The Occurrence of Simple Isoquinolines in Plants

  • J. Lundström
Conference paper
Part of the Proceedings in Life Sciences book series (LIFE SCIENCES)

Abstract

Simple isoquinoline alkaloids may be defined as those containing only one aromatic nucleus and no other cyclic structure except a methylenedioxy substituent. In general, they are derived from only one aromatic amino acid residue e.g. a phenylalanine or tyrosine moiety.

Keywords

Indole Bark Benzyl Quinoline qUinolones 

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References

  1. Ahn BC, Degen U, Lienjayetz C, Pachaly P, Zymalkowski F (1978) Inhaltstoffe von Cassia siamea. Arch Pharm 311: 569–578CrossRefGoogle Scholar
  2. Anonymous (1959) Peyotl. Bull Narcot UN Dep Social Affairs 11: 16–29Google Scholar
  3. Backeberg C (1966) Das Kakteenlexikon. Fischer, JenaGoogle Scholar
  4. Baser KH (1982) Isolation and identification of anisaldehyde and three alkaloids from leaves of Thalictrum minus var. microphyllum. J Nat Prod 45: 704–706CrossRefGoogle Scholar
  5. Bell EA, Nulu JR, Cone C (1971) L-Dopa and L-3-carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, a new amino acid from seeds of Mucuna mutisiana. Phytochemistry 10: 2191–2194CrossRefGoogle Scholar
  6. Bick IRC, Sévenet T, Sinchai W, Skelton BW, White AH (1981) Alkaloids of Cryptocarya longifolia: X-ray crystal structure of thalifoline and longifoline. Aust J Chem 34: 195–207CrossRefGoogle Scholar
  7. Bruhn JG (1971) Carnegia gigantea: The Saguaro and its uses. Econ Bot 25:320–329Google Scholar
  8. Bruhn JG, Holmstedt B (1974) Early peyote research. An interdisciplinary study. Econ Bot 28: 353–390CrossRefGoogle Scholar
  9. Bruhn JG, Lundström J (1976) Alkaloids of Carnegia gigantea. Arizonine, a new tetrahydroisoquinoline alkaloid. Lloydia 39: 197–203PubMedGoogle Scholar
  10. Canonica L, Galliani G, Lesma G, Tollari S (1981) Enzymatic transformations of alkaloids utilizing pure enzymes. Proc 1st Int Conf Chem Biotechnol Biol Act Nat Prod 1st vol. 2: 522–527Google Scholar
  11. Cava MP, Bessho K (1966) Hernandia alkaloids II. Hernandaline, a new elaborated aporphine structural type. Tetrahedron Lett 36: 4279–4282CrossRefGoogle Scholar
  12. Chen CR, Beal JL, Doskotch RW, Mitscher LA, Svoboda GH (1974) A phytochemical study of Doryphora sassafras II. Isolation of eleven crystalline alkaloids from the bark. Lloydia 37: 493–500PubMedGoogle Scholar
  13. Chen D, Liang X (1982) Studies on the constituents of lateral root of Aconitum carmichaeli Debt (Fu Zi), a traditional Chinese medicine I. Isolation and structural determination of salsolinol. Xaoxue Xuebao 17:793–794, CA 98: 40465kGoogle Scholar
  14. Dahlgren R (1975) A system of classification of the angiosperms to be used to demonstrate the distribution of characters. Bot Not 128: 119–147Google Scholar
  15. Daxenbichler ME, Kleiman R, Wiesleder D, VanEtten CH, Carlson KD (1972) A new amino acid, (—)-1-methyl-3-carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, from velvet beans. Tetrahedron Lett 18: 1801–1802CrossRefGoogle Scholar
