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(-)-Evodiakine, A Pair of Rearranged Rutaecarpine-Type Alkaloids From Evodia rutaecarpa |
| Yan-Hong Li1,2, Yu Zhang1, Li-Yan Peng1, Xiao-Nian Li1, Qin-Shi Zhao1, Rong-Tao Li1, Xing-De Wu1 |
1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2. Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, School of Ethnic Medicine, Yunnan Minzu University, Jingming South Road, Chenggong New District, Kunming 650504, Yunnan, People's Republic of China |
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Abstract (±)-Evodiakine (1a and 1b), a pair of rearranged rutaecarpine-type alkaloids with an unprecedented 6/5/5/7/6 ring system, were isolated from the nearly ripe fruits of Evodia rutaecarpa. Separation of the enantiomers have been achieved by chiral HPLC column. The structures of (±)-evodiakine were unambiguously elucidated by 1D and 2D NMR spectra, mass spectrometry, and single-crystal X-ray diffraction. Their absolute configurations were determined by comparison of experimental and calculated electronic circular dichroism spectra. A hypothetical biogenetic pathway for (±)-evodiakine was also proposed. Compounds 1a, 1b, and the racemate (1) were tested for their cytotoxic and anti-inflammatory activities.
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| Keywords
Evodia rutaecarpa
(±)-Evodiakine
Rutaecarpine-type alkaloids
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| Fund:This work was financially supported by the NSFC-Joint Foundation of Yunnan Province (No.U1502223);the National Natural Science Foundation of China (No.21402212),the Science and Technology Program of Yunnan province (No.2015FB173);and the CAS "Light of West China" Program and Youth Innovation Promotion Association CAS (X.-D.Wu) |
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Issue Date: 31 January 2018
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