Skip to main content
SpringerLink
Log in

The Pyrrolizidine Alkaloids

  • Chapter
Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Abstract

Previous chapters in this series by Warren appeared in 1955 (310) and 1966 (311). Since then an authoritative book by Bull, Culvenor, and Dick, on the chemistry and pharmacology of pyrrolizidine alkaloids has been published (60). Comprehensive reviews on the alkaloids (312), their chemotaxonomic significance (77), and general pyrrolizidine chemistry (243) are available. A series of Annual Reports including pyrrolizidine alkaloids was introduced in 1971 (245). The present review follows the format of previous articles in this series and covers the literature up to early 1981.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Aasen, A. J., and C. C. J. Culvenor: The Saturated Pyrrolizidinediols. A Partial Synthesis of Turneforcidine. Aust. J. Chem. 22, 2657 (1969).

    Article  CAS  Google Scholar 

  2. Aasen, A. J., and C. C. J. Culvenor: The Saturated Pyrrolizidinediols. II. The Total Synthesis and Stereochemistry of Macronecine. J. Org. Chem. 34, 4143 (1969).

    Article  CAS  Google Scholar 

  3. Aasen, A. J., C. C. J. Culvenor, and L. W. Smith: The Saturated Pyrrolizidinediols. I. Spectral Studies and the Conversion of an Ester of Dihydroxyheliotridane into the (+)-Enantiomer of Hastanecine. J. Org. Chem. 34, 4137 (1969).

    CAS  Google Scholar 

  4. Abdullaev, U. A., Ya. U. Rashkes, Kh. Shakhidoyatov, and S. Yu. Yunusov: Mass Spectra of Pyrrolizidine Alkaloids of the Heliotridane Series. Khim. Prir. Soedin. 1972, 634 [Chem. Abstr. 78, 84612 (1973)]; RASKHES, YA. V., U. A. ABDULLAEV, and S. Yu. YUNUSOV: Mass Spectra of Pyrrolizidine Alkaloids. Khim. Prir. Soedin. 1978, 153 [Chem. Abstr. 89, 163803 (1978)].

    Google Scholar 

  5. Abdullaev, U.A., Ya. V. Rashkes, and S. Yu. Yunusov: Mass Spectra of TV-Oxides of Pyrrolizidine Alkaloids. Khim. Prir. Soedin. 1974, 620 [Chem. Abstr. 82, 73270 (1975)].

    Google Scholar 

  6. Abdullaev, U.A., Ya. V. Rashkes, and S. Yu. Yunusov: Fragmentation of a Macrocyclic Ring of Alkaloids with an Otonecine Nucleus. Khim. Prir. Soedin. 1976, 66 [Chem. Abstr. 85, 177726 (1976)].

    Google Scholar 

  7. Adams, R., S. Miyano, and M. D. Nair: Synthesis of Substituted Pyrrolidines and Pyrrolizidines. J. Am. Chem. Soc. 83, 3323 (1961).

    Article  CAS  Google Scholar 

  8. Akramov, S. T., F. Kiyamitdinova, and S. Yu. Yunusov: Alkaloids of Heliotropium dasycarpum and H. arguzioides. Dokl. Akad. Nauk Uz. SSR 4, 30 (1961) [Chem. Abstr. 60, 16209 (1964)].

    Google Scholar 

  9. Akramov, S. T., F. Kiyamitdinova, and S. Yu. Yunusov: Alkaloids from Lindelofia stylosa. Dokl. Akad. Nauk Uz. SSR 1961, 35 [Chem. Abstr. 61, 4700 (1964)].

    Google Scholar 

  10. Akramov, S. T., F. Kiyamitdinova, and S. Yu. Yunusov: Alkaloids of Solenanthus turkestanicus, Lindelofia olgae, and Trachelanthus korolkovii. Dokl. Akad. Nauk Uz. SSR 19, 29 (1962) [Chem. Abstr. 61, 11005 (1964)].

    CAS  Google Scholar 

  11. Akramov, S. T., F. Kiyamitdinova, and S. Yu. Yunusov: Study of Rindera and Lindelofia. Dokl. Akad. Nauk Uz. SSR 22, 35 (1965) [Chem. Abstr. 63, 16770 (1965)].

    CAS  Google Scholar 

  12. Akramov, S. T., F. Kiyamitdinova, and S. Yu. Yunusov: The Alkaloids from Senecio francheti, Trachelanthus hissoricus, and T. korolkovii. Khim. Prir. Soedin. 1967, 351 [Chem. Abstr. 68, 47001 (1968)].

    Google Scholar 

  13. Akramov, S. T., A. S. Samatov, and S. Yu. Yunusov: Alkaloids of Solenanthus circinatus, Paracaryum himalayense, and Lindelofia pterocarpa. Dokl. Akad. Nauk. Uz. SSR 21, 28 (1964).

    Google Scholar 

  14. Ali, M. A., and G. A. Adil: Isolation and Structure of Crotalarine, a New Alkaloid from Crotolaria burhia. Pakistan J. Sci. Ind. Res. 16, 227 (1973).

    CAS  Google Scholar 

  15. Alieva, Sh. A., U. A. Abdullaev, M. V. Telezhenetskaya, and S. Yu. Yunusov: Alkaloids of Doronicum macrophyllum. Khim. Prir. Soedin. 1976, 194 [Chem. Abstr. 85, 108841 (1976)].

    Google Scholar 

  16. Allan, J. R., I. C. Hsu, and L. A. Carstens: Dehydroretronecine-induced Rhabdomyosarcomas in Rats. Cancer Res. 35, 997 (1975).

    Google Scholar 

  17. Alonso de Lama, J. M., and I. Ribas: Alkaloids of the Papilionaceae. XXIII. Alkaloids of Adenocarpus argyrophyllus from the Cañaveral Mountains of Cáceres, Spain. Anales Real Espan. Fis. Quirn. (Madrid) 49B, 711 (1953) [Chem. Abstr. 49, 4681 (1955).

    Google Scholar 

  18. Amal, H., and O. Ates: Echium italicum var. biebersteinii. Instanbul Univ. Eczacilik Fak. Mecm. 7, 85 (1971) [Chem. Abstr. 77, 72582 (1972)].

    Google Scholar 

  19. Atal, C. K.: Semisynthetic Derivatives of Pyrrolizidine Alkaloids of Pharmacodynamic Importance. A Review. Lloydia 41, 312 (1978).

    CAS  Google Scholar 

  20. Atal, C. K., C. C. J. Culvenor, R. S. Sawhney, and L. W. Smith: Crosemperine, a New Otonecine Ester from Crotalaria semperflorens Vent. Aust. J. Chem. 20, 805 (1967).

    Article  CAS  Google Scholar 

  21. Atal, C. K., C. C. J. Culvenor, R. S. Sawhney, and L. W. Smith: The Alkaloids of Crotalaria grahamiana. Grahamine, the 3′-[(—)-2-methylbutyryl]ester of Monocrotaline. Aust. J. Chem. 22, 1773 (1969).

    Article  CAS  Google Scholar 

  22. Atal, C. K., K. K. Kapur, C. C. J. Culvenor, and L. W. Smith: A New Pyrrolidine Aminoalcohol in Alkaloids from Crotalaria Species. Tetrahedron Lett. 1966, 537.

    Google Scholar 

  23. Atal, C. K., and R. S. Sawhney: The Pyrrolizidine Alkaloids from Indian Crotalarias. Indian J. Pharm. 35, 1 (1973).

    CAS  Google Scholar 

  24. Atal, C. K., R. K. Sharma, C. C. J. Culvenor, and L. W. Smith: Alkaloids of Crotalaria rubiginosa Willd. Trichodesmine and Junceine. Aust. J. Chem. 19, 2189 (1966).

    Article  CAS  Google Scholar 

  25. Bale, N. M, R. Cahill, N. M. Davies, M. B. Mitchell, E. H. Smith, and D. Whitehouse: Biosynthesis of the Necic Acids of the Pyrrolizidine Alkaloids. Further Investigations of the Formation of Senecic and Isatinecic Acids in Senecio Species. J. Chem. Soc., Perkin Trans. I 1978, 101.

    Google Scholar 

  26. Bale, N. M., and D. H. G. Crout: Determination of the Relative Rates of Incorporation of Arginine and Ornithine into Retronecine During Pyrrolizidine Alkaloid Biosynthesis. Cytochemistry 14, 2617 (1975).

    Article  CAS  Google Scholar 

  27. Barreiro, E. J., A. de Lima Pereira, L. Nelson, L. F. Gomes, and A. J. R. da Silva: Carbon-13 Nuclear Magnetic Resonance of Pyrrolizidine Alkaloids: a Reassignment. J. Chem. Res. (S) 1980, 330.

    Google Scholar 

  28. Bates, R. B., and S. R. Morehead: Absolute Configurations of Pyrrolizidine Alkaloids of the Loline Group. Tetrahedron Lett. 1972, 1629.

    Google Scholar 

  29. Batirov, E. Kh., S. A. Khamidkhodzhaev, V. M. Malikov, and S. Yu. Yunusov: Study of Alkaloids from Lolium cunateum. Khim. Prir. Soedin. 1976, 60 [Chem. Abstr. 85, 59556 (1976)].

    Google Scholar 

  30. Batirov, E. Kh., V. Malikov, and S. Yu. Yunusov: Lolidine, a New Chlorine Containing Alkaloid from Lolium cuneatum Seeds. Khim. Prir. Soedin. 1976, 63 [Chem. Abstr. 85, 74883 (1976)].

    Google Scholar 

  31. Batirov, E. Kh., V. Malikov, and S. Yu. Yunusov: Alkaloids from Lolium cuneatum Seeds. Khim. Prir. Soedin. 1976, 120 [Chem. Abstr. 86, 13792 (1977)].

    Google Scholar 

  32. Batra, V., R. N. Gandhi, and T. Rajagopalan: Structure of Crotastriatine. Indian J. Chem. 13, 989 (1975).

    CAS  Google Scholar 

  33. Batra, V., and T. R. Rajagopalan: Alkaloidal Constituents of Senecio scandens. Curr. Sci. 46, 141 (1977).

    CAS  Google Scholar 

  34. Benn, M., J. de Grave, C. Gnanasunderam, and R. Hutchins: Host-plant Pyrrolizidine Alkaloids in Nyctemera annulata Boisduval: Their Persistence Through the Life Cycle and Transfer to a Parasite. Experientia 35, 731 (1979).

    CAS  Google Scholar 

  35. Bhacca, N. S., and R. K. Sharma: Mucronatinine, a New Alkaloid from Crotalaria mucronata Desv. I. Tetrahedron 24, 6319 (1968).

    Article  CAS  Google Scholar 

  36. Birnbaum, G. I.: The Nature of Intramolecular N … C = O Interactions. Crystal Structure of the Senecio Alkaloid Senkirkine. J. Am. Chem. Soc. 96, 6165 (1974).

    CAS  Google Scholar 

  37. Birnbaum, K. B.: Structure and Absolute Configuration of the Alkaloid Clivorine. Acta Crystallogr. Sect. B 28, 2825 (1972).

    Article  CAS  Google Scholar 

  38. Birnbaum, K. B., A. Kläsek, P. Sedmera, G. Snatzke, L. F. Johnson, and F. Santavy: Revised Structure of the Alkaloid Clivorine. Tetrahedron Lett. 1971, 3421.

