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Crystallographic and NMR Investigation of Ergometrine and Methylergometrine, Two Alkaloids from Claviceps Purpurea

1
Department of Pharmaceutical Sciences, University of Milan, via L. Mangiagalli, 25, 20133 Milano, Italy
2
Department of Medical Biotechnology and Translational Medicine, University of Milan, Via Saldini 50, 20133 Milano, Italy
3
Chemical-Pharmaceutical Consulting and IP Management, Viale Giovanni da Cermenate 58, 20141 Milano, Italy
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(2), 331; https://doi.org/10.3390/molecules25020331
Received: 11 December 2019 / Revised: 9 January 2020 / Accepted: 10 January 2020 / Published: 14 January 2020
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. View Full-Text
Keywords: ergot; 9,10-unsaturated ergoline; alkaloids; 15N NMR; 13C NMR; 1H NMR; X-ray analysis; oxytocic activity ergot; 9,10-unsaturated ergoline; alkaloids; 15N NMR; 13C NMR; 1H NMR; X-ray analysis; oxytocic activity
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MDPI and ACS Style

Meneghetti, F.; Ferraboschi, P.; Grisenti, P.; Reza Elahi, S.; Mori, M.; Ciceri, S. Crystallographic and NMR Investigation of Ergometrine and Methylergometrine, Two Alkaloids from Claviceps Purpurea. Molecules 2020, 25, 331.

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