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2013 | 11 | 12 | 2120-2133
Article title

Study of lipophilicity of alpha-asarone derivatives and their deterrent activity against the Colorado potato beetle

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EN
Abstracts
EN
Five positional isomers and thirty derivatives of alpha-asarone wereobtained as a bioactive set of substances, and their deterrent activity against the Colorado potato beetle was studied. The lipophilicity values of thirty-six compounds were determined by using experimental, chromatographic and theoretical methods. The logk w values for all compounds were determined by reversed-phase high-performance liquid chromatography using five different columns. The octan-1-ol/water partition coefficients values were determined experimentally as a measure of lipophilicity. For the purpose of comparison, theoretical lipophilic parameters for all compounds were calculated with the use of chemical programs. The experimental, chromatographic and calculated values were compared using linear regression analysis. The most significant correlations were found between the chromatographic lipophilicities using methanol/water for all tested columns and calculated values. It has been found that 13 compounds have the lowest lipophilicities, which correspond to deterrent activity. The presented results show that the computational method is useful for determining the lipophilicity of a series of homologues, but not for positional isomers. In addition, this study shows that determination of lipophilicity using HPLC with various stationary phases is practical and reasonable for all alpha-asarone derivatives. [...]
Publisher

Journal
Year
Volume
11
Issue
12
Pages
2120-2133
Physical description
Dates
published
1 - 12 - 2013
online
26 - 9 - 2013
Contributors
  • Institute of Plant Protection - National Research Institute, Regional Experimental Station, BiaŁystok, 15-195, Poland, biuro@ior.bialystok.pl
  • Institute of Plant Protection - National Research Institute, Regional Experimental Station, BiaŁystok, 15-195, Poland
author
  • Institute of Plant Protection - National Research Institute, Department of Entomology, Poznań, 60-318, Poland
References
  • [1] Z. Chilimonczyk, D. Siluk, R. Kaliszan, B. Łozowicka, J. PopŁawski, S. Filipek, Pure Appl. Chem. 73, 1445 (2001) http://dx.doi.org/10.1351/pac200173091445[Crossref]
  • [2] C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Feny, Adv. Drug Deliv. 23, 3 (1997) http://dx.doi.org/10.1016/S0169-409X(96)00423-1[Crossref]
  • [3] H. Waterbeemd, D.A. Smith, B.C Jones, J. Comp.-Aided Mol. Des. 15, 273 (2001) http://dx.doi.org/10.1023/A:1008192010023[Crossref]
  • [4] K. Valko, J. Chromatogr. A 1037, 299 (2004) http://dx.doi.org/10.1016/j.chroma.2003.10.084[Crossref]
  • [5] J. Dai, L. Jin, S. Yao, L. Wang, Chemosphere 42, 899 (2001) http://dx.doi.org/10.1016/S0045-6535(00)00181-8[Crossref]
  • [6] E.C. Miller, A.B. Swanson, D.H. Philips, L. Fletcher, A. Liem, J.A. Miller, J. Cancer Res. 43, 1124 (1983)
  • [7] Malik, E. Sedlarova, J. Csollei, F. Andriamainty, J. Cizmarik, Chem. Pap. 61, 206 (2007) http://dx.doi.org/10.2478/s11696-007-0021-8[Crossref]
  • [8] S. Griffin, S.G. Wyllie, J. Markham, J. Chromatogr. A 24, 221 (1999) [Crossref]
  • [9] X. Liu, H. Tanaka, A. Yamauchi, B. Testa, H. Schuman, J. Chromatogr. A 1091, 51 (2005) http://dx.doi.org/10.1016/j.chroma.2005.07.029[Crossref]
  • [10] G. Cimpan, M. Hadaruga, V. Miclaus, J. Chromatogr. A 69, 49 (2008)
