Skip to main content

Advertisement

SpringerLink
Log in

Natural Seven-Membered Terpene Lactones: Synthesis and Biological Activity

  • Published:
Chemistry of Natural Compounds Aims and scope

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17

References

  1. J. K. Rugutt, K. J. Rugutt, and D. K. Berner, J. Nat. Prod., 64, 1434 (2001).

    Article  CAS  PubMed  Google Scholar 

  2. A. Kablan, R. A. Saunders, M. Szkudlarek-Mikho, A. J. B. Chin, R. M. Bosio, K. Fujii, J. Shapiro, and K.-V. Chin, J. Diabetes Metab., 1, 1 (2010).

    Article  CAS  Google Scholar 

  3. H. Y. Kim, D. G. Lee, K. H. Lee, and S. Lee, Hortic. Environ. Biotechnol., 53, 242 (2012).

    Article  CAS  Google Scholar 

  4. G. L. Gallardo, N. I. Pena, and G. M. Cabrera, Phytochem. Lett., 1, 155 (2008).

    Article  CAS  Google Scholar 

  5. H.-L. Ge, D.-W. Zhang, L. Li, D. Xie, J.-H. Zou, Y.-K. Si, and J. Dai, Chem. Pharm. Bull., 59, 1541 (2011).

    Article  CAS  PubMed  Google Scholar 

  6. Y. Ye, X.-Q. Li, C.-P. Tang, and S. Yao, Chin. J. Nat. Med., 11, 97 (2013).

    Article  CAS  PubMed  Google Scholar 

  7. A. A. Semenov, Outline of the Chemistry of Natural Compounds [in Russian], Nauka, Sib. Izd. Firma RAN, Novosibirsk, 2000.

    Google Scholar 

  8. J.-J. Fu, L.-Y. Wang, H.-L. Li, J.-J. Qin, Y.-H. Shen, J.-G. Cheng, H.-Z. Jin, and W.-D. Zhang, J. Asian Nat. Prod. Res., 14, 496 (2012).

    Article  CAS  PubMed  Google Scholar 

  9. Y. Fukuyama and J.-M. Huang, Stud. Nat. Prod. Chem., 32, 395 (2005).

    Article  CAS  Google Scholar 

  10. H. Jianmei and Y. Chunshu, Phytochemistry, 42, 1375 (1996).

    Article  CAS  Google Scholar 

  11. Q. Zhu, C.-P. Tang, C.-Q. Ke, W. Wang, H.-Y. Zhang, and Y. Ye, J. Nat. Prod., 72, 238 (2009).

    Article  CAS  PubMed  Google Scholar 

  12. D.-D. Wei, J.-S. Wang, Y. Zhang, and L.-Y. Kong, Chin. J. Nat. Med., 10, 20 (2012).

    Article  CAS  PubMed  Google Scholar 

  13. L. Fang, X.-J. Wang, S.-G. Ma, and S.-S. Yu, Acta Pharm. Sin. B, 1, 178 (2011).

    Article  CAS  Google Scholar 

  14. J.-F. Liu, Z.-Y. Jiang, Q. Zhang, Y. Shi, Y.-B. Ma, M.-J. Xie, X.-M. Zhang, and J.-J. Chen, Planta Med., 76, 152 (2010).

    Article  CAS  PubMed  Google Scholar 

  15. H.-M. Chung, J.-H. Su, T.-L. Hwang, J.-J. Li, J.-J. Chen, Y.-H. Chen, Y.-C. Chang, Y.-D. Su, Y.-H. Chen, L.-S. Fang, J.-H. Sheu, W.-H. Wang, and P.-J. Sung, Tetrahedron, 69, 2740 (2013).

    Article  CAS  Google Scholar 

  16. J. Wandji, J. D. Wansi, V. Fuendjiep, E. Dagne, D. A. Mulholland, F. Tillequin, Z. T. Fomum, B. L. Sondengam, B. C. Nkeh, and D. Njamen, Phytochemistry, 54, 811 (2000).

