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Secondary Plant Substances: Monoterpenoid Indole Alkaloids

  • Horst-Robert Schütte
Part of the Progress in Botany/Fortschritte der Botanik book series (BOTANY, volume 48)

Abstract

Tryptophan-derived alkaloids, which are found in higher plants and microorganisms, are the largest group (about one quarter) of known alkaloids. Most of them have been isolated and structurally determined during the last two decades. This was done with the aid of classic chemical degradation and modern analytical techniques (mass spectrometry, nuclear magnetic resonance, X-ray crystallography). Many indole alkaloids are biologically active and some are extremely useful therapeutic agents in human medicine, e.g., Catharanthus, Curare, ergot, Rauwolfia, Vinca alkaloids. Approximately 1100 indole alkaloids of this type are known. The overwhelming majority of monoterpenoid indole alkaloids are restricted to three plant families: Loganiaceae, Apocynaceae, and Rubiaceae, which belong to the order Gentianales (Contortae) (PHILLIPSON and ZENK 1980; KISAKUREK et al. 1983; KOSKINEN and LOUNASMAA 1983). The iridoid indole alkaloids were classified in eight different skeleton types: corynanthean (C)-(I), vincosan (D)-(II), vallesiachotaman (V)-(III), strychnan (S)-(IV), aspidospermatan (A)-(V), eburan (E)-(VI), plumeran (P)-(VII), and ibogan (I)-(VIII) types (Fig. 1). The C-, D-, V-, S-, and A-types possess a non-rearranged secologanin moiety and the E-, P-, and I-types a rearranged secologanin unit. The latter three more “complex” types occur exclusively in Plumerioideae, a subfamily of Apocynaceae.