    Google Scholar 

  39. Bohlmann, F., W. Klose, and K. Nikisch: Synthese des Dehydroheliotridins und des 3- Oxo-dehydroheliotridins. Tetrahedron Lett. 1979, 3699.

    Google Scholar 

  40. Bohlmann, F., and K.-H. Knoll: Zwei neue Acylpyrrole aus Kleinia kleinioides. Phytochemistry 17, 599 (1978).

    Article  CAS  Google Scholar 

  41. Bohlmann, F., K.-H. Knoll, C. Zdero, P. K. Mahanta, M. Grenz, A. Suwita, D. Ehlers, N. L. Van, W.-R. Abraham, and A. A. Natu: Terpen-Derivate aus Senecio- Arten. Phytochemistry 16, 965 (1977).

    Article  CAS  Google Scholar 

  42. Bohlmann, F., and C. Zdero: Neue C10-Säureamide, Furanoeremophilane und andere Inhaltsstoffe aus Bolivianischen Senecio-Arten. Phytochemistry 18, 125 (1979).

    Article  CAS  Google Scholar 

  43. Bohlmann, F., C. Zdero, D. Berger, A. Suwita, P. Mahanta, and C. Jeffrey: Neue Furanoeremophilane und weitere Inhaltsstoffe aus Südafrikanischen Senecio-Arten. Phytochemistry 18, 79 (1979).

    Article  CAS  Google Scholar 

  44. Bohlmann, F., C. Zdero, and M. Grenz: Natürlich vorkommende Terpen-Derivate, 78. Weitere Inhaltsstoffe aus Südafrikanischen Senecio-Arten. Chem. Ber. 110, 474 (1977).

    Article  CAS  Google Scholar 

  45. Bohlmann, F., C. Zdero, and A. A. Natu: Weitere Bisabolen-Derivate und andere Inhaltsstoffe aus Südafrikanischen Senecio-Arten. Phytochemistry 17, 1757 (1978).

    Article  CAS  Google Scholar 

  46. Bohlmann, F., C. Zdero, and G. Snatzke: Zur Stereochemie der Acylpyrrole aus Senecio-Arten. Chem. Ber. 111, 3009 (1978).

    Article  CAS  Google Scholar 

  47. Bohlmann, F., and J. Ziesche: Neue Germacren-Derivate aus Senecio-Arten. Phytochemistry 18, 1489 (1979).

    Article  CAS  Google Scholar 

  48. Boppré, M.: Chemical Communication, Plant Relationships, and Mimicry in the Evolution of Danaid Butterflies. Entomol. Exp. Appl. 24, 264 (1978).

    Article  Google Scholar 

  49. Boppré, M., R. L. Petty, D. Schneider, and J. Meinwald: Behaviorally Mediated Contacts Between Scent Organs: Another Prerequisite for Pheromone Production in Danaus chrysippus Males (Lepidoptera). J. Comp. Physiol., Sect. A 126, 97 (1978).

    Article  Google Scholar 

  50. Borges del Castillo, J., A. G. Espana de Aguirre, J. L. Bretón, A. G. González, and J. Trujillo: Loroquin, A New Necine Isolated from Urechtites karwinsky Mueller (1-Hydroxy-methylene-7-keto-dihydropyrrolizine). Tetrahedron Lett. 1970, 1219.

    Google Scholar 

  51. Bottomley, W., and T. A. Geissman: Pyrrolizidine Alkaloids. The Biosynthesis of Retronecine. Phytochemistry 3, 357 (1964).

    Article  CAS  Google Scholar 

  52. Brandänge, S., and I. Granelli: Studies on Orchidaceae Alkaloids. XXXVI. Alkaloids from some Vanda and Vandopsis Species. Acta Chem. Scand. 27, 1096 (1973).

    Article  Google Scholar 

  53. Brandänge, S., I. Granelli, and B. Lüning: Orchidaceae Alkaloids. XVIII. Isolation of Phalaenopsin La from Kingiella taenialis (Lindl.) Rolfe. Acta Chem. Scand. 24, 354 (1970).

    Article  Google Scholar 

  54. Brandänge, S., S. Josephson, and S. Vallen: Orchidaceae Alkaloids. XXXVIII. Asymmetric Synthesis of 2-isobutylmalic acid and 2-(cyclohexylmethyl)malic acid. Acta Chem. Scand. 27, 3668 (1973).

    Article  Google Scholar 

  55. Brandänge, S., and B. Lüning: Studies on Orchidaceae Alkaloids. XII. Pyrrolizidine Alkaloids from Phalaenopsis amabilis BL. and Ph. mannii Rchb. f. Acta Chem. Scand. 23, 1151 (1969).

    Article  Google Scholar 

  56. Brandänge, S., B. Lüning, C. Moberg, and E. Sjöstrand: Orchidaceae Alkaloids. XXIV. Pyrrolizidine Alkaloid from Phalaenopsis cornucervi. Acta Chem. Scand. 25, 349 (1971).

    Article  Google Scholar 

  57. Brandänge, S., B. Lüning, C. Moberg, and E. Sjöstrand: Orchidaceae Alkaloids. XXX. Fourteen Phalaenopsis Species. New Pyrrolizidine Alkaloid from Phalaenopsis equestris. Acta Chem. Scand. 26, 2558 (1972).

    Article  Google Scholar 

  58. Briggs, L. H., R. C. Cambie, B. J. Candy, G. M. O’Donovan, R. H. Russell, and R. N. Seelye: Alkaloids of New Zealand Senecio Species. Part II. Senkirkine. J. Chem. Soc. 1965, 2492.

    Google Scholar 

  59. Broch-Due, A. I., and A. A. Aasen: Alkaloids of Anchusa officinalis L. Identification of the Pyrrolizidine Alkaloid Lycopsamine. Acta Chem. Scand. Ser. B. 34, 75 (1980).

    Article  Google Scholar 

  60. Bruemmerhoff, S. W. D., and H. L. de Waal: Retrorsine from Crotalaria spartioides. J. S. African Chem. Inst. 14, 101 (1961).

    CAS  Google Scholar 

  61. Bull, L. B., C. C. J. Culvenor, and A. T. Dick: The Pyrrolizidine Alkaloids. North- Holland Publ., Amsterdam, 1968.

    Google Scholar 

  62. Cahill, R., D. H. G. Crout, M. B. Mitchell, and U. S. Müller: Isoleucine Biosynthesis and Metabolism: Stereochemistry of the Formation of L-isoleucine and of its conversion into Senecic and Isatinecic Acids in Senecio Species. J. Chem. Soc., Chem. Commun. 1980, 419.

    Google Scholar 

  63. Cava, M. P., K. V. Rao, J. A. Weisbach, R. F. Raffauf, and B. Douglas: The Alkaloids of Cacalia floridana. J. Org. Chem. 33, 3570 (1968).

    Article  CAS  Google Scholar 

  64. Chu, Y.-L., and J.-H. Chu: Pyrrolizidine Alkaloids. II. The Alkaloids of Senecio cruentus. Yao Hsueh Hsueh Pao 11, 168 (1964) [Chem. Abstr. 61, 1904d (1964)].

    Google Scholar 

  65. Coleman, P. C., E. D. Coucourakis, and J. A. Pretorius: Crystal Structure of Retrorsine. S. African J. Chem. 33, 116 (1980); STOECKLI-EVANS, H.: Retrorsine Hydrobromide Ethanol Solvate: A Pyrrolizidine Alkaloid. Acta Crystallogr., Sect. B 35, 2798 (1979).

    Google Scholar 

  66. Constantinescu, E., and D. Albulescu: The Isolation of an Alcamine from Senecio doria. Farmacia 9, 139 (1961) [Chem. Abstr. 56, 14396 (1962)].

    CAS  Google Scholar 

  67. Cooks, R. G., F. L. Warren, and D. H. Williams: Rhizophoraceae Alkaloids. Part III. Cassipourine. J. Chem. Soc. (C) 1967, 286.

    Google Scholar 

  68. Coucourakis, E. D., and C. G. Gordon-Gray: The Senecio Alkaloids. Suggested Structures for Isoline and Bisline, Two New Alkaloids from Senecio othonniformis Fourcade. J. Chem. Soc. (C) 1970, 2312.

    Google Scholar 

  69. Coucourakis, E. D., C. G. Gordon-Gray, and C. G. Whiteley: The Senecio Alkaloids. The Structure and Absolute Configuration of Isoline. J. Chem. Soc., Perkin Trans. I 1972, 2339.

    Google Scholar 

  70. Crout, D. H. G.: Pyrrolizidine Alkaloids. The Biosynthesis of Echimidinic Acid. J. Chem. Soc. (C) 1966, 1968.

    Google Scholar 

  71. Crout, D. H. G.: Pyrrolizidine Alkaloids. Biosynthesis of the Angelate Component of Heliosupine. J. Chem. Soc. (C) 1967, 1233.

    Google Scholar 

  72. Crout, D. H. G.: The Structure of Axillarine, a Novel Pyrrolizidine Alkaloid from Crotalaria axillaris Ait. Chem. Commun. 1968, 429; — Structures of Axillarine and Axillaridine, Novel Pyrrolizidine Alkaloids from Crotalaria axillaris Ait. J. Chem. Soc. (C) 1969, 1379.

    Google Scholar 

  73. Crout, D. H. G.: Pyrrolizidine and Seco-pyrrolizidine Alkaloids of Crotalaria laburnifolia L. Subspecies eldomae. J. Chem. Soc., Perkin Trans. I 1972, 1602.

    Google Scholar 

  74. Crout, D. H. G.: The Pyrrolizidine Alkaloids, their Physiological Activity and Biosynthesis in Higher Plants. Chimia 30, 270 (1976).

    Google Scholar 

  75. Crout, D. H. G., M. H. Benn, H. Imaseki, and T. A. Geissman: Pyrrolizidine Alkaloids. The Biosynthesis of Seneciphyllic Acid. Phytochemistry 5, 1 (1966).

    Article  CAS  Google Scholar 

  76. Crout, D. H. G., N. M. Davies, E. H. Smith, and D. Whitehouse: Pyrrolizidine Alkaloids. The Biosynthesis of Senecic Acid. J. Chem. Soc., Perkin Trans. 1 1972, 671; Crout, D. H. G., N. M. Davies, E. H. Smith, and D. Whitehouse: Biosynthesis of the C10 Necic Acids of the Pyrrolizidine Alkaloids. Chem. Commun. 1970, 635.

    Google Scholar 

  77. Crout, D. H. G., and D. Whitehouse: Absolute Configuration of 2,3-Dihydroxy-3-methylpentanoic Acid; an Intermediate in the Biosynthesis of Isoleucine, and its Identity with the Esterifying Acid of the Pyrrolizidine Alkaloid Strigosine. J. Chem. Soc., Perkin Trans. I 1977, 544.

    Google Scholar 

  78. Culvenor, C. C. J.: Pyrrolizidine Alkaloids — Occurrence and Systematic Importance in Angiosperms. Bot. Notiser 131, 473 (1978).

    CAS  Google Scholar 

  79. Culvenor, C. C. J., D. H. G. Crout, W. Klyne, W. P. Mose, J. D. Renwick, and P. M. Scopes: Circular Dichroism of Pyrrolizidine Alkaloids and Related Compounds. J. Chem. Soc. (C) 1971, 3653.

