Skip to main content

Advertisement

Log in

Triterpenoids with a Five-Membered a-Ring: Distribution in Nature, Transformations, Synthesis, and Biological Activity

  • Published:
Chemistry of Natural Compounds Aims and scope

The literature on the distribution in nature, structural variations, isolation, identification, and biosynthesis issues of triterpenoids with a five-membered A-ring was reviewed. The principal trends in approaches to the synthesis of structural analogs of such compounds were discussed. Information on the biological activity of natural and semi-synthetic A-pentacyclic triterpenoids was presented.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. P. Dzubak, M. Hajduch, D. Vydra, A. Hustova, M. Kvasnica, D. Biedermann, L. Markova, M. Urban, and J. Sarek, Nat. Prod. Rep., 23, 394 (2006).

    PubMed  CAS  Google Scholar 

  2. J.-L. Rios, J. Ethnopharmacol., 128, 1 (2010).

    PubMed  CAS  Google Scholar 

  3. D. J. Newman and G. M. Cragg, J. Nat. Prod., 75 (3), 311 (2012).

    PubMed Central  PubMed  CAS  Google Scholar 

  4. T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, and O. B. Flekhter, Russ. J. Bioorg. Chem., 32 (1), 37 (2006).

    CAS  Google Scholar 

  5. T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, and O. B. Flekhter, Russ. J. Bioorg. Chem., 32 (3), 261 (2006).

    CAS  Google Scholar 

  6. H. Itokawa, S. L. Morris-Natschke, T. Akiyama, and K.-H. Lee, J. Nat. Med., 62 (3), 263 (2008).

    PubMed  CAS  Google Scholar 

  7. B. K. Cassels and M. Asencio, Phytochem. Rev., 10, 545 (2011).

    CAS  Google Scholar 

  8. W.-H. Li, X.-M. Zhang, R.-R. Tian, Y.-T. Zheng, W.-M. Zhao, and M.-H. Qiu, J. Asian Nat. Prod. Res., 9 (6), 551 (2007).

    PubMed  CAS  Google Scholar 

  9. P. M. Giles, Jr., Pure Appl. Chem., 71 (4), 587 (1999).

    CAS  Google Scholar 

  10. A. A. Semenov and V. G. Kartsev, Principles of the Chemistry of Natural Compounds [in Russian], , Vol. 1, International Philanthropic Foundation “Scientific Partnership” [in Russian], MBFNP, Moscow, 2009, 624 pp.

  11. Q. Zeng, B. Guan, J.-J. Qin, C.-H. Wang, X.-R. Cheng, J. Ren, S.-K. Yan, H.-Z. Jin, and W.-D. Zhang, Phytochemistry, 80, 148 (2012).

    PubMed  CAS  Google Scholar 

  12. K. V. Raja Rao, L. J. M. Rao, and N. S. Prakasa Rao, Phytochemistry, 29 (4), 1326 (1990).

    Google Scholar 

  13. S. Taniguchi, Y. Imayoshi, E. Kobayashi, Y. Takamatsu, H. Ito, T. Hatano, H. Sakagami, H. Tokuda, H. Nishino, D. Sugita, S. Shimura, and T. Yoshida, Phytochemistry, 59 (3), 315 (2002).

    PubMed  CAS  Google Scholar 

  14. N. P. Thao, B. T. T. Luyen, B. H. Tai, S. Y. Yang, S. H. Jo, N. X. Cuong, N. H. Nam, Y. I. Kwon, C. V. Minh, and Y. H. Kim, Bioorg. Med. Chem. Lett., 24 (4), 1192 (2014).

