Chemistry of Natural Compounds

, Volume 36, Issue 5, pp 419–477 | Cite as

Hetisane - Type Diterpenoid Alkaloids

  • I. A. Bessonova
  • Sh. A. Saidkhodzhaeva
Article

Abstract

Data in the literature up to 1998 on hetisane-type diterpenoid alkaloids isolated from plants of the generaAconitum, Consolida, Delphinium, Thalictrum,andSpireaare reviewed and systematized. Data on the chemistry and physicochemical methods of studying the structures and pharmacology of hetisane alkaloids are generalized. An alphabetical list of 107 hetisane alkaloids with an indication of the plant source, structure, characteristic derivatives, physicochemical data, and references to the original literature is presented

Aconitum Consolida Delphinium Thalictrum (Ranunculaceae) Spirea (Rosaceae) hetisane-type C20alkaloids (chemical properties, spectral data, pharmacology) 

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REFERENCES

  1. 1.
    A. Katz and E. Staehelin, Tetrahedron Lett., 23, 1155 (1982).Google Scholar
  2. 2.
    E. S. Stern and J. F. Macfarlan, in: The Alkaloids. Chemistry and Physiology, R. H. F. Manske and H. L. Holmes, eds., Academic Press, New York (1954), Vol. IV, p. 275.Google Scholar
  3. 3.
    S. W. Pelletier, J. Nat. Prod., 55, 1 (1992).Google Scholar
  4. 4.
    M. S. Yunusov, Nat. Prod. Rep., 8, 499 (1991); M. S. Yunusov, Nat. Prod. Rep., 10, 471 (1993).Google Scholar
  5. 5.
    M. N. Sultankhodzhaev, in: Progress in Research on Alkaloid-Bearing Plants [in Russian], Kh. N. Aripov, ed., Fan, Tashkent (1993), p. 37.Google Scholar
  6. 6.
    Atta-ur-Rahman and M. Iqbal Choudhary, Nat. Prod. Rep., 12, 361 (1995).Google Scholar
  7. 7.
    M. S. Yunusov, Bashk. Khim. Zh., 3, 17 (1996).Google Scholar
  8. 8.
    Atta-ur-Rahman and M. Iqbal Choudhary, Nat. Prod. Rep., 14, 191 (1997).Google Scholar
  9. 9.
    Atta-ur-Rahman and M. Iqbal Choudhary, Nat. Prod. Rep., 16, 619 (1999).Google Scholar
  10. 10.
    R. Sh. Shakirov, M. V. Telezhenetskaya, I. A. Bessonova, et al., Khim. Prir. Soedin., a) 250, b) 250, c) 252, d) 341, e) 341, f) 415, g) 450, h) 451, i) 482, j) 676, k) 765, l) 766, m) 767, n) 788, o) 812, p) 841, q) 842, r) 857, s) 957, t) 960, u) 975 (1996).Google Scholar
  11. 11.
    A. Ulubelen, A. H. Mericli, F. Mericli, and F. Yilmaz, Phytochemistry, 41, 957 (1996).Google Scholar
  12. 12.
    B. S. Joshi, M. S. Puar, Y. Bai, A. M. Panu, and S. W. Pelletier, Tetrahedron, 50, 12283 (1994).Google Scholar
  13. 13.
    V. Venkateswarlu, S. K. Srivastava, B. S. Joshi, H. K. Desai, and S. W. Pelletier, J. Nat. Prod., 58, 1527 (1995).Google Scholar
  14. 14.
    Y. Bai, F. Sun, M. Benn, and W. Majak, Phytochemistry, 37, 1717 (1994).Google Scholar
  15. 15.
    J. A. Glinski, B. S. Joshi, Q. P. Jiang, and S. W. Pelletier, Heterocycles, 27, 185 (1988).Google Scholar
  16. 16.
    M. Benn, J. F. Richardson, and W. Majak, Heterocycles, 24, 1605 (1986).Google Scholar
  17. 17.
    A. G. Gonzalez, G. De la Fuente, M. Reina, and I. Timon, Heterocycles, 22, 667 (1984).Google Scholar
  18. 18.
