Natural Products and Bioprospecting    2016, Vol. 6 Issue (6) : 291-296     DOI: 10.1007/s13659-016-0113-7
Original article |
(-)-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
Download: PDF(1042 KB)   HTML ()  
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks    
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.
Keywords Evodia rutaecarpa      (±)-Evodiakine      Rutaecarpine-type alkaloids     
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)
Issue Date: 31 January 2018
Service
E-mail this article
E-mail Alert
RSS
Articles by authors
Yan-Hong Li
Yu Zhang
Li-Yan Peng
Xiao-Nian Li
Qin-Shi Zhao
Rong-Tao Li
Xing-De Wu
Trendmd:   
Cite this article:   
Yan-Hong Li,Yu Zhang,Li-Yan Peng, et al. (-)-Evodiakine, A Pair of Rearranged Rutaecarpine-Type Alkaloids From Evodia rutaecarpa[J]. Natural Products and Bioprospecting, 2016, 6(6): 291-296.
URL:  
http://npb.kib.ac.cn/EN/10.1007/s13659-016-0113-7     OR     http://npb.kib.ac.cn/EN/Y2016/V6/I6/291
1. C.J. Huang, Flora of China, vol. 43 (Science Press, Beijing, 1997), pp. 65-66
2. Q.Z. Wang, J.Y. Liang, Acta Pharm. Sinica 39, 605-608 (2004)
3. G.Y. Zuo, H.P. He, B.G. Wang, X. Hong, X.J. Hao, Acta Bot. Yunnanica 25, 103-106 (2003)
4. Q.Z. Wang, J.Y. Liang, X. Feng, Chin. Chem. Lett. 21, 596-599 (2010)
5. J. Teng, X.W. Yang, Heterocycles 68, 1691-1698 (2006)
6. N. Shoji, A. Umeyama, A. Iuchi, N. Saito, S. Arihara, K. Nomoto, Y. Ohizumi, J. Nat. Prod. 52, 1160-1162 (1989)
7. G.Y. Zuo, X.S. Yang, X.J. Hao, Chin. Chem. Lett. 11, 127-128 (2000)
8. Y.H. Li, J. He, Y. Li, X.D. Wu, L.Y. Peng, R.N. Du, X. Cheng, Q.S. Zhao, R.T. Li, Helv. Chim. Acta 97, 1481-1486 (2014)
9. M. Bubenyák, M. Pálfi, M. Takács, S. Béni, E. Szök} o, B. Noszál, J. Kökösi, Tetrahedron Lett. 49, 4937-4940 (2008)
10. M.J. Frisch, G.W. Trucks, H.B. Schlegel et al., Gaussian 03, revision D.01 (Gaussian Inc, Wallingford, 2005)
11. H. Shigemori, T. Kagata, J. Kobayashi, Heterocycles 59, 275-281 (2003)
12. I.J. Pachter, R.J. Mohrbacher, D.E. Zacharias, J. Am. Chem. Soc. 83, 635-642 (1961)
13. Z.J. Zhang, J. Yang, J. He, X.D. Wu, L.D. Shao, Y. Li, S.X. Huang, R.T. Li, Q.S. Zhao, Tetrahedron Lett. 55, 6490-6494 (2014)
14. C.Y. Gan, W.T. Robinson, T. Etoh, M. Hayashi, K. Komiyama, T.S. Kam, Org. Lett. 11, 3962-3965 (2009)
15. G.J. Huang, C.H. Pan, F.C. Liu, T.S. Wu, C.H. Wu, Food Chem. Toxicol. 50, 1485-1493 (2012)
16. Y.H. Li, H.M. Li, Y. Li, J. He, X. Deng, L.Y. Peng, L.H. Gao, Q.S. Zhao, R.T. Li, X.D. Wu, Tetrahedron 70, 8893-8899 (2014)
No related articles found!
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed