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Ecdysteroids of flowering plants (Angiospermae)

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Abstract

A review is given of the ecdysone-like substances found in recent years in flowering plants. The structures of new compounds are presented. The role of molting hormones in the ecological interrelationships between plants and insects is discussed.

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Literature cited

  1. 1.

    K. Nakanishi, M. Koreeda, S. Sasaki, M. L. Chang, and H. Y. Hsu, J. Chem. Soc. Chem. Commun., 915 (1966).

  2. 2.

    M. N. Galbraith, and D. H. S. Horn, J. Chem. Soc. Chem. Commun., 905 (1966).

  3. 3.

    S. Imai, T. Toyosato, M. Sakai, Y. Sato, S. Fujioka, E. Murata, and M. Goto, Chem. Pharm. Bull.,17, 335 (1969).

  4. 4.

    P. Karlson and C. Bode, J. Insect Physiol.,15, 111 (1969).

  5. 5.

    M. Kobayasi, T. Takemoto, S. Ogawa, and N. Nishimoto, J. Insect Physiol.,13, 1395 (1967).

  6. 6.

    J. N. Kaplanis, L. A. Tabor, M. J. Thompson, W. E. Robbins, and T. J. Shortino, Steroids,8, 625 (1966).

  7. 7.

    D. Adelung and P. Karlson, J. Insect Physiol.,15, 1301 (1969).

  8. 8.

    C. M. Williams, Biol. Bull.,134, 344 (1968).

  9. 9.

    T. Ohtaki, R. D. Milkman, and C. M. Williams, Proc. Natl. Acad. Sci.,58, 981 (1967).

  10. 10.

    Y. Sato, M. Sakai, S. Imai, and S. Fujioka, App. Ent. Zool.,3, 49 (1968).

  11. 11.

    C. J. Chihara, W. H. Petri, J. W. Fristrom, and D. S. King, J. Insect Physiol.,18, 1115 (1972).

  12. 12.

    A. A. Akhrem, I. S. Levina, and Yu. A. Titov, Ecdysones — Insect Steroid Hormones [in Russian], Minsk (1973).

  13. 13.

    W. E. Robbins, J. N. Kalanis, M. J. Thompson, T. J. Shortino, and S. C. Joyner, Steroids,16, 105 (1970).

  14. 14.

    M. Koreeda, K. Nakanishi, and M. Goto, J. Am. Chem. Soc.,92, 7512 (1970).

  15. 15.

    P. Karlson, Sem. Étude Thëme Prod. Natur. et Prot. Plant,41, 17 (1976).

  16. 16.

    Yu. D. Kholodova, Khim. Prir. Soedin., 227 (1977); Ukr. Biokhim. Zh.,51, 560 (1979).

  17. 17.

    M. R. Yakubova, G. L. Genkina, T. T. Shakirov, and N. K. Abubakirov, Khim. Prir. Soedin., 737 (1978).

  18. 18.

    N. Ikekawa, F. Hattori, J. Rubio-Lightbourn, H. Miyazaki, M. Ischibashi, and C. Mori, J. Chromatogr. Sci.,10, 233 (1972).

  19. 19.

    C. F. Poole, E. D. Morgan, and P. M. Bebbington, J. Chromatogr.,104, 172 (1975).

  20. 20.

    E. F. Morgan and C. E. Poole, J. Chromatogr.,116, 333 (1976).

  21. 21.

    D. A. Schooley, G. Weiss, K. Nakanishi, Steroids,19, 377 (1972).

  22. 22.

    S. Ogawa, A. Yoshida, and R. Kato, Chem. Pharm. Bull.,25, 904 (1977).

  23. 23.

    M. Hori, Steroids,14, 33 (1969).

  24. 24.

    H. N. Higg, M. J. Thompson, J. N. Kaplanis, J. A. Svoboda, and W. E. Robbins, Steroids,23, 507 (1974).

  25. 25.

    I. D. Wilson, C. R. Bielby, E. D. Morgan, and A. E. M. McLean, J. Chromatogr.,194, 343 (1980).

  26. 26.

    R. Lafont, P. Beydon, G. Somme-Martin, and C. Blais, Steroids,36, 185 (1980).

  27. 27.

