A pair of unprecedented cyclohexylethanoid enantiomers containing unusual trioxabicyclo[4.2.1]nonane ring from Clerodendrum bungei |
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| Authors: | Hucheng Zhu Lijun Huan Chunmei Chen Jing Yang Jiangbo He Yong Chen Guangmin Yao Zengwei Luo Yongbo Xue Yonghui Zhang |
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| Affiliation: | 1. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People’s Republic of China;2. College of Life Science, Hubei University, Wuhan 430062, People’s Republic of China;3. Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People’s Republic of China;4. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People’s Republic of China |
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| Abstract: | A pair of unprecedented enantiomers (1a/1b) of cyclohexylethanoid bearing an unusual trioxabicyclo[4.2.1]nonane ring, along with two known structurally related cyclohexylethanoids, (+)-rengyolone (2) and cleroindicin E (3), were isolated from the aerial parts of Clerodendrum bungei. The structures and absolute configurations of the enantiomers were determined by comprehensive spectroscopic analysis, single-crystal X-ray diffraction, and quantum mechanical calculation of the electronic circular dichroic (ECD) spectra. The postulated biogenetic pathway of 1a/1b was also discussed. |
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| Keywords: | Clerodendrum bungei Enantiomer X-ray ECD |
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