Abstract
The crystal structure of the natural product zeylenone, C21H18O7, was confirmed by single-crystal X-ray diffraction. The crystal structure has three chiral centers at positions C1, C5 and C6 of the cyclo-hexa-none ring, but the absolute configuration could not be determined reliably. The methyl benzoate and benzo-yloxy substituents at positions C1 and C5 of the cyclo-hexenone ring are on the same side of the ring with the dihedral angle between their mean planes being 16.25 (10)°. These rings are almost perpendicular to the cyclo-hexenone ring. The benzoate groups and two hydroxyl groups on the cyclo-hexenone ring form strong hydrogen bonds to consolidate the crystal structure. In addition, weak C-H⋯O hydrogen bonds also contribute to the packing of the structure.
Highlights
The crystal structure of the natural product zeylenone, C21H18O7, was confirmed by single-crystal X-ray diffraction
The methyl benzoate and benzoyloxy substituents at positions C1 and C5 of the cyclohexenone ring are on the same side of the ring with the dihedral angle between their mean planes being 16.25 (10)
Weak C—HÁ Á ÁO hydrogen bonds contribute to the packing of the structure
Summary
Zeylenone is a naturally occurring polyoxygenated cyclohexene derived from the shikimate pathway. It has been found in a few plant families such as Piperaceae and Annonaceae. The biological activity of zeylenone was reported as inducing apoptosis in the mitochondria of gastric cancer cells (Yang et al, 2018) and cervical carcinoma cells (Zhang et al, 2017). The absolute configuration of natural zeylenone was determined by CD spectroscopy to be (À)-zeylenone (Takeuchi et al, 2001)
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