    Google Scholar 

  80. Culvenor, C. C. J., J. A. Edgar, J. L. Frahn, and L. W. Smith: The Alkaloids of Symphytum x uplandicum (Russian Comfrey). Aust. J. Chem. 33, 1105 (1980).

    Article  CAS  Google Scholar 

  81. Culvenor, C. C. J., J. A. Edgar, J. L. Frahn, L. W. Smith, A. Ulubelen, and S. Doganca: The Structure of Anadoline. Aust. J. Chem. 28, 173 (1975).

    Article  CAS  Google Scholar 

  82. Culvenor, C. C. J., J. A. Edgar, M. V. Jago, A. Outteridge, J. E. Peterson, and L. W. Smith: Hepato- and Pneumotoxicity of Pyrrolizidine Alkaloids and Derivatives in Relation to Molecular Structure. Chem.-Biol. Interactions 12, 299 (1976).

    CAS  Google Scholar 

  83. Culvenor, C. C. J., J. A. Edgar, L. W. Smith, and I. Hirono: The Occurrence of Senkirkine in Tussilago farfara. Aust. J. Chem. 29, 229 (1976).

    Article  CAS  Google Scholar 

  84. Culvenor, C. C. J., M. L. Heffernan, and W. G. Woods: Nuclear Magnetic Resonance Spectra of Pyrrolizidine Alkaloids. I. The Spectra of Retronecine and Heliotridine. Aust. J. Chem. 18, 1605 (1965); CULVENOR, C. C. J., and W. G. WOODS: Nuclear Magnetic Resonance Spectra of Pyrrolizidine Alkaloids. II. The Pyrrolizidine Nucleus in Ester and Non-ester Alkaloids and their Derivatives. Aust. J. Chem. 18, 1625 (1965).

    Google Scholar 

  85. Culvenor, C. C. J., S. R. Johns, J. A. Lamberton, and L. W. Smith: The Isolation of Calycanthine and Pyrrolizidine Alkaloids from Bhesa archboldiana (Celastraceae): An Unusual Co-occurrence of Alkaloidal Types. Aust. J. Chem. 23, 1279 (1970).

    Article  CAS  Google Scholar 

  86. Culvenor, C. C. J., S. R. Johns, and L. W. Smith: Acetyllasiocarpine, an Alkaloid from Heliotropium europaeum. Aust. J. Chem. 28, 2319 (1975).

    Article  CAS  Google Scholar 

  87. Culvenor, C. C. J., J. D. Morrison, A. J. C. Nicholson, and L. W. Smith: Alkaloids of Crotalaria trifoliastrum Willd. II. l-Methoxymethyl-l,2-epoxypyrrolizidine. Aust. J. Chem. 16, 131 (1963).

    Article  CAS  Google Scholar 

  88. Culvenor, C. C. J., G. M. O’Donovan, and L. W. Smith: Alkaloids of Crotalaria trifoliastrum Willd. and C. aridicola Domin. III. Additional Pyrrolizidine Derivatives. Aust. J. Chem. 20, 757 (1967).

    Article  CAS  Google Scholar 

  89. Culvenor, C. C. J., G. M. O’Donovan, and L. W. Smith: The Identity of the Amino Alcohol of Retusamine with Otonecine. Aust. J. Chem. 20, 801 (1967).

    Article  CAS  Google Scholar 

  90. Culvenor, C. C. J., and L. W. Smith: The Alkaloids of Amsinckia Species: A. intermedia Fisch. et Mey., A. hispida (Ruiz et Pav.) Johnst. and A. lycopsioides Lehm. Aust. J. Chem. 19, 1955 (1966).

    CAS  Google Scholar 

  91. Culvenor, C. C. J., and L. W. Smith: Usaramine, a New Pyrrolizidine Alkaloid from Crotalaria usaramoensis E. G. Baker. Aust. J. Chem. 19, 2127 (1966).

    Article  CAS  Google Scholar 

  92. Culvenor, C. C. J., and L. W. Smith: The Alkaloids of Cynoglossum australe R. Br. and C. amabile Stapf. And Drummond. Aust. J. Chem. 20, 2499 (1967).

    CAS  Google Scholar 

  93. Culvenor, C. C. J., and L. W. Smith: A Quaternary N-Dihydropyrrolizinomethyl Derivative of Heliotrine from Heliotropium europaeum. Tetrahedron Lett. 1969, 3603.

    Google Scholar 

  94. Culvenor, C. C. J., and L. W. Smith: Crotanecine Ester Alkaloids of Crotalaria agatiflora. Anales de Quim. 68, 883 (1972).

    Google Scholar 

  95. Danilova, A. V., and L. M. Utkin: Structure of the Alkaloid Macrophylline. Zh. Obshch. Khim. 30, 345 (1960) [Chem. Abstr. 54, 22698 (I960)].

    CAS  Google Scholar 

  96. Danishefsky, S.: Electrophilic Cyclopropanes in Organic Synthesis. Acc. Chem. Res. 12, 66 (1979).

    Article  CAS  Google Scholar 

  97. Danishefsky, S., R. McKee, and R. K. Singh: Kinetically Controlled Total Syntheses of dl-Trachelanthamidine and dl-Isoretronecanol. J. Am. Chem. Soc. 99, 4783 (1977).

    Article  CAS  Google Scholar 

  98. Danishefsky, S., R. McKee, and R. K. Singh: Stereospecific Total Synthesis of dl-Hastanecine and dl-Dihydroxyheliotridane. J. Am. Chem. Soc. 99, 7711 (1977).

    Article  CAS  Google Scholar 

  99. Davies, N. M., and D. H. G. Crout: Pyrrolizidine Alkaloid Biosynthesis. Relative Rates of Incorporation of the Isomers of Isoleucine into the Necic Acid Component of Senecionine. J. Chem. Soc., Perkin Trans. I 1974, 2079.

    Google Scholar 

  100. Deagen, J. T., and M. L. Deinzer: Improvements in the Extraction of Pyrrolizidine Alkaloids. Lloydia 40, 395 (1977).

    CAS  Google Scholar 

  101. Deinzer, M. L., P. A. Thomson, D. M. Burgett, and D. L. Isaacson: Pyrrolizidine Alkaloids: Their Occurrence in Honey from Tansy Ragwort (Senecio jacobaea L.). Science 195, 497 (1977).

    Article  CAS  Google Scholar 

  102. Deinzer, M. L., P. Thomson, D. Griffin, and E. Dickinson: A Sensitive Analytical Method for Pyrrolizidine Alkaloids. The Mass Spectra of Retronecine Derivatives. Biomed. Mass Spectrom. 5, 175 (1978).

    Article  CAS  Google Scholar 

  103. Dickinson, J. O., M. P. Cooke, R. R. King, and P. A. Mohamed: Milk Transfer of Pyrrolizidine Alkaloids in Cattle. J. Am. Vet. Med. Assoc. 169, 1192 (1976).

    CAS  Google Scholar 

  104. Dimenna, G. P., T. P. Krick, and H. J. Segall: Rapid High-performance Liquid Chromatography Isolation of Monoesters, Diesters and Macrocyclic Diester Pyrrolidine Alkaloids from Senecio jacobaea and Amsinckia intermedia. J. Chromatogr. 192, 474 (1980).

    Article  CAS  Google Scholar 

  105. Drewes, S. E., I. Antonowitz, P. T. Kaye, and P. C. Coleman: 13C Nuclear Magnetic Resonance Spectra of the Senecio Alkaloids, Retrorsine, Swazine, Isoline, and Hygrophylline. J. Chem. Soc., Perkin Trans. I 1981, 287.

    Google Scholar 

  106. Edgar, J. A., M. Boppre, and D. Schneider: Pyrrolizidine Alkaloid Storage in African and Australian Danaid Butterflies. Experientia 35, 1447 (1979).

    Article  CAS  Google Scholar 

  107. Edgar, J. A., P. A. Cockrum, and J. L. Frahn: Pyrrolizidine Alkaloids in Danaus plexippus L. and D. chrysippus L. Experientia 32, 1532 (1976).

    Article  Google Scholar 

  108. Edgar, J. A., and C. C. J. Culvenor: Pyrrolizidine Alkaloids in Parsonsia Species (Family Apocynaceae) which Attract Danaid Butterflies. Experientia 31, 393 (1975).

    Article  CAS  Google Scholar 

  109. Edgar, J. A., N. J. Eggers, A. J. Jones, and G. B. Russell: Unusual Macrocyclic Pyrrolizidine Alkaloids from Parsonsia heterophylla A. Cunn and Parsonsia spiralis Wall. ( Apocynaceae ). Tetrahedron Lett. 1980, 2657.

    Google Scholar 

  110. Edwards, J. D., and T. Matsumoto: Senecio Alkaloids. Synthesis of Decanecic Acids. J. Org. Chem. 32, 1837 (1967).

    Article  CAS  Google Scholar 

  111. Eggers, N. J., and G. J. Gainsford: Parsonsine (C22H33NO8): A Pyrrolizidine Alkaloid from Parsonsia heterophylla A. Cunn. Cryst. Struct. Commun. 8, 597 (1979).

    CAS  Google Scholar 

  112. Evans, J. V., A. Peng, and C. J. Nielsen: The Gas Chromatographic Mass Spectrometric Analysis of the New Antitumor Drug Indicine N-oxide Utilizing a Novel Reaction Accompanying Trimethylsilylation. Biomed. Mass Spectrom. 6, 38 (1979).

    Article  CAS  Google Scholar 

  113. Ferry, S., and J. L. Brazier: Sur les Alcaloides de Quelques Senecio Indigènes II. Identification et Structures. Ann. Pharm. Fr. 34, 133 (1976).

    CAS  Google Scholar 

  114. Fridrichsons, J., A. M. Mathieson, and D. J. Sutor: Crystal Structure of Jacobine Bromohydrin. Acta Crystallogr., Sect. B 16, 1075 (1963).

    CAS  Google Scholar 

  115. Furuya, T., and K. Araki: Constituents of Crude Drugs. I. Alkaloids of Symphytum officinale. Chem. Pharm. Bull. (Japan) 16, 2512 (1968).

    Article  CAS  Google Scholar 

  116. Furuya, T., and M. Hikichi: Alkaloids and Triterpenoids of Symphytum officinale. Phytochemistry 10, 2217 (1971).

    Article  CAS  Google Scholar 

  117. Furuya, T., and M. Hikichi: Lindelofine and Supinine: Pyrrolizidine Alkaloids from Eupatorium stoechadosmum. Phytochemistry 12, 225 (1973).

    Article  CAS  Google Scholar 

  118. Furuya, T., M. Hikichi, and Y. Iitaka: Fukinotoxin, a New Pyrrolizidine Alkaloid from Petasites japonicus. Chem. Pharm. Bull. (Japan) 24, 1120 (1976).

    Article  CAS  Google Scholar 

  119. Furuya, T., K. Murakami, and M. Hikichi: Constituents of Crude Drugs. III. Senkirkine, a Pyrrolizidine Alkaloid from Farfugium japonicum. Phytochemistry 10, 3306 (1971).

    Article  CAS  Google Scholar 

  120. Gafner, G., and L. J. Admiraal: The Crystal and Molecular Structure of the Alkaloid Cassipourine. Acta Crystallogr. Sect. B 25, 2114 (1969).

    Article  CAS  Google Scholar 

  121. Gainsford, G. J.: The Second Form of the Alkaloid Parsonsine, C22H33NO8. Cryst. Struct. Commun. 9, 173 (1980).

    CAS  Google Scholar 

  122. Gandhi, R. N., T. R. Rajagopalan, and T. R. Seshadri: A New Alkaloid from the Seeds of Crotalaria striata. Curr. Sci. 37, 285 (1968).

