Antiviral properties of diterpenes and their derivatives

Capa

Citar

Texto integral

Resumo

The review focuses on low-molecular-weight natural metabolites of the diterpene series and their semi-synthetic analogues, which exhibit antiviral activity. Data on the antiviral activity of both plant extracts and their components are provided. The structures of biologically active natural diterpenoids and their derivatives with a pronounced antiviral effect are presented. Mechanisms of therapeutic action of diterpenoids and their derivatives with a pronounced antiviral effect are considered for different viruses. The review summarizes the data over the last 12 years (2011–2022). The bibliography includes 183 references.

Sobre autores

Olga Yarovaya

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistryof the Siberian Branch of Russian Academy of Sciences

Email: ooo@nioch.nsc.ru
Doctor of chemical sciences, Head Scientist Researcher

Sergey Laev

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistryof the Siberian Branch of Russian Academy of Sciences

Candidate of chemical sciences, Researcher

Nariman Salakhutdinov

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistryof the Siberian Branch of Russian Academy of Sciences

Email: anvar@nioch.nsc.ru
Doctor of chemical sciences, Professor

Bibliografia

  1. O.I.Yarovaya, N.F.Salakhutdinov. Russ. Chem. Rev., 90, 488 (2021)
  2. N.F.Salakhutdinov, K.P.Volcho, O.I.Yarovaya. Pure Appl. Chem., 89, 1105 (2017)
  3. S.Xiao, Z.Tian, Y.Wang, L.Si, L.Zhang, D.Zhou. Med. Res. Rev., 38, 951 (2018)
  4. M.T.Islam, S.K.Bardaweel, M.S.Mubarak, W.Koch, K.Gawe-Beben, B.Antosiewicz, J.Sharifi-Rad. Front. Immunol., 11, Art. ID 572136 (2020)
  5. A.P.Wardana, N.S.Aminah, M.Rosyda, M.I.Abdjan, A.N.Kristanti, K.N.W.Tun, M.I.Choudhary, Y.Takaya. Heliyon, 7, e07777 (2021)
  6. P.Saha, F.I.Rahman, F.Hussain, S.M.A.Rahman, M.M.Rahman. Front. Pharmacol., 12, Art. ID 820312 (2021)
  7. S.Bhakat, M.E.S.Soliman. J. Nat. Med., 69, 451 (2015)
  8. M.T.Islam, M.S.Mubarak. Phyther. Res., 34, 674 (2020)
  9. G.A.Tolstikov, T.G.Tolstikov, E.E.Shul'ts, S.E.Tolstikov, M.V.Khvostov. Smolyanye Kisloty Khvoinykh Rossii. Khimiya, Farmakologiya (Resin Acids of Coniferous Russia. Chemistry, Pharmacology). (Novosibirsk: Akad. Izd. GEO, 2011)
  10. M.A.Gonzalez. Eur. J. Med. Chem., 87, 834 (2014)
  11. T.Fonseca, B.Gigante, M.M.Marques, T.L.Gilchrist, E.De Clercq. Bioorg. Med. Chem., 12, 103 (2004)
  12. R.Gowda, S.V.Madhunapantula, O.F.Kuzu, A.Sharma, G.P.Robertson. Mol. Cancer Ther., 13, 1679 (2014)
  13. K.S.Kovaleva, A.A.Kononova, V.A.Korobeynikov, V.V.Zarubaev, A.A.Shtro, Y.R.Orshanskay, O.I.Yarovaya, A.G.Pokrovsky, N.F Salakhutdinov. Med. Chem., 6, 642 (2016)
  14. V.C.Roa-Linares, Y.M.Brand, L.S.Agudelo-Gomez, V.Tangarife-Castano, L.A.Betancur-Galvis, J.C.Gallego-Gomez, M.A.Gonzalez. Eur. J. Med. Chem., 108, 79 (2016)
  15. F.T.G.Sousa, C.Nunes, C.M.Romano, E.C.Sabino, M.A.Gonzalez-Cardenete. Rev. Inst. Med. Trop. Sao Paulo, 62, 2 (2020)