    Article  CAS  PubMed  Google Scholar 

  17. B. Nkeh, D. Njamen, J. Wandji, Z. Fomum, D. Dongmo, T. Nguelefack, D. Wansi, and A. Kamanyi, Pharm. Biol., 41, 26 (2003).

    Article  CAS  Google Scholar 

  18. C. A. Ospina, A. D. Rodriguez, J. A. Sanchez, E. Ortega-Barria, T. L. Capson, and A. M. S. Mayer, J. Nat. Prod., 68, 1519 (2005).

    Article  CAS  PubMed  Google Scholar 

  19. M. Govindan, G. N. Govindan, and D. G. Kingston, J. Nat. Prod., 58, 1174 (1995).

    Article  CAS  PubMed  Google Scholar 

  20. J. A. Toth, B. J. Burreson, P. J. Scheuer, J. Finer-Moore, and J. Clardy, Tetrahedron, 36, 1307 (1980).

    Article  CAS  Google Scholar 

  21. Y. Uchio, M. Nitta, M. Nakayama, T. Iwagawa, and T. Hase, Chem. Lett., 12 (4), 613 (1983).

    Article  Google Scholar 

  22. L.-F. Liang, L.-F. Lan, O. Taglialatela-Scafati, and Y.-W. Guo, Tetrahedron, 69, 7481 (2013).

    Article  CAS  Google Scholar 

  23. A. S. Anjaneyulu, G. V. Rao, K. S. Sagar, K. R. Kumar, and K. C. Mohan, Nat. Prod. Lett., 7, 183 (1995).

    Article  CAS  Google Scholar 

  24. A. S. R. Anjaneyulu, K. S. Sagar, and G. V. Rao, J. Nat. Prod., 60, 9 (1997).

    Article  CAS  Google Scholar 

  25. T. Wen, Y. Ding, Z. Deng, L. Ofwegen, P. Proksch, and W. Lin, J. Nat. Prod., 71, 1133 (2008).

    Article  CAS  PubMed  Google Scholar 

  26. A. Ma, Z. Deng, L. Ofwegen, M. Bayer, P. Proksch, and W. Lin, J. Nat. Prod., 71, 1152 (2008).

    Article  CAS  PubMed  Google Scholar 

  27. Y. Lu, H.-J. Su, H.-H. Chen, Z.-H. Wen, J.-H. Sheu, and J.-H. Su, Arch. Pharm. Res., 34, 1263 (2011).

    Article  CAS  PubMed  Google Scholar 

  28. K.-L. Lo, A. T. Khalil, Y.-H. Kuo, and Y.-C. Shen, Chem. Biodiversity, 6, 2227 (2009).

    Article  CAS  Google Scholar 

  29. K.-L. Lo, A. T. Khalil, Y. H. Kuo, and Y.-C. Shen, Helv. Chim. Acta, 93, 1329 (2010).

    Article  CAS  Google Scholar 

  30. J. Su, R. Yang, Y. Kuang, and L. Zeng, J. Nat. Prod., 63, 1543 (2000).

    Article  CAS  PubMed  Google Scholar 

  31. P.-W. Hsieh, F.-R. Chang, A. T. McPhail, K.-H. Lee, and Y.-C. Wu, Nat. Prod. Res., 17, 409 (2003).

    Article  CAS  PubMed  Google Scholar 

  32. H.-J. Shih, Y.-J. Tseng, C.-Y. Huang, Z.-H. Wen, C.-F. Dai, and J.-H. Sheu, Tetrahedron, 68, 244 (2012).

    Article  CAS  Google Scholar 

  33. Y.-J. Chen, J.-H. Su, C.-Y. Tsao, C.-T. Hung, H.-H. Chao, J.-J. Lin, M.-H. Liao, Z.-Y. Yang, H. H. Huang, F.-J. Tsai, S.-H. Weng, and Y.-J. Wu, Molecules, 18, 10146 (2013).

