Chemistry of Natural Compounds

, Volume 35, Issue 2, pp 107–149 | Cite as

Steroid alkaloids of the plant and animal Kingdoms

  • V. V. Kul'kova
  • R. Shakirov
  • A. L. D'yakonov
Article

Abstract

This review, which covers the literature for 1988–1996, gives new information on the occurrence of steroid alkaloids in Nature and discusses ecological and biogenetic aspects of their study.

Keywords

Steroid Organic Chemistry Alkaloid Animal Kingdom Steroid Alkaloid 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    M. M. Telitchenko and S. A. Ostroumov,Introduction to Problems of Biochemical Ecology [in Russian] Nauka, Moscow (1990).Google Scholar
  2. 2.
    BSÉ [Great Soviet Encyclopaedia] [in Russian], Vol.29 (1978), p. 597.Google Scholar
  3. 3.
    J. B. Harborne,An Introduction to Ecological Biochemistry, Academic Press, London (1977) [Russian translation, Mir, Moscow (1985, p. 312].Google Scholar
  4. 4.
    Atta-ur-Rahman and A. Muzaffar, in:The Alkaloids (ed. A. Brossi), Academic Press, San Diego, Vol.32, (1988), p. 79.Google Scholar
  5. 5.
    D. M. Harrison,Nat. Prod. Rep.,27, 139 (1990);CrossRefGoogle Scholar
  6. 6.
    R. Schakirov [Shakirov] and M. S. Yunusov,Nat. Prod. Rep.,27, 557 (1990).CrossRefGoogle Scholar
  7. 7.
    B. N. Orlov, D. B. Gelashvili, and A. K. Ibragimov,Poisonous Animals and Plants of the USSR [in Russian], Vysshaya Shkola, Moscow (1990), p. 272.Google Scholar
  8. 8.
    S. M. Shuraeva and L. M. Safronova, Byul. Glav. Botan. Sada,168, 101 (1993).Google Scholar
  9. 9.
    S. Begum, S. B. Usmani, B. S. Siddiqi, and S. Siddiqi,Phytochemistry,36, 1537 (1994).CrossRefGoogle Scholar
  10. 10.
    S. Siddiqi and B. A. Shamsuttdin,J. Sci. Ind. Res.,32, 1 (1989).Google Scholar
  11. 11.
    K. K. Bhutane, R. M. Vaid, M. Ali, R. Rapoor, S. R. Soodan, and D. Kumar,Phytochemistry,29, 969 (1990).CrossRefGoogle Scholar
  12. 12.
    Atta-ur-Rahman, M. Alam, H. Nasir, and E. Y. A. Dagne,Phytochemistry,29, 1293 (1990).CrossRefGoogle Scholar
  13. 13.
    Atta-ur-Rahman, Z. Igbal, M. I. Choudhary, and F. Talat,Heterocycles,31, 493 (1990).Google Scholar
  14. 14.
    Atta-ur-Rahman, Z. Igbal, and M. I. Choudhary,J. Nat. Prod.,53, 319 (1990).CrossRefGoogle Scholar
  15. 15.
    M. I. Choudhary, Atta-ur-Rahman, and M. Shamma,Phytochemistry,27, 1561 (1988).CrossRefGoogle Scholar
  16. 16.
    Atta-ur-Rahman, Z. Igbal, M. Alam, M. I. Choudhary, N. H. Igbal, and F. Talat,Phytochemistry,29, 683 (1990).CrossRefGoogle Scholar
  17. 17.
    Atta-ur-Rahman, M. Alam, and M. I. Choudhary,Phytochemistry,27, 3342 (1988).CrossRefGoogle Scholar
  18. 18.
    Atta-ur-Rahman,Pure and Appl. Chem.,61, 453 (1989).Google Scholar
  19. 19.
    Atta-ur-Rahman, A. Serfan, D. Ahmed, S. Bilge, and T. Sogul,J. Nat. Prod.,52, 1319 (1989).CrossRefGoogle Scholar
  20. 20.
    Atta-ur-Rahman, D. Ahmed, M. Choudhary, B. Sener, and S. Turkoz,Fitoterapia,26, 439 (1989).Google Scholar
  21. 21.
    Atta-ur-Rahman, D. Ahmed, E. Asif, S. A. Gamal, M. I. Choudhary, B. Sener, and S. Turkoz,Phytochemistry,30, 1295 (1991).CrossRefGoogle Scholar
  22. 22.
    B. U. Khodzhaev, M. R. Khodzhaeva, and Kh. Ubaev,Khim. Prir. Soedin., 907 (1993).Google Scholar
