New hydroxycinnamic acid derivatives were synthesized by reacting malonic acid and 4-hydroxybenzaldehydes with isobornyl and/or alkyl substituents. The antiradical, antioxidant, and membrane-protective activities were assessed in various in vitro models. The bulk of the substituent(s) in the o-position(s) relative to the phenol hydroxyl had a substantial effect on the antioxidant properties of the tested acids.
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G. R. Silveira, K. A. Campelo, G. R. S. Lima, L. P. Carvalho, S. S. Samarao, O. Vieira-da-Motta, L. Mathias, C. R. R. Matos, I. J. C. Vieira, E. J. Tenorio de Melo, and E. J. Maria, Molecules, 23, 774 (2018).
E. Pontiki, D. Hadjipavlou-Litina, K. Litinas, and G. Geromichalos, Molecules, 19, 9655 (2014).
M. Sova, Mini-Rev. Med. Chem., 12, 749 (2012).
P. De, M. Baltas, and F. Bedos-Belval, Curr. Med. Chem., 18, 1672 (2011).
X. Zhang, X. He, Q. Chen, J. Lu, S. Rapposelli, and R. Pi, Bioorg. Med. Chem., 26, 543 (2018).
N. F. Salakhutdinov, K. P. Volcho, and O. I. Yarovaya, Pure Appl. Chem., 89, 1105 (2017).
E. V. Kuzakov and E. N. Schmidt, Chem. Nat. Compd., 36, 245 (2000).
T. M. Plotnikova, G. A. Chernysheva, V. I. Smol′yakova, P. P. Shchetinin, A. V. Kuchin, I. Yu. Chukicheva, and M. B. Plotnikov, Byull. Eksp. Biol. Med., 157, 173 (2014) [T. M. Plotnikova, G. A. Chernysheva, V. I. Smol′yakova, P. P. Shchetinin, A. V. Kuchin, I. Yu. Chukicheva, and M. B. Plotnikov, Bull. Exp. Biol. Med., 157, 211 (2014)].
T. Plotnikova, M. Plotnikov, G. Chernysheva, V. Smol′yakova, P. Shchetinin, A. Kuchin, and I. Chukicheva, Key Eng. Mater., 683, 469 (2016).
O G. Shevchenko, S. N. Plyusnina, E. V. Buravlev, I. Yu. Chukicheva, I. V. Fedorova, O. V. Shchukina, and A. V. Kuchin, Izv. Akad. Nauk, Ser. Khim., No. 10, 1881 (2017) [O G. Shevchenko, S. N. Plyusnina, E. V. Buravlev, I. Yu. Chukicheva, I. V. Fedorova, O. V. Shchukina, and A. V. Kutchin, Russ. Chem. Bull., Int. Ed., 66, 1881 (2017)].
I. Yu. Chukicheva, I. V. Fedorova, N. A. Nizovtsev, A. A. Koroleva, O. G. Shevchenko, and A.V. Kuchin, Chem. Nat. Compd., 54, 875 (2018).
O. V. Shchukina, I. Yu. Chukicheva, O. G. Shevchenko, and A. V. Kutchin, Russ. J. Bioorg. Chem., 44, 787 (2018).
E. V. Buravlev, I. Yu. Chukicheva, I. A. Dvornikova, A. V. Churakov, and A. V. Kuchin, Zh. Org. Khim., 48, 943 (2012) [E. V. Buravlev, I. Yu. Chukicheva, I. A. Dvornikova, A. V. Churakov, and A. V. Kutchin, Russ. J. Org. Chem., 48, 938 (2012)].
E. V. Buravlev, I. Yu. Chukicheva, K. Yu. Suponitskii, and A. V. Kuchin, Zh. Org. Khim., 49, 69 (2013) [E. V. Buravlev, I. Yu. Chukicheva, K. Yu. Suponitskii, and A. V. Kutchin, Russ. J. Org. Chem., 49, 60 (2013)].
E. V. Buravlev, I. Yu. Chukicheva, A. V. Churakov, and A. V. Kuchin, Zh. Org. Khim., 48, 70 (2012) [E. V. Buravlev, I. Yu. Chukicheva, A. V. Churakov, and A. V. Kutchin, Russ. J. Org. Chem., 48, 64 (2012)].
G. M. Coppinger and T. W. Campbell, J. Am. Chem. Soc., 75, 734 (1953).
F. Michel, F. Thomas, S. Hamman, C. Philouze, E. Saint-Aman, and J.-L. Pierre, Eur. J. Inorg. Chem., 3684 (2006).
I. Yu. Chukicheva, L. V. Spirikhin, and A. V. Kuchin, Zh. Org. Khim., 44, 69 (2008) [I. Yu. Chukicheva, L. V. Spirikhin, and A. V. Kuchin, Russ. J. Org. Chem., 44, 62 (2008)].
V. B. Vol′eva, I. S. Belostotskaya, N. L. Komissarova, and L. N. Kurkovskaya, Zh. Org. Khim., 44, 814 (2008) [V. B. Vol′eva, I. S. Belostotskaya, N. L. Komissarova, and L. N. Kurkovskaya, Russ. J. Org. Chem., 44, 803 (2008)].
H. Chen, J. Wang, X. Hong, H.-B. Zhou, and C. Dong, Can. J. Chem., 90, 758 (2012).
C. I. Acker, R. Brandao, A. R. Rosario, and C. W. Nogueira, Environ. Toxicol. Pharmacol., 28, 280 (2009).
S. T. Stefanello, A. S. Prestes, T. Ogunmoyole, S. M. Salman, R. S. Schwab, C. R. Brender, L. Dornelles, J. B. T. Rocha, and F. A. A. Soares, Toxicol. in Vitro, 27, 1433 (2013).
R. Chawla, R. Arora, R. Kumar, A. Sharma, J. Prasad, S. Singh, R. Sagar, P. Chaudhary, S. Shukla, G. Kaur, R. K. Sharma, S. C. Puri, K. L. Dhar, G. Handa, V. K. Gupta, and G. N. Qazi, Mol. Cell. Biochem., 273, 193 (2005).
T. Asakawa and S. Matsushita, Lipids, 15, 137 (1980).
J. A. Buege and S. D. Aust, in: Methods in Enzymology, Vol. 52, S. Fleischer and L. Packer (eds.), Academic Press, New York, 1978, p. 302.
K. Sevgi, B. Tepe, and C. Sarikurkcu, Food Chem. Toxicol., 77, 12 (2015).
J. Takebayashi, J. Chen, and A. A. Tai, Methods Mol. Biol., 594, 287 (2010).
J. J. M. Van den Berg, J. A. F. Opden Kamp, B. H. Lubin, B. Roelofsen, and F. A. Kuypers, Free Radical Biol. Med., 12, 487 (1992).
Acknowledgment
The research was financially supported by the RFBR in the framework of science Project No. 18-03-00950_a.
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Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2019, pp. 565–570.
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Dvornikova, I.A., Buravlev, E.V., Fedorova, I.V. et al. Synthesis and Antioxidant Properties of Hydroxycinnamic Acid Derivatives Containing Isobornyl Substituents. Chem Nat Compd 55, 658–664 (2019). https://doi.org/10.1007/s10600-019-02772-x
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DOI: https://doi.org/10.1007/s10600-019-02772-x