Skip to main content
SpringerLink
Log in

Polymethyleneamine Alkaloids of Animal Origin: I. Metabolites of Marine and Microbial Organisms

  • Review Articles
  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

This review, issued in two parts, describes the information on the structure and biological activity of animal alkaloids derived from polymethyleneamines and produced by marine organisms, wasps, spiders, and microorganisms. Animal alkaloids are outstanding models for developing methods and drugs for the treatment of many human diseases. In the first part, we consider compounds produced by marine and microbial organisms. Some promising synthetic analogues of these alkaloids are used in developing modern preparations for the chelate therapy of excessive blood iron content and antituberculosis, antiproliferative, and immunosuppressive drugs.

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

Similar content being viewed by others

REFERENCES

  1. Casero, R.A. and Woster, J.P.M., J. Med. Chem., 2001, vol. 44, pp. 1–26.

    Article  PubMed  CAS  Google Scholar 

  2. Karigiannis, G. and Papaioannou, D., Eur. J. Org. Chem., 2000, pp. 1841–1863.

  3. Kuksa, V., Buchan, R., and Thoo Lin, P.K., Synthesis, 2000, no. 9, pp. 1189–1207.

  4. Niwa, H., Watanabe, M., and Yamada, K., Tetrahedron Lett., 1993, vol. 34, pp. 7441–7444.

    Article  CAS  Google Scholar 

  5. Montanari, A.M., Fenical, W., Lindquist, N., Lee, A.Y., and Clardy, J., Tetrahedron, 1996, vol. 15, pp. 5371–5380.

    Google Scholar 

  6. Honma, K., Tsuda, M., Mikami, Y., and Kobayashi, J., Tetrahedron, 1995, vol. 51, pp. 3745–3748.

    Article  CAS  Google Scholar 

  7. Tsukamoto, S., Kato, H., Hirota, H., and Fusetani, N., Tetrahedron Lett., 1996, vol. 37, pp. 5555–5556.

    CAS  Google Scholar 

  8. Tsukamoto, S., Yamashita, T., Matsunaga, S., and Fusetani, N., J. Org. Chem., 1999, vol. 64, pp. 3794–3795.

    Article  CAS  Google Scholar 

  9. Tsukamoto, S., Kato, H., Hirota, H., and Fusetani, N., Tetrahedron, 1996, vol. 52, pp. 8181–8186.

    Article  CAS  Google Scholar 

  10. Tsukamoto, S., Kato, H., Hirota, H., and Fusetani, N., Tetrahedron Lett., 1996, vol. 37, pp. 1439–1440.

    CAS  Google Scholar 

  11. Moore, K.S., Wehrli, S., Roder, H., Rogers, M., Forrest, J.N., McCrimmon, J.D., and Zasloff, M., Proc. Natl. Acad. Sci. USA, 1993, vol. 90, pp. 1354–1358.

    PubMed  CAS  Google Scholar 

  12. Rao, M.N., Shinnar, A.E., Noecker, L.A., Chao, T.L., Feibush, B., Snyder, B., Sharkansky, I., Sarkahian, A., Zhang, X., Jones, S.R., Kinney, W.A., and Zasloff, M., J. Nat. Prod., 2000, vol. 63, pp. 631–635.

    Article  PubMed  CAS  Google Scholar 

  13. Kashman, Y., Hirsch, S., McConnell, O.J., Ohtani, I., Kusumi, T., and Kakisawa, H., J. Am. Chem. Soc., 1989, vol. 111, pp. 8925–8926.

    Article  CAS  Google Scholar 

  14. Ohtani, I., Kusumi, T., and Kakisawa, H., Tetrahedron Lett., 1992, vol. 33, pp. 2525–2528.

    Article  CAS  Google Scholar 

  15. Berlinck, R.G.S., J. Nat. Prod., 1999, vol. 16, pp. 339–365.

    CAS  Google Scholar 

  16. Jare-Erijman, E.A., Sakai, R., and Rinehart, K.L., J. Am. Chem. Soc., 1991, vol. 56, pp. 5712–5715.

    Google Scholar 

  17. Jare-Erijman, E.A., Ingrum, A.L., Carney, J.R., Rinehart, K.L., and Sakai, R., J. Org. Chem., 1993, vol. 58, pp. 4805–4808.