  16. K.S.Kovaleva, O.I.Yarovaya, A.V.Shernyukov, V.V.Zarubaev, A.A.Shtro, Y.R.Orshanskaya, N.F.Salakhutdinov. Chem. Heterocycl. Compd., 53, 364 (2017)
  17. E.V.Tretyakova, I.E.Smirnova, E.V.Salimova, V.N.Odinokov. Bioorg. Med. Chem., 23, 6543 (2015)
  18. Y.-D.Wang, G.-J.Zhang, J.Qu, Y.-H.Li, J.-D.Jiang, Y.-B.Liu, S.-G.Ma, Y.Li, H.-N.Lv, S.-S.Yu. J. Nat. Prod., 76, 1976 (2013)
  19. G.-J.Zhang, Y.-H.Li, J.-D.Jiang, S.-S.Yu, J.Qu, S.-G.Ma, Y.-B.Liu, D.-Q.Yu. Tetrahedron, 69, 1017 (2013)
  20. G.-J.Zhang, Y.-H.Li, J.-D.Jiang, S.-S.Yu, X.-J.Wang, P.-Y.Zhuang, Y.Zhang, J.Qu, S.-G.Ma, Y.Li, Y.-B.Liu, D.-Q.Yu. Tetrahedron, 70, 4494 (2014)
  21. M.A.Gonzalez, R.J.Zaragoza. J. Nat. Prod., 77, 2114 (2014)
  22. S.Bahri, S.Jameleddine, V.Shlyonsky. Biomed. Pharmacother., 84, 569 (2016)
  23. S.Birtic, P.Dussort, F.-X.Pierre, A.C.Bily, M.Roller. Phytochemistry, 115, 9 (2015)
  24. H.-B.Shin, M.-S.Choi, B.Ryu, N.-R.Lee, H.-I.Kim, H.-E.Choi, J.Chang, K.-T.Lee, D.S.Jang, K.-S.Inn. Virol. J., 10, 303 (2013)
  25. A.Pariu, B.otrukelj, M.Renko, V.Turk, M.Pukl, A.Umek, B.D.Korant. J. Nat. Prod., 56, 1426 (1993)
  26. C.A.Bueno, F.M.Michelini, M.W.Pertino, C.A.Gomez, G.Schmeda-Hirschmann, L.E.Alche. Med. Microbiol. Immunol., 204, 575 (2015)
  27. Z.-y.Fang, M.Zhang, J.-n. Liu, X.Zhao, Y.-q.Zhang, L.Fang. Front. Pharmacol., 11, 1 (2020)
  28. D.Elebeedy, W.F.Elkhatib, A.Kandeil, A.Ghanem, O.Kutkat, R.Alnajjar, M.A.Saleh, A.I.Abd El Maksoud, I.Badawy, A.A.Al-Karmalawy. RSC Adv., 11, 29267 (2021)
  29. Z.-K.Yin, Z.-M.Feng, J.-S.Jiang, X.Zhang, P.-C.Zhang, Y.-N.Yang. J. Asian Nat. Prod. Res., 22, 24 (2020)
  30. Y.-H.Wu, Y.-R.Wu, B.Li, Z.-Y.Yan. Fitoterapia, 145, 104633 (2020)
  31. W.He, Y.Li, Y.Qin, X.Tong, Z.Song, Y.Zhao, R.Wei, L.Li, H.Dai, W.Wang, H.Luo, X.Ye, L.Zhang, X.Liu. Appl. Microbiol. Biotechnol., 101, 6365 (2017)
  32. D.Zhang, J.Guo, M.Zhang, X.Liu, M.Ba, X.Tao, L.Yu, Y.Guo, J.Dai. J. Nat. Prod., 80, 3241 (2017)
  33. V.K.Bajpai, N.-H.Kim, K.Kim, S.C.Kang. Pak. J. Pharm. Sci., 29, 1077 (2016)
  34. L.Yang, L.Li, S.Huang, J.Pu, Y.Zhao, Y.Ma, J.Chen, C.Leng, Z.Tao, H.Sun. Chem. Pharm. Bull., 59, 1102 (2011)
  35. J.-X.Zhao, C.-P.Liu, W.-Y.Qi, M.-L.Han, Y.-S.Han, M.A.Wainberg, J.-M.Yue. J. Nat. Prod., 77, 2224 (2014)
  36. X.-J.Li, Z.-Z.Jiang, L.Zhang. J. Ethnopharmacol., 155, 67 (2014)
  37. C.Xi, S.Peng, Z.Wu, Q.Zhou, J.Zhou. Biomed. Pharmacother., 90, 531 (2017)
  38. A.Salminen, M.Lehtonen, T.Paimela, K.Kaarniranta. Biochem. Biophys. Res. Commun., 394, 439 (2010)
  39. S.Isharwal, S.Modi, N.Arora, C.Uhlrich, B.Giri, U.Barlass, A.Soubra, R.Chugh, S.M.Dehm, V.Dudeja, A.Saluja, S.Banerjee, B.Konety. Prostate, 77, 584 (2017)
  40. J.-T.Liou, Z.-Y.Chen, L.-J.Ho, S.-P.Yang, D.-M.Chang, C.-C.Liang, J.-H.Lai. Eur. J. Pharmacol., 589, 288 (2008)
  41. Z.Wan, X.Chen. Retrovirology, 11, 88 (2014)
  42. L.Ni, J.Ma, C.Li, L.Li, J.Guo, S.Yuan, Q.Hou, Y.Guo, D.Zhang. Tetrahedron Lett., 56, 1239 (2015)
  43. A.Vasas, J.Hohmann. Chem. Rev., 114, 8579 (2014)
  44. R.K.Devappa, H.P.S.Makkar, K.Becker. J. Am. Oil Chem. Soc., 88, 301 (2011)