  16. Djerassi C, Smith CR, Marfey SP, McDonald RN, Lemin AJ, Figdor SK, Estrada H (1954) Alkaloid studies III. Isolation of pilocereine and anhalonidine from four cactus species. J Am Chem Soc 76: 3215–3217CrossRefGoogle Scholar
  17. Forgacs P, Desconclois JF, Mansard D, Provost J, Tiberghien R, Tocquer J, Touché A (1981) Dopamine et alcald des tétrahydroisoquinoléiques d’Annona reticulata L. Annonacées. Plant Med Phytother X V: 10–15Google Scholar
  18. Gharbo SA, Beal JL, Schlessinger RH, Cava MP, Svoboda GH (1965) A phytochemical study of Doryphora sassafras. I. Isolation of eight crystalline alkaloids from the leaves. Lloydia 28: 237–244Google Scholar
  19. Ghosal S, Metha R (1974) ß-Phenethylamine and tetrahydroisoquinoline alkaloids of Desmodium cephalotes. Phytochemistry 13: 1628–1629CrossRefGoogle Scholar
  20. Ghosal S, Srivastava RS (1973a) Chemical investigation of Alhagi pseudalhagi (Bieb.) Desv.: 13-Phenethylamine and tetrahydroisoquinoline alkaloids. J Pharm Sci 62: 1555–1556PubMedCrossRefGoogle Scholar
  21. Ghosal S, Srivastava RS (1973b) ß-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochemistry 12: 193–197CrossRefGoogle Scholar
  22. Hussain SF, Minard RD, Freyer AJ, Shamma M (1983a) New alkaloids from Fumaria parviflora. J Nat Prod 44: 169–178CrossRefGoogle Scholar
  23. Hussain SF, Nakkady S, Khan L, Shamma M (1983b) Oxyhydrastinine, an isoquinolone alkaloid from the Papaveraceae. Phytochemistry 22: 319–320CrossRefGoogle Scholar
  24. Iee IR, Lee MM (1982) Studies of chemical constituents of the genus Thalictrum in Korea I. Alkaloids from the root of Thalictrum uchiyamai Nakai. Saegyate Hakhoe Chi 13:132–135, CA 98: 221674yGoogle Scholar
  25. Irgashev T, Israilov IA, Batsuren D, Yunosov MS (1983) Corydalis stricta alkaloids. Khim Prir Soedin 1983:490–493, CA 100:82695aGoogle Scholar
  26. Iwasa K, Takao N (1982) Formation of alkaloids in Corydalis ophiocarpa callus culture. Phytochemistry 21: 611–614CrossRefGoogle Scholar
  27. Kapadia G, Fayez MBE (1970) Peyote constituents: Chemistry, biogenesis and biological effects. J Pharm Sci 59: 1699–1726PubMedCrossRefGoogle Scholar
  28. Kapadia G, Fayez MBE (1973) The chemistry of peyote alkaloids. Lloydia 36: 9–35PubMedGoogle Scholar
  29. Krane BD, Shamma M (1982) The isoquinolone alkaloids. J Nat Prod 45: 377–384CrossRefGoogle Scholar
  30. Kunitomo J-I, Murakami Y, Oshikata M, Shingu T, Lu S-T, Chen I-S, Akasu M (1981) The alkaloids of Stephania sasakii Hayata (13). On the tertiary minor bases. Yakugaku Zasshi 101: 431–436Google Scholar
  31. Kupchan SM, Yoshitake A (1969) Thalictrum alkaloids IX. The isolation, structural elucidation and synthesis of thalisopavine. J Org Chem 34: 1062–1065Google Scholar
  32. Lundström J (1971) Biosynthetic studies on mescaline and related cactus alkaloids. Acta Pharm Suec 8: 275–302PubMedGoogle Scholar
  33. Lundström J (1983) Simple isoquinoline alkaloids. In: Brossi A (ed) The Alkaloids, vol. XXI. Academic Press, London New York, pp 255–327Google Scholar
  34. Mata R, McLaughlin JL (1982) Cactus alkaloids 50. A comprehensive tabular summary. Rev Latinoam Quim 12: 95–117Google Scholar