    Google Scholar 

  18. Coffey, D.S., McDonald, A.I., Overman, L.E., and Stappenbeck, F., J. Am. Chem. Soc., 1999, vol. 121, pp. 6944–6945.

    Article  CAS  Google Scholar 

  19. Tsukamoto, S., Yamashita, T., Matsunaga, S., and Fusetani, N., Tetrahedron Lett., 1999, vol. 40, pp. 737–738.

    CAS  Google Scholar 

  20. Matsunaga, S., Yamashita, T., Tsukamoto, S., and Fusetani, N., J. Nat. Prod., 1999, vol. 62, pp. 1202–1204.

    Article  PubMed  CAS  Google Scholar 

  21. Kourany-Lefoll, E., Pais, M., Sevenet, T., Guittet, E., Montagnac, A., Fontaine, C., Guenard, D., Adeline, M.T., and Debitus, C., J. Org. Chem., 1992, vol. 57, pp. 3832–3835.

    Article  CAS  Google Scholar 

  22. Moriarty, R.M., Enache, L.A., Kinney, W.A., Allen, C.S., Canary, G.W., Tuladhar, S.M., and Guo, L., Tetrahedron Lett., 1995, vol. 36, pp. 5139–5142.

    CAS  Google Scholar 

  23. van Wagoner, R.M., Jompa, J., Tahir, A., and Ireland, C.M., J. Nat. Prod., 1999, vol. 62, pp. 794–797.

    PubMed  Google Scholar 

  24. Sata, N.U., Sugano, M., Matsunagana, S., and Fusetani, N., Tetrahedron Lett., 1999, vol. 40, pp. 719–722.

    Article  CAS  Google Scholar 

  25. Williams, D.E., Lassota, P., and Andersen, R.J., J. Org. Chem., 1998, vol. 63, pp. 4838–4841.

    CAS  Google Scholar 

  26. Onuki, H., Ito, K., Kobayashi, Y., Matsumori, N., and Tachibana, K., J. Org. Chem., 1998, vol. 63, pp. 3925–3932.

    Article  CAS  Google Scholar 

  27. Onuki, H. and Tachibana, K., Tetrahedron Lett., 1993, vol. 34, pp. 5609–5612.

    Article  CAS  Google Scholar 

  28. McCormick, K.D., Koayashi, K., Goldin, S.M., Reddy, N.L., and Meinwald, J., Tetrahedron, 1993, vol. 49, pp. 11 155–11 168.

    Article  CAS  Google Scholar 

  29. Ushio-Sta, N., Matsunaga, S., Fusetani, N., Honda, K., and Yasumuro, K., Tetrahedron Lett., 1996, vol. 37, pp. 225–228.

    Google Scholar 

  30. Exposito, M.A., Lopez, B., Fernandez, R., Vazquez, M., Debitus, C., Iglesias, T., Jiomenez, C., Quinoa, E., and Riguera, R., Tetrahedron, 1998, vol. 54, pp. 7539–7550.

    CAS  Google Scholar 

  31. Exposito, A., Fernandez-Suarez, M., Iglesias, T., Munoz, L., and Riguera, R., J. Org. Chem., 2001, vol. 66, pp. 4206–4213.

    Article  PubMed  CAS  Google Scholar 

  32. Kroger, N., Deutzmann, R., Bergsdorf, Ch., and Sumper, M., Proc. Natl. Acad. Sci. USA, 2000, vol. 97, pp. 14 133–14 138.

    Article  CAS  Google Scholar 

  33. Casapullo, A., Fontana, A., and Cimino, G., J. Org. Chem., 1996, vol. 61, pp. 7415–7419.

    Article  PubMed  CAS  Google Scholar 

  34. Jayatilake, G.S., Baker, B.J., and McClintock, J.B., Tetrahedron Lett., 1997, vol. 38, pp. 7507–7510.

    Article  CAS  Google Scholar 

  35. Kong, F. and Faulkner, D.J., J. Org. Chem., 1993, vol. 58, pp. 970–971.

    CAS  Google Scholar 

  36. Ponasik, J.A., Conova, S., Kinghorn, D., Kinney, W.A., Rittschof, D., and Ganem, B., Tetrahedron, 1998, vol. 54, pp. 6977–6986.

    Article  CAS  Google Scholar 

  37. Savage, P.B., Li, C.H., Taotafa, U., Ding, B.W., and Guan, Q.Y., FEMS Microbiol. Lett., 2002, vol. 217, pp. 1–7.

    Article  PubMed  CAS  Google Scholar 

  38. Zhou, X.D., Cai, F., and Zhou, W.S., Tetrahedron, 2002, vol. 58, pp. 10 293–10 299.

    Article  CAS  Google Scholar 

  39. US Patent 5 792 635, 1998.

  40. US Patent 5 721 226, 1998.

  41. US Patent 6 083 939, 2000.

  42. Khabnadideh, S., Tan, C.L., Croft, S.L., Kendrick, H., Yardley, V., and Gilbert, I.H., Bioorg. Med. Chem. Lett., 2000, vol. 10, pp. 1237–1239.