    PubMed  CAS  Google Scholar 

  15. K. Machida and M. Kikuchi, Chem. Pharm. Bull., 45 (12), 1928 (1997).

    CAS  Google Scholar 

  16. K. Machida and M. Kikuchi, Tetrahedron Lett., 38 (4), 571 (1997).

    CAS  Google Scholar 

  17. D. Lontsi, B. L. Sondengam, M. T. Martin, and B. Bodo, Phytochemistry, 30 (7), 2361 (1991).

    CAS  Google Scholar 

  18. X.-F. He, X.-N. Wang, S. Yin, L. Dong, and J.-M. Yue, Eur. J. Org. Chem., No. 28, 4818 (2009).

  19. C.-J. Ji, G.-Z. Zeng, J. Han, W.-J. He, Y.-M. Zhang, and N.-H. Tan, Bioorg. Med. Chem. Lett., 22 (20), 6377 (2012).

    PubMed  CAS  Google Scholar 

  20. D. B. Dominguez-Carmona, F. Escalante-Erosa, K. Garcia-Sosa, G. Ruiz-Pinell, D. Gutierrez-Yapu, M. J. Chan-Bacab, R. E. Moo-Puc, N. C. Veitch, A. Gimenez-Turba, and L. M. Pena-Rodriguez, J. Braz. Chem. Soc., 22 (7), 1279 (2011).

    CAS  Google Scholar 

  21. Y. Fujiwara, A. Hayashida, K. Tsurushima, R. Nagai, M. Yoshitomi, N. Daiguji, N. Sakashita, M. Takeya, S. Tsukamoto, and T. Ikeda, J. Agric. Food Chem., 59, 4544 (2011).

    PubMed  CAS  Google Scholar 

  22. P. L. Julian, J. Pikl, and R. Dawson, J. Am. Chem. Soc., 60, 77 (1938).

    CAS  Google Scholar 

  23. S. Erazo, N. Backhouse, C. Delporte, R. Negrete, O. Munoz, J. L. Lopez-Perez, and A. S. Feliciano, Bol. Soc. Chil. Quim., 43 (3), 297 (1998).

    CAS  Google Scholar 

  24. S. M. Lee, B. S. Min, C.-G. Lee, K.-S. Kim, and Y. H. Kho, Planta Med., 69 (11), 1051 (2003).

    PubMed  CAS  Google Scholar 

  25. S. Suksamrarn, P. Panseeta, S. Kunchanawatta, T. Distaporn, S. Ruktasing, and A. Suksamrarn, Chem. Pharm. Bull., 54 (4), 535 (2006).

    PubMed  CAS  Google Scholar 

  26. S. Ganapaty, P. S. Thomas, K. V. Ramana, G. Karagianis, and P. G. Waterman, Z. Naturforsch. B: Chem. Sci., 61, 87 (2006).

    CAS  Google Scholar 

  27. F. A. Aladedunye, D. A. Okorie, and O. M. Ighodaro, Nat. Prod. Res., 22 (12), 1067 (2008).

    PubMed  CAS  Google Scholar 

  28. S.-S. Lee, C.-J. Lin, and K. C. Liu, J. Nat. Prod., 55 (5), 602 (1992).

    CAS  Google Scholar 

  29. S.-J. Jou, C.-H. Chen, J.-H. Guh, C.-N. Lee, and S.-S. Lee, J. Chin. Chem. Soc., 51 (4), 827 (2004).

    CAS  Google Scholar 

  30. Y. Su, C. L. Chang, S. S. Lee, W. C. Chen, and C. F. Huang, Res. Commun. Mol. Pathol. Pharmacol., 100 (3), 313 (1998).

    PubMed  CAS  Google Scholar 

  31. M. A. Arai, C. Tateno, T. Hosoya, T. Koyano, T. Kowithayakorn, and M. Ishibashi, Bioorg. Med. Chem., 16, 9420 (2008).

    PubMed  CAS  Google Scholar 

  32. S.-S. Lee, S.-N. Shy, and K. C. S. Liu, Phytochemistry, 46 (3), 549 (1997).

    CAS  Google Scholar 

  33. S.-M. Lee, J.-G. Park, Y.-H. Lee, C.-G. Lee, B.-S. Min, J.-H. Kim, and H.-K. Lee, Biol. Pharm. Bull., 27 (11), 1883 (2004).

