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1H and 13C NMR spectral analysis of some necines of toxic pyrrolizidine alkaloids

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Summary

The total assignment of the 1H and 13C NMR spectra of the necines of toxic pyrrolizidine alkaloids (retronecine, heliotridine, crotanecine, otonecine), their hydrochlorides and their N-oxides has been performed. The characteristic chemical shift differences between retronecine and heliotridine, as well as the protonation and N-oxidation shift effects in NMR studies of necines at the corresponding position are proposed to be an additional assignment aid. The assignment of the spectra was achieved by the concerted use of 2D correlation spectroscopy.

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References

  1. Bull LB, Culvenor CCJ, Dick AT (1968) The pyrrolizidine alkaloids, North-Holland, Amsterdam, pp 2–19

    Google Scholar 

  2. Roeder E (1990) Phytochemistry 29:11–29

    Google Scholar 

  3. Roeder E (1991) In: Rizk AM (ed), Naturally occurring pyrrolizidine alkaloids, CRC Press, Boca Raton Ann Arbor Boston, pp 111–146

    Google Scholar 

  4. Jackman JM, Sternhell S (1967) Applications of nuclear magnetic resonance spectroscopy in organic chemistry, 2nd ed, Pergamon Press, London, p 180

    Google Scholar 

  5. Horsley W, Sternlicht H (1968) J Am Chem Soc 90:3738

    Google Scholar 

  6. Horsley W, Sternlicht H (1970) J Am Chem Soc 92:680

    Google Scholar 

  7. Morishima I, Yoshikawa K, Okada K, Yonezawa T, Goto K (1973) J Am Chem Soc 95:165

    Google Scholar 

  8. Roeder E, Liu K (1991) Phytochemistry 30:1734–1737

    Google Scholar 

  9. Wunderlich JA (1962) Chem Ind (London) p 2089

  10. Bull LB, Culvenor CCJ, Dick AT (1968) The pyrrolizidine alkaloids, North-Holland, Amsterdam, p 84

    Google Scholar 

  11. Culvenor CCJ, O'Donovan GM, Smith LW (1967) Aust J Chem 20:801–804

    Google Scholar 

  12. Ravi S, Lakshmanan AJ, Herz W (1990) Phytochemistry 29:361–364

    Google Scholar 

  13. Atal CK, Culvenor CCJ, Sawhney RS, Smith LW (1967) Aust J Chem 20:805–808

    Google Scholar 

  14. Mattocks AR (1967) J Chromatogr 27:505–508

    Google Scholar 

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Authors and Affiliations

  1. Pharmazeutisches Institut der Universität Bonn, An der Immenburg 4, W-5300, Bonn 1, Federal Republic of Germany

    E. Röder, K. Liu & T. Bourauel

Authors
  1. E. Röder
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  2. K. Liu
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  3. T. Bourauel
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Dedicated to Prof. Dr. Dr. Dres. h. c. Herbert Oelschläger, Frankfurt/Main, on the occasion of his 70th birthday

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Röder, E., Liu, K. & Bourauel, T. 1H and 13C NMR spectral analysis of some necines of toxic pyrrolizidine alkaloids. Fresenius J Anal Chem 342, 719–722 (1992). https://doi.org/10.1007/BF00321863

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  • DOI: https://doi.org/10.1007/BF00321863

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