    CAS  Google Scholar 

  123. Gharbo, S. A., and A. M. Habib: Phytochemical Investigation of Egyptian Senecio. II. Alkaloids of Senecio aegyptius, S. desfontainei, S. vulgaris, S. petasitis, and S. mikanoides. Lloydia 32, 503 (1969).

    CAS  Google Scholar 

  124. Gordon-Gray, C. G., and F. D. Schlosser: The Senecio Alkaloids. The Biosynthesis of the Necic Acids. J. South African Chem. Inst. 23, 13 (1970).

    CAS  Google Scholar 

  125. Gordon-Gray, C. G., R. B. Wells, N. Hallak, M. B. Hursthouse, S. Neidle, and T. P. Toube: Swazine, a New Alkaloid from Senecio swaziensis Compton: A Chemical and X-ray Crystal Study of a Novel Spiro Dilactone. Tetrahedron Lett. 1972, 707; GORDON-GRAY, C. G., and R. B. WELLS: Structure and Absolute Configuration of Swazine. J. Chem. Soc., Perkin Trans. I 1974, 1556.

    Google Scholar 

  126. Goss, G. J.: The Interaction Between Moths and Plants Containing Pyrrolizidine Alkaloids. Environ. Entomol. 8, 487 (1979).

    CAS  Google Scholar 

  127. Gupta, V. P., S. K. Handoo, and R. S. Sawhney: Experimental Analysis of Ultraviolet Spectra of Some Pyrrolizidine Esters. Indian J. Pure Appl. Phys. 13, 776 (1975); SIMANEK, V., A. KLASEK, and F. SANTAVY: Ultraviolet Absorption Spectroscopy of Some Pyrrolizidine Alkaloids. Collect. Czech. Chem. Commun. 34, 1832 (1969).

    Google Scholar 

  128. Gupta, V. P., S. K. Handoo, and R. S. Sawhney: Experimental Analysis of the Infrared Spectrum of Some Pyrrolizidine Esters. Curr. Sci. 44, 451 (1975).

    CAS  Google Scholar 

  129. Habib, A. A. M.: Senecionine, seneciphylline, jacobine, and otosenine from Senecio cineraria. Planta Med. 26, 279 (1974).

    Article  CAS  Google Scholar 

  130. Habib, A. A. M.: Phytochemical Investigation of Heliotropium ramosissimum. Bull. Fac. Sci., Riyadh Univ. 7, 67 (1975) [Chem. Abstr. 85, 119597 (1976)].

    Google Scholar 

  131. Habib, A. A. M., M. R. I. Saleh, and M. Farag: Isolation of Crispatine and Fulvine from Crotalaria madurensis. Lloydia 34, 455 (1971).

    CAS  Google Scholar 

  132. Hart, N. K., and J. A. Lamberton: Pyrrolizidine Alkaloids from Planchonella Species (Family Sapotaceae). I. The Alkaloids of Planchonella thyrsoidea C. T. White and P. anteridifera (White and Francis) H. J. Lam. Aust. J. Chem. 19, 1259 (1966).

    CAS  Google Scholar 

  133. Hayashi, K., A. Natorigawa, and H. Mitsuhashi: Integerrimine from Cacalia hastata L. subsp. orientalis Kitamura. Chem. Pharm. Bull. (Japan) 20, 201 (1972).

    Article  CAS  Google Scholar 

  134. Hikichi, M., Y. Asada, and T. Furuya: Ligularidine, a New Pyrrolizidine Alkaloid from Ligularia dentata. Tetrahedron Lett. 1979, 1233.

    Google Scholar 

  135. Hikichi, M., and T. Furuya: Syneilesine, a New Pyrrolizidine Alkaloid from Syneilesis palmata. Tetrahedron Lett. 1974, 3657.

    Google Scholar 

  136. Hikichi, M., and T. Furuya: Studies on Constituents of Crude Drugs. VII. Syneilesine and Acetylsyneilesine from Syneilesis palmata. Chem. Pharm. Bull. (Japan) 24, 3178 (1976).

    Article  CAS  Google Scholar 

  137. Hikichi, M., T. Furuya, and Y. Iitaka: Yamataimine, a New Pyrrolizidine Alkaloid from Cacalia yatabei. Tetrahedron Lett. 1978, 767.

    Google Scholar 

  138. Hirono, I., M. Haga, M. Fujii, S. Matsuura, N. Matsubara, M. Nakayama, T. Furuya, M. Hikichi, H. Takanashi, E. Uchida, S. Hosaka, and I. Ueno: Induction of Hepatic Tumors in Rats by Senkirkine and Symphytine. J. Natl. Cancer Inst. 63, 469 (1979).

    CAS  Google Scholar 

  139. Hirono, I., H. Mori, and M. Haga: Carcinogenic Activity of Symphytum officinale. J. Natl. Cancer Inst. 61, 865 (1978).

    CAS  Google Scholar 

  140. Hoque, M. S., A. Ghani, and H. Rashid: Alkaloids of Heliotropium indicum Linn. Grown in Bangladesh. Bangladesh Pharm. J. 5, 13 (1976).

    CAS  Google Scholar 

  141. Hoskins, W. M., and D. H. G. Crout: Pyrrolizidine Alkaloid Analogues. Preparation of Semisynthetic Esters of Retronecine. J. Chem. Soc., Perkin Trans. I 1977, 538.

    Google Scholar 

  142. Hrbek, J., L. Hruban, A. Klasek, N. K. Kochetkov, A. M. Likhosherstov, F. Santavy, and G. Snatzke: Pyrrolizidine Alkaloids. XVIII. Chiroptical Properties of some Pyrrolizidine Alkaloids. Collect. Czech. Chem. Commun. 37, 3918 (1972).

    CAS  Google Scholar 

  143. Hughes, C. A., R. Letcher, and F. L. Warren: The Senecio Alkaloids. Part XVI. The Biosynthesis of the “Necine” Bases from Carbon-14 Precursors. J. Chem. Soc. 1964, 4974.

    Google Scholar 

  144. Huizing, H. J., F. de Boer, and T. M. Malingre: Chloranil, a Sensitive Detection Reagent for Pyrrolizidine Alkaloids on Thin-Layer Chromatograms. J. Chromatogr. 195, 407 (1980); MOLYNEUX, R. J., and J. N. ROITMAN: Specific Detection of Pyrrolizidine Alkaloids on Thin-Layer Chromatograms. J. Chromatogr. 195, 412 (1980).

    Google Scholar 

  145. Huizing, H. J., and T. M. Malingre: Reduction of Pyrrolizidine N-oxides by the Use of a Redox Polymer. J. Chromatogr. 173, 187 (1979).

    Article  CAS  Google Scholar 

  146. Huizing, H. J., and T. M. Malingre: Purification and Separation of Pyrrolizidine Alkaloids from Boraginaceae on a Polystyrene-divinylbenzene Resin. J. Chromatogr. 176, 274 (1979).

    Article  CAS  Google Scholar 

  147. Huizing, H. J., and T. M. Malingré: Ion-pair Adsorption Chromatography of Pyrrolizidine Alkaloids. J. Chromatogr. 205, 218 (1981).

    Article  CAS  Google Scholar 

  148. Huxtable, R. J.: New Aspects of the Toxicology and Pharmacology of Pyrrolizidine Alkaloids. Gen. Pharmacol. 10, 159 (1979).

    CAS  Google Scholar 

  149. Jovceva, R. J., A. Boeva, H. Potfsilová, A. Klásek, and F. Santavy: Alkaloids from Senecio procerus L., var. procerus Stoj. Stef. et Kit. Collect. Czech. Chem. Commun. 43, 2312 (1978).

    CAS  Google Scholar 

  150. Karimov, A., M. V. Telezhenetskaya, K. L. Lutfullin, and S. Yu. Yunusov: Alkaloids of Echium vulgare and Berberís oblonga. Khim. Prir. Soedin. 1975, 433 [Chem. Abstr. 84, 14662 (1976)].

    Google Scholar 

  151. Keeler, R. F., K. R. van Kampen, and L. F. James (eds.): Effects of Poisonous Plants on Livestock. New York: Academic Press. 1978.

    Google Scholar 

  152. Khalilov, D. S.: Phytochemical Study of Different Species of Senecio from Azerbaidzhán Flora. Izvest. Akad. Nauk Azerb. SSR, Ser. Biol. Nauk 1971, 122 [Chem. Abstr. 77, 123781 (1972)].

    Google Scholar 

  153. Khalilov, D. S., and M. V. Telezhenetskaya: Alkaloids of Senecio. Khim. Prir. Soedin. 1973, 128 [Chem. Abstr. 78, 15643 (1973)].

    Google Scholar 

  154. Khalilov, D. S., M. V. Telezhenetskaya, and S. Yu. Yunusov: Doronine from Senecio othonnae. Khim. Prir. Soedin. 1977, 866 [Chem. Abstr. 88, 101593 (1978)].

    Google Scholar 

  155. Khan, H. A., and D. J. Robins: Pyrrolizidine Alkaloid Biosynthesis; Incorporation of 13C-Labelled Putrescines into Retronecine. J. Chem. Soc., Chem. Commun. 1981, 146.

    Google Scholar 

  156. Khan, H. A., and D. J. Robins: Pyrrolizidine Alkaloids. Evidence for N-(4-Aminobutyl)-l,4-diaminobutane (Homospermidine) as an Intermediate in Retronecine Biosynthesis. J. Chem. Soc., Chem. Commun. 1981, 554.

    Google Scholar 

  157. Khanna, P., and S. K. Manot: Production of Pyrrolizidine Alkaloid from in vitro Tissue Culture of Crotalaria júncea Linn. Indian J. Exp. Biol. 15, 807 (1977).

    CAS  Google Scholar 

  158. Khasanova, M. A., U. A. Abdullaev, M. V. Telezhenetskaya, and S. Yu. Yunusov: Structure of Uluganine. Khim. Prir. Soedin. 1974, 809 [Chem. Abstr. 82,140349 (1975)].

    Google Scholar 

  159. Kirfel, A., G. Will, H. Wiedenfeld, and E. Róder: (1aR,6bR,10R,11R)-9,15-Dioxo-10-hydroxy-10,11,13-trimethyl-1a,2,3,6b-tetrahydro-5H-Pyrrolizino-[1 a, 6b,6a — b,c]-1,8-dioxa-15-ds-tridecene, C18H25N05. Cryst. Struct. Commun. 9, 353 (1980).

    CAS  Google Scholar 

  160. Kirfel, A., G. Will, H. Wiedenfeld, and E. Róder: (2S,4R,5R)-2-Carboxymethyl-5-Carboxy-2,4,5-trimethyl-2,3,4,5-Tetrahydrofuran, C10H16O5. Cryst. Struct. Commun. 9, 363 (1980).

    CAS  Google Scholar 

  161. Kiyamitdinova, F., S. T. Akramov, and S. Yu. Yunusov: Alkaloids from the Family of Boraginaceae. Khim. Prir. Soedin. 1967, 411 [Chem. Abstr. 68, 75730 (1968)].

    Google Scholar 

  162. Kiyooka, S., and T. Hase: Pyrrolizidine Alkaloids: The Synthesis and Stereochemistry of a- and p-Retusanecic Acids. Bull. Chem. Soc. (Japan) 46, 3609 (1973).