    G. De la Fuente, J. A. Gavin, R. D. Acosta, and J. A. Morales, Heterocycles, 27, 1 (1988).Google Scholar
  19. 19.
    A. G. Gonzalez, G. De la Fuente, M. Reina, R. Diaz, and I. Timon, Phytochemistry, 25, 1971 (1986).Google Scholar
  20. 20.
    H. Takayama, Y. Hitotsuyanagi, K. Yamaguchi, N. Aimi, and S. Sakai, Chem. Pharm. Bull., 40, 2927 (1992).Google Scholar
  21. 21.
    G. Almanza, J. Bastida, C. Codina, and G. De la Fuente, Phytochemistry, 44, 739 (1997).Google Scholar
  22. 22.
    G. De la Fuente, M. Reina, and E. Valencia, Heterocycles, 29, 1577 (1989).Google Scholar
  23. 23.
    Atta-ur-Rahman, Handbook of Natural Products Data, Vol. 1, Diterpenoid and Steroidal Alkaloids, Elsevier Science Publ., Amsterdam, Neth. (1990), p. 240.Google Scholar
  24. 24.
    G. De la Fuente, J. A. Gavin, M. Reina, and R. D. Acosta, J. Org. Chem., 55, 342 (1990).Google Scholar
  25. 25.
    A. G. Gonzalez, G. De la Fuente, M. Reina, P. G. Jones, and P. R. Rathby, Tetrahedron Lett., 24, 3765 (1983).Google Scholar
  26. 26.
    S. A. Ross, B. S. Joshi, S. W. Pelletier, M. G. Newton, and A. J. Aasen, J. Nat. Prod., 56, 424 (1993).Google Scholar
  27. 27.
    A. Ulubelen, H. K. Desai, S. K. Srivastava, B. P. Hart, J. C. Park, B. S. Joshi, S. W. Pelletier, A. H. Mericli, F. Mericli, and R. Ilarslan, J. Nat. Prod., 59, 360 (1996).Google Scholar
  28. 28.
    H. Bando, K. Wada, T. Amiya, K. Kobayashi, Y. Fujimoto, and T. Sakurai, Heterocycles, 26, 2623 (1987).Google Scholar
  29. 29.
    Q. Jiang and S. W. Pelletier, J. Nat. Prod., 54, 525 (1991).Google Scholar
  30. 30.
    A. Ulubelen, A. H. Mericli, and F. Mericli, J. Nat. Prod., 56, 780 (1993).Google Scholar
  31. 31.
    A. Ulubelen, A. H. Mericli, F. Mericli, R. Ilarslan, and S. A. Matlin, Phytochemistry, 31, 3229 (1992).Google Scholar
  32. 32.
    T. Okamoto, H. Sanjoh, K. Yamaguchi, Y. Iitaka, and S. Sakai, Chem. Pharm. Bull., 31, 1431 (1983).Google Scholar
  33. 33.
    J. A. Grina, D. R. Schroeder, E. T. Wydallis, and F. R. Stermitz, J. Org. Chem., 51, 390 (1986).Google Scholar
  34. 34.
    M. H. Benn, Can. J. Chem., 44, 1 (1966).Google Scholar
  35. 35.
    S. W. Pelletier, F. M. Harraz, M. M. Badawi, S. Tantiraksachai, F.-P. Wang, and S.-Y. Chen, Heterocycles, 24, 1853 (1986).Google Scholar
  36. 36.
    A. Ulubelen, A. H. Mericli, F. Mericli, R. Ilarslan, and W. Voelter, Phytochemistry, 34, 1165 (1993).Google Scholar
  37. 37.
    P. Kulanthaivel and M. Benn, Heterocycles, 23, 2515 (1985).Google Scholar
  38. 38.
    Y. Bai, M. Benn, and W. Majak, Heterocycles, 31, 1233 (1990).Google Scholar
  39. 39.
    P. Kulanthaivel, S. W. Pelletier, and J. D. Olsen, Heterocycles, 27, 339 (1988).Google Scholar
  40. 40.
    S. W. Pelletier, J. A. Glinski, B. S. Joshi, and S.-Y. Chen, Heterocycles, 20, 1347 (1983).Google Scholar
  41. 41.
    K. I. Varughese and S. W. Pelletier, J. Nat. Prod., 47, 470 (1984).Google Scholar
  42. 42.
    B. Tashkhodjaev, I. M. Yusupova, B. T. Salimov, and B. T. Ibragimov, J. Inclusion Phenom. Mol. Recognit. Chem., 14, 311 (1992).Google Scholar
  43. 43.
