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Alkaloids from Narcissus angustifolius subsp. transcarpathicus (Amaryllidaceae).

Josep Labraña1, Alex King'ori Machocho, Vladimir Kricsfalusy

  • 1Departament de Productes Naturals, Facultat de Farmàcia, Universitat de Barcelona, Avda. Diagonal 643, E-08028 Barcelona, Spain.

Phytochemistry
|August 2, 2002
PubMed
Summary

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Researchers isolated seven alkaloids from Narcissus angustifolius bulbs, including a new compound, nangustine. Nangustine and pancracine showed in vitro activity against parasitic protozoa like Trypanosoma and Plasmodium.

Area of Science:

  • Phytochemistry
  • Natural Products Chemistry
  • Medicinal Chemistry

Background:

  • The Amaryllidaceae family is a rich source of alkaloids with diverse biological activities.
  • Narcissus species, particularly Narcissus angustifolius, are known to contain various alkaloids.
  • Understanding the chemical constituents of specific subspecies is crucial for discovering novel compounds.

Purpose of the Study:

  • To isolate and characterize alkaloids from fresh bulbs of Narcissus angustifolius subsp. transcarpathicus.
  • To elucidate the structure and stereochemistry of a newly discovered alkaloid, nangustine.
  • To evaluate the in vitro antiparasitic activity of isolated alkaloids against key protozoan pathogens.

Main Methods:

  • Alkaloid isolation from plant material using chromatographic techniques.

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  • Structure elucidation through comprehensive physical and spectroscopic methods (NMR, MS, etc.).
  • In vitro antiparasitic assays against Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Leishmania donovani, and Plasmodium falciparum.

    • Main Results:

    • Seven alkaloids were successfully isolated from Narcissus angustifolius subsp. transcarpathicus bulbs.
    • Nangustine, a novel 5,11-methanomorphanthridine alkaloid with C-3/C-4 substitution, was identified and characterized.
    • The structure and stereochemistry of nangustine and other known alkaloids were confirmed.
    • Spectroscopic data for pancracine were completed.
    • Both nangustine and pancracine demonstrated in vitro activity against the tested parasitic protozoa.

    Conclusions:

    • The study successfully identified novel and known alkaloids from Narcissus angustifolius subsp. transcarpathicus.
    • Nangustine represents a new structural class of 5,11-methanomorphanthridine alkaloids.
    • Nangustine and pancracine exhibit promising in vitro antiparasitic potential, warranting further investigation.