    Article  CAS  Google Scholar 

  163. Kiyooka, S., T. Hase, and J. D. Edwards: Pyrrolizidine Alkaloids. The Total Synthesis of Retusaminic Acid. Chem. Lett. 1973, 963.

    Google Scholar 

  164. Klásek, A., V. A. Mnatsakanyan, and F. Santavy: Alkaloids from Senecio cineraria D. C. Collect. Czech. Chem. Commun. 40, 2524 (1975).

    Google Scholar 

  165. Klásek, A., T. Reichstein, and F. Santavy: Die Pyrrolizidin-Alkaloide aus Senecio alpinus (L.) Scop., S. subalpinus Koch und S. incanus L. subsp. carniolicus (Willd.) Br.-Bl. Helv. Chim. Acta 51, 1088 (1968).

    Article  Google Scholar 

  166. Klásek, A., P. Sedmera, A. Boeva, and F. Santavy: Pyrrolizidine Alkaloids. XX. Nemorensine, an Alkaloid from Senecio nemorensis L. Collect Czech. Chem. Commun. 38, 2504 (1973).

    Google Scholar 

  167. Klásek, A., P. Sedmera, and F. Santavy: Pyrrolizidine Alkaloids. XV. Structure of the Alkaloid Clivorine. Collect. Czech. Chem. Commun. 35, 956 (1970).

    Google Scholar 

  168. Klásek, A., P. Sedmera, and F. Santavy: Pyrrolizidine Alkaloids. XVI. Alkaloids from Some Plants of the Genus Ligularia. Collect. Czech. Chem. Commun. 36, 2205 (1971).

    Google Scholar 

  169. Klásek, A., P. Sedmera, J. Vokoun, A. Boeva, S. Dvorackova, and F. Santavy: Oxynemorensine, an Alkaloid from Senecio nemorensis L., var. subdecurrens Griseb. Collect. Czech. Chem. Commun. 45, 548 (1980).

    Google Scholar 

  170. Klasek, A., B. Sula, and F. Santavy: Pyrrolizidine Alkaloids. XXI. Alkaloids from Senecio fluviatilis Wallr. Collect. Czech. Chem. Commun. 38, 2658 (1973).

    CAS  Google Scholar 

  171. Klasek, A., V. Svarovsky, S. S. Ahmed, and F. Santavy: Isolation of Pyrrolizidine Alkaloids from Senecio aegyptius L. and S. desfontainei Druce (Syn. S. coronopifolius Desf.). Coll. Czech. Chem. Commun. 33, 1738 (1968).

    CAS  Google Scholar 

  172. Klasek, A., P. Vrublovsky, and F. Santavy: Isolation of Pyrrolizidine Alkaloids from the Plants Senecio rivularis D. C. and Ligularia clivorum Maxim. Collect. Czech. Chem. Commun. 32, 2512 (1967).

    CAS  Google Scholar 

  173. Klose, W., K. Nikisch, and F. Bohlmann: Synthesis of 5,7a-Didehydroheliotridin-3-one, the Parent Compound of a New Class of Pyrrolizidine Alkaloids. Chem. Ber. 113, 2694 (1980).

    Article  CAS  Google Scholar 

  174. Kochetkov, N. K., A. M. Likhosherstov, and V.N. Kulakov: The Total Synthesis of Some Pyrrolizidine Alkaloids and Their Absolute Configuration. Tetrahedron 25, 2313 (1969).

    Article  CAS  Google Scholar 

  175. Kohlmuenzer, S., H. Tomczyk, and A. Saint-Fermin: Alkaloid Emiline, a New Otonecine Ester from Emilia flammea. Diss. Pharm. Pharmacol. 23, 419 (1971) [Chem. Abstr. 76, 96972 (1972)].

    CAS  Google Scholar 

  176. Kompis, I., and F. Santavy: Alkaloide des raukenblattrigen Kreuzkrauts (Senecio erucifolius L.). Collect. Czech. Chem. Commun. 27, 1413 (1962).

    CAS  Google Scholar 

  177. Konovalov, V. S., and G. P. Men’shikov: Alkaloids of Cacalia hastata. Zh. Obshch. Khim. 15, 328 (1945) [Chem. Abstr. 40, 3760 (1946)].

    Google Scholar 

  178. Kovach, J. S., M. M. Ames, G. Powis, C. G. Moertel, R. G. Hahn, and E. T. Creagan: Toxicity and Pharmacokinetics of a Pyrrolizidine Alkaloid, Indicine TV-oxide, in Humans. Cancer Res. 39, 4540 (1979).

    Google Scholar 

  179. Laing, M., and P. Sommerville: The Crystal and Molecular Structure of the Methiodide of Swazine, an Alkaloid from Senecio swaziensis Compton. Tetrahedron Lett. 1972, 5183.

    Google Scholar 

  180. Leander, K., and B. Luning: Studies on Orchidaceae Alkaloids. VII. Structure of a Glucosidic Alkaloid from Malaxis congesta comb. nov. (Rchb. f.). Tetrahedron Lett. 1967, 3477.

    Google Scholar 

  181. Lindstrom, B., and B. Luning: Studies on Orchidaceae Alkaloids. XIII. A New Alkaloid, Laburnine Acetate, from Vanda cristata Lindl. Acta Chem. Scand. 23, 3352 (1969).

    Article  CAS  Google Scholar 

  182. Lindstrom, B., and B. Luning: Orchidaceae Alkaloids. XXIII. Alkaloids of Liparis loeselii and Hammarbya paludosa. Acta Chem. Scand. 25, 895 (1971).

    Article  CAS  Google Scholar 

  183. Lindstrom, B., and B. Luning: Orchidaceae Alkaloids. XXXV. Alkaloids from Hammarbya paludosa and Liparis keitaoensis. Acta Chem. Scand. 26, 2963 (1972).

    Article  CAS  Google Scholar 

  184. Lindstrom, B., B. Luning, and K. Surala-Hansen: Orchidaceae Alkaloids. XXVI. New Glycosidic Alkaloid from Malaxis grandifolia. Acta Chem. Scand. 25, 1900 (1971).

    Article  CAS  Google Scholar 

  185. Locock, R. A., J. L. Beal, and R. W. Doskotch: Alkaloid Constituents of Eupatorium serotinum. Lloydia 29, 201 (1966).

    CAS  Google Scholar 

  186. Lu, S. T., C. N. Lin, T. S. Wu, and D. C. Shieh: Alkaloids of Senecio taiwanensis and S. morrisonensis. J. Chinese Chem. Soc. (Taipei) 19, 127 (1972) [Chem. Abstr. 77, 161936 (1972)].

    CAS  Google Scholar 

  187. Luning, B., and H. Tranker: Studies on Orchidaceae Alkaloids. X. A Pyrrolizidine Alkaloid from Chysis bractescens Lindl. Acta Chem. Scand. 22, 2324 (1968).

    CAS  Google Scholar 

  188. McGaw, B. A., and J. G. Woolley: The Biosynthesis of Angelic Acid in Cynoglossum officinale. Phytochemistry 18, 1647 (1979).

    Article  CAS  Google Scholar 

  189. Mahran, G., G. Wassel, B. El-Menshawi, G. El-Hossary, and A. Saeed: Pyrrolizidine Alkaloids of Crotalaria aegyptiaca and Crotalaria madurensis. Acta Pharm. Suec. 16, 333 (1979).

    CAS  Google Scholar 

  190. Man’ko, I. V.: Alkaloids of Cynoglossum officinale. Ukr. Khim. Zh. 25, 627 (1959) [Chem. Abstr. 54, 12494 (I960)].

    Google Scholar 

  191. Man’ko, I. V.: Alkaloids of Cynoglossum officinale and Echium vulgare and Standard Drug Preparation from C. officinale. Farm. Zh. (Kiev) 19, 22 (1964) [Chem. Abstr. 64, 4125 (1966)].

    Google Scholar 

  192. Man’ko, I. V., M. P. Korotkova, and N. M. Shevtsova: Alkaloids of Some Symphytum Species. Rast. Resur. 5, 508 (1969) [Chem. Abstr. 72, 87175 (1970)].

    Google Scholar 

  193. Man’ko, I. V., and B. K. Kotovskii: Asperumine, a New Alkaloid from the Plant Symphytum asperum, and its Structure. J. Gen. Chem. U.S.S.R. 40, 2506 (1970).

    Google Scholar 

  194. Man’ko, I. V., B. K. Kotovskii, and Y. G. Denisov: Level of Alkaloids in Symphytum officinale Dependent on the Phase of Plant Development. Rast Resur. 6, 409 (1970) [Chem. Abstr. 74, 61608 (1971)].

    Google Scholar 

  195. Man’ko, I. V., B. K. Kotovskii, and Y. G. Denisov: Accumulation of Alkaloids in Symphytum asperum Dependent on the Phase of Plant Development. Rast. Resur. 6, 582 (1970) [Chem. Abstr. 74, 84023 (1971)].

    Google Scholar 

  196. Man’ko, I. V., and L. G. Marchenko: Alkaloids from Paracynoglossum imeretinum. Khim. Prir. Soedin. 537 (1971) [Chem. Abstr. 75, 126598 (1971)].

    Google Scholar 

  197. Man’ko, I. V., and L. G. Marchenko: Pictumine, a New Alkaloid from Cynoglossum pictum. Khim. Prir. Soedin. 1972, 655 [Chem. Abstr. 78, 84611 (1973)].

    Google Scholar 

  198. Man’ko, I. V., Z. V. Mel’kumova, and U. F. Malysheva: Accumulation of Alkaloids in Different Organs of Symphytum caucasicum. Rast. Resur. 8, 538 (1972) [Chem. Abstr. 78, 82085 (1973)].

    Google Scholar 

  199. Man’ko, I. V., and P. N. Vasil’kov: Lappula intermedia Alkaloids. I. Trudy Leningrad, Khim. Farm. Inst. 26, 166 (1968) [Chem. Abstr. 73, 73849 (1970)].

    Google Scholar 

  200. Marquez, V. C.: Chromatographic Separation of the Alkaloids of Bulnesia retamo, Heliotropium arborescens, and Cestrum auriculatum. Biol. Soc. Quim. Peru 27,161 (1961) [Chem. Abstr. 61, 15032 (1964)].

    CAS  Google Scholar 

  201. Matsumoto, T., K. Fukui, and J. D. Edwards: Pyrrolizidine Alkaloids. Synthesis and Configuration of Fulvinic and Crispatic Acids. Chem. Lett. 1973, 283.

    Google Scholar 

  202. Matsumoto, T., T. Okabe, and K. Fukui: Senecio Alkaloids. The Synthesis and Configuration of (±)-Latifolic Acid. Chem. Lett. 1972, 29.

    Google Scholar 

  203. Matsumoto, T., T. Okabe, and K. Fukui: Pyrrolizidine Alkaloids. The Absolute Configuration of Latifolic Acid and its Stereoisomers. Chem. Lett. 1973, 773.

    Google Scholar 

  204. Matsumoto, T., M. Takahashi, and Y. Kashihara: Pyrrolizidine Alkaloids. The Synthesis and Absolute Configuration of All Stereoisomers of Monocrotalic Acid. Bull. Chem. Soc. Japan 52, 3329 (1979).

