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Alkaloids from Nerine filifolia.

Jerald J Nair1, William E Campbell, Reto Brun

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

Phytochemistry
|February 1, 2005
PubMed
Summary

Three novel alkaloids, including N-demethylbelladine and filifoline, were isolated from Nerine filifolia bulbs. Their structures were elucidated, and filifoline showed no cytotoxicity or anti-protozoal activity.

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Area of Science:

  • Phytochemistry
  • Natural Product Chemistry
  • Organic Chemistry

Background:

  • The Amaryllidaceae family is a rich source of alkaloids with diverse biological activities.
  • Nerine filifolia bulbs are known to contain various chemical constituents.

Purpose of the Study:

  • To isolate and characterize novel and known alkaloids from Nerine filifolia.
  • To investigate the structure, stereochemistry, and biological properties of isolated compounds, particularly filifoline.

Main Methods:

  • Isolation of compounds using chromatographic techniques.
  • Structure elucidation via 1D and 2D NMR and mass spectrometry.
  • Circular dichroism (CD) studies and semi-synthetic derivatization.
  • Cytotoxicity assays against myoblast (L6) cells.

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  • In vitro anti-protozoal activity screening.

    • Main Results:

    • Isolation of three new alkaloids: N-demethylbelladine, 6alpha-methoxybuphanidrine, and filifoline.
    • Identification of five known alkaloids and phenol.
    • Determination of structures and stereochemistry using advanced spectroscopic methods.
    • Filifoline exhibited an unusual circular dichroism response, prompting further synthetic studies.
    • Filifoline demonstrated no cytotoxicity to L6 cells and no anti-protozoal activity against tested parasites.

    Conclusions:

    • Nerine filifolia is a source of novel Amaryllidaceae alkaloids.
    • The study elucidated the chemical profile and initial biological evaluation of compounds from Nerine filifolia.
    • Filifoline's unique CD properties warrant further investigation into its stereochemistry and potential applications.