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Abstract

The term peptide alkaloids, first proposed by Goutarel and co-workers (32) in 1964, has been applied to a rapidly expanding group of closely related polyamide plant bases composed largely of simple amino acids. Although these compounds have also been called basic peptides (12), it seems generally accepted that the emphasis of the first term is more appropriate in view of their relatively small size and the fact that each incorporates a fragment which is not (or at least is no longer) a common amino acid (61). For the purpose of the present review a peptide alkaloid is defined as a plant base containing two or more amide groups. By this definition are included certain polyamide bases (e. g. lunarine, homaline) whose amino acid origin is less obvious*. This review follows the suggestion of Goutarel and co-workers (32) that, in spite of their polyamide nature, the ergot alkaloids logically belong with the indole alkaloids because of the importance of lysergic acid in their structures. Moreover, the basic lysergic acid portion is distant from the polyamide part and has usually been cleaved from it during chemical investigation. Therefore, these compounds are not treated here. The peptide compounds isolated by Wieland and co-workers from Amanita species are also excluded since most of them are not basic and they have been reviewed recently (58).

Keywords

Ergot Alkaloid High Resolution Mass Spectroscopy Tetrahedron Letter Macrocyclic Ring Simple Amino Acid 
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. 1.
    Bertho, A. und W.S. Liang: Notiz über ein Alkaloid aus Ceanothus americanus. Arch. Pharmaz. 271, 273 (1933).CrossRefGoogle Scholar
  2. 2.
    Bladon, P., M. Chaigneau, M.-M. Janot, J. Le Men, P. Potier et A. Melera: Isolement de Dérivés Diphényliques par Fusion Alcaline de la Lunarine. Tetrahedron Letters 1961, 321.Google Scholar
  3. 3.
    Bladon, P., R. Ikan, F.-S. Spring and A.D. Tait: The Chemistry of Lunaria Alkaloids. I. Tetrahedron Letters 1959, No. 9, 18.Google Scholar
  4. 4.
    Blanpin, O., M. Païs et M.A. Quevauviller: Étude Pharmacodynamique d’Adouétine Z, Alcaloïde du Waltheria americana. Ann. pharm. franc. 21, 147 (1963).Google Scholar
  5. 5.
    Boit, H.-G.: Über die Alkaloide von Lunaria biennis. Chem. Ber. 87, 1082 (1954).CrossRefGoogle Scholar
  6. 6.
    Clark, A.H.: The Alkaloids of Ceanothus americanus. Amer. J. Pharm. 98, 147 (1926).Google Scholar
  7. 7.
    Clark, A.H.: The Alkaloids of Ceanothus americanus. II. Extraction of the Alkaloid. Amer. J. Pharm. 100, 240 (1928).Google Scholar
  8. 8.
    Clinch, J.H.M.: Analysis of the Leaves of Ceanothus americanus L. Amer. J. Pharm. 56, 131 (1884).Google Scholar
  9. 9.
    Fehlhaber, H.-W.: Massenspektrometrische Strukturermittlung von Peptid-Alkaloiden. Z. analyt. Chem. 235, 91 (1968).CrossRefGoogle Scholar
  10. 10.
    Gerlach, F.C.: Ceanothus. Amer. J. Pharm. 63, 332 (1891).Google Scholar
  11. 11.
    Gordin, H.M.: On the Alkaloids of Ceanothus americanus. Pharm. Rev. 18, 266 (1900).Google Scholar