    Article  CAS  Google Scholar 

  205. Mattocks, A. R.: Minor Alkaloids of Heliotropium indicum L. J. Chem. Soc. (C) 1967, 329.

    Google Scholar 

  206. Mattocks, A. R.: Toxicity and Metabolism of Senecio Alkaloids. “Phytochemical Ecology” ed. J. B. HARBORNE, p. 179. London and New York: Academic Press. 1972.

    Google Scholar 

  207. Mattocks, A. R.: Pyrrolizidine Alkaloid Analogues. Part 2. Further Hydroxymethyl-1-methyl-3-pyrrolines (Synthanecines), and the Preparation and Esterification of Some Hydroxymethylpyrroles. J. Chem. Soc., Perkin Trans. 1 1978, 896; — The Distribution of Radioactivity in Rats given [3H]2,3-Bisacetoxymethyl-l-methylpyrrole, a Pneumotoxic Analogue of Labile Pyrrolizidine Alkaloid Metabolites. Toxicol. Lett. 3, 79 (1979).

    CAS  Google Scholar 

  208. Mattocks, A. R., R. Schoental, H. C. Crowley, and C.C.J. Culvenor: Indicine: the Major Alkaloid of Heliotropium indicum L. J. Chem. Soc. 1961, 5400.

    Google Scholar 

  209. Medvedeva, R. G., and Z. M. Zolotavina: Dynamics of Alkaloids in Heliotropium arguzioides. Trudy Inst. Bot., Akad. Nauk Kaz. SSR 29, 181 (1971) [Chem. Abstr. 76, 56583 (1972)].

    Google Scholar 

  210. Méndez, M. R., and I. Ribas: Papilionaceous Alkaloids. XXX. Alkaloids of Adenocarpus grandiflorus. Anales Real. Soc. Espan. Fis. Quim. (Madrid) 54B, 161 (1958) [Chem. Abstr. 52, 17313e (1958)].

    Google Scholar 

  211. Mody, N. V., R. S. Sawhney, and S. W. Pelletier: Carbon-13 Nuclear Magnetic Resonance Spectral Assignments for Pyrrolizidine Alkaloids. J. Natural Products 42, 417 (1979).

    Article  CAS  Google Scholar 

  212. Mohanraj, S., P. S. Subramanian, C. C. J. Culvenor, J. A. Edgar, J. L. Frahn, L. W. Smith, and P. A. Cockrum: Curassavine, an Alkaloid from Heliotropium curassavicum Linn, with a C8 Necic Acid Skeleton. J. Chem. Soc., Chem. Commun. 1978, 423; b) SUBRAMANIAN, P. S., S. MOHANRAJ, P. A. COCKRUM, C. C. J. CULVENOR, J. A. EDGAR, J. L. FRAHN, and L. W. SMITH: The Alkaloids of Heliotropium curassavicum. Aust. J. Chem. 33, 1357 (1980).

    Google Scholar 

  213. Molyneux, R. J., A. E. Johnson, J. N. Roitman, and M. E. Benson: Chemistry of Toxic Range Plants. Determination of Pyrrolizidine Alkaloid Content and Composition in Senecio species by Nuclear Magnetic Resonance Spectroscopy. J. Agrie. Food Chem. 27, 494 (1979).

    Article  CAS  Google Scholar 

  214. Montidome, M., and P. C. Ferreira: Alkaloids from the Genus Senecio. Rev. Fac. Farm. Bioquim. Univ. Sao Paulo 4, 175 (1966) [Chem. Abstr. 67, 79670 (1967)].

    Google Scholar 

  215. Neuner-Jehle, N., H. Nesvadba, and G. Spiteller: Anwendung der Massenspektrometrie zur Strukturaufklárung von Alkaloiden, 6. Mitt. Monatsh. Chem. 96, 321 (1965).

    Article  CAS  Google Scholar 

  216. Nghia, N. T., P. Sedmera, A. Klásek, A. Boeva, L. Drjanovska, L. Dolejs, and F. Santavy: Bulgarsenine and Retroisosenine, Alkaloids from Senecio nemorensis L., var. bulgaricus (Vel.) Stoj. et Stef. Collect. Czech. Chem. Commun. 41, 2952 (1976).

    Google Scholar 

  217. Nishikawa, K., M. Miyamura, and Y. Hirata: Chemotaxonomical Alkaloid Studies. Structures of Liparis Alkaloids. Tetrahedron 25, 2723 (1969).

    Article  CAS  Google Scholar 

  218. Nowacki, E., and R. U. Byerrum: A Study on the Biosynthesis of the Crotalaria Alkaloids. Life Sci. 1, 157 (1962).

    Article  CAS  Google Scholar 

  219. O’Kelly, J., and K. Sargeant: Supinine from the Seeds of Trichodesma zeylanicum, R.Br. J. Chem. Soc. 1961, 484.

    Google Scholar 

  220. Pais, M., F. X. Jarreau, P. Fouché, and R. Goutarel: Adulteration of Strophanthus gratus Seeds. Alafine, a New Alkaloid Isolated from the Seeds of Alafia species and Alafia multiflora (Apocynaceae). Ann. Pharm. Fr. 29, 57 (1971).

    CAS  Google Scholar 

  221. Panizo, F. M., and B. Rodriguez Gonzales: Chemical Study of Peninsular Senecios. III. Alkaloids of S. durieui and S. auricola. Anales de Quim. 70, 1043 (1974).

    Google Scholar 

  222. Pass, D. A., G. G. Hogg, R. G. Russell, J. A. Edgar, I. M. Tence, and L. Rikard-Bell: Poisoning of Chickens and Ducks by Pyrrolizidine Alkaloids of Heliotropium europaeum. Aust. Vet. J. 55, 284 (1979).

    CAS  Google Scholar 

  223. Pedersen, E.: Minor Pyrrolizidine Alkaloids from Cynoglossum officinale. Dansk. Tidsskr. Farm. 44, 287 (1970) [Chem. Abstr. 74, 72780 (1971)].

    Google Scholar 

  224. Pedersen, E.: Pyrrolizidine Alkaloids in Danish Species of the Family Boraginaceae. Arch. Pharm. Chem. Sci. Ed. 3, 55 (1975).

    CAS  Google Scholar 

  225. Pedersen, E.: Echinatine and Supinine: Pyrrolizidine Alkaloids from Eupatorium cannabinum. Phytochemistry 14, 2086 (1975).

    Article  CAS  Google Scholar 

  226. Pedersen, E., and E. Larsen: Mass Spectrometry of Some Pyrrolizidine Alkaloids. Org. Mass Spectrom. 4, 249 (1970).

    Article  CAS  Google Scholar 

  227. Pérez-Salazar, A.: Crystal Structure of the Alkaloid Jacobine by X-Ray Diffraction. Anales de Quim. 74, 196 (1978); PÉREZ-SALAZAR, A., F. H. CANO, and S. GARCÍA- BLANCO: The Alkaloid Jacobine (C18H25NO6): A Refinement. Cryst. Struct. Commun. 1978, 105.

    Google Scholar 

  228. Pérez-Salazar, A., F. H. Cano, J. Fayos, S. Martínez-Carrera, and S. García-Blanco: The Alkaloid Otosenine. Evidence of a Weak —N:·· C—O Intra-Annular Bond. Acta Crystallogr., Sect. B 33, 3525 (1977).

    Article  Google Scholar 

  229. Pilbeam, D. J., R. M. Polhill, and E. A. Bell: Free Amino Acids and Alkaloids of South American, Asian and Australian Crotalaria species. Bot. J. Linn. Soc. 79, 259 (1979).

    Article  CAS  Google Scholar 

  230. Pimenov, M. G., L. D. Yakhontova, D. Pakalne, and L. A. Sapunova: Intraspecific Chemical Differentiation of Adenostyles rhombifolia in Northern Caucasus. Rastit. Resur. 11, 72 (1975) [Chem. Abstr. 82, 152218 (1975)].

    Google Scholar 

  231. Pizzorno, M. T., and S. M. Albonico: Cycloaddition to Propargylic Aldehyde: a Single Step Synthesis of a Pheromone. Chem. Ind. ( London ) 1978, 349.

    Google Scholar 

  232. Plescia, S., G. Daidone, and V. Sprio: Compositae. Senecio nebrodensis L. var sicula. Phytochemistry 15, 2026 (1976).

    Google Scholar 

  233. Porter, L. A., and T. A. Geissman: Angularine, a New Pyrrolizidine Alkaloid from Senecio angulatus L. J. Org. Chem. 27, 4132 (1962).

    Article  CAS  Google Scholar 

  234. Puri, S. C., R. S. Sawhney, and C. K. Atal: Genus Crotalaria. XIII. Crobarbatine, a New Pyrrolizidine Alkaloid of C. barbata. Experientia 29, 390 (1973).

    Article  CAS  Google Scholar 

  235. Puri, S. C., R. S. Sawhney, and C. K. Atal: Genus Crotalaria. XVI. Pyrrolizidine Alkaloids of C. leiloba Bartl., C. stipularia Desv. and C. tetragona Roxb. J. Indian Chem. Soc. 51, 628 (1974).

    CAS  Google Scholar 

  236. Qualls, C. W., and H. J. Segall: Rapid Isolation and Identification of Pyrrolizidine Alkaloids (Senecio vulgaris) by Use of High-Performance Liquid Chromatography. J. Chromatogr. 150, 202 (1978).

    Article  CAS  Google Scholar 

  237. Rajagopalan, T. R., and V. Batra: Monocrotalinine, a New Alkaloid from Crotalaria grahamiana. Indian J. Chem., Sect. B 15, 455 (1977).

    Google Scholar 

  238. Rajagopalan, T. R., and V. Batra: Alkaloidal Constituents of Heliotropium curassavicum. Indian J. Chem., Sect. B 15, 494 (1978).

    Google Scholar 

  239. Rao, P. G., R. S. Sawhney, and C. K. Atal: Genus Crotalaria: Part XXIII - Croburhine, a Novel Pyrrolizidine Alkaloid from Crotalaria burhia Buch.-Ham. Indian J. Chem. 13, 835 (1975).

    CAS  Google Scholar 

  240. Rao, P. G., R. S. Sawhney, and C. K. Atal: Genus Crotalaria XXL Isocromadurine, a Novel Pyrrolizidine Alkaloid of C. madurensis R. Wight. Experientia 31, 878 (1975).

    Article  CAS  Google Scholar 

  241. Rao, P. G., R. S. Sawhney, and C. K. Atal: Genus Crotalaria: Part XX — Cromadurine, a New Pyrrolizidine Alkaloid from Crotalaria madurensis R. Wight. Indian J. Chem. 13, 870 (1975).

    CAS  Google Scholar 

  242. Ribas, I., and J. M. Alonso de Lama: Alkaloids of the Papilionaceae. XII. Alkaloids of Adenocarpus hispanicus from the Guadarrama Mountains, Madrid. Farmacognosia (Madrid) 13, 367 (1953).

    CAS  Google Scholar 

  243. Ribas, I., and J. J. Barreiro: Alkaloids of the Papilionaceae. XVIII. Alkaloids of Adenocarpus decorticans. Anales Asoc. Quim. Arg. 41, 27 (1953) [Chem. Abstr. 48, 3987i (1954)].

    Google Scholar 

  244. Robertson, K. A., J. L. Seymour, M.-T. Hsia, and J. R. Allen: Covalent Interaction of Dehydroretronecine, a Carcinogenic Metabolite of the Pyrrolizidine Alkaloid, Monocrotaline, with Cysteine and Glutathione. Cancer Res. 37, 3141 (1977).