    L. N. Dunan, P. L. Donnahey, H. H. Rees, and T. W. Goodwin, J. Chromatogr.,205, 139 (1981).

  28. 28.

    M. B. Gorovits, I. L. Zatsny, N. K. Abubakirov, Rast. Res.,10, No. 2, 261 (1974).

  29. 29.

    T. Takemoto, S. Ogawa, N. Nishimoto, S. Arihara, and K. Bue, J. Pharm. Soc. Japan,87, 1414 (1967).

  30. 30.

    P. Karlson, H. Hoffmeister, W. Hoppe, and R. Huber, Ann. Chem., 662, 1 (1963).

  31. 31.

    P. Karlson, Naturwissenschaften,53, 445 (1966).

  32. 32.

    U. Baltaev, M. B. Gorovin, N. D. Abdullaev, Ya. V. Rashkes, M. R. Yagudaev, and N. K. Abubakirov, Khim. Prir. Soedin., 457 (1978).

  33. 33.

    B. Z. Usmanov, M. B. Gorovits, and N. K. Abubakirov, Khim. Prir. Soedin., 535 (1971).

  34. 34.

    Z. Saatov, B. Z. Usmanov, and N. I. Abubakirov, Khim. Prir. Soedin., 422 (1977).

  35. 35.

    B. Z. Usmanov, Z. Saatov, and N. K. Abubakirov, Khim. Prir. Soedin., 710 (1977).

  36. 36.

    B. Z. Usmanov, Ya. V. Rashkes, and N. K. Abubakirov, Khim. Prir. Soedin., 215 (1978).

  37. 37.

    B. Z. Usmanov, M. B. Gorovits, and N. K. Abubakirov, Khim. Prir. Soedin., 125 (1973).

  38. 38.

    B. Z. Usmanov, M. B. Gorovits, and N. K. Abubakirov, Khim. Prir. Soedin., 466 (1975).

  39. 39.

    Ya. K. Yatsyuk and G. M. Segal', Khim. Prir. Soedin., 281 (1970).

  40. 40.

    I. L. Zatsny, M. B. Gorovits, and N. K. Abubakirov, Khim. Prir. Soedin., 840 (1971).

  41. 41.

    I. L. Zatsny, M. B. Gorovits, and N. K. Abubakirov, Khim. Prir. Soedin., 175 (1973).

  42. 42.

    I. L. Novosel'skaya, M. B. Gorovits, and N. K. Abubakirov, Khim. Prir. Soedin., 429 (1975).

  43. 43.

    H. Rimpler, Tetrahedron Lett., 329 (1969).

  44. 44.

    I. L. Zatsny, M. B. Gorovits, Ya. V. Rashkes, and N. K. Abubakirov, Khim. Prir. Soedin., 155 (1975).

  45. 45.

    U. Blataev, M. B. Gorovits, S. A. Khamidkhdzhaev, and N. K. Abubakirov, Khim. Prir. Soedin., 406 (1974).

  46. 46.

    U. Baltaev, M. B. Gorovits, N. D. Abdullaev, M. R. Yagudaev, and N. K. Abubakirov, Khim. Prir. Soedin., 813 (1977).

  47. 47.

    U. Baltaev, M. B. Gorovits, Ya. V. Rashkes, and N. K. Abubakirov, Khim. Prir. Soedin., 463 (1978).

  48. 48.

    N. K. Abubakirov, Khim. Zhizn', No. 11, 57 (1975).

  49. 49.

    Yu. D. Kholodova, U. Baltaev, V. O. Volovenko, M. B. Gorovits, and N. K. Abubakirov, Khim. Prir. Soedin., 171 (1979).

  50. 50.

    E. Ohnishi, T. Mizuno, F. Chatani, N. Ikekawa, and S. Sakurai, Science,197, No. 4298, 66 (1977).

  51. 51.

    Y. K. Chong, M. N. Galbraith, and D. H. S. Horn, J. Chem. Soc. Chem. Commun., 1217 (1970).

  52. 52.

    Z. Saatov, B. Z. Usmanov, and N. K. Abubakirov, Khim. Prir. Soedin., 793 (1979).

  53. 53.

