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Diterpenoid alkaloids from Delphinium davisii

A Ulubelen1, H K Desai, S K Srivastava

  • 1Faculty of Pharmacy, University of Istanbul, Turkey.

Journal of Natural Products
|April 1, 1996
PubMed
Summary

Three novel diterpenoid alkaloids, davisinol, 18-benzoyldavisinol, and Davisin, were isolated from Delphinium davisii Munz. Their structures were determined, along with new NMR assignments for related alkaloids, advancing natural product chemistry.

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Area of Science:

  • Natural Product Chemistry
  • Organic Chemistry
  • Pharmacognosy

Background:

  • Delphinium species are known sources of biologically active alkaloids.
  • Diterpenoid alkaloids, particularly hetisane-type, exhibit diverse pharmacological properties.
  • The chemical investigation of Delphinium davisii Munz. is crucial for discovering novel compounds.

Purpose of the Study:

  • To isolate and characterize new hetisane-type diterpenoid alkaloids from Delphinium davisii Munz.
  • To elucidate the structures of these novel compounds using comprehensive spectroscopic methods.
  • To provide accurate spectroscopic assignments for known related alkaloids.

Main Methods:

  • Isolation of alkaloids using chromatographic techniques.
  • Structure elucidation via detailed 1H and 13C Nuclear Magnetic Resonance (NMR) spectroscopy.

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  • Mass spectrometry for molecular weight determination.

    • Main Results:

    • Three new hetisane-type diterpenoid alkaloids: davisinol (6), 18-benzoyldavisinol (7), and Davisin (9) were identified.
    • Structures of these new compounds were established through extensive spectroscopic analysis.
    • Accurate 1H and 13C-NMR assignments were made for kobusine (8) and karakoline (5).
    • Known alkaloids, including 14-acetylperegrine (4), 6-deacetylperegrine (3), karakoline (5), hetisine, and hetisinone, were also isolated.

    Conclusions:

    • The study successfully identified and characterized novel diterpenoid alkaloids from Delphinium davisii Munz.
    • The findings expand the known chemical diversity of Delphinium alkaloids.
    • This research provides valuable spectroscopic data for future studies on related natural products.