Original Article |
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Pharmacological and Predicted Activities of Natural Azo Compounds |
Valery M. Dembitsky1, Tatyana A. Gloriozova2, Vladimir V. Poroikov2 |
1. National Scientific Center of Marine Biology, 17 Palchevsky Str., Vladivostok, Russia 690041; 2. Institute of Biomedical Chemistry, Moscow, Russia 119121 |
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Abstract This paper describes research on natural azo compounds isolated from fungi, plant, bacteria, and invertebrates. More than 120 biologically active diazene containing alkaloids demonstrate confirmed pharmacological activity, including antitumor, antimicrobial, and antibacterial effects. The structures, origin, and biological activities of azo compounds are reviewed. Utilizing the computer program PASS, some structure-activity relationship new activities are also predicted, pointing toward possible new applications of these compounds. This article emphasizes the role of natural azo compounds as an important source of drug prototypes and leads for drug discovery.
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Keywords
Azo metabolites
Alkaloids
Fungi
Plant
Bacteria
Sponges
SAR
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Fund:The work was partially supported (TAG and VVP) in the framework of the Russian State Academies of Sciences Fundamental Research Program for 2013-2020. |
About author: 10.1007/s13659-016-0117-3 |
Issue Date: 06 February 2018
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1. H.E. Bigelow, Chem. Rev. 9, 117-167 (1931) 2. T.A. La Rue, Lloydia 40, 307-321 (1977) 3. C.C. Nawrat, C.J. Moody, Nat. Prod. Rep. 28, 1426-1444 (2011) 4. L.M. Blair, J.J. Sperry, Nat. Prod. 76, 794-812 (2013) 5. V.M. Dembitsky, Phytomedicine 21, 1559-1581 (2014) 6. V.M. Dembitsky, J. Nat. Med. (Tokyo) 62, 1-33 (2008) 7. V.M. Dembitsky, Eur. J. Med. Chem. 43, 223-251 (2008) 8. F.M.D. Ismail, D.O. Levitsky, V.M. Dembitsky, Eur. J. Med. Chem. 44, 3373-3387 (2009) 9. D.M. Pereira, P. Valentao, P.B. Andrade, Dyes Pigm. 111, 124-134 (2014) 10. A.B. Soliev, K. Hosokawa, K. Enomoto, Evid. Based Complement. Altern. Med. 670349 (2011). doi:10.1155/2011/670349 11. V.M. Dembitsky, T. Ř ezanka, Folia Microbiol. 50, 363-391 (2005) 12. V.M. Dembitsky, Chem. Biodivers. 1, 673-781 (2004) 13. A. Sergeiko, V.V. Poroikov, L.O. HanuŠ, V.M. Dembitsky, Open Med. Chem. J. 2, 26-37 (2008) 14. A. Torres, M. Hochberg, I. Pergament, R. Smoum, V. Niddam, V.M. Dembitsky, Eur. J. Biochem. 271, 780-784 (2004) 15. M. Wainwright, Biotech. Histochem. 85, 341-354 (2010) 16. A.M. Bode, Z. Dong, Cancer Prev. Res. (Phila.) 