Department of Pharmaceutical Sciences, University of Milan, via L. Mangiagalli, 25, 20133 Milano, Italy.
Department of Medical Biotechnology and Translational Medicine, University of Milan, Via Saldini 50, 20133 Milano, Italy.
Molecules. 2020 Jan 14;25(2):331. doi: 10.3390/molecules25020331.
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 H, C, and N 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.
麦角新碱和甲基麦角新碱是两种生物碱，它们被用作马来酸盐，用于预防和控制产后出血。尽管这两种分子已经为人所知很长时间了，但文献中可用的晶态和 NMR 光谱数据很少且不一致。为了提供更确凿的数据，我们对麦角新碱、甲基麦角新碱及其马来酸盐的 H、C 和 N NMR 信号进行了仔细的 NMR 研究，以完成它们的完全归属。这些信息使它们的构象平衡得到了更好的定义。此外，通过单晶 X 射线衍射对两种马来酸盐在固态下的立体化学和分子间相互作用进行了深入研究，表明这些衍生物既可以作为氢键供体，也可以作为氢键受体，并且证明了分子间相互作用的数量与其不同溶解度之间存在相关性。