  45. S.Wang, X.Wu, M.Tan, J.Gong, W.Tan, B.Bian, M.Chen, Y.Wang. J. Ethnopharmacol., 140, 33 (2012)
  46. S.-Z.Huang, Q.-Y.Ma, W.-W.Fang, F.-Q.Xu, H.Peng, H.-F.Dai, J.Zhou, Y.-X.Zhao. J. Asian Nat. Prod. Res., 15, 750 (2013)
  47. S.-Z.Huang, X.Zhang, Q.-Y.Ma, Y.-T.Zheng, F.-Q.Xu, H.Peng, H.-F.Dai, J.Zhou, Y.-X.Zhao. Fitoterapia, 91, 224 (2013)
  48. N.N.Win, H.Ngwe, I.Abe, H.Morita. J. Nat. Med., 71, 579 (2017)
  49. N.N.Win, T.Ito, T.Matsui, S.Aimaiti, T.Kodama, H.Ngwe, Y.Okamoto, M.Tanaka, Y.Asakawa, I.Abe, H.Morita. Bioorg. Med. Chem. Lett., 26, 1789 (2016)
  50. N.N.Win, T.Kodama, Z.P.Htoo, S.Y.Y.Hnin, H.Ngwe, I.Abe, H.Morita. Fitoterapia, 151, 104870 (2021)
  51. W.Jing, X.Zhang, H.Zhou, Y.Wang, M.Yang, L Long, H.Gao. Fitoterapia, 134, 226 (2019)
  52. R.W.Jiang, S.C.Ma, P.P.H.But, T.C.W.Mak. J. Nat. Prod., 64, 1266 (2001)
  53. J.Wu, G.Chen, X.Xu, X.Huo, S.Wu, Z.Wu, H.Gao. Fitoterapia, 92, 168 (2014)
  54. S.Kamikawa, S.Oshimo, E.Ohta, T.Nehira, H.Ômura, S.Ohta. Phytochemistry, 121, 50 (2016)
  55. J.Xu, X.Cao, F.Liu, J.Ma, X.Liu, L.Tong, G.Su, Y.Ohizumi, D.Lee, L.Wang, Y.Guo. Fitoterapia, 113, 144 (2016)
  56. S.-N.Liu, J.Hu, S.H.Tan, Q.Wang, J.Xu, Y.Wang, Y.Yuan, Q.Gu. RSC Adv., 7, 46938 (2017)
  57. Z.Dang, K.Jung, L.Zhu, H.Xie, K.-H.Lee, C.-H.Chen, L.Huang. ACS Med. Chem. Lett., 6, 355 (2015)
  58. C.-H.Chao, J.-C.Cheng, D.-Y.Shen, T.-S.Wu. J. Nat. Prod., 77, 22 (2014)
  59. Y.Ma, X.-Y.Mao, L.-J.Huang, Y.-M.Fan, W.Gu, C.Yan, T.Huang, J.-X.Zhang, C.-M.Yuan, X.-J.Hao. Fitoterapia, 109, 8 (2016)
  60. B.Wang, Y.Wei, X.Zhao, X.Tian, J.Ning, B.Zhang, S.Deng, D.Li, X.Ma, C.Wang. Bioorg. Chem., 81, 234 (2018)
  61. J.Li, X.Feng, D.Liu, Z.Zhang, X.Chen, R.Li, H.Li. Chem. Biodivers., 16, 2 (2019)
  62. S.-J.Lin, T.-C.Su, C.-N.Chu, Y.-C.Chang, L.-M.Yang, Y.-C.Kuo, T.-J.Huang. J. Nat. Prod., 79, 3057 (2016)
  63. T.-J.Huang, C.-L.Yang, Y.-C.Kuo, Y.-C.Chang, L.-M.Yang, B.-H.Chou, S.-J.Lin. Bioorg. Med. Chem., 23, 720 (2015)
  64. W.-F.Li, J.Wang, J.-J.Zhang, X.Song, C.-F.Ku, J.Zou, J.-X.Li, L.-J.Rong, L.-T.Pan, H.-J.Zhang. Int. J. Mol. Sci., 16, 27978 (2015)
  65. H.-C.Liu, Z.-B.Xiang, Q.Wang, B.-Y.Li, Y.-S.Jin, H.-S.Chen. Fitoterapia, 118, 94 (2017)
  66. D.R.Littler, M.Liu, J.L.McAuley, S.A.Lowery, P.T.Illing, B.S.Gully, A.W.Purcell, I.R.Chandrashekaran, S.Perlman, D.F.J.Purcell, R.J.Quinn, J.Rossjohn. J. Biol. Chem., 297, 101362 (2021)
  67. T.Klc, G.Topcu, A.C.Goren, Z.Aydogmus, A.Karagoz, Y.K.Yildiz, I.Aslan. Rec. Nat. Prod., 14, 256 (2020)
  68. W.Lai, L.Huang, L.Zhu, G.Ferrari, C.Chan, W.Li, K.-H.Lee, C.-H.Chen. J. Med. Chem., 58, 8638 (2015)
  69. L.Huang, P.Ho, J.Yu, L.Zhu, K.-H.Lee, C.-H.Chen. PLoS One, 6, e26677 (2011)
  70. L.Huang, W.H.Lai, L.Zhu, W.Li, L.Wei, K.H.Lee, L.Xie, C.H.Chen. ACS Med. Chem. Lett., 9, 268 (2018)
  71. Y.Asada, A.Sukemori, T.Watanabe, K.J.Malla, T.Yoshikawa, W.Li, K.Koike, C.-H.Chen, T.Akiyama, K.Qian, K.Nakagawa-Goto, S.L.Morris-Natschke, K.-H.Lee. Org. Lett., 13, 2904 (2011)
  72. M.Yan, Y.Lu, C.-H.Chen, Y.Zhao, K.-H.Lee, D.-F.Chen. J. Nat. Prod., 78, 2712 (2015)