  • [11] F. Darrouzain, P. Dallet, J.P. Dubost, L. Ismaili, F. Pehourcq, B. Bannwarth, M. Matoga, Y.C. Guillaume, J. Pharm. Biomed. Anal. 41, 228 (2006) http://dx.doi.org/10.1016/j.jpba.2005.11.011[Crossref]
  • [12] G.T. Balogh, Z. Szanto, E. Forrai, W. Gyorffy, A. Lopata, J. Pharm. Biomed. Anal. 39, 1057 (2005) http://dx.doi.org/10.1016/j.jpba.2005.05.019[Crossref]
  • [13] K. Sztanke, W. Markowski, R. Swieboda, B. Polak, Eur. J. Med. Chem. 45, 2644 (2010) http://dx.doi.org/10.1016/j.ejmech.2010.01.068[Crossref]
  • [14] B. Hallgas, T. Patonay, A. Kiss-Szikszai, Z. Dobos, F. Hollosy, D. Eros, L. Orfi, G. Keri, M. Idei, J. Chromatogr. B 801, 229 (2004) http://dx.doi.org/10.1016/j.jchromb.2003.11.021[Crossref]
  • [15] M. Remko, Chem. Pap. 61, 133 (2007) http://dx.doi.org/10.2478/s11696-007-0010-y[Crossref]
  • [16] F. Hollosy, J. Seprodi, L. Orfi, D. Eros, G. Keri, M. Idei, J. Chromatogr. B 780, 355 (2002) http://dx.doi.org/10.1016/S1570-0232(02)00545-7[Crossref]
  • [17] C. Sarbu, R.D. Nascu-Briciu, D. Casoni, A. Kot-Wasik, A. Wasik, J. Namiesnik, J. Chromatogr. A 1266, 53 (2012) http://dx.doi.org/10.1016/j.chroma.2012.10.007[Crossref]
  • [18] D. Casoni, A. Kot-Wasik, J. Namiesnik, C. Sarbu, J. Chromatogr. A 1216, 2456 (2009) http://dx.doi.org/10.1016/j.chroma.2009.01.029[Crossref]
  • [19] M. Remko, C.W. von der Lieth, Bioorg. Med. Chem. 12, 5395 (2004) http://dx.doi.org/10.1016/j.bmc.2004.07.049[Crossref]
  • [20] M. Ilijas, I. Malnar, V. Gabelica Markovic, V. Stepanic, J. Pharm. Biomed. Anal. 76, 104 (2013) http://dx.doi.org/10.1016/j.jpba.2012.11.043[Crossref]
  • [21] P. Nemecek, T. Durcekova, J. Mocak, K. Waisser, Chem. Pap. 63, 84 (2009) http://dx.doi.org/10.2478/s11696-008-0089-9[Crossref]
  • [22] M. Remko, M. Swart, F.M. Bickelhaupt, Bioorg. Med. Chem. 14, 1715 (2006) http://dx.doi.org/10.1016/j.bmc.2005.10.020[Crossref]
  • [23] E. Dreassi, A.T. Zizzari, F. Falchi, S. Schenone, A. Santucci, G. Maga, M. Botta, Eur. J. Med. Chem. 44, 3712 (2009) http://dx.doi.org/10.1016/j.ejmech.2009.03.039[Crossref]
  • [24] E.H. Kerns, D. Li, Drug-Like Properties: Concept, Structure Design and Methods (Elsevier, San Diego, CA, USA, 2008)
  • [25] R. Enriquez, M. Chavez, F. Jauregui, Phytochemistry 19, 2024 (1980) http://dx.doi.org/10.1016/0031-9422(80)83029-9[Crossref]
  • [26] A.K.M. El-Nahal, G.H. Schmidt, E.M. Risha, J. Stored Prod. Res. 25, 211 (1989) http://dx.doi.org/10.1016/0022-474X(89)90026-X[Crossref]
  • [27] O. Koul, M.J. Smirle, M.B. Isman, J. Chem. Ecol. 16, 1911 (1990) http://dx.doi.org/10.1007/BF01020504[Crossref]
  • [28] G.Q. Liu, J.N. Sun, Z.Z. He, Y. Jiang, Acta Pharm. Sinica 4, 95 (1983)
  • [29] G. Matolcsy, A.I. Farag, L. Varjas, I. Belai, Y.M. Darwish, In: G.E. Pratt, G.T. Brooks (Eds.), Juvenile Hormone Biochemistry (Elsevier/North-Holland Biomedical Press, Amsterdam, Netherlands, 1981) 383
  • [30] C. Park, S. Kim, J. Ahn, J. Stored Prod. Res. 39, 333 (2003) http://dx.doi.org/10.1016/S0022-474X(02)00027-9[Crossref]
  • [31] B. Łozowicka, P. Kaczyński, Pest Manag. Sci. 69, 964 (2013) http://dx.doi.org/10.1002/ps.3461[Crossref]
  • [32] J. Popławski, B. Łozowicka, A.T. Dubis, B. Lachowska, Z. Winiecki, J. Nawrot, Pest Manag. Sci. 56, 560 (2000) http://dx.doi.org/10.1002/(SICI)1526-4998(200006)56:6<560::AID-PS171>3.0.CO;2-X[Crossref]
  • [33] B. Szafranek, E. Synak, D. Waligóra, J. Szafranek, J. Nawrot, Chemoecology 18, 205 (2008) http://dx.doi.org/10.1007/s00049-008-0407-2[Crossref]
