Citation: GUO Hui, ZHANG Shuan, ZHANG Ke-Yao, ZHU Hai-Yan, LIU Jing-Li, LIU Dong-Mei, WANG Chang-Li, SU Zhuo. Antitumor Activity and Theoretical Calculation of Evodiamine and Rutaecarpine[J]. Chinese Journal of Structural Chemistry, ;2016, 35(8): 1174-1180. doi: 10.14102/j.cnki.0254-5861.2011-1235 shu

Antitumor Activity and Theoretical Calculation of Evodiamine and Rutaecarpine

1.
a Department of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang 712046, China;
2.
b Institute of Modern Physics, Northwest University, Xi'an 710069, China

Received Date: 7 April 2016
Available Online: 1 June 2016
Fund Project: Supported by the National Natural Science Foundation of China (81001669, 81373944) (81001669, 81373944) and the Natural Science Basic Research Plan in Shaanxi Province (2016JM8028) (2016JM8028)

The antitumor activities of two alkaloids, evodiamine (EVO) and rutaecarpine (RUT), against MCF-7, SMMC-7721 and SW-1353 cells growth in vitro were investigated by MTT assay. The results showed that the anti-tumor effects of two alkaloids were remarkably different. In order to discover the relationship of antitumor activity and structures of the compounds, the dihedral angle, Natural Electron Configuration, frontier molecular orbital profiles (HOMO, LUMO) and bandgaps of these two compounds have been studied based on density functional theory (DFT) by means of DFT-B3LYP/6-31G (d) in Gaussian 03. The calculation results of dihedral angle showed that EVO, due to the existence of methyl group attached to the N(14) atom, have non-planar and twisted structures, which decrease the stability of EVO and increase the activity of EVO. Furthermore, the bandgaps of RUT are lower than that of EVO, indicating RUT has higher stability than EVO, so the activity of EVO is higher than that of RUT. In addition, the negative charge of N14 atom in EVO is lower than that of in RUT, so the positive charge of N(14) atom in EVO is higher than that of in RUT, which suggests that the nucleophile is easier to aggress the N(14) atom in EVO than that in RUT, so the reason of the different antitumor activities of EVO and RUT may be attacked by nucleophile.
- evodiamine and rutaecarpine,
- anticancer activity,
- density functional theory,
- MTT
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