8, 1-8 (2015) 17. A.S. Shawali, N.A. Samy, J. Adv. Res. 6, 241-254 (2015) 18. V.M. Dembitsky, Tetrahedron 59, 4701-4720 (2003) 19. D.A. Filimonov, A.A. Lagunin, T.A. Gloriozova, A.V. Rudik, Chem. Heterocycl. Compd. 50, 444-457 (2014) 20. V.V. Poroikov, D.A. Filimonov, Y.V. Borodina, A.A. Lagunin, J. Chem. Inf. Comput. Sci. 40, 1349-1355 (2000) 21. V.M. Dembitsky, T. Gloriozova, V.V. Poroikov, Mini Rev. Med. Chem. 5, 319-336 (2005) 22. V.M. Dembitsky, T. Gloriozova, V.V. Poroikov, Mini Rev. Med. Chem. 7, 571-589 (2007) 23. V.M. Dembitsky, T. Gloriozova, V.V. Poroikov, Phytomedicine 22, 183-202 (2015) 24. D.O. Levitsky, T.A. Gloriozova, V.V. Poroikov, V.M. Dembitsky, Mathews J. Pharm. Sci. 1, 003 (2016) 25. M. Yamato, H. Iinuma, H. Naganawa, Y. Yamagishi, M. Hamada, T. Masuda, H. Umezawa, V. Abe, M. Hori, J. Antibiot. 39, 184-191 (1986) 26. Y. Ma, R.J. Parry, Microbiology 146, 345-352 (2000) 27. G. Bianchi, D. Dallavalle, L. Merlini, G. Nasini, S. Quaroni, Planta Med. 69, 574-576 (2003) 28. W.J. McGahren, M.P. Kunstmann, J. Am. Chem. Soc. 91, 2808-2810 (1969) 29. W.J. McGahren, M.P. Kunstmann, J. Am. Chem. Soc. 92, 1587-1590 (1970) 30. M. Nakayama, Y. Takahashi, H. Itoh, K. Kamiya, M. Shiratsuchi, G. Otani, J. Antibiot. 42, 1535-1540 (1989) 31. M. Fujiu, S. Sawairi, H. Shimada, H. Takaya, Y. Aoki, T. Okuda, K. Yokose, J. Antibiot. 47, 833-835 (1994) 32. Y. Aoki, M. Kondoh, M. Nakamura, T. Fujii, T. Yamazaki, H. Shimada, M. Arisawa, J. Antibiot. 47, 909-916 (1994) 33. T.H. Haskell, A. Ryder, Q.R. Bartz, Antibiot. Chemother. (Northfield) 4, 141-144 (1954) 34. J. Ehrlich, L.E. Anderson, G.L. Coffey, W.H. Feldman, Antibiot. Chemother. (Northfield) 4, 338-342 (1954) 35. L.E. Anderson, J. Ehrlich, S.H. Sun, P.R. Burkholder, Antibiot. Chemother. (Northfield) 6, 100-115 (1956) 36. K. Ohkuma, G. Nakamura, S. Yamashita, J. Antibiot. 10, 224-225 (1957) 37. L. Ding, B.S. Ndejouong, A. Maier, H.H. Fiebig, C. Hertweck, J. Nat. Prod. 75, 1729-1734 (2012) 38. N. Manderscheid, S.E. Helaly, A. Kulik, J. Wiese, J. Antibiot. 66, 85-88 (2013) 39. S. Omura, K. Otoguro, N. Imamura, H. Kuga, J. Antibiot. 40, 623-629 (1987) 40. N. Imamura, H. Kuga, K. Otoguro, H. Tanaka, S. Omura, J. Antibiot. 42, 156-158 (1989) 41. K. Tsuzuki, F.S. Yan, K. Otoguro, S. Omura, J. Antibiot. 44, 774-784 (1991) 42. J.R. Egerton, D.A. Ostlind, L.S. Blair, C.H. Eary, Antimicrob. Agents Chemother. 15, 372-378 (1979) 43. A. Sugawara, M. Kubo, T. Nakashima, T. Hirose, Tetrahedron 71, 2149-2157 (2015) 44. G. Le Goff, M.T. Martin, B.I. Iorga, E. Adelin, J. Nat. Prod. 76, 142-149 (2013) 45. Y. Abe, J.I. Kadokura, A. Shimazu, H. Seto, N. Otake, Agric. Biol. Chem. 47, 2703-2705 (1983) 46. W.Y. Chan, T.B. Ng, J.S. Lam, J.H. Wong, Appl. Microbiol. Biotechnol. 