  73. A.H.H.El-Desoky, K.Eguchi, N.Kishimoto, T.Asano, H.Kato, Y.Hitora, S.Kotani, T.Nakamura, S.Tsuchiya, T.Kawahara, M.Watanabe, M.Wada, M.Nakajima, T.Watanabe, S.Misumi, S.Tsukamoto. J. Med. Chem., 65, 3460 (2022)
  74. Q.Liu, Y.-Y.Cheng, W.Li, L.Huang, Y.Asada, M.-T.Hsieh, S.L.Morris-Natschke, C.-H.Chen, K.Koike, K.-H.Lee. J. Med. Chem., 62, 6958 (2019)
  75. K.Otsuki, W.Li, Y.Asada, C.-H.Chen, K.-H.Lee, K.Koike. Org. Lett., 22, 11 (2020)
  76. V.Vidal, O.Potterat, S.Louvel, F.Hamy, M.Mojarrab, J.-J.Sanglier, T.Klimkait, M.Hamburger. J. Nat. Prod., 75, 414 (2012)
  77. S.Z.Huang, X.J.Zhang, X.Y.Li, L.M.Kong, H.Z.Jiang, Q.Y.Ma, Y.Q.Liu, J.M.Hu, Y.T.Zheng, Y.Li, J.Zhou, Y.X.Zhao. Phytochemistry, 75, 99 (2012)
  78. Y.-Y.Liu, Y.-P.Liu, X.-P.Wang, Z.-H.Qiao, X.-M.Yu, Y.-Z.Zhu, L.Xie, L.Qiang, Y.-H.Fu. Bioorg. Chem., 105, 104388 (2020)
  79. S.F.Li, X.Liang, X.K.Wu, X.Gao, L.W.Zhang. J. Nat. Prod., 84, 1022 (2021)
  80. F.Olivon, S.Remy, G.Grelier, C.Apel, C.Eydoux, J.-C.Guillemot, J.Neyts, L.Delang, D.Touboul, F.Roussi, M.Litaudon. J. Nat. Prod., 82, 330 (2019)
  81. Y.-Y.Cheng, H.Chen, H.-P.He, Y.Zhang, S.-F.Li, G.-H.Tang, L.-L.Guo, W.Yang, F.Zhu, Y.-T.Zheng, S.-L.Li, X.-J.Hao. Phytochemistry, 96, 360 (2013)
  82. S.-F.Li, Y.Zhang, N.Huang, Y.-T.Zheng, Y.-T.Di, S.-L.Li, Y.-Y.Cheng, H.-P.He, X.-J.Hao. Phytochemistry, 93, 216 (2013)
  83. P.-M.Allard, P.Leyssen, M.-T.Martin, M.Bourjot, V.Dumontet, C.Eydoux, J.-C.Guillemot, B.Canard, C.Poullain, F.Gueritte, M.Litaudon. Phytochemistry, 84, 160 (2012)
  84. P.-M.Allard, M.-T.Martin, M.-E.Tran Huu Dau, P.Leyssen, F.Gueritte, M.Litaudon. Org. Lett., 14, 342 (2012)
  85. M.Bourjot, P.Leyssen, J.Neyts, V.Dumontet, M.Litaudon. Molecules, 19, 3617 (2014)
  86. R.K.Devappa, C.C.Malakar, H.P.S.Makkar, K.Becker. Nat. Prod. Res., 27, 1459 (2013)
  87. L.-F.Nothias-Scaglia, C.Pannecouque, F.Renucci, L.Delang, J.Neyts, F.Roussi, J.Costa, P.Leyssen, M.Litaudon, J.Paolini. J. Nat. Prod., 78, 1277 (2015)
  88. N.Marquez, M.A.Calzado, G.Sanchez-Duffhues, M.Perez, A.Minassi, A.Pagani, G.Appendino, L.Diaz, M.A.Munoz-Fernandez, E.Munoz. Biochem. Pharmacol., 75, 1370 (2008)
  89. H.Chen, R.Zhang, R.-H.Luo, L.-M.Yang, R.-R.Wang, X.-J.Hao, Y.-T.Zheng. Molecules, 22, 1498 (2017)
  90. Y.Asada, A.Sukemori, T.Watanabe, K.J.Malla, T.Yoshikawa, W.Li, X.Kuang, K.Koike, C.-H.Chen, T.Akiyama, K.Qian, K.Nakagawa-Goto, S.L.Morris-Natschke, Y.Lu, K.-H Lee. J. Nat. Prod., 76, 852 (2013)
  91. P.A.Cox. Pharm. Biol., 39, 33 (2001)
  92. G.Miana, M.Riaz, S.Shahzad-ul-Hussan, R.Paracha, U.Paracha. Mini-Rev. Med. Chem., 15, 1122 (2015)
  93. H.Shang, J.Ding, S.Yu, T.Wu, Q.Zhang, F.Liang. Acta Pharmacol. Sin., 36, 908 (2015)
  94. L.-L.Pan, P.-L.Fang, X.-J.Zhang, W.Ni, L.Li, L.-M.Yang, C.-X.Chen, Y.-T.Zheng, C.-T.Li, X.-J.Hao, H.-Y.Liu. J. Nat. Prod., 74, 1508 (2011)
  95. M.Bourjot, L.Delang, V.H.Nguyen, J.Neyts, F.Gueritte, P.Leyssen, M.Litaudon. J. Nat. Prod., 75, 2183 (2012)
  96. E.J.Beans, D.Fournogerakis, C.Gauntlett, L.V.Heumann, R.Kramer, M.D.Marsden, D.Murray, T.-W.Chun, J.A.Zack, P.A.Wender. Proc. Natl. Acad. Sci. USA, 110, 11698 (2013)
