Isolation, crystal structure, and Hirshfeld surface analysis of artapshin

Sesquiterpenes are widely regarded as key and often defining compounds within the Artemisia genus. This group of natural products is highly diverse, with more than 5,000 identified molecules to date. They have attracted significant interest due to their broad spectrum of biological activities, including antitumor, antimicrobial, anti-inflammatory, antioxidant, antidiabetic, anti-vitiligo, cytotoxic, and neuroprotective effects [1]. However, despite these beneficial properties, terpenoids may also produce adverse effects such as respiratory distress, central nervous system disturbances, nausea, and vomiting [2]. During the investigation of the chemical composition of Artemisia scotina, the compound artapshin, previously known but lacking a characterized crystal structure, was successfully isolated. Analysis of the spectral data (UV, IR, and NMR), together with comparison to the published literature and an authentic reference sample, confirmed that the isolated compound is artapshin [3]. As part of our continued work, both the isolation and crystal structure of artapshin (1) were further examined. According to the X-ray analysis results, the asymmetric unit in the crystal consists of four molecules of the compound. Compound 1 was found to crystallize in the orthorhombic system (P2₁, Z=4). In the crystal, O—H⋯O and C—H⋯O hydrogen bonds link the molecules into infinite chains with a C₁₅H₂₄O₅ chain motif along the c-axis direction. Hirshfeld surface analysis showed that the structures are dominated by H···H, H···C/C···H and H···O/O···H contacts; these interactions present in the determined molecular structure were characterized as stabilizing factors in the unit cell.

References

1. Fattahian M., et al. Phytochemistry 203: 113411.
2. Ding, L. F., et al. Phytochemistry 216: 113871.
3. Serkerov S. V. et al. Chemistry of Natural Compounds 19(5): 543-546.