Preparation and Crystal Structure of Acetyl Hemerocallin and Structural Revision of Hemerocallin
10.3969/j.issn.1674-6348.2013.02.014
- Author:
Yan-ze LIU
1
Author Information
1. Institute of Medicinal Plant Development
- Publication Type:Journal Article
- Keywords:
Acetyl hemerocallin;
Binaphthalene;
Crystal structure;
Hemerocallin;
Hemerocallis fulva
- From:
Chinese Herbal Medicines
2014;5(2):158-162
- CountryChina
- Language:Chinese
-
Abstract:
Objective: To revise the structure of hemerocallin, an active and toxic compound isolated from the roots of Hemerocallis fulva, which was first reported in 1974 based on the chemical and spectral data. Methods: The structure of acetyl hemerocallin was determined through the acetyl derivative preparing and X-ray diffraction. Results: The title compound acetyl hemerocallin (1) has been prepared and structurally characterized by X-ray single-crystal diffraction method. X-ray analysis revealed that the two naphthalene rings in compound 1 were significantly twisted with an average dihedral angle of 44.1°. The two acetate groups in each naphthalene ring adopted anti-parallel conformation. In addition, the π-π stacking interactions were found in the crystal structure, the molecules were linked into a supramolecular network, and the crystal structure was stabilized. Conclusion: The structure of hemerocallin is identified as 2,2'-bi(1,8-dihydroxy-6-methyl-7-acetylnaphthalene) (3). © 2013 Tianjin Press of Chinese Herbal Medicines.
