Swertisin dihydrate.

Area of Science:

• Natural Product Chemistry
• Crystallography
• Structural Biology

Background:

• Flavonoids are a diverse class of natural products with various biological activities.
• C-glycosylflavones represent a specific subclass characterized by a direct carbon-carbon bond between the sugar and the aglycone.
• Understanding the three-dimensional structure of these compounds is crucial for elucidating their properties and interactions.

Purpose of the Study:

• To determine the crystal structure of 6-C-glucopyranosyl-7-O-methylapigenin dihydrate.
• To analyze the molecular conformation and intermolecular interactions within the crystal lattice.
• To provide insights into the structural basis of C-glucosylflavone stability and properties.

Main Methods:

• Single-crystal X-ray diffraction analysis was performed on 6-C-glucopyranosyl-7-O-methylapigenin dihydrate.
• The crystal structure was solved and refined to determine atomic positions and bond lengths.
• Intermolecular interactions, including hydrogen bonding and stacking, were analyzed.

Main Results:

• The crystal structure of 6-C-glucopyranosyl-7-O-methylapigenin dihydrate was successfully elucidated.
• The flavone skeleton exhibited a nearly planar conformation, with a small dihedral angle between the pyran moiety and the 4-hydroxyphenyl ring (9.8 degrees).
• The glucose moiety's pyranosyl ring was oriented nearly perpendicular to the benzopyran ring system, and molecules formed stacked layers stabilized by hydrogen bonds.

Conclusions:

• The crystal structure reveals specific conformational preferences and intermolecular interactions in this C-glucosylflavone.
• The layered arrangement, with alternating hydrophobic flavone and hydrophilic glucose/water layers, contributes to the compound's stability.
• These findings enhance our understanding of natural C-glucosylflavones and their structural characteristics.