  97. G.Tong, Z.Liu, P.Li. Chem., 4, 2944 (2018)
  98. F.Olivon, H.Palenzuela, E.Girard-Valenciennes, J.Neyts, C.Pannecouque, F.Roussi, I.Grondin, P.Leyssen, M.Litaudon. J. Nat. Prod., 78, 1119 (2015)
  99. Y.Lu, Y.-S.Huang, C.-H.Chen, T.Akiyama, S.L.Morris-Natschke, Y.-Y.Cheng, I.-S.Chen, S.-Z.Yang, D.-F.Chen, K.-H.Lee. Phytochemistry, 174, 112360 (2020)
  100. L.S.Abreu, Y.M.do Nascimento, R.dos S.Costa, M.L.S.Guedes, B.N.R.F.Souza, L.J.Pena, V.C.D.O.Costa, M.T.Scotti, R.Braz-Filho, J.M.Barbosa-Filho, M.S.da Silva, E.D.S.Velozo, J.F.Tavares. J. Nat. Prod., 82, 2721 (2019)
  101. L.-F.Nothias, S.Boutet-Mercey, X.Cachet, E.De La Torre, L.Laboureur, J.-F.Gallard, P.Retailleau, A.Brunelle, P.C.Dorrestein, J.Costa, L.M.Bedoya, F.Roussi, P.Leyssen, J.Alcami, J.Paolini, M.Litaudon, D.Touboul. J. Nat. Prod., 80, 2620 (2017)
  102. H.E.De la Torre-Tarazona, R.Jimenez, P.Bueno, S.Camarero, L.Roman, J.L.Fernandez-Garcia, M.Beltran, L.F.Nothias, X.Cachet, J.Paolini, M.Litaudon, J.Alcami, L.M.Bedoya. Biochem. Pharmacol., 177, 113937 (2020)
  103. M.Esposito, L.-F.Nothias, P.Retailleau, J.Costa, F.Roussi, J.Neyts, P.Leyssen, D.Touboul, M.Litaudon, J.Paolini. J. Nat. Prod., 80, 2051 (2017)
  104. F.Olivon, P.-M.Allard, A.Koval, D.Righi, G.Genta-Jouve, J.Neyts, C.Apel, C.Pannecouque, L.-F.Nothias, X.Cachet, L.Marcourt, F.Roussi, V.L.Katanaev, D.Touboul, J.-L.Wolfender, M.Litaudon. ACS Chem. Biol., 12, 2644 (2017)
  105. S.-Z.Huang, X.Zhang, Q.-Y.Ma, H.Peng, Y.-T.Zheng, J.-M.Hu, H.-F.Dai, J.Zhou, Y.-X.Zhao. Fitoterapia, 95, 34 (2014)
  106. J.B.F.Tostes, A.L.D.Carvalho, A.J.Ribeiro da Silva, P.J.P.Mourao, A.D.Rossi, A.Tanuri, A.C.Siani. J. Nat. Prod., 84, 1666 (2021)
  107. https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=BasicSearch.process. (n.d.) (Last access 11.01.2023)
  108. S.M.Ogbourne, P.G.Parsons. Fitoterapia, 98, 36 (2014)
  109. G.Jiang, E.A.Mendes, P.Kaiser, D.P.Wong, Y.Tang, I.Cai, A.Fenton, G.P.Melcher, J.E.K.Hildreth, G.R.Thompson, J.K.Wong, S.Dandekar. PLoS Pathog., 11, e1005066 (2015)
  110. J.Brogdon, W.Ziani, X.Wang, R.S.Veazey, H.Xu. Sci. Rep., 6, 39032 (2016)
  111. D.Pandelo Jose, K.Bartholomeeusen, R.D.da Cunha, C.M.Abreu, J.Glinski, T.B.F.da Costa, A.F.M.Bacchi Rabay, L.F.Pianowski Filho, L.W.Dudycz, U.Ranga, B.M.Peterlin, L.F.Pianowski, A.Tanuri, R.S.Aguiar. Virology, 462-463, 328 (2014)
  112. G.Jiang, E.A.Mendes, P.Kaiser, S.Sankaran-Walters, Y.Tang, M.G.Weber, G.P.Melcher, G.R.Thompson, A.Tanuri, L.F.Pianowski, J.K.Wong, S.Dandekar. AIDS, 28, 1555 (2014)
  113. C.M.Abreu, S.L.Price, E.N.Shirk, R.D.Cunha, L.F.Pianowski, J.E.Clements, A.Tanuri, L.Gama. PLoS One, 9, e97257 (2014)
  114. A.M.Spivak, E.T.Larragoite, M.L.Coletti, A.B.Macedo, L.J.Martins, A.Bosque, V.Planelles. Retrovirology, 13, 88 (2016)
  115. D.C.Cary, K.Fujinaga, B.M.Peterlin. PLoS One, 11, e0168027 (2016)
  116. Q.Liu, W.Li, L.Huang, Y.Asada, S.L.Morris-Natschke, C.-H.Chen, K.-H.Lee, K.Koike. Eur. J. Med. Chem., 156, 618 (2018)
  117. P.Wang, P.Lu, X.Qu, Y.Shen, H.Zeng, X.Zhu, Y.Zhu, X.Li, H.Wu, J.Xu, H.Lu, Z.Ma, H.Zhu. Sci. Rep., 7, 9451 (2017)