    S. W. Pelletier, L. H. Keiths, and P. C. Parthasarathy, J. Am. Chem. Soc., 89, 4146 (1967).Google Scholar
  44. 44.
    S. Sakai, I. Yamamoto, K. Hotoda, K. Yamaguchi, N. Aimi, E. Yamanaka, J. Haginiwa, and T. Okamoto, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 104, 222 (1984).Google Scholar
  45. 45.
    S. Sakai, K. Yamaguchi, I. Yamamoto, and T. Okamoto, Chem. Pharm. Bull., 30, 4573 (1982).Google Scholar
  46. 46.
    S. W. Pelletier and N. V. Mody, The Alkaloids: Chemistry and Physiology, R. H. F. Manske and R. G. A. Rodrigo, eds., Academic Press, New York, London, Toronto, Sydney, San Francisco (1981), Vol. XVIII, p. 99.Google Scholar
  47. 47.
    S. W. Pelletier, S. W. Page, and G. Newton, Tetrahedron Lett., No. 11, 795 (1971).Google Scholar
  48. 48.
    S. Sakai, K. Yamaguchi, I. Yamamoto, K. Hotoda, T. Okazaki, N. Aimi, J. Haginiwa, and T. Okamoto, Chem. Pharm. Bull., 31, 3338 (1983).Google Scholar
  49. 49.
    Z. Yuanlong and Z. Renhong, Heterocycles, 17, 607 (1982).Google Scholar
  50. 50.
    Ref. Zh. Khim., 11Zh 513 (1967); Acta Pharm. Sinica, 13, No. 3, 186 (1966).Google Scholar
  51. 51.
    M. G. Reinecke, D. E. Minter, D. C. Chen, and W. M. Yan, Tetrahedron, 42, 6621 (1986).Google Scholar
  52. 52.
    I. A. Bessonova, Khim. Prir. Soedin., 123 (1999).Google Scholar
  53. 53.
    M. Reina, J. A. Gavin, A. Madinaveitia, R. D. Acosta, and G. de la Fuente, J. Nat. Prod., 59, 145 (1996).Google Scholar
  54. 54.
    S. Sakai, I. Yamamoto, K. Yamaguchi, H. Takayama, M. Ito, and T. Okamoto, Chem. Pharm. Bull., 30, 4579 (1982).Google Scholar
  55. 55.
    S. A. Ross, B. S. Joshi, H. K. Desai, S. W. Pelletier, M. G. Newton, X. Zhang, and J. K. Snyder, Tetrahedron, 47, 9585 (1991).Google Scholar
  56. 56.
    B. S. Joshi, H. Desai, El.-S. A. El-Kashoury, S. W. Pelletier, and J. D. Olsen, Phytochemistry, 28, 1561 (1989).Google Scholar
  57. 57.
    T. Okamoto, H. Sanjoh, K. Yamaguchi, A. Yoshino, T. Kaneko, Y. Iitaka, and S. Sakai, Chem. Pharm. Bull., 30, 4600 (1982).Google Scholar
  58. 58.
    S. W. Pelletier, S. W. Page, and M. G. Newton, Tetrahedron Lett., No. 55, 4825 (1970).Google Scholar
  59. 59.
    K. Wada, H. Bando, and N. Kawahara, Heterocycles, 31, 1081 (1990).Google Scholar
  60. 60.
    S. W. Pelletier and L. H. Keith, The Alkaloids. Chemistry and Physiology, R. H. F. Manske, ed., Academic Press, New York and London (1970), Vol. XII, p. 136.Google Scholar
  61. 61.
    M. Reina, A. Madinaveitia, J. A. Gavin, and G. de la Fuente, Phytochemistry, 41, 1235 (1996).Google Scholar
  62. 62.
    H. Takayama, T. Okazaki, K. Yamaguchi, N. Aimi, J. Haginiwa, and S. Sakai, Chem. Pharm. Bull., 36, 3210 (1988).Google Scholar
  63. 63.
    S. W. Pelletier, L. H. Wright, M. G. Newton, and H. Wright, J. Chem. Soc., Chem. Commun., 98 (1970).Google Scholar
  64. 64.
    G. de la Fuente, J. A. Gavin, R. D. Acosta, and F. Sanchez-Ferrande, Phytochemistry, 34, 553 (1993).Google Scholar
  65. 65.
    F. Wang and Q. Fang, Planta Med., 42, 375 (1981).Google Scholar
  66. 66.
    F. Wang and X. Liang, Planta Med., 443 (1985).Google Scholar
