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.
Crystallographic and NMR Investigation of Ergometrine and Methylergometrine, Two Alkaloids from Claviceps purpurea / F. Meneghetti, P. Ferraboschi, P. Grisenti, S. Reza Elahi, M. Mori, S. Ciceri. - In: MOLECULES. - ISSN 1420-3049. - 25:2(2020), pp. 331.1-331.11.
|Titolo:||Crystallographic and NMR Investigation of Ergometrine and Methylergometrine, Two Alkaloids from Claviceps purpurea|
CICERI, SAMUELE (Corresponding)
|Parole Chiave:||13C NMR; 15N NMR; 1H NMR; 9,10-unsaturated ergoline; X-ray analysis; alkaloids; ergot; oxytocic activity|
|Settore Scientifico Disciplinare:||Settore BIO/10 - Biochimica|
|Data di pubblicazione:||2020|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.3390/molecules25020331|
|Appare nelle tipologie:||01 - Articolo su periodico|