Abstract
Extracts of garlic (Allium sativum L.) were obtained using supercritical carbon dioxide extraction and were separated into individual compounds using preparative high performance liquid and gas chromatography. A series of nonsymmetrical allyl disulfides with different substituents were synthesized. The compounds isolated from the supercritical garlic extract and the synthetic nonsymmetrical allyl disulfides (SNA) were tested as potential antimicrobial agents using a number of test objects: Candida utilis, Bacillus cereus, Pseudomonas aurantiaca, and Escherichia coli. It was shown that the SNA exhibit high antimicrobial activity, which was much higher that the activities of individual components of garlic and in some cases were comparable in efficiency with antibiotics of the floxacin series widely used in clinical practice. The data obtained suggest the potential for using SNA as antimicrobial agents.
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References
K. Harjai, R. Kumar, and S. Singh, FEMS Immunol. Med. Microbiol. 58, 161 (2010).
E. A. Palombo, Evidence-Based Complem. Altern. Med. 2011, 680354 (2011).
S. D. Chavah, N. L. Shetty, and M. Kanuri, Oral. Health Rev. Dent. 8, 369 (2010).
E. J. Nya and B. Austin, J. Fish Dis. 32, 9635 (2009).
A. Hannan, UllahM. Ikram, M. Usman, S. Hussian, M. Absar, and J. K. Pak, J. Pharm. Sci. 24, 81 (2011).
R. Ruiz, M. P. Garcia, A. Lara, and L. A. Rubio, Vet. Microbiol. 144, 110 (2010).
S. Liu, Y. Sun, W. Li, H. Yu, X. Li, et al., FEMS Microbiol. Lett. 303, 183 (2010).
M. N. Palaksha, M. Ahmed, and S. Das, J. Nat. Sci., Biol. Med. 1, 12 (2010).
G. Goncagul and E. Ayaz, Recent Pat. Antiinfect. Drug Discov. 5, 91 (2010).
J. F. Ayala-Zavala and G. A. Gonzalez-Agular, J. Food Sci. 75, M398 (2010).
J. F. Ayala-Zavala, G. A. Gonzalez-Agular, and L. del Toro Sanchez, J. Food Sci. 74, R84 (2009).
A. Stoll and E. Seebeck, Adv. Enzymol. 11, 377 (1951).
E. Block, S. Ahmad, J. L. Catalfamo, M. K. Jain, and R. Apiz-Castro, J. Am. Chem. Soc. 108, 7045 (1986).
H. Borjihan, A. Ogita, K. Fujita, T. Kirasawa, and T. Tanaka, J. Antibiot. (Tokyo) 62, 691 (2009).
H. Borjihan, A. Ogita, K. Fujita, M. Doe, and T. Tanaka, Planta Med. 76, 1864 (2010).
F. C. Velkers, K. Dieho, F. W. Pecher, J. C. Vernooij, J. H. van Eck, and W. J. Landman, Poult. Sci. 90, 364 (2011).
A. Coppi, M. Cabinian, D. Mirelman, and P. Sinnis, Vet. Antimicrob. Agents Chemother., 1737 (2006).
M. Alam, V. Dwivwdi, A. A. Khan, and O. Mohammad, Nanomedicine (London) 4, 713 (2009).
A. Khodavandi, N. S. Hormal, et al., Phytomedicine 19, 56 (2011).
C.-H. Chen, T.-W. Chou, L.-H. Cheng, and C.-W. Ho, J. Taiwan Inst. Chem. Eng. 42, 228 (2011).
M. Arzanlou and S. Bohlooli, J. Med. Microbiol. 59, 1044 (2010).
C. Dini, A. Fabbri, and A. Geraci, Ann. Ist. Super. Sanita 47, 465 (2011).
R. Gupta, B. Thakur, P. Singh, et al., Ind. J. Med. Res. 131, 809 (2010).
I. Gull, M. Saeed, H. Shaukat, S. M. Aslam, Z. Samra, and A. Athar, Ann. Clin. Microbiol. Antimicrob. 11, 8 (2012).
S. Rahman, A. K. Parves, R. Islam, and M. H. Khan, Ann. Clin. Microbiol. Antimicrob. 10, 10 (2011).
US Patent No. 20120189710.
E. M. Calvey, J. E. Matusik, K. D. White, R. DeOrazio, D. Sha, and E. J. Block, Agric. Food Chem. 45, 4406 (1997).
D. P. Ilic, V. D. Nikolic, L. B. Nikolic, M. Z. Stankovic, and L. P. Stanojevic, Hem. Ind. 64, 85 (2010).
R. R. Culter and P. Wilson, Brit. J. Biomed. Sci. 61, 71 (2004).
T. Miron, A. Rabinkov, D. Mirelman, M. Wilchek, and L. Weiner, Biochim. Biophys. Acta 1463, 20 (2000).
US Patent No. 20100204337.
US Patent No. 2004022280.
US Patent No. 4049665.
S. Casella, M. Leonardi, B. Melai, F. Fratini, and L. Pistelli, Phytother. Res. 27, 380 (2012).
K. H. Kyung, Curr. Opin. Biotechnol. 23, 142 (2012).
D. Yu. Zalepugin, N. A. Tilkunova, Yu. S. Yashin, I. V. Chernyshova, V. S. Mishin, and A. L. Mulyukin, Russ. J. Phys. Chem. B 4, 1103 (2010).
S. K. Spangler, M. A. Visalli, M. R. Jacobs, and P. C. Appelbaum, Antimicrob. Agents Chemother. 40, 772 (1996).
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Original Russian Text © D.Yu. Zalepugin, N.A. Tilkunova, I.V. Chernyshova, M.I. Vlasov, A.L. Mulyukin, 2014, published in Sverkhkriticheskie Flyuidy: Teoriya i Praktika, 2014, Vol. 9, No. 3, pp. 73–82.
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Zalepugin, D.Y., Tilkunova, N.A., Chernyshova, I.V. et al. Components of supercritical extracts of garlic and synthetic nonsymmetrical allyl disulfides as potential antimicrobial preparations. Russ. J. Phys. Chem. B 9, 1059–1064 (2015). https://doi.org/10.1134/S1990793115070155
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DOI: https://doi.org/10.1134/S1990793115070155