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7-Hydroxywithanolides from datura ferox

Veleiro1, Cirigliano, Oberti

  • 1Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, (1428) Buenos Aires, and Departamento de Quimica Organica and IMBIV (CONICET), Facultad de Cie.

Journal of Natural Products
|July 30, 1999
PubMed
Summary

Three novel withanolides were identified from Datura ferox leaves. Structural elucidation utilized advanced spectroscopic techniques and molecular modeling for these unique compounds.

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Analytical chemistry·2000

Area of Science:

  • Phytochemistry
  • Natural Product Chemistry
  • Organic Chemistry

Background:

  • Datura ferox is a plant species known for its rich phytochemical profile.
  • Withanolides are a class of steroidal lactones with diverse biological activities.
  • Exploring the chemical constituents of medicinal plants can lead to the discovery of novel compounds.

Purpose of the Study:

  • To isolate and characterize new withanolides from Datura ferox leaves.
  • To elucidate the chemical structures of these novel compounds.
  • To contribute to the understanding of Datura ferox phytochemistry.

Main Methods:

  • Extraction and isolation of compounds from Datura ferox leaves.
  • Structure elucidation using Nuclear Magnetic Resonance (NMR) spectroscopy.

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  • Mass Spectrometry (MS) for molecular weight determination.
  • Molecular modeling for structural confirmation.

    • Main Results:

    • Three new withanolides, compounds 1, 2, and 3, were successfully isolated.
    • Compound 1: (17R,20S,22R)-5alpha,6alpha, 7beta,12alpha-tetrahydroxy-1-oxowitha-2,24-dienolide.
    • Compound 2: (17R,20S, 22R,24S,25S)-24,25-epoxy-5alpha,6alpha,7beta, 12alpha-tetrahydroxy-1-oxowitha-2-enolide.
    • Compound 3: (17R,20S, 22R)-5alpha,6alpha-epoxy-7alpha-hydroxy-1,12-dioxowitha-2, 24-dienolide.

    Conclusions:

    • The study successfully identified three previously unknown withanolides from Datura ferox.
    • The structures were rigorously determined using a combination of spectroscopic and computational methods.
    • This discovery expands the known chemical diversity of withanolides and Datura species.