    Article  PubMed  CAS  Google Scholar 

  43. Hirota, H., Matsunaga, S., and Fusetani, N., Tetrahedron Lett., 1990, vol. 31, pp. 4163–4164.

    CAS  Google Scholar 

  44. Kobayashi, Y., Onuki, H., and Tachibana, K., Bioorg. Med. Chem., 1999, vol. 7, pp. 2073–2081.

    PubMed  CAS  Google Scholar 

  45. Guo, H.Y., Naser, S.A., Ghobrial, G., and Phanstiel, O., J. Med. Chem., 2002, vol. 45, pp. 2056–2063.

    Article  PubMed  CAS  Google Scholar 

  46. Pierre, J.L. and Gautier-Luneau, I., BioMetals, 2000, vol. 13, pp. 91–96.

    Article  PubMed  CAS  Google Scholar 

  47. Wang, G.Y.S., Graziani, E., Waters, B., Pan, W., Li, X., McDermott, J., Meurer, G., Saxena, G., Andersen, R.J., and Davies, J., Organic Letters, 2000, vol. 2, pp. 2401–2404.

    PubMed  CAS  Google Scholar 

  48. Durand, P., Peralba, P., and Renaut, P., Tetrahedron, 2001, vol. 57, pp. 2757–2760.

    Article  CAS  Google Scholar 

  49. Overman, L.E. and Tomasi, A.L., J. Am. Chem. Soc., 1998, vol. 120, pp. 4039–4040.

    Article  CAS  Google Scholar 

  50. Frontier, A., Raghavan, S., and Danishefsky, S., J. Am. Chem. Soc., 2000, vol. 122, pp. 6151–6159.

    Article  CAS  Google Scholar 

  51. Hegde, R., Silver, J.E., Patel, M.G., Gullo, V.P., Das, P.R., and Puar, M.S., J. Nat. Prod., 1995, vol. 58, pp. 843–847.

    CAS  Google Scholar 

  52. Evidente, A., Capasso, R., Cutignano, A., Taglialatela-Scafati, O., Vurro, M., Zonno, M.C., and Motta, A., Phytochemistry, 1998, vol. 48, pp. 1131–1137.

    CAS  Google Scholar 

  53. Wang, Q.X., Phanstiel IV, O., J. Org. Chem., 1998, vol. 63, pp. 1491–1495.

    CAS  Google Scholar 

  54. Shenker, M., Ghirlando, R., Oliver, I., Helmann, M., Hadar, Y., and Chen, Y., Soil Sci. Soc. Am. J., 1995, vol. 59, pp. 837–843.

    CAS  Google Scholar 

  55. Durand, P., Richard, P., and Renaut, P., J. Org. Chem., 1998, vol. 63, pp. 9723–9727.

    Article  CAS  Google Scholar 

  56. Lebreton, L., Annat, J., Derrepas, P., Dutartre, P., and Renaut, P., J. Med. Chem., 1999, vol. 42, pp. 277–290.

    PubMed  CAS  Google Scholar 

  57. Lebreton, L., Jost, E., Carboni, B., Annat, J., Vaultier, M., Dutartre, P., and Renaut, P., J. Med. Chem., 1999, vol. 42, pp. 4749–4763.

    PubMed  CAS  Google Scholar 

  58. Nishimura, K., Ohki, Y., Fukuchi-Shimogori, T., Sakata, K., Saiga, K., Beppu, T., Shirahata, A., Kashiwagi, K., and Igarashi, K., Biochem. J., 2002, vol. 363, pp. 761–768.

    Article  PubMed  CAS  Google Scholar 

  59. Kawada, M., Someno, T., Iinuma, H., Masuda, T., Ishizuka, M., and Takeuchi, T., J. Antibiot., 2000, vol. 53, pp. 705–710.

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Vorozhtsov Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. akademika Lavrent'eva 5, Novosibirsk, 630090, Russia

    L. N. Rogosa, N. F. Salakhutdinov & G. A. Tolstikov

Authors
  1. L. N. Rogosa
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. F. Salakhutdinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. A. Tolstikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. N. Rogosa.

Additional information

__________

Translated from Bioorganicheskaya Khimiya, Vol. 31, No. 6, 2005, pp. 563–577.

Original Russian Text Copyright © 2005 by Rogosa, Salakhutdinov, Tolstikov.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rogosa, L.N., Salakhutdinov, N.F. & Tolstikov, G.A. Polymethyleneamine Alkaloids of Animal Origin: I. Metabolites of Marine and Microbial Organisms. Russ J Bioorg Chem 31, 507–520 (2005). https://doi.org/10.1007/s11171-005-0070-0

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11171-005-0070-0

Key words

Search

Navigation