    Article  CAS  PubMed  Google Scholar 

  34. T. Aceret, J. Coll, Y. Uchio, and P. Sammarco, Comp. Biochem. Physiol., Part C: Pharmacol., Toxicol., Endocrinol., 120, 121 (1998).

    CAS  Google Scholar 

  35. T. L. Aceret, L. Brown, J. Miller, J. C. Coll, and P. W. Sammarco, Toxicon, 34, 1165 (1996).

    Article  CAS  PubMed  Google Scholar 

  36. K. Mori, S. Suzuki, K. Iguchi, and Y. Yamada, Chem. Lett., 4, 1515 (1983).

    Article  Google Scholar 

  37. Y.-Y. Lin, Y.-H. Jean, H.-P. Lee, W.-F. Chen, Y.-M. Sun, J.-H. Su, Y. Lu, S.-Y. Huang, H.-C. Hung, P.-J. Sung, J.-H. Sheu, and Z.-H. Wen, PLos One, 8, 1 (2013).

    Google Scholar 

  38. L.-C. Hu, W.-H. Yen, J.-H. Su, M. Chiang, Z.-H. Wen, W.-F. Chen, T.-C. Lu, Y.-W. Chang, Y.-H. Chen, W.-H. Wang, Y.-C. Wu, and P.-J. Sung, Mar. Drugs, 11, 2154 (2013).

    Article  PubMed Central  PubMed  CAS  Google Scholar 

  39. M. Herin and B. Tursch, Bull. Soc. Chim. Belg., 85, 707 (1979).

    Article  Google Scholar 

  40. Y.-S. Lin, C.-H. Chen, C.-C. Liaw, Y.-C. Chen, Y.-H. Kuo, and Y.-C. Shen, Tetrahedron, 65, 9157 (2009).

    Article  CAS  Google Scholar 

  41. Y. Li, A.-H. Gao, H. Huang, J. Li, E. Mollo, M. Gavagnin, G. Cimino, Y.-C. Gu, and Y.-W. Guo, Helv. Chim. Acta, 92, 1341 (2009).

    Article  CAS  Google Scholar 

  42. Y. Lu, C.-Y. Huang, Y.-F. Lin, Z.-H. Wen, J.-H. Su, Y.-H. Kuo, M. Y. Chiang, and J.-H. Sheu, J. Nat. Prod., 71, 1754 (2008).

    Article  CAS  PubMed  Google Scholar 

  43. A. Ma, Z. Deng, L. Ofwegen, M. Bayer, P. Proksch, and W. Lin, J. Nat. Prod., 71, 1152 (2008).

    Article  CAS  PubMed  Google Scholar 

  44. P. P. Guerrero, R. W. Read, M. Batley, and G. C. Janairo, J. Nat. Prod., 58, 1185 (1995).

    Article  CAS  Google Scholar 

  45. P.-J. Sung, C.-H. Chao, Y.-P. Chen, J.-H. Su, W.-P. Hu, and J.-H. Sheu, Tetrahedron Lett., 47, 167 (2006).

    Article  CAS  Google Scholar 

  46. P.-J. Sung, Y.-D. Su, G.-Y. Li, M. Y. Chiang, M.-R. Lin, I.-C. Huang, J.-J. Li, L.-S. Fang, and W.-H. Wang, Tetrahedron, 65, 6918 (2009).

    Article  CAS  Google Scholar 

  47. C. A. Ospina, A. D. Rodriguez, E. Ortega-Barria, and T. L. Capson, J. Nat. Prod., 66, 357 (2003).

    Article  CAS  PubMed  Google Scholar 

  48. C. A. Ospina and A. D. Rodriguez, J. Nat. Prod., 69, 1721 (2006).

    Article  CAS  PubMed  Google Scholar 

  49. A. D. Rodriguez and O. M. Cobar, Tetrahedron, 51, 6869 (1995).

    Article  CAS  Google Scholar 

  50. S. Hirsch and Y. Kashman, J. Nat. Prod., 51, 1243 (1988).

    Article  CAS  Google Scholar 

  51. R. A. Keyzers, P. T. Northcote, and M. T. Davies-Coleman, Nat. Prod. Rep., 23, 321 (2006).

    Article  CAS  PubMed  Google Scholar 

  52. A. C. Pinto, M. L. A. Goncalves, R. B. Filho, A. Neszmelyi, and G. Lukacs, J. Chem. Soc. Chem. Commun., 5, 293 (1982).