  12. 12.
    Goutarel, R.: Peptides Basiques, Un Type Nouveau d’Alcaloïde. Colloq. Int. Centre Nat. Rech. Sci. No. 144, 159 (1966).Google Scholar
  13. 13.
    Groot, J.T.: Pharmacology of Ceanothus americanus. I. Preliminary Studies: Hemodynamics and the Effects of Coagulation. J. Pharmacol. Exp. Therapeut. 30, 275 (1927).Google Scholar
  14. 14.
    Hairs, E.: Un Alcaloïde des Graines du Lunaria biennis. Bull. Acad. roy. Belgique 1909, 1042 [Chem. Abstr. 4, 1892 (1910)].Google Scholar
  15. 15.
    Hansen, O.R.: Lunarine, an Alkaloid from Lunaria biennis. Acta Chem. Scand. 1, 656 (1947).CrossRefGoogle Scholar
  16. 16.
    Heyns, K. und H.-F. Grutzmacher: Massenspektren von Freien und N-Acetylierten Aminosäuren. Liebigs Ann. Chem. 667, 194 (1963).CrossRefGoogle Scholar
  17. 17.
    Heyns, K. und H.-F. Grutzmacher: Massenspektrometrische Untersuchungen von acylierten Peptiden. Tetrahedron Letters 1963, 1761.Google Scholar
  18. 18.
    Huneck, S.: Über die Alkaloide von Lunaria rediviva L. Naturwiss. 49, 233 (1962).CrossRefGoogle Scholar
  19. 19.
    Janot, M.-M. et J. Le Men: Sur les Alcaloïdes de Lunaria biennsis Moench. (Crucifères). Bull. soc. chim. France 1956, 1840.Google Scholar
  20. 20.
    Klein, F.K. and H. Rapoport: Ceanothus Alkaloids. Americine. J. Amer. Chem. Soc. 90, 2398 (1968).CrossRefGoogle Scholar
  21. 21.
    Klein, F.K. and H. Rapoport: The Structure of Ceanothine-B. J. Amer. Chem. Soc. 90, 3576 (1968).CrossRefGoogle Scholar
  22. 22.
    Ma, J.C.N. and E.W. Warnhoff: On the Use of Nuclear Magnetic Resonance for the Detection, Estimation, and Characterization of N-Methyl Groups. Canad. J. Chem. 43, 1849 (1965).CrossRefGoogle Scholar
  23. 23.
    Manian, A.A.: A Study of a Purified Alkaloidal Principle of Ceanothus americanus. Ph. D. Thesis. Purdue University, 1954.Google Scholar
  24. 24.
    Marchand, J., X. Monseur et M. Païs: Alcaloïdes Peptidiques — VII (5). Myrianthines A, B et C., Alcaloïdes du Myrianthus arboreus P. Beauv. (Urticacées). Ann. pharm. franc. 26, 771 (1968).Google Scholar
  25. 25.
    Marchand, J., M. Païs, X. Monseur et F.-X. Jarreau: Alcaloïdes Peptidiques — VII. Les Lasiodines A et B, Alcaloïdes du Lasiodiscus marmoratus C.H. Wright (Rhamnacées). Tetrahedron 25, 937 (1969).CrossRefGoogle Scholar
  26. 26.
    Menard, E.L., J.M. Müller, A.F. Thomas, S.S. Bhatnagar und N.J. Dastoor: Über die Inhaltsstoffe von Zizyphus oenoplia Mill. 1. Mitteilung: Isolierung der Inhaltsstoffe. Helv. Chim. Acta 46, 1801 (1963).CrossRefGoogle Scholar
  27. 27.
    Païs, M., F.-X. Jarreau, X. Lusinchi et R. Goutarel: Alcaloïdes Peptidiques, III (1). Pandamine et Pandaminine, Alcaloïdes du Panda oleosa Pierre (Pandacées). Ann. chimie 1966, 83.Google Scholar
  28. 28.
    Païs, M., J. Mainil et R. Goutarel: Les Adouétines X, Y et Z, Alcaloïdes du Waltheria americana L. (Sterculiacées). Ann. pharm. franc. 21, 139 (1963).Google Scholar
  29. 29.
    Païs, M., J. Marchand, F.-X. Jarreau et R. Goutarel: Alcaloïdes Peptidiques. V. Structures des Adouetines X, Y, Y′ et Z, Alcaloïdes du Waltheria americana L. (Sterculiacées). Bull. soc. chim. France 1968, 1145.Google Scholar
