Crystallographic and NMR Investigation of Ergometrine and Methylergometrine, Two Alkaloids from <i>Claviceps Purpurea</i>

Abstract

Ergometrine and methylergometrine are two alkaloids that are used as maleate salts for the prevention and control of postpartum hemorrhage. Although the two molecules have been known for a long time, few and discordant crystallographic and NMR spectroscopic data are available in the literature. With the aim of providing more conclusive data, we performed a careful NMR study for the complete assignment of the 1H, 13C, and 15N NMR signals of ergometrine, methylergometrine, and their maleate salts. This information allowed for a better definition of their conformational equilibria. In addition, the stereochemistry and the intermolecular interactions in the solid state of the two maleate salts were deeply investigated by means of single-crystal X-ray diffraction, showing the capability of these derivatives to act as both hydrogen-bond donors and acceptors, and evidencing a correlation between the number of intermolecular interactions and their different solubility.

Keywords

• ergot
• 9,10-unsaturated ergoline
• alkaloids
• ¹⁵n nmr
• ¹³c nmr
• ¹h nmr
• x-ray analysis
• oxytocic activity