    PubMed  CAS  Google Scholar 

  34. X.-Y. Zhang, X.-H. Cai, and X.-D. Luo, Chin. J. Nat. Med., 10 (1), 36 (2012).

    PubMed  Google Scholar 

  35. Y.-P. Liu, X.-H. Cai, T. Feng, Y. Li, X.-N. Li, and X.-D. Luo, J. Nat. Prod., 74 (5), 1161 (2011).

    PubMed  CAS  Google Scholar 

  36. X.-C. Li, L. Cai, and C. D. Wu, Phytochemistry, 46 (1), 97 (1997).

    PubMed  CAS  Google Scholar 

  37. I. C. R. Leal, K. R. N. dos Santos, I. I. Junior, O. A. C. Antunes, A. Porzel, L. Wessjohann, and R. M. Kuster, Planta Med., 76, 47 (2010).

    PubMed  CAS  Google Scholar 

  38. S. R. Giacomelli, G. Maldaner, C. Stucker, C. Marasciulo, J. Shmidt, L. Wessjohann, I. I. Dalcol, and A. F. Morel, Planta Med., 73, 499 (2007).

    PubMed  CAS  Google Scholar 

  39. L. Yu, B. P. Jiang, D. Luo, X. C. Shen, S. Guo, J. A. Duan, and Y. P. Tang, Phytomedicine, 19 (3–4), 239 (2012).

    PubMed  CAS  Google Scholar 

  40. H. Yeo, S.-Y. Park, and J. Kim, Phytochemistry, 48 (8), 1399 (1998).

    CAS  Google Scholar 

  41. Q.-W. Tan, M.-A. Ouyang, and B. Gao, Molecules, 19 (4), 4897 (2014).

    PubMed  CAS  Google Scholar 

  42. L.-J. Zhang, J.-J. Cheng, C.-C. Liao, H.-L. Cheng, H.-T. Huang, L.-M. Y. Kuo, and Y.-H. Kuo, Planta Med., 78 (14), 1584 (2012).

    PubMed  CAS  Google Scholar 

  43. F. Wang, X.-M. Li, and J.-K. Liu, Chem. Pharm. Bull., 57 (5), 525 (2009).

    PubMed  CAS  Google Scholar 

  44. X.-F. He, X.-N. Wang, L.-S. Gan, S. Yin, L. Dong, and J.-M. Yue, Org. Lett., 10 (19), 4327 (2008).

    PubMed  CAS  Google Scholar 

  45. S. Pointinger, S. Promdang, S. Vajrodaya, C. M. Pannell, O. Hofer, K. Mereiter, and H. Greger, Phytochemistry, 69 (15), 2696 (2008).

    PubMed  CAS  Google Scholar 

  46. K. Machida and M. Kikuchi, Chem. Pharm. Bull., 45 (10), 1589 (1997).

    CAS  Google Scholar 

  47. K. Machida and M. Kikuchi, Tetrahedron Lett., 37 (24), 4157 (1996).

    CAS  Google Scholar 

  48. H.-K. Liu, T.-H. Tsai, T.-T. Chang, C.-J. Chou, and L.-C. Lin, Phytochemistry, 70 (4), 558 (2009).

    PubMed  CAS  Google Scholar 

  49. S.-S. Lee, B.-J. You, and K.-C. Wang, J. Chin. Chem. Soc., 40 (2), 213 (1993).

    CAS  Google Scholar 

  50. S.-S. Lee, W.-C. Chen, C.-F. Huang, and Y. Su, J. Nat. Prod., 61 (11), 1343 (1998).

    PubMed  CAS  Google Scholar 

  51. K. Nakagawa-Goto, K. Yamada, M. Taniguchi, H. Tokuda, and K.-H. Lee, Bioorg. Med. Chem. Lett., 19 (13), 3378 (2009).

    PubMed Central  PubMed  CAS  Google Scholar 

  52. S.-S. Lee, W.-C. Su, and K. C. Liu, J. Nat. Prod., 54 (2), 615 (1991).

    CAS  Google Scholar 

  53. P. Rambabu, K. V. Ramana, and S. Ganapaty, Int. J. Chem. Sci., 9 (3), 1014 (2011).

    CAS  Google Scholar 

  54. K. Sekar, S. Parthasarathy, A. B. Kundu, and B. R. Barik, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 48, 2251 (1992).

  55. S. Guo, J.-A. Duan, Y.-P. Tang, N.-Y. Yang, D.-W. Qian, S.-L. Su, and E.-X. Shang, J. Agric. Food Chem., 58 (10), 6285 (2010).