  23. 23.
    M. Qui, R. Nie, Z. Li, and J. Zhou,Acta Bot. Sin.,32, 626 (1990).Google Scholar
  24. 24.
    M. Qui, C. He, R. Nie, and Q. Zheng,Zhou Jun, Yunnan Zhiwu Yanjiu,12, 111 (1990);Chem. Abstr.,113, 148873j (1990).Google Scholar
  25. 25.
    M. Qui, Z. Li, D. Cao, and R. Nie,Zhiwu Xuebao,35, 885 (1993);Chem. Abstr.,121, 78257a (1994).Google Scholar
  26. 26.
    Y. Mimaki and Y. Sashida,Chem. Pharm. Bull.,38, 1090 (1990).Google Scholar
  27. 27.
    Atta-ur-Rahman, A. Faroog, M. I. Choudhary, A. H. Gilani, F. Shaheen, R. A. Ali, F. Noor-e-ain, and B. Sener,Planta Med.,60, 377 (1994);Chem. Abstr.,121, 226438c (1994).PubMedGoogle Scholar
  28. 28.
    Y. J. Xu, D. M. Xu, D. B. Cui, J. S. Gao, E. X. Huang, S. Y. Liu, and D. Q. Yu,Yaoxue Xuebao,29, 200 (1994).Google Scholar
  29. 29.
    P. Li, X. G. Li, G. J. Xu, and K. Kaneko,J. China Pharm. Univ.,21, 198 (1990).Google Scholar
  30. 30.
    G. Lin, J.-P. Ho, P. Li, and X. G. Li,J. Nat. Prod.,58, 1662 (1995).CrossRefPubMedGoogle Scholar
  31. 31.
    J. Zhang, A. Lao, and R. Xu,Zhiwu Xuebao,35, 238 (1993);Chem. Abstr.,120, 129485n (1994).Google Scholar
  32. 32.
    Y. Kitamura, K. Kaneko, M. Shiro, Yuh-Pan Chen, Hong-Yen Hsu, Ping Lee, and Guo-Jun Xu,Chem. Pharm. Bull.,37, 1514 (1989).Google Scholar
  33. 33.
    Shichun Yu and Peigen Xiao,Zhongcaoyao,21, 2 (1990);Chem. Abstr.,113, 112481r (1990).Google Scholar
  34. 34.
    D. M. Xu, M. L. Xu, S. Q. Wang, E. X. Hung, X. G. Wen, S. Arihara, and N. Shoji,J. Nat. Prod. 53, 549 (1990).PubMedGoogle Scholar
  35. 35.
    Y. Kitamura, M. Nishizawa, and K. Kaneko,Tetrahedron Lett.,30, 37, 4891 (1989).Google Scholar
  36. 36.
    D. M. Xu, C. H. He, S. Q. Wang, E. X. Huang, M. L. Xu, Y. X. Zhang, and X. G. Wen,Yaoxue Xuebao,23, 902 (1988).Google Scholar
  37. 37.
    D. M. Xu, C. H. He, S. Q. Wang, E. X. Huang, M. L. Xu, and X. Y. Wen,Yaoxue Xuebao,25, 127 (1990).Google Scholar
  38. 38.
    Y. Kitamura, M. Nishizawa, K. Kaneko, M. Shiro, Yuh-Pan Chen, and Hong-Yen Hsu,Tetrahedron,45, 7281 (1989).CrossRefGoogle Scholar
  39. 39.
    Jian-Xing Zhang, Ai-na Lao, and Rensheng Xu,Zhiwu Xuebao,35, 963 (1993).Google Scholar
  40. 40.
    W. H. Xu and Z. Xue,Yaoxue Xuebao,23, 61 (1988).Google Scholar
  41. 41.
    U. T. Shakirova and R. Shakirov,Khim. Prir. Soedin., 524 (1994).Google Scholar
  42. 42.
    B. Tashkhodzhaev, S. Nasirov, A. Nabiev, R. Shakirov, K. Samikov, and M. R. Yagudaev,Khim. Prir. Soedin., 384 (1991).Google Scholar
  43. 43.
    A. K. Choudhary, B. C. Sen, M. F. Hashim, and M. Ahmed,Pharmazie,48, 628 (1993).Google Scholar
  44. 44.
    V. E. Sokolov,Madagascar [in Russian], Progress, Moscow (1990).Google Scholar
  45. 45.
    A. Charkravarty, B. Das, and S. J. Mekhopadhyay,J. Nat. Prod.,55, 965 (1992).Google Scholar
  46. 46.
    M. I. Choudhary, B. Sener, and S. Turkoz,Phytochemistry,30, 368 (1991).CrossRefGoogle Scholar
  47. 47.
    Atta-ur-Rahman, Rahat Azhar Ali, G. Anwar-l-Hassan, M. I. Choudhary, K. Aftab, B. Sener, and S. Turkoz,Planta Med.,59, 969 (1993).Google Scholar
  48. 48.
    R. Shakirov, V. V. Kul'kova, and I. Nakhatov,Khim. Prir. Soedin., 100 (1995).Google Scholar
  49. 49.