  118. Y.-S.Huang, Y.Lu, C.-H.Chen, K.-H.Lee, D.-F.Chen. J. Nat. Prod., 82, 1587 (2019)
  119. A.A.Okoye, R.Fromentin, H.Takata, J.H.Brehm, Y.Fukazawa, B.Randall, M.Pardons, V.Tai, J.Tang, J.Smedley, M.Axthelm, J.D.Lifson, L.J.Picker, D.Favre, L.Trautmann, N.Chomont. PLoS Pathog., 18, e1010245 (2022)
  120. L.-F.Nothias-Scaglia, I.Schmitz-Afonso, F.Renucci, F.Roussi, D.Touboul, J.Costa, M.Litaudon, J.Paolini. J. Chromatogr. A, 1422, 128 (2015)
  121. L.-F.Nothias-Scaglia, V.Dumontet, J.Neyts, F.Roussi, J.Costa, P.Leyssen, M.Litaudon, J.Paolini. Fitoterapia, 105, 202 (2015)
  122. M.Fattahian, M.Ghanadian, Z.Ali, I.A.Khan. Phytochem. Rev., 19, 265 (2020)
  123. L.M.Bedoya, N.Marquez, N.Martinez, S.Gutierrez-Eisman, A.Alvarez, M.A.Calzado, J.M.Rojas, G.Appendino, E.Munoz, J.Alcami. Biochem. Pharmacol., 77, 965 (2009)
  124. L.-F.Nothias-Scaglia, P.Retailleau, J.Paolini, C.Pannecouque, J.Neyts, V.Dumontet, F.Roussi, P.Leyssen, J.Costa, M.Litaudon. J. Nat. Prod., 77, 1505 (2014)
  125. M.Esposito, L.-F.Nothias, H.Nedev, J.-F.Gallard, P.Leyssen, P.Retailleau, J.Costa, F.Roussi, B.I.Iorga, J.Paolini, M.Litaudon. J. Nat. Prod., 79, 2873 (2016)
  126. Z.-P.Mai, G.Ni, Y.-F.Liu, Y.-H.Li, L.Li, J.-Y.Li, D.-Q.Yu. J. Org. Chem., 83, 167 (2018)
  127. C.-S.Huang, S.-H.Luo, Y.-L.Li, C.-H.Li, J.Hua, Y.Liu, S.-X.Jing, Y.Wang, M.-J.Yang, S.-H.Li. Nat. Prod. Bioprospect., 4, 91 (2014)
  128. Y.Tian, W.Xu, C.Zhu, S.Lin, Y.Li, L.Xiong, S.Wang, L.Wang, Y.Yang, Y.Guo, H.Sun, X.Wang, J.Shi. J. Nat. Prod., 74, 1221 (2011)
  129. M.Dong, X.-Q.Chen, C.-H.Chen, R.-T.Li. Chem. Biodivers., 15, e1700560 (2018)
  130. S.Remy, F.Olivon, S.Desrat, F.Blanchard, V.Eparvier, P.Leyssen, J.Neyts, F.Roussi, D.Touboul, M.Litaudon. J. Nat. Prod., 81, 901 (2018)
  131. K.Ogawa, S.Nakamura, K.Hosokawa, H.Ishimaru, N.Saito, K.Ryu, M.Fujimuro, S.Nakashima, H.Matsuda. J. Nat. Med., 72, 439 (2018)
  132. P.R.S.Stephens, C.C.Cirne-Santos, C.de Souza Barros, V.L.Teixeira, L.A.D.Carneiro, L.dos S.C.Amorim, J.S.P.Ocampo, L.R.R.Castello-Branco, I.C.N.de Palmer Paixao. J. Appl. Phycol., 29, 775 (2017)
  133. L.Miceli, V.Teixeira, H.Castro, C.Rodrigues, J.Mello, M.Albuquerque, L.Cabral, M.de Brito, A.de Souza. Mar. Drugs, 11, 4127 (2013)
  134. V.Garrido, G.A.P.B.Teixeira, V.L.Teixeira, P.Ocampo, W.J.Ferreira, D.N.Cavalcanti, S.M.N.Campos, M.de M.B.Pedruzzi, P.Olaya, C.C.C.dos Santos, V.Giongo, I.C.P.Paixao. Rev. Bras. Farmacogn., 21, 209 (2011)
  135. A.Pardo-Vargas, I.de Barcelos Oliveira, P.Stephens, C.Cirne-Santos, I.de Palmer Paixao, F.Ramos, C.Jimenez, J.Rodriguez, J.Resende, V.Teixeira, L.Castellanos. Mar. Drugs, 12, 4247 (2014)
  136. A.Pardo-Vargas, F.A.Ramos, C.C.Cirne-Santos, P.R.Stephens, I.C.P.Paixao, V.L.Teixeira, L.Castellanos. Bioorg. Med. Chem. Lett., 24, 4381 (2014)
  137. F.Amaya-Garcia, M.L.Sanchez Nunez, F.A.Ramos, M.Puyana, I.C.Nunes de Palmer Paixao, V.L.Teixeira, L.Castellanos. Rev. Colomb. Quim., 46, 5 (2017)
  138. F.Amaya-Garcia, C.Cirne-Santos, C.de Souza Barros, A.M.Pinto, M.L.Sanchez Nunez, V.L.Teixeira, J.A.L.C.Resende, F.A.Ramos, I.C.Nunes de Palmer Paixao, L.Castellanos. J. Nat. Prod., 84, 1373 (2021)