    CAS  Google Scholar 

  245. Robins, D. J.: Advances in Pyrrolizidine Chemistry. Adv. Heterocyclic Chem. 24, 247 (1969).

    Article  Google Scholar 

  246. Robins, D. J.: Senecioneae — Chemical Review in The Biology and Chemistry of the Compositae (Heywood, V. H., J. B. Harborne, and B. L. Turner, eds.), p. 831. London and New York: Academic Press. 1977.

    Google Scholar 

  247. Robins, D. J.: Pyrrolizidine Alkaloids in The Alkaloids (Grundon, M. F., ed.). The Chemical Society, London, 1978–1981, Vols. 8–11; see also earlier volumes: SAXTON, J. E.: 1971–1975, Vols. 1–5; CROUT, D. H. G.: 1976–1977, Vols. 6–7.

    Google Scholar 

  248. Robins, D. J., N. M. Bale, and D. H. G. Crout: Pyrrolizidine Alkaloids. Biosynthesis of Monocrotalic Acid, the Necic Acid Component of Monocrotaline. J. Chem. Soc., Perkin Trans. I 1974, 2082.

    Google Scholar 

  249. Robins, D. J., and D. H. G. Crout: Pyrrolizidine Alkaloids. The Stereochemistry of Monocrotalic and Trichodesmic Acids. J. Chem. Soc. (C) 1969, 1386.

    Google Scholar 

  250. Robins, D. J., and D. H. G. Crout: Pyrrolizidine Alkaloids. The Absolute Configuration at C-2 in Monocrotalic Acid. J. Chem. Soc. (C) 1970, 1334.

    Google Scholar 

  251. Robins, D. J., and S. Sakdarat: Synthesis of the 8p-Pyrrolizidine Bases (+)-Isoretronecanol, (+)-Laburnine, and (+)-Supinidine. J. Chem. Soc., Chem. Commun. 1979, 1181.

    Google Scholar 

  252. Robins, D. J., and S. Sakdarat: Synthesis of the Pyrrolizidine Base, (+)-Supinidine. J. Chem. Soc., Perkin Trans. I 1979, 1734.

    Google Scholar 

  253. Robins, D. J., and S. Sakdarat: Pyrrolizidine Alkaloids. Synthesis of 13,13-Dimethyl-l,2-didehydrocrotalanine. J. Chem. Soc., Chem. Commun. 1980, 282.

    Google Scholar 

  254. Robins, D. J., and S. Sakdarat: Synthesis of Optically Active Pyrrolizidine Bases. J. Chem. Soc., Perkin Trans. I 1981, 909.

    Google Scholar 

  255. Robins, D. J., and J. R. Sweeney: Pyrrolizidine Alkaloids. Evidence for the Involvement of Spermidine and Spermine in the Biosynthesis of Retronecine. J. Chem. Soc., Chem. Commun. 1979, 120.

    Google Scholar 

  256. Roder, E., and H. Wiedenfeld: Isolierung und Strukturaufklârung des Alkaloids Fuchsisenecionin aus Senecio fuchsii. Phytochemistry 16, 1462 (1977).

    Article  Google Scholar 

  257. Roder, E., H. Wiedenfeld, and M. Frisse: Pyrrolizidinalkaloide aus Senecio doronicum. Phytochemistry 19, 1275 (1980).

    Article  Google Scholar 

  258. Roder, E., H. Wiedenfeld, and U. Pastewka: Pyrrolizidinalkaloide aus Senecio vernalis. Planta Med. 37, 131 (1979).

    Article  Google Scholar 

  259. Rodriguez, F. D., and A. G. Gonzalez: Canary Plant Alkaloids. XI. Secondary Alkaloids of Senecio kleinia. Farm. Nueva 36, 803 (1971) [Chem. Abstr. 76, 83573 (1972)].

    Google Scholar 

  260. Rodriguez, F. D., and A. G. Gonzalez: Canary Plant Alkaloids. XII. Alkaloids of Senecio antieuphorbium. Farm. Nueva 36, 810 (1971) [Chem. Abstr. 76, 83572 (1972)].

    Google Scholar 

  261. Rothschild, M., R. T. Aplin, P. A. Cockrum, J. A. Edgar, P. Fairweather, and R. Lees: Pyrrolizidine Alkaloids in Arctiid Moths (Lep.) with a Discussion on Host Plant Relationships and the Role of these Secondary Plant Substances in the Arctiidae. Biol. J. Linn. Soc. 12, 305 (1979).

    Article  Google Scholar 

  262. Rouffiac, R., and J. Parello: Étude Chimique des Alkaloides du Phyllanthus niruri L. (Euphorbiaceés). Présence de l’Antipode Optique de la Norsécurinine. Plant. Med. Phytother. 3, 220 (1969).

    CAS  Google Scholar 

  263. Sadritinov, F. S.: Pharmacology of Alkaloids of 1-Methylpyrrolizidine and their Derivatives. Farmacol. Prirod. Soedin. Tashkent 1979, 29 [Chem. Abstr. 93, 18681 (1980)].

    Google Scholar 

  264. Saito, S., T. Tanaka, K. Kotera, H. Nakai, N. Sugimoto, Z. Horii, M. Ikeda, and Y. Tamura: Structures of Norsecurinine and Dihydronorsecurinine. Chem. Pharm. Bull. (Japan) 13, 786 (1965).

    Article  CAS  Google Scholar 

  265. Sasaki, K., and Y. Hirata: The Structures of Two New Zwitterionic Alkaloids from Anodendron affine Druce. Tetrahedron Lett. 1969, 4065; The Alkaloids of Anodendron affine Druce. Tetrahedron 26, 2119 (1970).

    CAS  Google Scholar 

  266. Sawhney, R. S., and C. K. Atal: Genus Crotalaria. X. Methylethers of Supinidine and Heliotridine from C. medicaginea Lam. J. Indian Chem. Soc. 47, 741 (1970).

    CAS  Google Scholar 

  267. Sawhney, R. S., and C. K. Atal: Genus Crotalaria XII. Identity of Crotalaburnine as Anacrotine. J. Indian Chem. Soc. 48, 887 (1971).

    CAS  Google Scholar 

  268. Sawhney, R. S., and C. K. Atal: Croalbidine, a New Pyrrolizidine Alkaloid from Crotalaria albida Heyne ex Roth. Indian J. Chem. 11, 88 (1973).

    CAS  Google Scholar 

  269. Sawhney, R. S., C. K. Atal, C. C. J. Culvenor, and L. W. Smith: Genus Crotalaria. XVII. The Stereochemistry of Croalbinecine. Aust. J. Chem. 27, 1805 (1974).

    Article  CAS  Google Scholar 

  270. Sawhney, R. S., R. N. Girotra, C. K. Atal, C. C. J. Culvenor, and L. W. Smith: Phytochemical Studies on Genus Crotalaria: Part VII - Major Alkaloids of C. mucronata, C. brevifolia and C. laburnifolia. Indian J. Chem. 5, 655 (1967).

    CAS  Google Scholar 

  271. Schoental, R.: Pancreatic Islet-Cell and other Tumors in Rats Given Heliotrine, a Monoester Pyrrolizidine Alkaloid, and Nicotinamide. Cancer Res. 35, 2020 (1975); — Biochemical Basis of Liver Necrosis Caused by Pyrrolizidine Alkaloids and other Hepatotoxins. Biochem. Soc. Trans. 3, 292 (1975).

    CAS  Google Scholar 

  272. Schoental, R.: Alkylation of Coenzymes and the Acute Effects of Alkylating Hepatotoxins. FEBS Lett. 61, 111 (1976).

    Article  CAS  Google Scholar 

  273. Sedmera, P., A. Klasek, A. M. Duffield, and F. Santavy: Pyrrolizidine Alkaloids. XIX. Structure of the Alkaloid Erucifoline. Collect. Czech. Chem. Commun. 37, 4112 (1972).

    CAS  Google Scholar 

  274. Segall, H. J.: Pyrrolizidine Alkaloids from Senecio jacobaea. Toxicol. Lett. 1, 279 (1978).

    Article  CAS  Google Scholar 

  275. Segall, H. J.: Reverse Phase Isolation of Pyrrolizidine Alkaloids. J. Liq. Chromatogr. 2,429 (1979); — Preparative Isolation of Pyrrolizidine Alkaloids Derived from Senecio vulgaris. J. Liq. Chromatogr. 2, 1319 (1979).

    CAS  Google Scholar 

  276. Segall, H. J., and R. J. Molyneux: Identification of Pyrrolizidine Alkaloids (Senecio longilobus). Res. Commun. Chem. Pathol. Pharmacol. 19, 545 (1978).

    CAS  Google Scholar 

  277. Sethi, M. L., and C. K. Atal: Phytochemical Studies on the Genus Crotalaria. Indian J. Pharm. 25, 159 (1963) [Chem. Abstr. 59, 4206 (1963)].

    Google Scholar 

  278. Sheveleva, G. P., N. V. Plekhanova, and D. S. Sargazakov: Alkaloids from Plants of the Borage, Thistle, and Lily Families of Kirghiz Flora. Mater. Nauch. Konf., Posvyashch. 100-Sto-Letiyu Period. Zakona D. I. Mendeleeva, 1969, 107 [Chem. Abstr. 76, 23067 (1972)].

    Google Scholar 

  279. Siddiqi, M. A., K. A. Suri, O. P. Suri, and C. K. Atal: Genus Crotalaria: Part XXXIV — Cronaburmine, a New Pyrrolizidine Alkaloid from Crotalaria nana Burm. Indian J. Chem. Sect. B 16, 1132 (1978).

    Google Scholar 

  280. Siddiqi, M. A., K. A. Suri, O. P. Suri, and C. K. Atal: A New Pyrrolizidine Alkaloid from Caccinia glauca. Phytochemistry 17, 2049 (1978).

    Article  CAS  Google Scholar 

  281. Siddiqi, M. A., K. A. Suri, O. P. Suri, and C. K. Atal: Novel Pyrrolizidine Alkaloid from Crotalaria nana. Phytochemistry 17, 2143 (1978).

    Article  CAS  Google Scholar 

  282. Siddiqi, M. A., K. A. Suri, O. P. Suri, and C. K. Atal: New Pyrrolizidine Alkaloids from Crotalaria candicans. Phytochemistry 18, 1413 (1979).

    Article  CAS  Google Scholar 

  283. Soto, J. P.: Decorticasine. Acta Cient. Compostelana 6, 37 (1969) [Chem. Abstr. 73, 109943 (1970)].

    Google Scholar 

  284. Stermitz, F. R., and J. A. Adamovics: Alkaloids of Caltha leptosepala and Caltha biflora. Phytochemistry 16, 500 (1977).

    Article  CAS  Google Scholar 

  285. Stermitz, F. R., and T. R. Suess: Pyrrolizidine Alkaloids in Castilleja rhexifolia (Scrophulariaceae). Phytochemistry 17, 2142 (1978).

    Article  CAS  Google Scholar 

  286. Stillman, A. E., R. Huxtable, P. Consroe, P. Kohnen, and S. Smith: Hepatic Venoocclusive Disease Due to Pyrrolizidine (Senecio) Poisoning in Arizona. Gastroenterology 73, 349 (1977).

