Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate

Area of Science:

• Natural Product Chemistry
• Mycology
• Crystallography

Background:

• Endophytic fungi residing in medicinal plants like Taxus sp. are a rich source of bioactive compounds.
• Alternariol 9-O-methyl ether (AME) is a specific metabolite with potential biological relevance.
• Understanding the solid-state structure of natural products is crucial for elucidating their properties and interactions.

Purpose of the Study:

• To isolate and characterize a novel compound from an unidentified endophytic fungus of Taxus sp.
• To determine the crystal structure of the isolated compound, alternariol 9-O-methyl ether (AME), in its dimethyl sulfoxide (DMSO) monosolvate form.
• To analyze the intermolecular interactions and crystallographic symmetry of AME within the crystal lattice.

Main Methods:

• Isolation of the compound from fungal cultures.
• Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.
• Analysis of hydrogen bonding, π-π stacking, and other non-covalent interactions.

Main Results:

• The compound, identified as alternariol 9-O-methyl ether (AME), was successfully isolated and its structure elucidated.
• The crystal structure of AME·DMSO revealed crystallographic mirror symmetry for both AME and DMSO molecules.
• Specific interactions including bifurcated hydrogen bonds, π-π stacking (3.6184 Å centroid distance), and C-H⋯O contacts were observed, organizing the crystal packing.

Conclusions:

• The study successfully characterized a new natural product, AME, from an endophytic fungus.
• The detailed crystallographic analysis provides insights into the self-assembly and intermolecular forces governing the solid-state structure of AME.
• The findings contribute to the understanding of fungal secondary metabolites and their structural diversity.