  139. C.C.Cirne-Santos, C.de Souza Barros, M.C.de Oliveira, V.W.-H.Rabelo, R.C.Azevedo, V.L.Teixeira, D.F.Ferreira, I.C.Nunes de Palmer Paixao. Sci. Rep., 10, 8263 (2020)
  140. C.de Souza Barros, C.C.Cirne-Santos, V.Garrido, I.Barcelos, P.R.S.Stephens, V.Giongo, V.L.Teixeira, I.C.Nunes de Palmer Paixao. J. Appl. Phycol., 28, 2523 (2016)
  141. C.de Souza Barros, V.Garrido, V.Melchiades, R.Gomes, M.W.L.Gomes, V.L.Teixeira, I.C.Nunes de Palmer Paixao. J. Appl. Phycol., 29, 769 (2017)
  142. R.dos S.Souza Marinho, M.C.R.Vieira, C.de Souza Barros, C.C.Cirne-Santos, J.P.G.Leite, V.L.Teixeira, I.C.Nunes de Palmer Paixao, A.M.V.Pinto. Arch. Biomed. Eng. Biotechnol., 3 (2), Art. ID 000557 (2019)
  143. R.Li, S.L.Morris-Natschke, K.-H.Lee. Nat. Prod. Rep., 33, 1166 (2016)
  144. L.Li, L.Chen, Y.Li, S.Sun, S.Ma, Y.Li, J Qu. Phytochemistry, 174, 112343 (2020)
  145. X.Gang, Z.Fang, Y.Xian-Wen, Z.Juan, Y.Li-Xin, X.-L.Shen, Y.-J.Hu, Q.-S.Zhao. Nat. Prod. Bioprospect., 1, 81 (2011)
  146. D.Zhang, X.Tao, G.Gu, Y.Wang, W.Zhao, W.Zhao, Y.Ren, S.Dai, L.Yu. Front. Microbiol., 12, Art. ID 662321 (2021);
  147. https://doi.org/10.3389/fmicb.2021.662321; https://doi.org/10.3389/fmicb.2021.662321
  148. T.Wu, Q.Wang, C.Jiang, S.L.Morris-Natschke, H.Cui, Y.Wang, Y.Yan, J.Xu, K.-H.Lee, Q.Gu. J. Nat. Prod., 78, 500 (2015); https://doi.org/10.1021/np500988m
  149. B.Fois, A.Corona, E.Tramontano, S.Distinto, E.Maccioni, R.Meleddu, P.Caboni, C.Floris, F.Cottiglia. J. Enzyme Inhib. Med. Chem., 36, 749 (2021)
  150. Z.-X.Yu, C.-J.Zheng, G.-Y.Chen, R.-L.Huang, X.-M.Zhou, Z.-G.Niu, X.-B.Li, C.-R.Han, X.-P.Song. J. Nat. Prod., 82, 27 (2019)
  151. C.Lhullier, E.de Oliveira Tabalipa, F.Nienkotter Sarda, L.Sandjo, N.Zanchett Schneider, J.Carraro, C.Oliveira Simees, E.Schenkel. Mar. Drugs, 17, 57 (2019)
  152. Q.T.N.Tran, W.S.F.Wong, C.L.L.Chai. Pharmacol. Res., 124, 43 (2017)
  153. B.Zeng, A.Wei, Q.Zhou, M.Yuan, K.Lei, Y.Liu, J.Song, L.Guo, Q.Ye. Phyther. Res., 36, 336 (2022)
  154. S.Gupta, K.P.Mishra, L.Ganju. Arch. Virol., 162, 611 (2017)
  155. R.Latif, C.-Y.Wang. Chin. J. Nat. Med., 18, 760 (2020)
  156. P.Wintachai, P.Kaur, R.C.H.Lee, S.Ramphan, A.Kuadkitkan, N.Wikan, S.Ubol, S.Roytrakul, J.J.H.Chu, D.R.Smith. Sci. Rep., 5, 14179 (2015)
  157. P.Panraksa, S.Ramphan, S.Khongwichit, D.R.Smith. Antiviral Res., 139, 69 (2017)
  158. J.-C.Lee, C.-K.Tseng, K.-C.Young, H.-Y.Sun, S.-W.Wang, W.-C.Chen, C.-K.Lin, Y.-H.Wu. Br. J. Pharmacol., 171, 237 (2014)
  159. B.Yu, C.Dai, Z.Jiang, E.Li, C.Chen, X.Wu, J.Chen, Q.Liu, C.Zhao, J.He, D.Ju, X.Chen. Chin. J. Integr. Med., 20, 540 (2014)
  160. T.-H.Shi, Y.-L.Huang, C.-C.Chen, W.-C.Pi, Y.-L.Hsu, L.-C.Lo, W.-Y.Chen, S.-L.Fu, C.-H.Lin. Biochem. Biophys. Res. Commun., 533, 467 (2020)
  161. W.Cai, H.Wen, Q.Zhou, L.Wu, Y.Chen, H.Zhou, M.Jin. Antiviral Res., 181, 104885 (2020)
  162. W.Cai, S.Chen, Y.Li, A.Zhang, H.Zhou, H.Chen, M.Jin. Antiviral Res., 133, 95 (2016)
  163. S.Seubsasana, C.Pientong, T.Ekalaksananan, S.Thongchai, C.Aromdee. Med. Chem., 7, 237 (2011)