    PubMed  CAS  Google Scholar 

  56. S.-S. Lee, B.-F. Lin, and K. C.-S. Chen, Chin. Pharm. J., 47 (6), 511 (1995).

    CAS  Google Scholar 

  57. S. Guo, J.-A. Duan, Y. Tang, Y. Qian, J. Zhao, and D. Qian, Biochem. Syst. Ecol., 39, 880 (2011).

    CAS  Google Scholar 

  58. Y. Che, S.-T. Li, and Y.-Q. Zhang, Linchan Huaxue Yu Gongye, 32 (4), 83 (2012).

    CAS  Google Scholar 

  59. P. Rambabu, K. V. Ramana, and S. Ganapaty, Int. J. Chem. Sci., 8 (2), 1231 (2010).

    CAS  Google Scholar 

  60. S. Guo, Y. P. Tang, J. A. Duan, S. L. Su, and A. W. Ding, Chin. Chem. Lett., 20 (2), 197 (2009).

    Google Scholar 

  61. S. G. Jagadeesh, G. L. Krupadanam, G. L. David, and G. Srimannarayana, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 39, 396 (2000).

    Google Scholar 

  62. L.-M. Li, X. Liao, S.-L. Peng, and L.-S. Ding, J. Integr. Plant Biol., 47 (4), 494 (2005).

    CAS  Google Scholar 

  63. K. Yoshikawa, Y. Kondo, E. Kimura, and S. Arihara, Phytochemistry, 49 (7), 2057 (1998).

    CAS  Google Scholar 

  64. L. F. Silva, Jr., Tetrahedron, 58 (45), 9137 (2002).

    CAS  Google Scholar 

  65. B. Achari and S. C. Pakrashi, Tetrahedron, 32 (6), 741 (1976).

    CAS  Google Scholar 

  66. T. S. Li, J. X. Wang, and X. J. Zheng, J. Chem. Soc. Perkin Trans. 1, 3957 (1998).

    Google Scholar 

  67. S. Lavoie, A. Pichette, F. X. Garneau, M. Girard, and D. Gaudet, Synth. Commun., 31 (10), 1565 (2001).

    CAS  Google Scholar 

  68. J. A. R. Salvador, R. M. A. Pinto, R. C. Santos, C. Le Roux, A. M. Beja, and J. A. Paixao, Org. Biomol. Chem., 7, 508 (2009).

    PubMed  CAS  Google Scholar 

  69. H. Schulze and K. Pieroh, Chem. Ber., 55, 2332 (1922).

    Google Scholar 

  70. O. Dischendorfer and H. Juvan, Monatsh. Chem., 56, 272 (1930).

    CAS  Google Scholar 

  71. G. R. Pettit, B. W. Green, and W. J. Bowyer, J. Org. Chem., 26, 2879 (1961).

    CAS  Google Scholar 

  72. V. Jarolim, K. Hejno, M. Streibl, M. Horak, and F. Sorm, Collect. Czech. Chem. Commun., 26, 459 (1961).

    CAS  Google Scholar 

  73. V. Jarolim, K. Hejno, and F. Sorm, Collect. Czech. Chem. Commun., 28, 2443 (1963).

    CAS  Google Scholar 

  74. W. Voser, D. E. White, H. Heusser, O. Jeger, and L. Ruzicka, Helv. Chim. Acta, 35 (3), 830 (1952).

    CAS  Google Scholar 

  75. D. H. R. Barton, D. A. J. Ives, and B. R. Thomas, J. Chem. Soc., 903 (1954).

  76. P. Crabbe, G. Ourisson, and T. Takahashi, Tetrahedron, 3, (3), 279 (1958).

    CAS  Google Scholar 

  77. G. R. Pettit and J. R. Dias, Can. J. Chem., 47 (6), 1091 (1969).

    CAS  Google Scholar 

  78. C. W. Shoppee, N. W. Hughes, R. E. Lack, and J. T. Pinhey, J. Chem. Soc. C, 1443 (1970).

  79. G. R. Pettit and J. R. Dias, J. Org. Chem., 37 (7), 973 (1972).

    PubMed  CAS  Google Scholar 

  80. T. Honda and G. W. Gribble, J. Org. Chem., 63, 4846 (1998).

    CAS  Google Scholar 

  81. N. I. Medvedeva, O. B. Flekhter, O. S. Kukovinets, F. Z. Galin, G. A. Tolstikov, I. Baglin, and C. Caved, Russ. Chem. Bull., 56 (4), 835 (2007).