Keywords

Cell Suspension Culture Vinca Alkaloid Indole Alkaloid Mevalonic Acid Plant Cell Report 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. Anderson, L.A., Keene, A.T., Phillipson, J.D.: Planta Med. 46, 25–27 ( 1982) .PubMedCrossRefGoogle Scholar
  2. Balague, C., Wilson, G.: Physiol. Veg. 20, 515–522 (1982)Google Scholar
  3. Balsevich, J.: Planta Med. 1985, 128–132Google Scholar
  4. Balsevich, J., Kurz, W.G.W.: Planta Med 49, 79–84 (1983)PubMedCrossRefGoogle Scholar
  5. Balsevich, J., Constabel, F., Kurz, W.G.W.: Planta Med. 44, 231–233 (1982)PubMedCrossRefGoogle Scholar
  6. Bartlett, M.F., Lambert, B.F., Werblood, H.M. Taylor, W.I.: J. Am. Chem. Soc. 85, 475–477 (1982)CrossRefGoogle Scholar
  7. Battersby, A.R., Kutney, J.P., Aweryn, B., Choi, L.S.L., Kolodziejczyk, P., Kurz, W.G.W., Chatson, K.B., Constabel, F.: Helv. Chim. Acta 65, 1271–1278 (1982)CrossRefGoogle Scholar
  8. Kutney, J.P., Choi, L.S.L., Honda, T., Lewis, N.G., Sato, T., Stuart, K.L., Worth, B.R.: Helv. Chim. Acta 65, 2088–2101 (1982b)CrossRefGoogle Scholar
  9. Kutney, J.P., aweryn, B., Choi, L.S.L., Honda, T., Kolodziejczyk, P., Lewis, N.G., Sato, T., Sleigh, S.K., Stuart, K.L., Worth, B.R., Kurz, W.G.W., Chatson, K.B., Constabel, F.: Tetrahedron 39, 3781–3795 (1983)CrossRefGoogle Scholar
  10. Kutney, J.P., Aweryn, B., Chatson, K.B., Choi, L.S.L., Kurz, W.G.W.: Plant Cell Rep. 4, 259–262 (1985).CrossRefGoogle Scholar
  11. Lee, S.L., Cheng, K.D., Scott, A.I.: Phytochemistry 20, 1841–1843 (1981)CrossRefGoogle Scholar
  12. Leete, E.: J. Nat. Prod. 43, 130–135 (198017Google Scholar
  13. Madyastha, K.M., Coscia, C.J.: Recent Adv. Phytochem. 85–129 (1979a);–J. Biol. Chem. 254, 2419–2427 (1979b)PubMedGoogle Scholar
  14. Madyastha, K.M., Meehan, T. D., Coscia, C.J.: Biochemistry 15, 1097–1102 (1976)PubMedCrossRefGoogle Scholar
  15. Majumdar, S.P., Poisson, J., Potier, P.: Phytochemistry 12, 1 167–1169 (1973)Google Scholar
  16. Mangeney, P., Andriamialisoa, R.Z., Langlois, N., Langlois, Y., Potier, P.: J. Am. Chem. Soc. 101, 2243–2245 (1979)CrossRefGoogle Scholar
  17. Mcfarlane, J., Madyastha, K.M., Coscia, C.J.: Biochem. Biophys. Res. Commun. 66, 1263–1269 (1975).CrossRefGoogle Scholar
  18. Mclauchlan, W.R., Hasan, M., Baxter, R.L., Scott, A.I.: Tetrahedron 39, 3777–3780 (1983)CrossRefGoogle Scholar
  19. Meehan, T.D., Coscia, C.J.: Biochem. Biophys. Res. Commun. 53, 1043–1048 (1973)CrossRefGoogle Scholar
  20. Merillon, J.M., Chenieux, J.C., Rideau, M.: Planta Med. 47, 169–176 (1983)CrossRefGoogle Scholar
  21. Merillon, J.M., Rideau, M., Chenieux, J.C.: Planta Med. 50, 497–501 (1984)CrossRefGoogle Scholar
  22. Mizukami, H., Nordlöv, H., Lee, S.L., Scott, A.I.: Biochemistry 18, 3760–3763 (1979).PubMedCrossRefGoogle Scholar
  23. Morris, P., Fowler, M.W.: Biochem. Soc. Trans. 8, 630–631 (1980)PubMedGoogle Scholar
  24. Mulder-Krieger, T.: Pharm. Weekbl. 120, 761–768 (1985)Google Scholar
  25. Mulder-Krieger, T., Verpoorte, R., Baerheim–Svendsen, A.: Planta Med. 44, 237–240 (1982a)PubMedCrossRefGoogle Scholar
  26. Mulder-Krieger, T., Verpoorte, R., de Graaf, Y.P., van der Kreek, M., Baerheim–Svendsen, A.: Planta Med. 46. 15–18 (1982b)Google Scholar
  27. Mulder-Krieger, T., Verpoorte, R., de Water, A., van Gessel, M., van Oeveren, B.C.J.A., Baerheim-Svendsen, A.: Planta Med. 46, 19–24 (1982c).PubMedCrossRefGoogle Scholar
  28. Nagakura, N., Rüffer, M., Zenk, M.H.: J. Chem. Soc. Perkin I 1979, 2308–2312Google Scholar
  29. Neumann, D., Krauss, G., Hieke, M., Gröger, D.: Planta Med. 48, 20–23 (1983)PubMedCrossRefGoogle Scholar
  30. Noe, W., Mollenschott, C., BERLIN, J.: Plant Mol. Biol. 3, 281–288 (1984).CrossRefGoogle Scholar
  31. Pawelka, K.H., Stöckigt, J.: Plant Cell Reports 2, 105–107 (1983)CrossRefGoogle Scholar
  32. Pfitzner, A., Stöckigt, J.: Phytochemistry 21, 1585–1588 (1982); - Chem. Commun. 1983a, 459–460; - Tetrahedron Lett. 24, 1695–1698 (1983b); Tetrahedron Lett. 24, 5197–5200 (1983c); - Planta Med. 48, 221–227 (1983d)Google Scholar
  33. Pfitzner, A., Krausch, B., Stöckigt, J.: Tetrahedron 40, 1691–1699 (1984)CrossRefGoogle Scholar
