transl.), 2012, 48, 184 [Zh. Org. Khim., 2012, 48, 197].
T.-K. Yang, R.-Y. Chen, D.-S. Lee, W.-S. Peng, Y.-Z. Jiang, A.-Q. Mi, T.-T. Jong, J. Org. Chem., 1994, 59, 914.
A. Banch, J. Scianowski, P. Ozimek, Phosphorus, Sulfur, and Silicon, 2014, 189, 274.
M. A. Cooper, J. R. Salmon, D. Whittaker, J. Chem. Soc. B, 1967, 12, 1259.
H. Ohle, G. Berend, J. Am. Chem. Soc., 1925, 58, 2585.
N. Lunu, K. Seelhorst, S. Kahl, K. Tscherch, C. Stacke, S. Rohn, J. Thiem, U. Hahn, C. Meier, Chem. Eur. J., 2013, 19, 17379.
R. Daniellou, C. Le Narvor, Adv. Synth. Catal., 2005, 347, 1863.
P. J. Garegg, B. Samuelsson, J. Chem. Soc., Perkin Trans. 1, 1980, 2866.
C. J. Goodwin, Carbohydr. Res., 1989, 195, 150.
M. A. Martins Alho, N. B. D´Accorso, I. M. E. Thiel, J. Heterocycl. Chem., 1996, 33, 1339.
G. Carchon, F. Chrétien, Y. Chapleur, Tetrahedron Lett., 2003, 44, 5715.
M. Adinolfi, D. Capasso, S. Di Gaetano, A. Iadonisi, L. Leone, A. Pastore, Org. Biomol. Chem., 2011, 9, 6278.
E. S. Izmestév, D. V. Sudarikov, S. A. Rubtsova, P. A. Slepukhin, A. V. Kuchin, Chem. Nat. Compd. (Engl. Transl.), 2011, 47, 46 [Khim. Prirod. Soedin., 2011, 1, 43].
L. A. Subluskey, L. C. King, J. Am. Chem. Soc., 1951, 73, 2647.
M. Llana-Ruiz-Cabello, S. Maisanaba, D. Gutiérrez-Praena, A. I. Prieto, S. Pichardo, Á. Jos, F. J. Moreno, A.-M. Cameán, Food Chem., 2015, 166, 423.
T. Asakawa, S. Matsushita, Lipids, 1980, 15, 137.
J. J. M. van den Berg, J. A. F. Op den Kamp, B. H. Lubin, B. Roelofsen, F. A. Kuypers, Free Radical Biol. Med., 1992, 12, 487.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences V. I. Minkin on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0723—0731, March, 2015.
Rights and permissions
About this article
Cite this article
Pestova, S.V., Izmest´ev, E.S., Shevchenko, O.G. et al. Synthesis and membranoprotective properties of new disulfides with monoterpene and carbohydrate fragments. Russ Chem Bull 64, 723–731 (2015). https://doi.org/10.1007/s11172-015-0926-2
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-015-0926-2