    Z. Saatov, B. Z. Usmanov, and N. K. Abubakirov, Khim. Prir. Soedin., 797 (1979).

  54. 54.

    P. Karlson, H. Bugany, H. Döpp, and G. A. Hoyer, Z. Physiol. Chem., 353, 1610 (1972).

  55. 55.

    P. Karlson and J. Koolman, Insect Biochem.,3, 409 (1973).

  56. 56.

    Ya. V. Rashkes and N. K. Abubakirov, Khim. Prir. Soedin.,518 (1980).

  57. 57.

    H. Hikino, S. Arihara, and T. Takemoto, Tetrahedron,25, 3909 (1969).

  58. 58.

    E. T. Tegisbaev, T. K. Chumbalov, and N. K. Abubakirov, Rast. Res.,1, 102 (1965).

  59. 59.

    W. Klyne, Biochem. J., xli, 47 (1950).

  60. 60.

    T. Takemoto, S. Ogawa, N. Nishimoto, H. Hirayama, and S. Tanigushi, J. Pharm. Soc. Jpn.,87, 748 (1967).

  61. 61.

    H. Heftman, H. H. Sauer, and R. D. Bennett, Naturwissenschafter,55, 37 (1968).

  62. 62.

    H. H. Sauer, R. D. Bennett, and E. Heftmann, Phytochemistry,7, 2027 (1968).

  63. 63.

    R. A. Joly, C. M. Svahn, R. D. Bennett, and E. Heftmann, Phytochemistry,8, 1917 (1969).

  64. 64.

    H. Hikino, T. Kohama, and T. Takemoto, Chem. Pharm. Bull.,17, 415 (1969).

  65. 65.

    H. Hikino, T. Hohama, and T. Takemoto. Phytochemistry,9, 367 (1970).

  66. 66.

    N. J. de Souza, E. L. Ghisalberti, H. H. Rees, and T. W. Goodwin, Phytochem.,9, 1247 (1970).

  67. 67.

    T. Matsuoka, S. Imai, M. Sakai, and M. Kamada, Annu. Rept. Takeda Res. Lab.,28, 221 (1969).

  68. 68.

    M. N. Galbraith, D. H. S. Horn, E. J. Middleton, and J. A. Thompson, J. Chem. Soc. Chem. Commun., 179 (1970).

  69. 69.

    N. J. de Souza and N. Nes, Science,162, 363 (1968).

  70. 70.

    M. E. Lowe, D. H. S. Horn, and M. N. Galbraith, Experientia,24, 518 (1968).

  71. 71.

    A. J. Clark and K. Bloch, J. Biol. Chem.,234, 2578, 2589 (1959).

  72. 72.

    E. Kodicek and H. Z. Levinson, Nature (London),188, 1023 (1960).

  73. 73.

    R. H. Dadd and T. L. Mittler, Experientia,22, 823 (1966).

  74. 74.

    P. Ehrhardt, Experientia,24, 82 (1968).

  75. 75.

    H. Z. Levinson, J. Insect Physiol.,8, 191 (1962).

  76. 76.

    J. A. Svoboda, R. F. N. Hutchins, M. J. Thompson, and W. E. Robbins, Steroids,14, 469 (1969).

  77. 77.

    G. S. Fraenkel, Science,129, 1466 (1959).

  78. 78.

    H. Schildknecht, R. Siewerdt, and U. Maschwitz, Angew. Chem.,78, 392 (1966).

  79. 79.

    H. Schildknecht and H. Birringer, Z. Naturforsch.,24b, 1529 (1969).

  80. 80.

    I. L. Novosel'skaya, M. B. Gorovits, and N. K. Abubakirov, Khim. Prir. Soedin.,401 (1981).

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Additional information

Plenary lecture at the 6th Indo-Soviet Symposium on the Chemistry of Natural Compounds, Poona, January 28 to February 1, 1981.

Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 685–702, November–December, 1981.

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Abubakirov, N.K. Ecdysteroids of flowering plants (Angiospermae). Chem Nat Compd 17, 489–503 (1981). https://doi.org/10.1007/BF00574363

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Keywords

  • Stigmasterol
  • Ecdysone
  • Ecdysterone
  • Molting Hormone
  • Vegetable Kingdom