85, 985-993 (2010) 47. H. Nakano, M. Hara, T. Katsuyama, Y. Uozaki, K. Gomi, U.S. Chem. Abstr. 119, 158353 (1993) 48. M. Nakaynma, H. Ito, I. Watanabe, M. Shiratsuchi, US Patent 4,981,954 (1991) 49. H. Umezawa, T. Takeuchi, H. Iinuma, M. Ito, M. Ishizuka, J. Antibiot. 28, 87-90 (1975) 50. R. Calvino, R. Fruttero, A. Gasco, A. Miglietta, L. Gabriel, J. Antibiot. 39, 864-868 (1986) 51. A. Gasco, A. Serafino, V. Mortarinin, E. Menziani, Tetrahedron Lett. 38, 3431-3432 (1974) 52. O. Brossa, E. Gadoni, A. Olivero, M. Seccia, A. Miglietta, L. Gabriel, E. Gravela, Res. Commun. Chem. Pathol. Pharmacol. 70, 143-153 (1990) 53. D. Boschi, C. Cena, R. Fruttero, M.I. Brenciaglia, Pharmazie 56, 670-672 (2001) 54. A. Miglietta, E. Gadoni, M. Buffa, A. Olivero, L. Gabriel, Eur. J. Drug Metab. Pharm. 20, 249-254 (1995) 55. T. Okuda, N. Nakayama, A. Fujiwara, Nippon Kingakukai Kaiho 23, 225-234 (1982) 56. T. Okuda, A. Fujiwara, Nippon Kingakkai Kaiho 23, 235-239 (1984) 57. B. Kopcke, A.A.H. Mayer, O. Sterner, Nat. Prod. Lett. 13, 41-46 (1999) 58. T. Kamo, M. Kashiwabara, K. Tanaka, S. Ando, H. Shibata, M. Hirota, Nat. Prod. Res. 20, 507-510 (2006) 59. Y. Takaishi, Y. Murakami, M. Uda, T. Ohashi, N. Hamamura, Phytochemistry 45, 997-1001 (1997) 60. F. Burkhard, A. Siegbert, W. Steglich, J. Fleischhauer, Eur. J. Org. Chem. 16, 3097-3104 (2001) 61. N. Claydon, J. Invertebr. Pathol. 32, 319-324 (1978) 62. D.W. Roberts, in Microbia Control of Pests and Plant Diseases 1970-1980, ed. by H.D. Burges (Academic Press, New York, 1981), pp. 441-464 63. W. Steglich, in Biologically Active Molecules (1989), pp. 1-8 64. T. Suortti, Food Chem. Toxicol. 22, 579-581 (1984) 65. T. Suortti, A. von Wright, J. Chromatogr. 255, 529-532 (1983) 66. S. Yannai, Dictionary of food compounds with CD-ROM:Additives, flavors, and ingredients (Chapman & Hall/CRC, Boca Raton, 2004) 67. M. Gill, R.J. Strauch, Z. Naturforsch. C 39, 1027-1029 (1984) 68. A.T. Gillespie, N. Claydon, Pesticide Sci. 27, 203-215 (1989) 69. M.J. Bidochka, G.G. Khachatourians, J. Insect. Pathol. 58, 106-117 (1991) 70. G.G. Khachatourians, Biochemistry and molecular biology of entomopathogenic fungi, in The Mycota VI. Human and Animal Relationships, ed. by D.H. Howard, J.D. Miller (Springer, Berlin, 1996), pp. 331-363 71. D.N. Pegler, Mushrooms and Toadstools (Mitchell Beazley, London, 1983) 72. C. Dickinson, J. Lucas, The Encyclopedia of Mushrooms (G. P. Putnam's Sons, New York, 1979) 73. Y.Y. Guo, H. Li, Z.X. Zhou, X.M. Mao, Org. Lett. 17, 6114-6117 (2015) 74. R. Wang, The investigation of biologically active secondary metabolites produced by diatoms. Ph.D. Dissertation, University of Rhode Island (1992) 75. Y. Shimizu, Chem. Rev. 