  67. 67.
    S. Sakai, K. Yamaguchi, H. Takayama, I. Yamamoto, and T. Okamoto, Chem. Pharm. Bull., 30, 4576 (1982).Google Scholar
  68. 68.
    Q. Jiang and S. W. Pelletier, Tetrahedron Lett., 29, 1875 (1988).Google Scholar
  69. 69.
    I. A. Bessonova, Sh. A. Saidkhodzhaeva, and M. F. Faskhutdinov, Khim. Prir. Soedin., 838 (1995).Google Scholar
  70. 70.
    I. A. Bessonova and Sh. A. Saidkhodzhaeva, Khim. Prir. Soedin., 576 (1996).Google Scholar
  71. 71.
    A. Katz, J. Nat. Prod., 52, 430 (1989).Google Scholar
  72. 72.
    T. Okamoto, H. Sanjoh, K. Yamaguchi, Y. Iitaka, and S. Sakai, Chem. Pharm. Bull., 31, 360 (1983).Google Scholar
  73. 73.
    Y.-C. Wu, T.-S. Wu, M. Niwa, S. T. Lu, and Y. Hirata, Phytochemistry, 27, 3949 (1988).Google Scholar
  74. 74.
    Y.-C. Wu, T.-S. Wu, M. Niwa, S. T. Lu, and Y. Hirata, Heterocycles, 26, 943 (1987).Google Scholar
  75. 75.
    G. Goto, K. Sasaki, N. Sakabe, and Y. Hirata, Tetrahedron Lett., No. 11, 1369 (1968).Google Scholar
  76. 76.
    F. Sun, X. T. Liang, and D. Q. Yu, J. Nat. Prod., 50, 923 (1987).Google Scholar
  77. 77.
    F. Sun, X. T. Liang, and D. Q. Yu, J. Nat. Prod., 51, 50 (1988).Google Scholar
  78. 78.
    Z. M. Vaisov, I. A. Bessonova, and V. A. Tel´nov, Khim. Prir. Soedin., 86 (1993).Google Scholar
  79. 79.
    B. S. Joshi, D. H. Chen, X. Zhang, J. K. Snyder, and S. W. Pelletier, Heterocycles, 32, 1793 (1991).Google Scholar
  80. 80.
    X. Zhang and J. K. Snyder, Heterocycles, 31, 1879 (1990).Google Scholar
  81. 81.
    A. S. Narzullaev, N. D. Abdullaev, M. S. Yunusov, V. M. Matveev, and S. G. Yunusova, Izv. Ross. Akad. Nauk, Ser. Khim., No. 1, 187 (1997).Google Scholar
  82. 82.
    S. Sakai, T. Okazaki, K. Yamaguchi, H. Takayama, and N. Aimi, Chem. Pharm. Bull., 35, 2615 (1987).Google Scholar
  83. 83.
    E. Wenkert, Chem. Ind., 282 (1955).Google Scholar
  84. 84.
    Y. Ichinohe, M. Yamaguchi, N. Katsui, and S. Kakimoto, Tetrahedron Lett., 2323 (1970).Google Scholar
  85. 85.
    M. N. Sultankhodzhaev and A. A. Nishanov, Khim. Prir. Soedin., 337 (1995).Google Scholar
  86. 86.
    I. M. Yusupova, B. Tashkhodzhaev, I. A. Bessonova, M. S. Yunusov, M. R. Yagudaev, V. G. Kondrat´ev, and A. I. Shreter, Khim. Prir. Soedin., 378 (1990).Google Scholar
  87. 87.
    B. T. Salimov, B. Tashkhodzhaev, I. M. Yusupova, S. V. Lindeman, and Yu. T. Struchkov, Khim. Prir. Soedin., 375 (1992).Google Scholar
  88. 88.
    I. M. Yusupova, B. T. Salimov, and B. Tashkhodzhaev, Khim. Prir. Soedin., 382 (1992).Google Scholar
  89. 89.
    Z. Karimov and M. G. Zhamierashvili, Khim. Prir. Soedin., 335 (1981).Google Scholar
  90. 90.
    Z. M. Vaisov and M. S. Yunusov, Khim. Prir. Soedin., 407 (1987).Google Scholar
  91. 91.
    I. A. Bessonova, L. N. Samusenko, M. S. Yunusov, and V. G. Kondrat1ev, Khim. Prir. Soedin., 383 (1990).Google Scholar
  92. 92.
    S. W. Pelletier, K. N. Iyer, L. H. Wright, M. G. Newton, and N. Singh, J. Am. Chem. Soc., 93, 5942 (1971).Google Scholar
  93. 93.
    P. Kulanthaivel, E. M. Holt, J. D. Olsen, and S. W. Pelletier, Phytochemistry, 29, 293 (1990).Google Scholar
