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Catharanthinol and dihydrocatharanthinol: two Iboga-class alkaloids.

Lionel Moisan1, Eric Doris, Bernard Rousseau

  • 1CEA/Saclay, DSV/SMMCB, Bâtiment 547, 91191 Gif-sur-Yvette, France.

Acta Crystallographica. Section C, Crystal Structure Communications
|November 6, 2004
PubMed
Summary

This study details two indole alkaloids, catharanthinol methanol solvate and dihydrocatharanthinol monohydrate. Their structures feature fused indole and isoquinuclidine rings, with differences in bonding influencing hydrogen interactions.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Structural Chemistry

Background:

  • The Iboga class of indole alkaloids are known for their complex structures and diverse biological activities.
  • Understanding the precise molecular architecture of these compounds is crucial for exploring their potential applications.
  • Catharanthinol and its derivatives represent a significant subclass within Iboga alkaloids.

Purpose of the Study:

  • To elucidate the crystal structures of catharanthinol methanol solvate and dihydrocatharanthinol monohydrate.
  • To identify key structural differences between the two related indole alkaloids.
  • To investigate the role of solvent molecules and functional groups in hydrogen bonding.

Main Methods:

  • X-ray crystallography was employed to determine the three-dimensional structures of both compounds.

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  • Detailed crystallographic analysis was performed to identify atomic positions and bonding.
  • Comparative structural analysis was conducted to highlight variations between the solvate and the hydrate.

    • Main Results:

    • The crystal structure of catharanthinol methanol solvate (C(20)H(24)N(2)O.CH(4)O) was determined, revealing a fused indole and isoquinuclidine system.
    • The crystal structure of dihydrocatharanthinol monohydrate (C(20)H(26)N(2)O.H(2)O) was also elucidated.
    • A key difference identified was the presence of a C=C double bond in the isoquinuclidine ring of the methanol solvate, absent in the hydrate.
    • Both structures exhibit intra- and/or intermolecular hydrogen bonding involving amine, hydroxy, and solvent (methanol or water) groups.

    Conclusions:

    • The structural characterization provides a detailed understanding of catharanthinol methanol solvate and dihydrocatharanthinol monohydrate.
    • The identified structural variations, particularly the C=C bond, are significant for understanding the chemical properties of these Iboga alkaloids.
    • Hydrogen bonding interactions play a critical role in the solid-state architecture of these compounds.