93, 1685-1698 (1993) 76. B. Levenberg, J. Biol. Chem. 239, 2267-2274 (1964) 77. S. Hilbig, T. Andries, W. Steglich, T. Anke, Angew. Chem. 97, 1063-1069 (1985) 78. K. Dornberger, W. Ihn, W. Schade, D. Tresselt, A. Zureck, L. Radics, Tetrahedron Lett. 27, 559-566 (1986) 79. J.Y. Cho, H.C. Kwon, P.G. Williams, P.R. Jensen, W. Fenical, Org. Lett. 8, 2471-2474 (2006) 80. M. Bahi, Bandamycin as new antifungal agent and further secondary metabolites from terrestrial and marine microorganisms. Ph.D. Dissertation, Gottingen (2012) 81. K. Yoshida, M. Okamoto, K. Umehara, M. Iwami, J. Antibiot. 35, 151-156 (1982) 82. H. Tanaka, K. Yoshida, Y. Itoh, H. Imanaka, J. Antibiot. 35, 157-163 (1982) 83. S. Omura, H. Tomoda, Q.M. Xu, Y. Takahashi, Y. Iwai, J. Antibiot. 39, 1211-1218 (1986) 84. H. Tomoda, K. Igarashi, S. Omura, Biochim. Biophys. Acta 921, 595-598 (1987) 85. H. Ui, A. Ishiyama, H. Sekiguchi, M. Namatame, A. Nishihara, Y. Takahashi, K. Shiomi, K. Otoguro, S. Omura, J. Antibiot. 60, 220-222 (2007) 86. S. Kosemura, S. Yamamura, Tetrahedron Lett. 38, 3025-3026 (1997) 87. V.V. Smirnov, E.A. Kiprianova, A.D. Garagulya, S.E. Esipov, S.A. Dovjenko, FEMS Microbiol. Lett. 153, 357-361 (1997) 88. H.J. Lindner, G. Schaden, Chem. Ber. 105, 1949-1955 (1972) 89. K. Hirata, H. Nakagami, J. Takashina, T. Mahmud, M. Kobayashi, Heterocycles 43, 1513-1519 (1996) 90. M. Mojzych, J. Chem. Soc. Pak. 33, 698-702 (2011) 91. T. Hosoe, K. Nozawa, N. Kawahara, K. Fukushima, Mycopathologia 146, 9-12 (1999) 92. J.M. Ames, G. MacLeod, Phytochemistry 29, 1201-1207 (1990) 93. P.W. Brian, Bot. Rev. 17, 357-430 (1951) 94. K. Wang, L. Guo, Y. Zou, Y. Li, J. Wu, J. Antibiot. 60, 325-327 (2007) 95. R. Grote, Y. Chen, A. Zeeck, J. Antibiot. 41, 595-601 (1988) 96. H. Bockholt, J.M. Beale, J. Rohr, Angew. Chem. 106, 1733-1735 (1994) 97. K. Hirasawa, K. Isono, J. Antibiot. 31, 628-629 (1978) 98. K. Susugiura, G.H. Hitchings, L.F. Cavalieri, C.C. Stock, Cancer Res. 10, 178-185 (1950) 99. K. Anzai, J. Nagatsu, S. Suzuki, J. Antibiot. 14, 340-342 (1961) 100. K. Anzai, S. Suzuki, J. Antibiot. 14, 253 (1961) 101. A. Stachelska-Wierzchowska, J. Wierzchowski, A. Bzowska, B. Wielgus-Kutrowska, B Mol. 21, 44-49 (2016) 102. M.B. Hossain, D. van der Helm, Acta Crystallogr. 41C, 1199-1202 (1985) 103. V. Ludovic, M.C. Groleau, V. Dekimpe, E. Deziel, Prod. J. Microbiol. Biotechnol. 17, 1407-1429 (2007) 104. J. Franke, K. Ishida, M. Ishida-Ito, C. Hertweck, Angew. Chem. Int. Ed. 52, 8271-8275 (2013) 105. T. Wieland, H. Faulstich, C.R.C. Crit, Rev. Biochem. 5, 185-260 (1978) 106. F. Enjalbert, S. Rapiorm, J. Nouguier-Soulém, S. Guillon, N. Amouroux, C. Cabot, J. Toxicol. Clin. Toxicol. 