    W. Zhao, Y. Tezuka, T. Kikuchi, J. Chen, and Y. Guo,Chem. Pharm. Bull.,37, 2920 (1989).Google Scholar
  50. 50.
    W. Zhao, Y. Tezuka, T. Kikuchi, J. Chen, and Y. Guo,Chem. Pharm. Bull.,39, 549 (1991).Google Scholar
  51. 51.
    M. Mizuno, Ren-Xiang Tan, Pei Zhen, Zhi-Da Min, M. Iinuma, and T. Tanaka,Phytochemistry,29, 359 (1990).CrossRefGoogle Scholar
  52. 52.
    H. Ripperger and A. Porzel,Phytochemistry 35, 813 (1994).CrossRefGoogle Scholar
  53. 53.
    P. F. Coll, M. I. Rodriguez, C. Perez, and G. Adam,Rev. Cubana Quim.,6, 66 (1992).Google Scholar
  54. 54.
    H. Ripperger and A. Porzel,Phytochemistry,30, 1299 (1991).CrossRefGoogle Scholar
  55. 55.
    H. Ripperger,Phytochemistry 29, 3375 (1990).CrossRefGoogle Scholar
  56. 56.
    A. K. Chakravarty and S. C. PakrashiPhytochemistry,27, 956 (1988).CrossRefGoogle Scholar
  57. 57.
    A. K. Chakravarty and S. C. Pakrashi,Indian J. Chem., B,27, 311 (1988).Google Scholar
  58. 58.
    G.-N. Lin, C.-M. Lu, M.-K. Cheng, and K.-H. Gan,J. Nat. Prod.,53, 513 (1990).CrossRefPubMedGoogle Scholar
  59. 59.
    S. F. Osman, S. L. Sinden, P. Irwin, K. Deahl, and W. M. Tingey,Phytochemistry,30, 3161 (1991).CrossRefGoogle Scholar
  60. 60.
    W. Dopke, S. Duday, and N. Matos,Z. Chem.,28, 185 (1988).Google Scholar
  61. 61.
    R. Puri, T. C. Wong, and R. K. Puri,J. Nat. Prod.,57, 587 (1994).CrossRefPubMedGoogle Scholar
  62. 62.
    Y. Tomoyuki, F. Nobuyo, Y. Shoji, N. Toshiro, K. Syuji, and F. Kunimitsu,Chem. Pharm. Bull.,38, 827 (1990).Google Scholar
  63. 63.
    A. Maxwell, M. Seepersoud, R. Pingal, D. R. Mootoo, and W. F. Reynolds,58, 625 (1995).Google Scholar
  64. 64.
    J. C. Kim, Q. M. Che, A. A. Z. Gunatilaka, and D. G. I. Kingston,J. Nat. Prod.,59, 283 (1996).CrossRefPubMedGoogle Scholar
  65. 65.
    J. Jurek, P. J. Scheuer, and M. Kelly-Borges,J. Nat. Prod.,57, 1004 (1994).CrossRefPubMedGoogle Scholar
  66. 66.
    S. Fukuzawa, S. Matsunaga, and N. Fusetani,J. Org. Chem.,59, 6164 (1994).CrossRefGoogle Scholar
  67. 67.
    S. Fukuzawa, S. Matsunaga, and N. Fusetani,J. Org. Chem.,60, 608 (1995).CrossRefGoogle Scholar
  68. 68.
    G. R. Pettit, M. Inoue, Y. Kamano D. L. Herald, C. Arm, C. Dufresne, N. D. Christie, J. M. Schmidt, D. L. Doubek, and T. S. Krupa,J. Am. Chem. Soc.,110, 2006 (1988).CrossRefGoogle Scholar
  69. 69.
    G. R. Pettit, M. Inoue, Y. Kamano, C. Dufresne, N. Christie, M. L. Niven, and D. L. Herald,J. Chem. Soc., Chem. Commun., 865 (1988).Google Scholar
  70. 70.
    G. R. Pettit, Y. Kamano, C. Dufresne, M. Inoue, N. Christie, J. M. Schmidt and D. L. Doubek,Can. J. Chem.,67, 1509 (1989).Google Scholar
  71. 71.
    E. Novacki, M. Jurrysta, and P. A. Gorski,Biochem. Physiol. Plants,169, 1030 (1976).Google Scholar
  72. 72.
    K. G. Ramaval, M. Rideau, and J. Chenieux,Phytochemistry,24, 441 (1988).Google Scholar
  73. 73.
    L. N. Bereznegovskaya,Rastit. Resurs.,19, 370 (1983).Google Scholar
  74. 74.
    O. A. Gorelova and V. Rzherzhabek,Dokl. Akad. Nauk SSSR,279, 253 (1984).Google Scholar
  75. 75.
    P. M. Frischknecht and T. W. Baumann,Phytochemistry,25, 2255, (1985).CrossRefGoogle Scholar
  76. 76.