  30. 30.
    Païs, M., J. Marchand, X. Monseur, F.-X. Jarreau et R. Goutarel: Alcaloïdes Peptidiques. IV. Structure de l’Hymenocardine, Alcalo’ide de l’Hymenocardia acida Tul. (Euphorbiacées). C.R. hebd. scéances Acad. Sci., Sér. C, 264, 1409 (1967).Google Scholar
  31. 31.
    Païs, M., J. Marchand, G. Ratle et F.-X. Jarreau: Alcaloïdes Peptidiques. (VI) (1). l’Hymenocardine, Alcaloïde de l’Hymenocardia acida Tul. (Hymenocardiacées). Bull. soc. chim. France 1968, 2979.Google Scholar
  32. 32.
    Païs, M., X. Monseur, X. Lusinchi et R. Goutarel: Alcaloïdes Peptidiques. II. Structure de la Pandamine, Alcaloïde du Panda oleosa Pierre (Pandacees). Bull. soc. chim. France 1964, 817.Google Scholar
  33. 33.
    Païs, M., G. Ratle, R. Sarfati and F.-X. Jarreau: L’homaline, Nouveau Type d’Alcaloïde Isolé d’un Homalium Sp. Africain (Flacourtiacées). C.R. hebd. scéances Acad. Sci., Ser. C, 266, 37 (1968).Google Scholar
  34. 34.
    Païs, M., G. Ratle, R. Sarfati and F.-X. Jarreau: A Propos de la Structure de l’Homaline. C.R. hebd. scéances Acad. Sci., Ser. C, 267, 82 (1968).Google Scholar
  35. 35.
    Potier, P. et J. Le Men: Étude Chimique de la Lunarine, Alcaloïde du Lunaria biennis Moench. (Cruciferes). Bull. soc. chim. France 1959, 456.Google Scholar
  36. 36.
    Potier, P., J. Le Men et M.-M. Janot: Sur la Numismine, Nouvel Alcaloïde Isolé des Graines du Lunaria biennis. Bull. soc. chim. France 1959, 201.Google Scholar
  37. 37.
    Potier, P., J. Le Men, M.-M. Janot and P. Bladon: The Isolation of Spermidine by Degradation of Lunarine. Tetrahedron Letters 1960, No. 18, 36.Google Scholar
  38. 38.
    Potier, P., J. Le Men, M.-M. Janot, P. Bladon, A.G. Brown and C.S. Wilson: The Structure of Lunarine. Tetrahedron Letters 1963, 293.Google Scholar
  39. 39.
    Poupat, C., B. Rodriguez, H.-P. Husson, P. Potier et M.-M. Janot: Nouveaux Alcaloïdes des Graines de la Monnaie du Pape, Lunaria biennis Moench (Cruciferes). C.R. hebd. scéances Acad. Sci., Sér. C., 269, 335 (1969).Google Scholar
  40. 40.
    Richards, L.W. and E.V. Lynn: An Examination of Ceanothus velutinus. J. Amer. Pharm. Assoc. 23, 332 (1934).CrossRefGoogle Scholar
  41. 41.
    Roscoe, C.W. and N.A. Hall: A Preliminary Study of the Alkaloidal Principles of Ceanothus americanus and Ceanothus velutinus. J. Amer. Pharm. Assoc. Sci. Ed. 49, 108 (1960).CrossRefGoogle Scholar
  42. 42.
    Servis, R.E. and A.I. Kosak: A Revised Structure for Ceanothine-B. J. Amer. Chem. Soc. 90, 4179 (1968).CrossRefGoogle Scholar
  43. 43.
    Servis, R.E., A.I. Kosak, R. Tschesche, E. Frohberg and H.W. Fehlhaber: Peptide Alkaloids from Ceanothus americanus L. (Rhamnaceae). J. Amer. Chem. Soc. 91, 5619 (1969).CrossRefGoogle Scholar
  44. 44.
    Steinegger, E. and T. Reichstein: Lunarin, das kristallisierte Alkaloid aus Lunaria biennis. Pharmac. Acta. Helv. 22. 258 (1947).Google Scholar
  45. 45.
    Svec., H.J. and G.A. Junk: The Mass Spectra of Dipeptides. J. Amer. Chem. Soc. 86, 2278 (1964).CrossRefGoogle Scholar
