Abstract
The synthesis of the alkaloid (–)-monophyllidin is described. The molecule is a hybrid of xanthoxyline and (S)-proline, accessible in one-step through a Mannich reaction. In the solid-state, defined structural arrangements with different physical properties are formed. Single crystal X-ray diffraction revealed structures of six distinct polymorphs. In the crystalline state, the alkaloid can host small polar molecules (preferably water), while the (S)-proline moiety is present in the zwitterionic state. Combined with the chelate, which is already present in the xanthoxyline substructure, an ideal disposition for multiple hydrogen bond networks evolve. Therefore, highly water-soluble polymorphs of monophyllidin can form. This structural flexibility explains the many faces of the molecule in terms of structure as well as analytical data. Furthermore, speculations about the biological role of the molecule, with regard to the manifold interactions with water, are presented.
Highlights
The species of Z. monophyllum is endemic in Middle and South America as well as the Caribbean [2]
Z. monophyllum is considered as a promising source for new biologically active alkaloids
We describe an efficient one -step synthesis of (–)-monophyllidin (3a) and (+)-monophyllidin (3b)
Summary
The synthesis of the alkaloid (–)-monophyllidin is described. The molecule is a hybrid of xanthoxyline and (S)-proline, accessible in one-step through a Mannich reaction. The alkaloid can host small polar molecules (preferably water), while the (S)-proline moiety is present in the zwitterionic state. Highly water-soluble polymorphs of monophyllidin can form. This structural flexibility explains the many faces of the molecule in terms of structure as well as analytical data. Speculations about the biological role of the molecule, with regard to the manifold interactions with water, are presented. Z. monophyllum is considered as a promising source for new biologically active alkaloids. (–)-Monophyllidin (3a) is a hybrid of two natural products, xanthoxyline (1) and (S)-proline (2a), respectively (Scheme 1).
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