    Article  Google Scholar 

  53. A. C. Pinto, T. C. Scofield, and R. B. Filho, Tetrahedron Lett., 24, 5043 (1983).

    Article  CAS  Google Scholar 

  54. J.-D. Chen, Y. Qiu, Z.-W. Yang, P. Lin, and Y.-M. Lin, Helv. Chim. Acta, 91, 2292 (2008).

    Article  CAS  Google Scholar 

  55. B. C. M. Potts, R. J. Capon, and D. J. Faulkner, J. Org. Chem., 57, 2965 (1992).

    Article  CAS  Google Scholar 

  56. W.-L. Xiao, R.-T. Li, S.-X. Huang, J.-X. Pu, and H.-D. Sun, Nat. Prod. Rep., 25, 871 (2008).

    Article  CAS  PubMed  Google Scholar 

  57. W.-L. Xiao, S.-X. Huang, R.-R. Wang, J.-L. Zhong, X.-M. Gao, F. He, J.-P. Pu, Y. Lu, Y.-T. Zheng, Q.-T. Zheng, and H.-D. Sun, Phytochemistry, 69, 2862 (2008).

    Article  CAS  PubMed  Google Scholar 

  58. A. Hisham, G. Jayakumar, M. D. Ajitha Bai, and Y. Fujimoto, Nat. Prod. Res., 18, 329 (2004).

    Article  CAS  PubMed  Google Scholar 

  59. S. S. Nathan, A. Hisham, and G. Jayakumar, Fitoterapia, 79, 106 (2008).

    Article  CAS  PubMed  Google Scholar 

  60. S. Senthil-Nathan, M.-Y. Choi, H.-Y. Seo, C.-H. Paik, and K. Kalaivani, Ecotoxicol. Environ. Saf., 72, 1156 (2009).

    Article  CAS  PubMed  Google Scholar 

  61. Atta-ur-Rahman, N. Habib, S. E. Asif, A. Safdar, I. Zahida, M. I. Choudhary, and J. Clardy, Tetrahedron, 48, 3577 (1992).

  62. X.-M. Gao, J.-X. Pu, W.-L. Xiao, S.-X. Huang, L.-G. Lou, and H.-D. Sun, Tetrahedron, 64, 11673 (2008).

    Article  CAS  Google Scholar 

  63. W. Ma, J. He, L. Li, and L. Qin, Helv. Chim. Acta, 92, 2086 (2009).

    Article  CAS  Google Scholar 

  64. R. Sun, H.-C. Song, C.-R. Wang, K.-Z. Shen, Y.-B. Xu, Y.-X. Gao, Y.-G. Chen, and J.-Y. Dong, Bioorg. Med. Chem. Lett., 21, 961 (2011).

    Article  CAS  PubMed  Google Scholar 

  65. Y.-B. Xue, J.-H. Yang, X.-N. Li, X. Du, J.-X. Pu, W.-L. Xiao, J. Su, W. Zhao, Y. Li, and H.-D. Sun, Org. Lett., 13, 1564 (2011).

    Article  CAS  PubMed  Google Scholar 

  66. Q.-Y. Song, K. Jiang, Q.-Q. Zhao, K. Gao, X.-J. Jin, and X.-J. Yao, Org. Biomol. Chem., 11 (7), 1251 (2013).

    Article  CAS  PubMed  Google Scholar 

  67. G.-F. Chen, Z.-L. Li, D.-J. Pan, C.-M. Tang, X. He, G.-Y. Xu, K. Chen, and K.-H. Lee, J. Nat. Prod., 56, 1114 (1993).