  34. Pfitzner, U., Zenk, M.H.: Planta Med. 46, 10–14 (1982)PubMedCrossRefGoogle Scholar
  35. Phillipson, J.D., Zenk, M.H. (eds): Indole and Biogenetically Related Alkaloids. London: Academic Press 1980.Google Scholar
  36. Rapoport, H., Moore, R.E.: J. Org. Chem. 27, 2981–2985 (1962)CrossRefGoogle Scholar
  37. Renaudin, J.P.: Plant Sei. Lett. 22, 59–65(1981)Google Scholar
  38. Renaudin, J.P., Guern, J.: Physiol. Veg. 20, 533–5T7 (1982)Google Scholar
  39. Roja, P.C., Benjamin, B.D., Heble, M.R., Chadha, M.S.: Planta Med. 1985, 73–74Google Scholar
  40. Roustan, J.P., Ambid, C., Fallot, J.: Physiol. Veg. 20, 523–532 (1982).Google Scholar
  41. Sasse, F., Buchholz, M., Berlin, J.: Z. Naturforsch. 38c, 910–915 (1983a)Google Scholar
  42. Sasse, F., Buchholz, M., Berlin, J.: Z. Naturforsch. 38c, 916–922 (1983b)Google Scholar
  43. Schallenberg, J., Berlin, J.: Z. Naturforsch. 34c, 541–545 (1979)Google Scholar
  44. Schübel, H., Stöckigt, J.: Plant Cell Reports 3, 72–74 (1984)CrossRefGoogle Scholar
  45. Scott, A.I,, Lee, S.L., Hirata, T., Culver, M.G.: Rev. Latinoam. Quirn. 9, 131–138 (1978)Google Scholar
  46. Scott, A.I., Mizukami, H., Hirata, I., Lee, S.L.: PKytochemistry 19, 488–489 (1980)CrossRefGoogle Scholar
  47. Scott, A.I., Lee, S.L.: Phytochemistry 19, 488–4W (1980)CrossRefGoogle Scholar
  48. Scott, A.I., Lee, S.L., Nordlöv, H., Dorschel, C.A., mizukami, H., Mac Kenzie, N.E.: Heterocycles 15, 1257–1274 (1981)CrossRefGoogle Scholar
  49. Shimolina, L.L., Minina, S.A.: Khim. Prir. Soedin. 1981, 807Google Scholar
  50. Spitsberg, V., Coscia, C.J., Krueger, R.J.: Plant Cell Reports 1, 43–47 (1981)CrossRefGoogle Scholar
  51. Staba, F.J., Chung, A.C.: Phytochemistry 20, 2495–2498 (1981)CrossRefGoogle Scholar
  52. Stafford, A., Fowler, M.W.: Plant Cell Tissue Organ Culture 2, 239–251 (1983)CrossRefGoogle Scholar
  53. Stafford, A., Smith, L., Fowler, M.W.: Plant Cell Tissue Organ Culture 4, 83–94 (1985)CrossRefGoogle Scholar
  54. Stöckigt, J.: Chem. Commun. 1978, 1097–1099;–113–141 in: Indole and Biogenetically Related Alkaloids, eds. J.D. Phillipson, M.H. Zenk. London: Academic Press 1980Google Scholar
  55. Stöckigt, J., Soll, H.J.: Planta Med. 40, 22–30 (1980)CrossRefGoogle Scholar
  56. Stöckigt, J., Höfle, G., Pfitzner, A.: Tetrahedron Lett. 2, 1925–1926 (1980a)CrossRefGoogle Scholar
  57. Stöckigt, J., Rüffer, M., Kan-Fan, Ch., HUSSON, H.P.: Planta Med. 39, 73–76 (1980b)CrossRefGoogle Scholar
  58. Stöckigt, J. , Pfitzner, A. , Firl, J. : Plant Cell Rep. 1, 36–39 (1981 )CrossRefGoogle Scholar
  59. Stöckigt, J., Pawelka, K.–H., Rother, A., Deus, B.: Z. Naturforsch. 37c, 857–860 (1982)Google Scholar
  60. Stöckigt, J., Pfitzner, A., Keller, P.J.: Tetrahedron Lett. 2A, 2485–2486 (1983)CrossRefGoogle Scholar
  61. Stöckigt, J., Gundlach, H., Deus–Neumann, B.: Helv. Chim. Acta 48, 315–318 (1985)CrossRefGoogle Scholar
  62. Stuart, K.L., Kutney, J.P., Honda, T., Lewis, N.G., Worth, B.R.: Heterocycles 9, 647–652 (1978).CrossRefGoogle Scholar
  63. Tanahashi, T., Nagakura, N., Inouye, H., Zenk, M.H.: Phytochemistry 23, 1917–1922 (1984)CrossRefGoogle Scholar
  64. Tietze, L-F.: Angew. Chem. 95, 840–853 (1983).CrossRefGoogle Scholar
  65. Uesato, S., Matsuda, S., Inouye, H.: Yakugaku Zasshi HM, 1232–1243 (1984a)? - Chem. Pharm. Bull. 32, 1671–1674 (1984b)Google Scholar
  66. Uesato, S., matsuda, S., Iida, A., Inouye, H., Zenk, M.H.: Chem. Pharm. Bull. 32, 3764–3767 (1984c).Google Scholar
  67. Westekemper, P., Wieczorek, U., Gueritte, F., langlois, N., Langlois, Y., Potier, P., Zenk, M.H.: Planta Med. 39, 24–37 (1980)Google Scholar
  68. Woodward, R.B.: Angew. Chem. 68, 13–20 (1956).CrossRefGoogle Scholar
  69. Zenk, M.H.: J. Nat. Prod. 43, 438–451 (1980)CrossRefGoogle Scholar
  70. Zenk, M.H., Deus, B.: 391–394 in: Plant Tissue Culture, ed. A. Fujiwara. Tokyo: Maruzen 1982.Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1986

Authors and Affiliations

  • Horst-Robert Schütte
    • 1
  1. 1.Akademie der Wissenschaften der DDRInstitut für Biochemie der Pflanzen HalleHalle (Saale)Germany

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