整合生物学期刊网

应用天然产物 ›› 2016, Vol. 6 ›› Issue (6): 291-296.DOI: 10.1007/s13659-016-0113-7

• Original article • 上一篇    下一篇

(-)-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. 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
  • 收稿日期:2016-11-03 修回日期:2016-11-03 出版日期:2016-12-24 发布日期:2018-01-31
  • 通讯作者: Xing-De Wu,e-mail:wuxingde@mail.kib.ac.cn
  • 基金资助:
    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)

(-)-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. 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
  • Received:2016-11-03 Revised:2016-11-03 Online:2016-12-24 Published:2018-01-31
  • Supported by:
    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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摘要： (±)-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.

关键词: Evodia rutaecarpa, (±)-Evodiakine, Rutaecarpine-type alkaloids

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.

Key words: Evodia rutaecarpa, (±)-Evodiakine, Rutaecarpine-type alkaloids

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