    Article  CAS  PubMed  Google Scholar 

  68. P. Kleinwachter, N. Anh, T. T. Kiet, B. Schlegel, H.-M. Dahse, A. Hartl, and U. Grafe, J. Nat. Prod., 64, 236 (2001).

    Article  CAS  PubMed  Google Scholar 

  69. L. N. Ofodile, L. E. Attah, A. Williams, and M. S. Simmonds, Afr. Res. Review, 1 (1), 65 (2007).

    Google Scholar 

  70. L. N. Ofodile, N. Uma, R. J. Grayer, O. T. Ogundipe, and M. S. Simmonds, Phytother. Res., 26, 748 (2012).

    Article  CAS  PubMed  Google Scholar 

  71. K. Chen, Q. Shi, Z.-L. Li, C.-D. Poon, R.-J. Tang, and K.-H. Lee, J. Asian Nat. Prod. Res., 1, 207 (1998).

    Article  CAS  Google Scholar 

  72. T. Zhou, H. Zhang, N. Zhu, and P. Chiu, Tetrahedron, 60, 4931 (2004).

    Article  CAS  Google Scholar 

  73. G.-F. Chen, Z.-L. Li, D.-J. Pan, C.-M. Tang, X. He, K. Chen, and K.-H. Lee, Tetrahedron Lett., 24, 3413 (1990).

    Google Scholar 

  74. G.-F. Chen, Z.-L. Li, C.-M. Tang, X. He, K. Chen, D.-J. Pan, C.-Q. Hu, R. Donald, A. T. McPhail, and K.-H. Lee, Heterocycles, 31, 1903 (1990).

    Article  CAS  Google Scholar 

  75. J.-M. Tan, Y.-H. Qiu, X.-Q. Tan, and C.-H. Tan, Helv. Chim. Acta, 94, 1697 (2011).

    Article  CAS  Google Scholar 

  76. G. F. Chen, C. H. Tan, Z. L. Li, S. H. Jiang, and D. Y. Zhu, Helv. Chim. Acta, 86, 787 (2003).

    Article  CAS  Google Scholar 

  77. G. F. Chen, Z. L. Li, K. Chen, C. M. Tang, X. He, D. J. Pan, C.-Q. Hu, D. R. McPhail, A. T. McPhail, and K. H. Lee, J. Chem. Soc. Chem. Commun., 1113 (1990).

  78. G.-F. Chen, Z.-L. Li, D.-J. Pan, S.-H. Jiang, and D.-Y. Zhu, J. Asian Nat. Prod. Res., 3, 321 (2001).

    Article  CAS  PubMed  Google Scholar 

  79. X.-M. Gao, J.-X. Pu, W.-L. Xiao, S.-X. Huang, L.-G. Lou, and H.-D. Sun, Tetrahedron, 64, 1163 (2008).

    Google Scholar 

  80. J.-X. Pu, R.-T. Li, W.-L. Xiao, N.-B. Gong, S.-X. Huang, Y. Lu, Q.-T. Zheng, L.-G. Lou, and H.-D. Sun, Tetrahedron, 62, 6073 (2006).

    Article  CAS  Google Scholar 

  81. J.-H. Yang, J.-X. Pu, J. Wen, X.-N. Li, F. He, Y.-B. Xue, Y.-Y. Wang, and Y. Li, J. Nat. Prod., 73, 12 (2010).

    Article  CAS  PubMed  Google Scholar 

  82. J.-X. Pu, L.-M. Yang, W.-L. Xiao, R.-T. Li, C. Lei, X.-M. Gao, S.-X. Huang, S.-H. Li, Y.-T. Zheng, H. Huang, and H.-D. Sun, Phytochemistry, 69, 1266 (2008).