    CAS  Google Scholar 

  82. N. I. Medvedeva, O. B. Flekhter, E. V. Tretyakova, F. Z. Galin, L. A. Baltina, L. V. Spirikhin, and G. A. Tolstikov, Russ. J. Org. Chem., 40 (8), 1092 (2004).

    CAS  Google Scholar 

  83. O. B. Kazakova, D. V. Kazakov, E. Yu. Yamansarov, N. I. Medvedeva, G. A. Tolstikov, K. Yu. Suponitsky, and D. E. Arkhipov, Tetrahedron Lett., 52, 976 (2011).

    CAS  Google Scholar 

  84. O. B. Kazakova, I. E. Smirnova, E. F. Khusnutdinova, O. S. Zhukova, L. V. Fetisova, G. N. Apryshko, N. I. Medvedeva, E. Yu. Yamansarov, I. P. Baikova, T. T. Nguyen, and H. Do Thi Thu, Russ. J. Bioorg. Chem., 40 (5), 558 (2014).

    CAS  Google Scholar 

  85. O. B. Kazakova, E. F. Khusnutdinova, A. N. Lobov, N. I. Medvedeva, and L. V. Spirikhin, Chem. Nat. Compd., 47, 579 (2011).

    CAS  Google Scholar 

  86. O. B. Kazakova, E. F. Khusnutdinova, G. A. Tolstikov, and K. Yu. Suponitskii, Russ. J. Org. Chem., 48 (3), 460 (2012).

    CAS  Google Scholar 

  87. N. I. Medvedeva, O. B. Flekhter, L. A. Baltina, F. Z. Galin, and G. A. Tolstikov, Chem. Nat. Compd., 40, 247 (2004).

    CAS  Google Scholar 

  88. O. B. Kazakova, E. F. Khusnutdinova, A. N. Lobov, T. I. Zvereva, Yu. V. Legostaeva, G. A. Tolstikov, and V. N. Khrustalev, Russ. Chem. Bull., 60 (8), 1781 (2011).

    CAS  Google Scholar 

  89. M. Kvasnica, I. Tislerova, J. Sarek, J. Sejbal, and I. Cisarova, Collect. Czech. Chem. Commun., 70, 1447 (2005).

    CAS  Google Scholar 

  90. M. Kvasnica, I. Rudovska, I. Cisarova, and J. Sarek, Tetrahedron, 64 (17), 3736 (2008).

    CAS  Google Scholar 

  91. M. Kvasnica, I. Rudovska, M. Hajduch, and J. Sarek, Monatsh. Chem., 141, 233 (2010).

    CAS  Google Scholar 

  92. A. Garcia-Granados, J. Duenas, E. Melguizo, J. N. Moliz, A. Parra, F. L. Perez, J. A. Dobado, and J. Molina, J. Chem. Res., 211 (2000).

  93. A. Garcia-Granados, P. E. Lopez, E. Melguizo, J. N. Moliz, A. Parra, and Y. Simeo, J. Org. Chem., 68, 4833 (2003).

    PubMed  CAS  Google Scholar 

  94. L. R. Mikhailova, L. A. Baltina, R. M. Kondratenko, O. Kunert, L. V. Spirikhin, F. Z. Galin, and G. A. Tolstikov, Chem. Nat. Compd., 42, 553 (2006).

    CAS  Google Scholar 

  95. B. Rickborn and R. M. Gerkin, J. Am. Chem. Soc., 90, 4193 (1968).

    CAS  Google Scholar 

  96. H. Suga and H. Miyake, Synthesis, 5, 394 (1988).

    Google Scholar 

  97. H. O. House and R. L. Wasson, J. Am. Chem. Soc., 79 (6), 1488 (1957).

    CAS  Google Scholar 

  98. G. Magnusson and S. Thoren, J. Org. Chem., 38 (7), 1380 (1973).

    CAS  Google Scholar 

  99. S. N. Bose and S. K. Chanda, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 40 (6), 510 (2001).

    Google Scholar 

  100. B. P. Pradhan, S. Chakraborty, G. C. Subba, and P. Weyerstahl, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 30 (4), 390 (1991).