40, 715-757 (2002) 107. C. Karlson-Stiber, H. Persson, Toxicon 42, 339-349 (2003) 108. J. Garcia, V.M. Costa, A. Carvalho, P. Baptista, P.G. de Pinho, M. de Lourdes Bastos, F. Carvalho, Food Chem. Toxicol. 86, 41-55 (2015) 109. E. Falck-Pedersen, P.W. Morris, D.L. Venton, Int. J. Peptide Protein Res. 21, 431-439 (1983) 110. E.S. Falck-Pedersen, Synthesis and characterization of 70-azo-camatoxins. Ph.D. Dissertation, University of Illinois. University Microfilms International, Ann Arbor, Michigan (1981) 111. V.M. Dembitsky, A.A.A. Al Quntar, M. Srebnik, Chem. Rev. 111, 209-237 (2011) 112. T. Wieland, Peptides of Poisonous Amanita Mushrooms (Springer, Berlin, 1986) 113. W. Zhang, X.J. Huang, S.-Y. Zhang, D.-M. Zhang, R.-W. Jiang, J.-Y. Hu, X.-Q. Zhang, L. Wang, W.-C. Ye, J. Nat. Prod. 78, 2036-2044 (2015) 114. Q. Lu, L. Zhang, G.-R. He, H.-X. Liang, G.-H. Du, Y.-X. Cheng, Chem. Biodivers. 4, 2948-2952 (2007) 115. M. Porwal, B.K. Mehta, D.N. Gupta, Nat. Acad. Sci. Lett. 2, 81-84 (1988) 116. F. Rana, M. Avijit, Int. J. Res. Pham. Chem. 2, 1035-1039 (2012) 117. X. Wang, Z. Lib, B. Yanga, Fitoterapia 75, 789-791 (2004) 118. P. Spencer, R.C. Fry, G.E. Kisby, Front. Genet. 3, 192-194 (2012) 119. G.L. Laqueur, M. Spatz, Cancer Res. 28, 2262-2267 (1968) 120. R.W. Morgan, G.R. Hoffmann, Mutat. Res. 114, 19-58 (1983) 121. D. Schneider, M. Wink, F. Sporer, P. Lounibos, Naturwis-senschaften 89, 281-294 (2002) 122. A. Prado, J. Ledezma, L. Cubilla-Rios, J.C. Bede, D.M. Windsor, J. Chem. Ecol. 37, 736-740 (2011) 123. S.F. Dossaji, Totins in certain indigenous Kenya plants. Ph.D. Thesis, University of Nairobi (1971) 124. T. Tanaka, H. Kohno, M. Murakami, R. Shimada, S. Kagami, Oncol. Rep. 7, 501-508 (2000) 125. K. Nishida, A. Kobayashi, T. Nagahama, T. Numata, Bull. Agric. Chem. Soc. Jpn. 23, 460-464 (1959) 126. T. Nagahama, T. Numata, K. Nishida, K. Agric, Chem. Soc. Jpn. 23, 556-559 (1959) 127. S.S. Chang, Y.L. Chan, M.L. Wu, J.F. Deng, T. Chiu, J. Toxicol. Clin. Toxicol. 42, 49-54 (2004) 128. F. Yagi, K. Tadera, Biochim. Biophys. Acta 1289, 315-321 (1996) 129. D.-F. Hwang, T.-Y. Chen, Ref. Modul. Food Sci. 326-330 (2016) 130. W.W. Wells, M.G. Yang, W. Bolzer, O. Mickelsen, Anal. Biochem. 25, 325-329 (1968) 131. A. Moretti, S. Sabato, G. Siniscalco, Phytochemistry 20, 1415-1416 (1981) 132. P. Lindblad, K. Tadera, F. Yagi, Environ. Exp. Bot. 30, 429-434 (1990) 133. J.E. Poulton, ACS Symp. Ser. 533, 170-190 (1993) 134. Y. Kariya, T. Kubota, J. Fromont, J. Kobayashi, Tetrahedron Lett. 47, 997-998 (2006) 135. Y. Kariya, T. Kubota, J. Fromont, J. Kobayashi, Bioorg. Med. Chem. 14, 8415-8419 (2006) 136. T. Kubota, K. Kura, J. Fromont, J. 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