    Article  CAS  PubMed  Google Scholar 

  83. Q.-G. Tan and X.-D. Luo, Chem. Rev., 111, 7437 (2011).

    Article  CAS  PubMed  Google Scholar 

  84. S. H. Qi, L. Chen, D. G. Wu, Y. B. Ma, and X. D. Luo, Tetrahedron, 59, 4193 (2003).

    Article  CAS  Google Scholar 

  85. X.-H. Cai, Z.-Z. Du, and X.-D. Luo, Helv. Chim. Acta, 90, 1980 (2007).

    Article  CAS  Google Scholar 

  86. S. N. J. Grosvenor, K. Mascoll, S. McLean, W. F. Reynolds, and W. F. Tinto, J. Nat. Prod., 69, 1315 (2006).

    Article  CAS  PubMed  Google Scholar 

  87. A. Quader, A. I. Gray, P. G. Waterman, C. Lavaud, G. Massiot, and I. H. Sadler, Tetrahedron, 47, 3611 (1991).

    Article  Google Scholar 

  88. J. F. Ayafor, B. L. Sondengam, A. N. Bilon, and J. D. Connolly, J. Nat. Prod., 49, 583 (1986).

    Article  CAS  PubMed  Google Scholar 

  89. B.-D. Lin, H.-D. Chen, J. Liu, S. Zhang, Y. Wu, L. Dong, and J.-M. Yue, Phytochemistry, 71, 1596 (2010).

    Article  CAS  PubMed  Google Scholar 

  90. Y. Ge, K. Liu, J. Zhang, S. Mu, and X. Hao, J. Agric. Food Chem., 60, 4289 (2012).

    Article  CAS  PubMed  Google Scholar 

  91. J.-S. Wang, Y. Zhang, X.-B. Wang, and L.-Y. Kong, Tetrahedron, 68, 3963 (2012).

    Article  CAS  Google Scholar 

  92. Y. Zhang, J.-S. Wang, X.-B. Wang, Y.-C. Gu, D.-D. Wei, C. Guo, M.-H. Yang, and L.-Y. Kong, J. Agric. Food Chem., 61, 2171 (2013).

    Article  CAS  PubMed  Google Scholar 

  93. O. Koul, W. M. Daniewski, J. S. Multani, M. Gumulka, and G. Singh, J. Agric. Food. Chem., 51, 7271 (2003).

    Article  CAS  PubMed  Google Scholar 

  94. Y. Zhang, J.-S. Wang, X.-B. Wang, Y.-C. Gu, D.-D. Wei, C. Guo, M.-H. Yang, and L.-Y. Kong, Tetrahedron Lett., 52, 2590 (2011).

    Article  CAS  Google Scholar 

  95. L.-G. Lin, C.-P. Tang, C.-Q. Ke, Y. Zhang, and Y. Ye, J. Nat. Prod., 71, 628 (2008).

    Article  CAS  PubMed  Google Scholar 

  96. B. T. Ngadjui, J. F. Ayafor, B. L. Sondengam, and J. D. Connolly, J. Nat. Prod., 52, 832 (1989).

    Article  CAS  Google Scholar 

  97. J. Liu, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 40, 644 (2001).

  98. S. Hasegawa, R. D. Bennett, and Z. Herman, Phytochemistry, 25, 1984 (1986).

    Article  CAS  Google Scholar 

  99. A. P. Breksa III, T. Kahn, A. A. Zukas, M. B. Hidalgo, and M. L. Yuen, J. Sci. Food Agric., 91, 1789 (2001).

    Article  CAS  Google Scholar 

  100. A. P. Breksa III, M. B. Hidalgo, and M. L. Yuen, Food Chem., 117, 739 (2009).

    Article  CAS  Google Scholar 

  101. V.S. P. Chaturvedula, J. K. Schilling, J. H. Wisse, J. S. Miller, R. Evans, and D. G. I. Kingston, Magn. Reson. Chem., 41, 139 (2003).