    Google Scholar 

  101. V. Georgian and N. Kundu, Tetrahedron, 19, 1037 (1963).

    CAS  Google Scholar 

  102. M. H. A. Elgamal, B. A. H. El-Tawil, and M. B. E. Fayez, J. Pharm. Sci., 62, 1557 (1973).

    PubMed  CAS  Google Scholar 

  103. A. D. Kacharov, S. V. Yemets, V. N. Nemykin, L. M. Kacharova, A. A. Fokin, and P. A. Krasutsky, RSC Adv., 3, 19057 (2013).

    CAS  Google Scholar 

  104. Y. Wei, C.-M. Ma, and M. Hattori, Bioorg. Med. Chem., 17, 3003 (2009).

    PubMed  CAS  Google Scholar 

  105. L. A. Tapondjou, F. N. Ngounou, D. Lontsi, B. L. Sondengam, and J. D. Connolly, Tetrahedron, 54, 2099 (1998).

    CAS  Google Scholar 

  106. A. V. Shernyukov, N. F. Salakhutdinov, and G. A. Tolstikov, Russ. Chem. Bull., 62 (4), 878 (2013).

    CAS  Google Scholar 

  107. J. Hao, P. Zhang, X. Wen, and H. Sun, J. Org. Chem., 73, 7405 (2008).

    PubMed  CAS  Google Scholar 

  108. P. Zhang, L. Xu, K. Qian, J. Liu, L. Zhang, K.-H. Lee, and H. Sun, Bioorg. Med. Chem. Lett., 21, 338 (2011).

    PubMed Central  PubMed  CAS  Google Scholar 

  109. T. Konoike, K. Takahashi, Y. Kitaura, and Y. Kanda, Tetrahedron, 55, 14901 (1999).

    CAS  Google Scholar 

  110. M. V. Khudobko, L. R. Mikhailova, L. A. Baltina, Jr., L. V. Spirikhin, and L. A. Baltina, Chem. Nat. Compd., 47, 76 (2011).

    CAS  Google Scholar 

  111. A. V. Shernyukov, I. Ya. Mainagashev, D. V. Korchagina, A. M. Genaev, N. I. Komarova, N. F. Salakhutdinov, and G. A. Tolstikov, Helv. Chim. Acta, 96, 1757 (2013).

    CAS  Google Scholar 

  112. A. V. Shernyukov, I. Ya. Mainagashev, D. V. Korchagina, Yu. V. Gatilov, N. F. Salakhutdinov, and G. A. Tolstikov, Dokl. Chem., 429 (1), 286 (2009).

    CAS  Google Scholar 

  113. A. V. Pereslavtseva, I. A. Tolmacheva, P. A. Selpukhin, O. S. El′tsov, I. I. Kucherov, V. F. Eremin, and V. V. Grishko, Chem. Nat. Compd., 49, 1059 (2014).

    CAS  Google Scholar 

  114. V. V. Grishko, N. V. Galaiko, I. A. Tolmacheva, I. I. Kucherov, V. F. Eremin, E. I. Boreko, O. V. Savinova, and P. A. Slepukhin, Eur. J. Med. Chem., 83, 601 (2014).

    PubMed  CAS  Google Scholar 

Download references

Acknowledgment

The work was sponsored by the RAS Presidium Program “Basic Science – Medicine” (Grant No. 12-R-3-1009) and a grant from the RFBR (No. 14-03-96007-r_ural-a).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. V. Grishko.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2015, pp. 5–24.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Grishko, V.V., Tolmacheva, I.A. & Pereslavtseva, A.V. Triterpenoids with a Five-Membered a-Ring: Distribution in Nature, Transformations, Synthesis, and Biological Activity. Chem Nat Compd 51, 1–21 (2015). https://doi.org/10.1007/s10600-015-1193-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-015-1193-z

Keywords

Navigation