  35. Michel K-H, Sandberg F (1968) Occurrence of tyramine and N-methyltyramine in Haloxylon salicornum. Acta Pharm Suec 5: 67–70PubMedGoogle Scholar
  36. Mohamed YAH, Chang C-j, McLaughlin JL (1979) Cactus alkaloids XXXIX. A glucotetrahydro-isoquinoline from the Mexican cactus Pterocereus gaumeri. J Nat Prod 42: 197–202CrossRefGoogle Scholar
  37. Müller P, Schütte HR (1971) Biosynthesis and metabolism of phenolic latex amino acids. Biochem Physiol Pflanz 162: 234–244Google Scholar
  38. Obata-Sasamoto H, Komamine A (1981) Biosynthesis of 3-carboxy-67,-dihydroxy-1,2,3,4-tetra-hydroisoquinoline in a callus culture of Stizolobium hassjoo. Z Naturforsch 36: 921–924Google Scholar
  39. Ordaz C, Ferrigni NR, McLaughlin JL (1983) Dehydroheliamine, a trace alkaloid from the saguaro, Carnegia gigantea ( Cactaceae ). Phytochemistry 22: 2101–2102Google Scholar
  40. Orekhov A, Proskurnina N (1934) Alkaloids of Salsola richten II. Constitution of salsoline. Ber 67B: 878–884Google Scholar
  41. Pummangura S, Mohamed YAH, Chang C-j, McLaughlin JL (1982) Two simple tetrahydroisoquinoline alkaloid N-oxides from cacti. Phytochemistry 21: 2375–2377CrossRefGoogle Scholar
  42. Ranieri RL, McLaughlin JL (1976) ß-Phenethylamine and tetrahydroisoquinoline alkaloids from the Mexian cactus Dolichothele longimamma. J Org Chem 41: 319–323CrossRefGoogle Scholar
  43. Ranieri RL, McLaughlin JL (1977) Cactus alkaloids XXXI. ß-Phenethylamines and tetrahydro-isoquinolines from the Mexican cactus Dolichothele uberiformis. Lloydia 40: 173–177PubMedGoogle Scholar
  44. Shamma M, Rothenberg AS (1978) The alkaloids of Thalictrum dioicum. Lloydia 41: 169–178Google Scholar
  45. Shamma M, Foy JE, Miana GA (1974) Baluchistanamine. Novel type dimeric isoquinoline alkaloid. J Am Chem Soc 96: 7809–7810Google Scholar
  46. Tani C, Nagakura N, Sugiyama N (1975) Studies on the alkaloids of Papaveraceous plants XXI. Alkaloids of Corydalis speciosa Maxim. The isolation of the tertiary bases by the multi-buffered DCCC Yakugaku Zasshi 95: 838–842Google Scholar
  47. Tani C, Nagakura N, Kuriyama C (1978) Studies on the alkaloids of papaveraceous plants XXXI. Separation of the alkaloids by droplet countercurrent chromatography. The alkaloids of Corydalis ophiocarpa Hook. et Thorns. Yakugaku Zasshi 98: 1243–1251PubMedGoogle Scholar
  48. Theuns HG, Vlietstra EJ, Salemink CA (1983) Corypalline and 0-methylcorypalline, two alkaloids from Papaver bracteatum. Phytochemistry 22: 247–250CrossRefGoogle Scholar
  49. Urzt a A, Cassels BK (1978) Alkaloid chemosystematics, chemotaxonomy and biogenesis in the Atherospermataceae. Lloydia 41: 98–113Google Scholar
  50. Verpoorte R, Siwon J, van Essen GFA, Tieken M, Baerheim-Svendsen A (1982) Studies on the Indonesian medicinal plants VII. Alkaloids of Archangelisia (lava. J Nat Prod 45: 582–584CrossRefGoogle Scholar
  51. White EP (1944) Alkaloids of the Leguminosae. N Z J Sci Tech 25B: 137–162Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1985

Authors and Affiliations

  • J. Lundström
    • 1
  1. 1.Astra Läkemedel ABSödertäljeSweden

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