    Article  CAS  Google Scholar 

  102. X.-H. Yan, Y.-T. Di, X. Fang, S.-Y. Yang, H.-P. He, S.-L. Li, Y. Lu, and X. J. Hao, Phytochemistry, 72, 508 (2011).

    Article  CAS  PubMed  Google Scholar 

  103. Q. Khuong-Huu, A. Chiaroni, C. Riche, H. Nguyen-Ngoc, K. Nguyen-Viet, and F. Khuong-Huu, J. Nat. Prod., 64, 634 (2001).

    Article  CAS  PubMed  Google Scholar 

  104. D. A. Mulholland, D. Naidoo, M. Randrianarivelojosia, P. K. Cheplogoi, and P. H. Coombes, Phytochemistry, 64, 631 (2003).

    Article  CAS  PubMed  Google Scholar 

  105. D. Mulholland, H. Mahomed, M. Kotsos, M. Randrianarivelojosia, C. Lavaud, G. Massiot, and J. M. Nuzillard, Tetrahedron, 55, 11547 (1999).

    Article  CAS  Google Scholar 

  106. L. Pan, L. B. Kardono, S. Riswan, H. Chai, E. J. Carcache de Blanco, C. M. Pannell, D. D. Soejarto, T. G. McCloud, D. J. Newman, and A. D. Kinghorn, J. Nat. Prod., 73, 1873 (2010).

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  107. V. U. Ahmad, K. A. Alvi, and M. A. Khan, J. Nat. Prod., 49, 249 (1986).

    Article  CAS  Google Scholar 

  108. A. A. Ahmed, T. K. Mohamed, H. J. Williams, A. I. Scott, and J. H. Reibenspies, Nat. Prod. Lett., 10, 239 (1997).

    Article  CAS  Google Scholar 

  109. A. Ahmed, A. Kattab, S. Bodige, Y. Mao, D. Minter, M. Reinecke, W. Watson, and T. Mabry, J. Nat. Prod., 64, 106 (2001).

    Article  CAS  PubMed  Google Scholar 

  110. Y.-L. Ku, G. V. Rao, C.-H. Chen, C. Wu, J.-H. Guh, and S.-S. Lee, Helv. Chim. Acta, 86, 697 (2003).

    Article  CAS  Google Scholar 

  111. M. S. Gachet, O. Kunert, M. Kaiser, R. Brun, M. Zehl, W. Keller, R. A. Munoz, R. Bauer, and W. Schuehly, J. Nat. Prod., 74, 559 (2011).

    Article  CAS  PubMed  Google Scholar 

  112. U. Sotanaphun, R. Suttisri, V. Lipipun, and R. Bavovada, Chem. Pharm. Bull., 48, 1347 (2000).

    Article  CAS  PubMed  Google Scholar 

  113. M. M. Farimani, S. N. Ebrahimi, P. Salehi, M. B. Bahadori, A. Sonboil, H. R. Khavasi, S. Zimmermann, M. Kaiser, and M. Hamburger, J. Nat. Prod., 76, 1806 (2013).

    Article  CAS  Google Scholar 

  114. B. M. Reyes, M. T. Ramirez-Apan, R. A. Toscano, and G. Delgado, J. Nat. Prod., 73, 1839 (2010).

    Article  CAS  PubMed  Google Scholar 

  115. A. T. C. Taketa, J. Lozada-Lechuga, M. Fragoso-Serrano, M. L. Villarreal, and R. Pereda-Miranda, J. Nat. Prod., 67, 644 (2004).

    Article  CAS  Google Scholar 

  116. J. O. Hoberg, Tetrahedron, 54, 12631 (1998).

    Article  CAS  Google Scholar 

  117. G. Yu. Ishmuratov, V. A. Vydrina, Yu. A. Galkina, M. P. Yakovleva, R. R. Muslukhov, and G. A. Tolstikov, Russ. J. Org. Chem., 50, 1704 (2014).