  • [34] L. Ebrahimi, G. Niknam, E.E. Lewis, BioControl 56, 781 (2011) http://dx.doi.org/10.1007/s10526-011-9343-0[Crossref]
  • [35] A. Alyokhin, M. Baker, D. Mota-Sanchez, G. Dively, E. Grafius, Am. J. Potato Res. 85, 395 (2008) http://dx.doi.org/10.1007/s12230-008-9052-0[Crossref]
  • [36] J.W. Martel, A.R. Alford, J.C. Dickens, Crop Prot. 26, 822 (2007) http://dx.doi.org/10.1016/j.cropro.2006.08.002[Crossref]
  • [37] N. Gandhi, S. Pillai, P. Patel, Int. J. Agric. Biol. 12, 616 (2010)
  • [38] S. Tooba, N.F. Usmani, T. Abbas, Pakistan J. Bot. 37, 149 (2005)
  • [39] D.A. Collins, J. Stored Prod. Res. 42, 395 (2006) http://dx.doi.org/10.1016/j.jspr.2005.08.001[Crossref]
  • [40] I.V. Tetko, V.Y. Tanchuk, J. Chem. Inf. Comput. Sci. 42, 1136 (2002) http://dx.doi.org/10.1021/ci025515j[Crossref]
  • [41] I.V. Tetko, V.Y. Tanchuk, A.E. Villa, J. Chem. Inf. Comput. Sci. 41, 1407 (2001) http://dx.doi.org/10.1021/ci010368v[Crossref]
  • [42] I.V. Tetko, V.Y. Tanchuk, T.N. Kasheva, A.E. Villa, J. Chem. Inf. Comput. Sci. 41, 1488 (2001) http://dx.doi.org/10.1021/ci000392t[Crossref]
  • [43] I.V. Tetko, G.I. Poda, J. Med. Chem. 47, 5601 (2004) http://dx.doi.org/10.1021/jm049509l[Crossref]
  • [44] VCCLAB, Virtual Computational Chemistry Laboratory (2005), http://www.vcclab.org.
  • [45] R. Mannhold, H.J. Waterbeemd, Comput.-Aided Mol. Des. 15, 337 (2001) http://dx.doi.org/10.1023/A:1011107422318[Crossref]
  • [46] C.M.M. Medic-Sari, A. Mornar, I. Jasprica, Acta Pharm. 54, 91 (2004)
  • [47] OECD, Guidelines for Testing of Chemicals, No. 107, OECD, Paris (1992)
  • [48] E. Soczewiński, C.A. Wachtmeister, J. Chromatogr. 7, 311 (1962) http://dx.doi.org/10.1016/S0021-9673(01)86422-0[Crossref]
  • [49] X. Belles, F. Camps, J. Coll, M.D. Piulachs, J. Chem. Ecol. 11, 1439 (1985) http://dx.doi.org/10.1007/BF01012143[Crossref]
  • [50] J. Nawrot, E. Bloszczyk J. Harmatha, Acta Entomol. Bohem. 83, 327 (1986)
  • [51] M. Gao, M. Wang, G.D. Hutchins, O.H. Zheng, Bioorg. Med. Chem. Let. 20, 2529 (2010) http://dx.doi.org/10.1016/j.bmcl.2010.02.094[Crossref]
  • [52] C. Cohen, J. Blaney, C. Humblet, P. Gung, D. Barry, J. Med. Chem. 33, 883 (1990) http://dx.doi.org/10.1021/jm00165a001[Crossref]
  • [53] J. Polański, R. Gieleciak, T. Magdziarz, A. Bąk, J. Chem. Inf. Comput. Sci. 44, 1423 (2004) http://dx.doi.org/10.1021/ci049960l[Crossref]
  • [54] C. Markopoulou, T. Tweedlie, D. Watson, G. Skellern, H. Reda, P. Petersson, H. Bradstock, M. Euerby, Chromatographia 70, 705 (2009) http://dx.doi.org/10.1365/s10337-009-1224-7[Crossref]
  • [55] D.H. Marchand, K. Croes, J.W. Dolan, L.R. Snyder, J. Chromatogr. A 1062, 57 (2005) http://dx.doi.org/10.1016/j.chroma.2004.11.015[Crossref]
  • [56] I. Wolska, J. Popławski, B. Łozowicka, Pol. J. Chem. 72, 2331 (1998)
  • [57] Q. Feng, T. Kumagai, Y. Nakamura, K. Uchida, T. Osawa, 2003. Mutat. Res. 537, 101 (2003) [Crossref]
  • [58] R. Rosso, T.O. Vieira, P.C. Leal, R.J. Nunes, R.A. Yunesb, T.B. Creczynski-Pasa, Bioorg. Med. Chem. 14, 6409 (2006) http://dx.doi.org/10.1016/j.bmc.2006.05.038[Crossref]
  • [59] M. Kostecka, A. Niewiadomy, R. Czeczko, Chromatographia 62, 121 (2005) http://dx.doi.org/10.1365/s10337-005-0597-5[Crossref]
  • [60] L. Gyurosiova, E. Sedlerova, J. Cizmarik, Chem. Pap. 56, 340 (2002)
  • [61] C. Hansch, A. Leo, S.B. Mekapati, A. Kurup, Bioorg. Med. Chem. 12, 3391 (2004) http://dx.doi.org/10.1016/j.bmc.2003.11.037[Crossref]
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-013-0336-y
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