  164. M.M.Uttekar, T.Das, R.S.Pawar, B.Bhandari, V.Menon, Nutan, S.K.Gupta, S.V.Bhat. Eur. J. Med. Chem., 56, 368 (2012)
  165. F.Li, E.M.Lee, X.Sun, D.Wang, H.Tang, G.-C.Zhou. Eur. J. Med. Chem., 187, 111925 (2020)
  166. H.Chen, Y.-B.Ma, X.-Y.Huang, C.-A.Geng, Y.Zhao, L.-J.Wang, R.-H.Guo, W.-J.Liang, X.-M.Zhang, J.-J.Chen. Bioorg. Med. Chem. Lett., 24, 2353 (2014)
  167. L.Yuan, C.Zhang, H.Sun, Q.Liu, J.Huang, L.Sheng, B.Lin, J.Wang, L.Chen. Bioorg. Med. Chem. Lett., 26, 769 (2016)
  168. K.Dai, J.K.Tan, W.Qian, R.C.H.Lee, J.J.Hann Chu, G.-C.Zhou. Biochem. Pharmacol., 194, 114820 (2021)
  169. Y.P.Tan, S.D.Houston, N.Modhiran, A.I.Savchenko, G.M.Boyle, P.R.Young, D.Watterson, C.M.Williams. Chem.-Eur. J., 25, 5664 (2019)
  170. Y.P.Tan, Y.Xue, A.I.Savchenko, S.D.Houston, N.Modhiran, C.L.D.McMillan, G.M.Boyle, P.V.Bernhardt, P.R.Young, D.Watterson, C.M.Williams. J. Nat. Prod., 82, 2828 (2019)
  171. L.Zhao, K.-L.Xiang, R.-X.Liu, Z.-P.Xie, S.-M.Zhang, S.-J.Dai. Bioorg. Chem., 96, 103651 (2020)
  172. Q.T.N.Tran, R.C.H.Lee, H.J.Liu, D.Ran, V.Z.L.Low, D.Q.To, J.J.H.Chu, C.L.L.Chai. Eur. J. Med. Chem., 230, 114110 (2022)
  173. T.Yamamoto, N.Izumi, H.Ui, A.Sueki, R.Masuma, K.Nonaka, T.Hirose, T.Sunazuka, T.Nagai, H.Yamada, S.O-mura, K.Shiomi. Tetrahedron, 68, 9267 (2012)
  174. A.S.Volobueva, O.I.Yarovaya, M.V.Kireeva, S.S.Borisevich, K.S.Kovaleva, I.Y.Mainagashev, Y.V.Gatilov, M.G.Ilyina, V.V.Zarubaev, N.F.Salakhutdinov. Molecules, 26, 6794 (2021)
  175. O.I.Yarovaya, K.S.Kovaleva, S.S.Borisevich, T.V.Rybalova, Y.V.Gatilov, E.O.Sinegubova, A.S.Volobueva, V.V.Zarubaev, N.F.Salakhutdinov. Mendeleev Commun., 32, 609 (2022)
  176. D.Kwong Jia Ye, J.-A.Richard. Tetrahedron Lett., 55, 2183 (2014)
  177. Z.-Y.Jiang, Y.-J.Yu, C.-G.Huang, X.-Z.Huang, Q.-F.Hu, G.-Y.Yang, H.-B.Wang, X.-Y.Zhang, G.-P.Li. Planta Med., 81, 241 (2015)
  178. S.Techer, E.Girard-Valenciennes, P.Retailleau, J.Neyts, F.Gueritte, P.Leyssen, M.Litaudon, J.Smadja, I.Grondin. Phytochem. Lett., 12, 313 (2015)
  179. J.Wu, X.Li, X.Guo, Z.Cheng, J.Meng, W.Cheng, W.Lin. Bioorg. Chem., 105, 104423 (2020)
  180. S.-Y.Cheng, S.-K.Wang, C.-Y.Duh. Mar. Drugs, 12, 6028 (2014)
  181. H.-S.Gu, S.-G.Ma, Y.-H.Li, Y.-D.Wang, Y.-B.Liu, L.Li, Y.Li, J.Qu, H.-N.Lv, X.-G.Chen, J.-D.Jiang, S.-S.Yu. Tetrahedron, 70, 7476 (2014)
  182. L.Yang, Y.-B.Zhang, L.Zhuang, T.Li, N.-H.Chen, Z.-N.Wu, P.Li, Y.-L.Li, G.-C.Wang. Planta Med., 83, 111 (2016)
  183. T.Morita, K.Miyakawa, S.S.Jeremiah, Y.Yamaoka, M.Sada, T.Kuniyoshi, J.Yang, H.Kimura, A.Ryo. Viruses, 13, 1669 (2021)
  184. L.Li, J.Zou, C.Xu, S.You, Z.Deng, G.Chen, Y.Liu, Q.Wang. J. Agric. Food Chem., 69, 13637 (2021)

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar

Согласие на обработку персональных данных

 

Используя сайт https://journals.rcsi.science, я (далее – «Пользователь» или «Субъект персональных данных») даю согласие на обработку персональных данных на этом сайте (текст Согласия) и на обработку персональных данных с помощью сервиса «Яндекс.Метрика» (текст Согласия).