    Article  CAS  Google Scholar 

  118. V. A. Vydrina, Yu. A. Galkina, R. R. Muslukhov, A. A. Kravchenko, and G. Yu. Ishmuratov, Chem. Nat. Compd., 50, 774 (2014).

    Article  CAS  Google Scholar 

  119. A. S. Kende and J. Chen, J. Am. Chem. Soc., 107, 7184 (1985).

    Article  CAS  Google Scholar 

  120. M. Stiles, Ann. N. Y. Acad. Sci., 88, 332 (1960).

    Article  CAS  Google Scholar 

  121. R. U. Lemieux and E. von Rudloff, Can. J. Chem., 33, 1701 (1955).

    Article  CAS  Google Scholar 

  122. T.-P. Loh and Q.-Y. Hu, Org. Lett., 3, 279 (2001).

    Article  CAS  PubMed  Google Scholar 

  123. A. L. Gemal and J. L. Luche, J. Am. Chem. Soc., 103, 5454 (1981).

    Article  CAS  Google Scholar 

  124. A. E. Wick, D. Felix, K. Steen, and A. Eschenmoser, Helv. Chim. Acta, 47, 2425 (1964).

    Article  CAS  Google Scholar 

  125. M. T. Crimmins and J. M. Ellis, J. Am. Chem. Soc., 127, 17200 (2005).

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  126. M. T. Crimmins, M. C. Mans, and A. D. Rodriguez, Org. Lett., 12, 5028 (2010).

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  127. J. R. Green, Chem. Commun., No. 16, 1751 (1998).

  128. A. M. M. Castro, Chem. Rev., 104, 2939 (2004).

    Article  CAS  Google Scholar 

  129. J. R. Green and A. A. Tjeng, J. Org. Chem., 74, 7411 (2009).

    Article  CAS  PubMed  Google Scholar 

  130. P. Basabe, O. Bodero, I. S. Marcos, D. Diez, M. DeRoman, A. Blanco, and J. G. Urones, Tetrahedron, 63, 11838 (2007).

    Article  CAS  Google Scholar 

  131. P. Basabe, O. Bodero, I. Marcos, D. Diez, A. Blanco, M. Roman, and J. Urones, J. Org. Chem., 74, 7750 (2009).

    Article  CAS  PubMed  Google Scholar 

  132. P. Langer, J. Prakt. Chem., 342, 728 (2000).

    Article  CAS  Google Scholar 

  133. E. Haslam, Tetrahedron, 36, 2409 (1980).

    Article  CAS  Google Scholar 

  134. M. R. Kernan and D. J. Faulkner, J. Org. Chem., 53, 2773 (1988).

    Article  CAS  Google Scholar 

  135. G. Stork and D. E. Kahne, J. Am. Chem. Soc., 105, 1072 (1983).

    Article  CAS  Google Scholar 

  136. D. Fischer and E. A. Theodorakis, Eur. J. Org. Chem., 25, 4193 (2007).

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The work was financed partially by NSh 2625.2014.3 “Synthetic transformations of compounds obtained from domestic plant raw material as a core strategy for developing drugs with high social significance.”

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Russian Academy of Sciences, Russia, Republic of Bashkortostan, 450054, Ufa, Prosp. Oktyabrya, 71

    G. Yu. Ishmuratov, V. A. Vydrina, Yu. A. Galkina, M. P. Yakovleva, N. M. Ishmuratova & A. G. Tolstikov

Authors
  1. G. Yu. Ishmuratov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Vydrina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. A. Galkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. P. Yakovleva
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. M. Ishmuratova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. G. Tolstikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. Yu. Ishmuratov.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2015, pp. 871–892.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ishmuratov, G.Y., Vydrina, V.A., Galkina, Y.A. et al. Natural Seven-Membered Terpene Lactones: Synthesis and Biological Activity. Chem Nat Compd 51, 1011–1034 (2015). https://doi.org/10.1007/s10600-015-1483-5

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-015-1483-5

Keywords

Search

Navigation