    H. Ripperger and K. Schreiber, in:The Alkaloids (ed. R. H. F. Manske and R. G. A. Rodrigo), Academic Press, New York, Vol.XIX (1981), p. 81.Google Scholar
  77. 77.
    L. N. Bereznegovskaya,Biologicheskie Nauki, 17 (1988).Google Scholar
  78. 78.
    K. Schreiber in:The Alkaloids (ed. R. H. F. Manske), Academic Press, New York, Vol.X (1968), p. 117.Google Scholar
  79. 79.
    R. B. Herbert, in:The Alkaloids (ed. M. F. Grundon), Royal Society of Chemistry, London, Vol.9 (1979), p. 27.Google Scholar
  80. 80.
    K. Kaneko, M. W. Tanaka, and H. Mitsuhashi,Phytochemistry,16, 1247 (1977).CrossRefGoogle Scholar
  81. 81.
    L. Canonica, F. Ronchetti, G. Russo, and G. Sportoletti,J. Chem. Soc., Chem. Commun., 286 (1977).Google Scholar
  82. 82.
    R. Tschesche and H. R. Brennecke,Phytochemistry 19, 1449 (1980).Google Scholar
  83. 83.
    S. F. Osman, S. L. Sinden, P. Irwin, K. Deahl, and W. M. Tingey,Phytochemistry,30, 3161 (1991).CrossRefGoogle Scholar
  84. 84.
    F. Coll, A. Preiss, M. Bastereschea, J. L. Mola, and G. Adam,Phytochemistry,22, 2099 (1983).CrossRefGoogle Scholar
  85. 85.
    F. Coll, A. Preiss, M. Bastereschea, L. Kutschabsky, J. L. Mola, K. Schreiber, and G. Adam,Phytochemistry,23, 883 (1984).CrossRefGoogle Scholar
  86. 86.
    K. Kaneko, U. Nakaoka, M. Tanaka, H. Yoshida, and N. Mitsuhashi,Phytochemistry,20, 157 (1981).CrossRefGoogle Scholar
  87. 87.
    K. Kaneko, M. Tanaka, U. Makaoka, Y. Tahaka, N. Yoshida, and H. Mitsuhashi,Phytochemistry,20, 327 (1981).CrossRefGoogle Scholar
  88. 88.
    S. F. Osman, in:Isoprenoids in Plants (ed. W. D. Nes, G. Fuller, and L.-S. Tsoi), Marcel Dekker, New York (1984), p. 519.Google Scholar
  89. 89.
    G. J. Bird, D. J. Collins, F. W. Eastwood, and J. M. Swan,Aust. J. Chem.,32, 611 (1979).Google Scholar
  90. 90.
    K. Kaneko, M. Watanabe, S. Taira, and H. Mitsuhashi,Phytochemistry,11, 3199 (1972).CrossRefGoogle Scholar
  91. 91.
    Y. Sashida, Y. Mimaki, and S. Shimomura,Chem. Lett., 897 (1989).Google Scholar
  92. 92.
    K. Kaneko, M. Tanaka, K. Haruki, N. Naruse, and H. Mitsuhashi,Tetrahedron Lett., 3737 (1979).Google Scholar
  93. 93.
    K. Kaneko, N. Naruse, R. Haruki, and H. Mitsuhashi,Chem. Pharm. Bull.,28, 1345 (1980).Google Scholar
  94. 94.
    V. V. Kul'kova,Author's Abtract of Dissertation … Candidate of Chemical Science [in Russian], Tashkent (1995).Google Scholar
  95. 95.
    Y. Kitamura, M. Nishizawa, and K. Kaneko,Tetrahedron 45, 5755 (1989).CrossRefGoogle Scholar
  96. 96.
    R. Goutarel, inThe Alkaloids (ed. J. E. Saxton), The Chemical Society, Burlington House, London, Vol.1 (1971), p. 382.Google Scholar
  97. 97.
    G. Habermehl, in:The Alkaloids (ed. R. H. F. Manske), Academic Press, New York, Vol.IX (1967), p. 436.Google Scholar
  98. 98.
    T. P. Anatsulova and S. M. Nikolaev,Rastit. Resurs.,27, 75 (1991).Google Scholar
  99. 99.
    Yu. R. Mirzaev, K. Samikov, R. Shakirov, V. V. Kul'kova, D. U. Abdullaeva, and F. N. Dzhakhangirov,Kimë va Farmatsiya, No.4, 62 (1996).Google Scholar

Copyright information

© Kluwer Academic/Plenum Publishers 1999

Authors and Affiliations

  • V. V. Kul'kova
  • R. Shakirov
  • A. L. D'yakonov

There are no affiliations available

Personalised recommendations