  46. 46.
    Tamura, C., G.A. Sim, J.A.D. Jeffreys, P. Bladon and G. Ferguson: Lunarine. Chem. Commun. 1965, 485.Google Scholar
  47. 47.
    Tschesche, R., L. Behrendt und H.-W. Fehlhaber: Alkaloide aus Rhamnaceen, VI. Aralionin, ein Peptid-Alkaloid aus Araliorhammus vaginatus Perrier. Chem. Ber. 102, 50 (1969).CrossRefGoogle Scholar
  48. 48.
    Tschesche, R., E. Frohberg und H.-W. Fehlhaber: Alkaloide aus Rhamnaceen, IV. Integerrin, ein weiteres Peptid-Alkaloid aus Ceanothus integerrimus Hook und Arn. Tetrahedron Letters 1968, 1311.Google Scholar
  49. 49.
    Tschesche, R. und H. Last: Alkaloide aus Rhamnaceen, V. Franganin und Frangufolin. Zwei weitere Peptid-Alkaloide aus Rhamnus frangula L. Tetrahedron Letters 1968, 2993.Google Scholar
  50. 50.
    Tschesche, R., H. Last und H.-W. Fehlhaber: Alkaloide aus Rhamnaceen, III. Frangulanin, ein Peptid-Alkaloid aus Rhamnus frangula L. Chem. Ber. 100, 3937 (1967).CrossRefGoogle Scholar
  51. 51.
    Tschesche, R. und I. Reutel: Alkaloïde aus Sterculiaceen, I. Über Peptidalkaloide aus Melochia corchorifolia. Tetrahedron Letters 1968, 3817.Google Scholar
  52. 52.
    Tschesche, R., J. Rheingans, H.-W. Fehlhaber und G. Legler: Integerrissin und Integerrenin, zwei Peptid-Alkaloide aus Ceanothus integerrimus Hook und Arn. Chem. Ber. 100, 3924 (1967).CrossRefGoogle Scholar
  53. 53.
    Tschesche, R., R. Welters und H.-W. Fehlhaber: Alkaloide aus Rhamnaceen, I. Scutianin, ein cyclisches Peptid-Alkaloid aus Scutia buxifolia Reiss. Chem. Ber. 100, 323 (1967).CrossRefGoogle Scholar
  54. 54.
    Warnhoff, E.W., J.C.N. Ma and P. Reynolds-Warnhoff: Ceanothine-B, a Naturally Occurring Oxazacylononadiene. J. Amer. Chem. Soc. 87, 4198 (1965).CrossRefGoogle Scholar
  55. 55.
    Warnhoff, E.W., S.K. Pradhan and J.C.N. Ma: Ceanothus Alkaloids I. Isolation, Separation and Characterization. Canad. J. Chem. 43, 2594 (1965).CrossRefGoogle Scholar
  56. 56.
    Warnhoff, E.W. unpublished results.Google Scholar
  57. 57.
    Wastl, H.: Influence of Tea from Leaves of Ceanothus americanus on Blood Pressure of Hypertensive Rats. Federat. Proc. (Amer. Soc. Exp. Biol.) 7, 131 (1948).Google Scholar
  58. 58.
    Wieland, Th.: The Toxic Peptides of Amanita Phalloides. Fortschr. Chem. organ. Naturstoffe 25, 214 (1967).Google Scholar
  59. 59.
    Wiesner, K., D.M. Macdonald, C. Bankiewicz and D.E. Orr: Structure of Pithecolobine. II. Canad. J. Chem. 46, 1881 (1968).CrossRefGoogle Scholar
  60. 60.
    Wiesner, K., Z. Valenta, D.E. Orr, V. Liede and G. Kohan: Structure of Pithecolobine. III. The Synthesis of the 1,5-and 1,3-Desoxypithecolobines. Canad. J. Chem. 46, 3617 (1968).CrossRefGoogle Scholar
  61. 61.
    Zbiral, E., E.L. Ménard und J.M. Müller: Über die Inhaltsstoffe von Zizyphus oenoplia Mill. 2. Mitteilung. Zur Konstitutionsermittlung des Zizyphins. Helv. Chim. Acta. 48, 404 (1965).CrossRefGoogle Scholar

Copyright information

© Springer-Verlag/Wien 1970

Authors and Affiliations

  • E. W. Warnhoff
    • 1
  1. 1.LondonCanada

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