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Tetrahydroberberine, a pharmacologically active naturally occurring alkaloid.

Subramanya Pingali1, James P Donahue2, Florastina Payton-Stewart1

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Tetrahydroberberine, a natural alkaloid, was crystallized as a racemic mixture. Its bent molecular structure and intermolecular hydrogen bonds influence crystal packing.

Keywords:
C—H...O hydrogen bondingalkaloidberberine derivativebiological activitycanadinecrystal structurequinolizidine coretetrahydroberberine

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Area of Science:

  • Natural Product Chemistry
  • Crystallography
  • Organic Chemistry

Background:

  • Tetrahydroberberine is a naturally occurring alkaloid with a C20H21NO4 chemical formula.
  • Alkaloids are a diverse group of naturally occurring organic compounds that contain at least one nitrogen atom.
  • Berberine alkaloids are widely distributed in plants and have shown various pharmacological activities.

Purpose of the Study:

  • To determine the crystal structure of tetrahydroberberine.
  • To investigate the molecular conformation and intermolecular interactions in the crystal lattice.
  • To provide insights into the solid-state properties of this natural product.

Main Methods:

  • Single-crystal X-ray diffraction analysis was performed on a racemic mixture of tetrahydroberberine.
  • The crystal structure was solved and refined to determine the molecular geometry and packing arrangement.
  • Intermolecular interactions, including hydrogen bonds, were identified and analyzed.

Main Results:

  • Tetrahydroberberine crystallized as a racemic mixture, adopting a bent molecular conformation.
  • An angle of 24.72(5)° was measured between the terminal arene rings across the reduced quinolizinium core.
  • Key intermolecular interactions, such as 1,3-benzodioxole -CH2···OCH3 and -OCH3···OCH3 hydrogen bonds, were identified as crucial for crystal packing.

Conclusions:

  • The crystal structure reveals a distinct bent conformation for tetrahydroberberine.
  • Intermolecular hydrogen bonding significantly influences the packing of tetrahydroberberine molecules in the solid state.
  • This structural information is valuable for understanding the physical properties and potential applications of tetrahydroberberine.