  94. 94.
    G. D. Manners, R. Y. Wong, M. Benson, M. H. Ralphs, and J. A. Pfister, Phytochemistry, 42, 875 (1996).Google Scholar
  95. 95.
    S. Sakai, I. Yamamoto, and T. Okamoto, Chem. Pharm. Bull., 30, 4583 (1982).Google Scholar
  96. 96.
    K. Wada, H. Bando, and N. Kawahara, Heterocycles, 32, 1297 (1991).Google Scholar
  97. 97.
    W. Nagata and H. Itazaki, Chem. Ind., 26, 1194 (1964).Google Scholar
  98. 98.
    H. E. Wright, G. Newton, and S. W. Pelletier, J. Chem. Soc., Chem. Commun., 507 (1969).Google Scholar
  99. 99.
    A. J. Solo and S. W. Pelletier, J. Am. Chem. Soc., 81, 4439 (1959).Google Scholar
  100. 100.
    S. W. Pelletier, N. V. Mody, J. Finer-Moore, A. M. M. Ateya, and L. C. Schramm, J. Chem. Soc., Chem. Commun., 327 (1981).Google Scholar
  101. 101.
    S. W. Pelletier, J. A. Glinski, K. I. Varughese, J. Maddry, and N. V. Mody, Heterocycles, 20, 413 (1983).Google Scholar
  102. 102.
    B. S. Joshi, J. A. Glinski, K. I. Varughese, and S. W. Pelletier, Heterocycles, 27, 195 (1988).Google Scholar
  103. 103.
    Q. Jiang, J. A. Glinski, B. S. Joshi, J. A. Maddry, M. G. Newton, and S. W. Pelletier, Heterocycles, 27, 925 (1988).Google Scholar
  104. 104.
    P. R. Story, J. Am. Chem. Soc., 83, 3347 (1961).Google Scholar
  105. 105.
    H. C. Brown and H. M. Bell, J. Org. Chem., 27, 1928 (1962).Google Scholar
  106. 106.
    H. C. Brown and H. M. Bell, J. Am. Chem. Soc., 85, 2324 (1963).Google Scholar
  107. 107.
    Ya. V. Rashkes, M. S. Yunusov, E. G. Sirotenko, and Z. M. Vaisov, Khim. Prir. Soedin., 542 (1987).Google Scholar
  108. 108.
    E. G. Mil'grom, Ya. V. Rashkes, and I. A. Bessonova, Khim. Prir. Soedin., 82 (1992).Google Scholar
  109. 109.
    S. K. Usmanova, V. A. Tel´nov, and N. D. Abdullaev, Khim. Prir. Soedin., 412 (1993).Google Scholar
  110. 110.
    M. G. Reinecke, W. H. Watson, D. C. Chen, and W. M. Yan, Heterocycles, 24, 49 (1986).Google Scholar
  111. 111.
    L. Jinghan, H. Zhigang, and Z. Shouxun, J. China Pharm. Univ., 19, 238 (1988).Google Scholar
  112. 112.
    B. S. Joshi, H. K. Desai, S. W. Pelletier, E. M. Holt, and A. J. Aasen, J. Nat. Prod., 51, 265 (1988).Google Scholar
  113. 113.
    V. A. Tel´nov, S. K. Usmanova, and N. D. Abdullaev, Khim. Prir. Soedin., 409 (1993).Google Scholar
  114. 114.
    I. A. Bessonova, L. N. Samusenko, M. S. Yunusov, M. R. Yagudaev, and V. G. Kondrat1ev, Khim. Prir. Soedin., 91 (1991).Google Scholar
  115. 115.
    B. T. Salimov, Zh. K. Kuzibaeva, and F. N. Dzhakhangirov, Khim. Prir. Soedin., 384 (1996).Google Scholar
  116. 116.
    B. T. Sagdullaev, A. Yu. Abramov, A. I. Gagel´gans, F. N. Dzhakhangirov, and P. B. Usmanov, Khim. Prir. Soedin., 523 (1998).Google Scholar

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© Plenum Publishing Corporation 2000

Authors and Affiliations

  • I. A. Bessonova
    • 1
  • Sh. A. Saidkhodzhaeva
    • 1
  1. 1.S. Yu. Yunusov Institute of the Chemistry of Plant SubstancesAcademy of Sciences of the Republic of UzbekistanTashkent

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