    CAS  Google Scholar 

  287. Stoeckli-Evans, H.: Monocrotaline. A Pyrrolizine Alkaloid. Acta Crystallogr., Sect. B 35, 231 (1979).

    Article  Google Scholar 

  288. Stoeckli-Evans, H.: Bulgarsenine (R: R)-(+)-bitartrate: a Pyrrolizidine Alkaloid. Acta Crystallogr. Sect. B 36, 3150 (1980).

    Article  Google Scholar 

  289. Stoeckli-Evans, H., and D. H. G. Crout: The Crystal Structure of Axillarine Hydrobromide Ethanol Solvate: A Pyrrolizidine Alkaloid. Helv. Chim. Acta 59, 2168 (1976).

    Article  CAS  Google Scholar 

  290. Subramanian, S. S., S. Nagarajan, and M. N. Ghosh: The Major Alkaloid of Crotalaria paniculata Seeds. Indian J. Pharm. 30, 153 (1968).

    CAS  Google Scholar 

  291. Suri, K. A., R. S. Sawhney, and C. K. Atal: Pyrrolizidine Alkaloids from Cynoglossum lanceolatum, C. glochidiatum, and Lindelofia angustifolia. Indian J. Pharm. 37, 69 (1975).

    CAS  Google Scholar 

  292. Suri, K. A., R. S. Sawhney, and C. K. Atal: Genus Crotalaria: Part XXV — Secopyrrolizidine Alkaloids of Crotalaria walkeri Arnott. Indian J. Chem., Sect. B 14, 471 (1976).

    Google Scholar 

  293. Suri, K. A., O. P. Suri, K. L. Dhar, and C. K. Atal: Chemical Components of Lapulla glochidiata and Crotalaria anagyroides. Indian J. Chem. Sect. B 16, 78 (1978).

    Google Scholar 

  294. Suri, O. P., R. S. Jamwal, K. A. Suri, and C. K. Atal: Ehretinine, a novel pyrrolizidine alkaloid from Ehretia aspera. Phytochemistry 19, 1273 (1980).

    Article  CAS  Google Scholar 

  295. Suri, O. P., R. S. Sawhney, and C. K. Atal: Pyrrolizidine Alkaloids from Heliotropium eichwaldii and Lindelofia spectabilis. Indian J. Chem. 13, 505 (1975).

    CAS  Google Scholar 

  296. Suri, O. P., R. S. Sawhney, M. S. Bhatia, and C. K. Atal: Novel Secopyrrolizidine Alkaloids from Crotalaria verrucosa. Phytochemistry 15, 1061 (1976).

    Article  CAS  Google Scholar 

  297. Sussman, J. L., and S. J. Wodak: The Crystal Structure of Fulvine: A Pyrrolizidine Alkaloid. Acta Crystallogr. Sect. B 29, 2918 (1973).

    Article  CAS  Google Scholar 

  298. Tandon, H. D., B. N. Tandon, R. Tandon, and N. C. Nayak: A Pathological Study of the Liver in an Epidemic Outbreak of Veno-occlusive Disease. Indian J. Med. Res. 65, 679 (1977).

    CAS  Google Scholar 

  299. Tandon, H. D., B. M. Tandon, and A. R. Mattocks: An Epidemic of Veno-occlusive Disease of the Liver in Afghanistan. Amer. J. Gastroenterol. 70, 607 (1978).

    CAS  Google Scholar 

  300. Tanino, H., S. Inoue, K. Nishikawa, and Y. Hirata: Syntheses of Tetraacetyl Malaxin and Kuramerine. Tetrahedron 25, 3033 (1969).

    Article  CAS  Google Scholar 

  301. Tashkhodzhaev, B., M. V. Telezhenetskaya, and S. Yu. Yunusov: Crystal and Molecular Structure of the Macrocyclic Pyrrolizidine Alkaloid Incanine. Khim. Prir. Soedin. 1979, 363 [Chem. Abstr. 92, 111199 (1980)].

    Google Scholar 

  302. Tashkhodzhaev, B., M. R. Yagudaev, and S. Yu. Yunusov: Crystal and Molecular Structure of the Macrocyclic Pyrrolizidine Alkaloid Trichodesmine. Khim. Prir. Soedin. 1979, 368 [Chem. Abstr. 92, 111194 (1980)].

    Google Scholar 

  303. Tittel, G., H. Hinz, and H. Wagner: Quantitative Bestimmung der Pyrrolizidin- Alkaloide in Symphyti Radix durch HPLC. Planta Med. 37, 1 (1979).

    Article  CAS  Google Scholar 

  304. Tomczyk, H., and S. Kohlmuenzer; Isolation of a New Pyrrolizidine Alkaloid from Emilia flammea (Compositae). Herba Pol. 17, 226 (1971) [Chem. Abstr. 77, 19848 (1972)].

    CAS  Google Scholar 

  305. Tsuda, Y., and L. Marion: The Alkaloids of Eupatorium maculatum L. Can. J. Chem. 41, 1919 (1963).

    Article  CAS  Google Scholar 

  306. Tufariello, J. F., and G. E. Lee: Functionalized Nitrones. A Highly Stereoselective and Regioselective Synthesis of dl-Retronecine. J. Am. Chem. Soc. 102, 373 (1980).

    Article  CAS  Google Scholar 

  307. Tufariello, J. F., and G. E. Lee: Synthesis in the Pyrrolizidine Class of Alkaloids. dl-Supinidine. J. Org. Chem. 40, 3866 (1975).

    Article  CAS  Google Scholar 

  308. Ulubelen, A., and S. Doganca: Anadoline, a New Senecio alkaloid from Symphytum Orientale. Tetrahedron Lett. 1970, 2583.

    Google Scholar 

  309. Ulubelen, A., and S. Doganca: Boraginaceae. Alkaloidal and Other Constituents of Symphytum Orientale. Phytochemistry 10, 441 (1971).

    Article  CAS  Google Scholar 

  310. Ulubelen, A., and F. Öcal: Alkaloids and other Compounds of Symphytum tuberosum. Phytochemistry 16, 499 (1977).

    Article  CAS  Google Scholar 

  311. Valverde, S., and F. M. Panizo: Chemical Study of the Peninsula Senecio. II. Basic Components of Senecio tournefortii. Anales de Quirn. 67, 425 (1971) [Chem. Abstr. 75, 110484 (1971)].

    Google Scholar 

  312. Warren, F. L.: The Pyrrolizidine Alkaloids. I. Fortschr. Chem. org. Naturstoffe 12, 198 (1955).

    CAS  Google Scholar 

  313. Warren, F. L.: The Pyrrolizidine Alkaloids. II. Fortschr. Chem. org. Naturstoffe 24, 329 (1966).

    CAS  Google Scholar 

  314. Warren, F. L.: Senecio Alkaloids. IN: The Alkaloids (R. H. F. , ed.), Vol. XII. New York: Academic Press. 1970.

    Google Scholar 

  315. Wang, S.-T.: The Crystal Structure of Monocrotaline. K’o Hsueh T’ung Pao 23, 670 (1978) [Chem. Abstr. 90, 187191 (1979)].

    Google Scholar 

  316. White, E. P.: Alkaloids of Some Herbaceous Senecio Species in New Zealand. New Zealand J. Sci. 12, 165 (1969).

    CAS  Google Scholar 

  317. White, E. P., and F. L. Warren: The Senecio Alkaloids. Sarracine TV-oxide and Sarracine from Senecio sylvaticus L. Anales de Quim. 68, 723 (1972).

    Google Scholar 

  318. Wiedenfeld, H., and E. Roder: Das Pyrrolizidinalkaloid Senecionin aus Seneciofuchsii. Phytochemistry 18, 1083 (1979).

    Article  CAS  Google Scholar 

  319. Willette, R. E., and L. V. Cammarato: Phytochemical Study of Connecticut. I. Isolation of Monocrotaline from Crotalaria sagittalis Fruit. J. Pharm. Sci. 61, 122 (1972).

    CAS  Google Scholar 

  320. Wright, W. G., and F. L. Warren: Rhizophoraceae Alkaloids. Part I. Four Sulphur-containing Bases from Cassipourea spp. J. Chem. Soc. (C) 1967, 283.

    Google Scholar 

  321. Wunderlich, J. A.: The Molecular Structures of Retusamine, Otosenine, Renardine and Onetine. Chem. Ind. (London) 1962,2089; — The Crystal Structure of Retusamine, α-Bromo-D-camphor-irajw-Tt-sulphonate Monohydrate. Acta Crystallogr. 23, 846 (1967).

    CAS  Google Scholar 

  322. Yakhontova, L. D., M. G. Pimenov, and L. A. Sapunova: Alkaloids of Adenostyles alliariae. Khim. Prir. Soedin. 1976, 122 [Chem. Abstr. 85, 59575 (1976)].

    Google Scholar 

  323. Yamada, K., H. Tatematsu, M. Suzuki, Y. Hirata, M. Haga, and I. Hirono: Isolation and the Structures of Two New Alkaloids, Petasitenine and Neopetasitenine from Petasites japonicus Maxim. Chem. Lett. 1976, 461; YAMADA, K., H. TATEMATSU, Y. HIRATA, M. HAGA, and I. HIRONO: Stereochemistry of Petasitenine, the Carcinogenic Alkaloid from Petasites japonicus Maxim, and Transformation of Petasitenine to Senkirkine. Chem. Lett. 1976, 1123.

    Google Scholar 

  324. Yamada, K., H. Tatematsu, R. Unno, and Y. Hirata: Petasinine and Petasinoside, Two Minor Alkaloids Possessing a New Necine Isolated from Petasites japonicus Maxim. Tetrahedron Lett. 1978, 4543.

    Google Scholar 

  325. Yates, S. G., and H. L. Tookey: Festucine, an Alkaloid from Tall Fescue (Festuca arundinaceae Schreb.): Chemistry of the Functional Groups. Aust. J. Chem. 18, 53 (1965).

    Article  CAS  Google Scholar 

  326. Zalkow, L. H., L. Gelbaum, and E. Keinan: Isolation of the Pyrrolizidine Alkaloid Europine N-oxide from Heliotropium maris-mortui and H. rotundifolium. Phytochemistry 17, 172 (1978).

    Article  CAS  Google Scholar 

  327. Zalkow, L. H., S. Bonetti, L. Gelbaum, M. M. Gordon, B. B. Patil, A. Shani, and D. van Derveer: Pyrrolizidine Alkaloids from Middle Eastern Plants. J. Natural Prod. 42, 603 (1979).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Glasgow, Scotland

    D. J. Robins

Authors
  1. D. J. Robins
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Chemistry, The Florida State University, Tallahassee, Florida, USA

    W. Herz (Professor of Chemistry) (Professor of Chemistry)

  2. Biologisches Institut II, Lehrstuhl für Biochemie der Pflanzen, Albert-Ludwigs-Universität, Freiburg i. Br., Federal Republic of Germany

    H. Grisebach

  3. Chemistry Department, The University, Glasgow, Scotland

    G. W. Kirby Sc. D. (Regius Professor of Chemistry) (Regius Professor of Chemistry)

Rights and permissions

Reprints and permissions

Copyright information

© 1982 Springer-Verlag/Wien

About this chapter

Cite this chapter

Robins, D.J. (1982). The Pyrrolizidine Alkaloids. In: Herz, W., Grisebach, H., Kirby, G.W. (eds) Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 41. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8656-5_4

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-8656-5_4

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-8658-9

  • Online ISBN: 978-3-7091-8656-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation