Citation: Li Li, Bei-Bei Yang, Yi-Kang Si. Chiroptical properties of artemisinin and artemether investigated using time-dependent density functional theory[J]. Chinese Chemical Letters, ;2014, 25(12): 1586-1590. doi: 10.1016/j.cclet.2014.07.008 shu

Chiroptical properties of artemisinin and artemether investigated using time-dependent density functional theory

1.
Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China

Corresponding author: Li Li,
Received Date: 25 April 2014
Available Online: 3 July 2014
Fund Project: This study was supported by the Fundamental Research Funds for the Central Institutes of China (No. 2012ZD03). (No. 2012ZD03)

Chiroptical properties including electronic circular dichroism (ECD) and optical rotatory dispersion (ORD) of artemisinin and artemether have been fully studied using quantum-chemical calculation based on time-dependent density functional theory. Both theoretical ECD and ORD of these two compounds were in good match with the experimental data. ECD spectrum of artemether could be totally attributed to the peroxide group, and that of artemisinin was an overlay of contribution from δ-lactone and peroxide moieties, which leading to a positive maximum at 260 nm. Our results showed that peroxide group could produce a broad ECD band in the far-UV region originated from electron transitions of HOMO→LUMO, HOMO 1→LUMO and HOMO 2→LUMO in the case of artemether. This work provided a theoretical interpretation of the ECD behavior of peroxide bond.
- Chiroptical properties,
- Artemisinin,
- Peroxide group,
- Absolute configuration,
- Time-dependent density functional theory
1. [1]
  [1] N.M. Douglas, N.M. Anstey, B.J. Angus, F. Nosten, R.N. Price, Artemisinin combination therapy for vivax malaria, Lancet Infect. Dis. 10 (2010) 405-416.
2. [2]
  [2] W.E. Ho, H.Y. Peh, T.K. Chan, W.S. Wong, Artemisinins: pharmacological actions beyond antimalarial, Pharmocol. Therapeut. 142 (2014) 126-139.
3. [3]
  [3] D.K. Ro, E.M. Paradise, M. Ouellet, et al., Production of the antimalarial drug precursor artemisinic acid in engineered yeast, Nature 440 (2006) 940-943.
4. [4]
  [4] J.M. Liu, M.Y. Ni, J.F. Fan, et al., Structure and reaction of Arteannuin, Acta Chim. Sin. 37 (1979) 129-143.
5. [5]
  [5] Qinghaosu Research Group, Crystal structure and absolute configuration of Qinghaosu, Sci. Sin. 11 (1979) 1114-1128.
6. [6]
  [6] G. Schmid, W. Hofheinz, Total synthesis of Qinghaosu, J. Am. Chem. Soc. 105 (1983) 624-625.
7. [7]
  [7] X.T. Liang, Circular dichroism of the peroxidic linkage, Acta Chim. Sin. 40 (1982) 287-288.
8. [8]
  [8] J.J. Liu, G.L. Duan, X.T. Liang, An ab initio study on the correlation between the absolute configuration and the CD spectra of organic peroxides, Chin. Chem. Lett. 2 (1991) 245-248.
9. [9]
  [9] P.L. Polavarapu, Renaissance in chiroptical spectroscopic methods for molecular structure determination, Chem. Rec. 7 (2007) 125-136.
10. [10]
  [10] N. Berova, L.D. Bari, G. Pescitelli, Application of electronic circular dichroism in configurational and conformational analysis of organic compounds, Chem. Soc. Rev. 36 (2007) 914-931.
11. [11]
  [11] L. Li, C. Li, Y.K. Si, D.L. Yin, Absolute configuration of Buagafuran: an experimental and theoretical electronic circular dichroism study, Chin. Chem. Lett. 24 (2013) 500-502.
12. [12]
  [12] MOE 2009.10, Chemical Computing Group Inc., http://www.chemcomp.com.
13. [13]
  [13] Gaussian 09, revision C.01, Gaussian, Inc., http://www.gaussian.com.
14. [14]
  [14] J.N. Lisgarten, B.S. Potter, C. Bantuzeko, R.A. Palmer, Structure, absolute configuration, and conformation of the antimalarial compound, Artemisinin, J. Chem. Crystallogr. 28 (1998) 539-543.
15. [15]
  [15] I. Fernandez, A. Robert, Peroxide bond strength of antimalaria drugs containing an endoperoxide cycle. Relation with biological activity, Org. Biomol. Chem. 9 (2011) 4098-4107.
16. [16]
  [16] The State Pharmacopoeia Committee of China, The Pharmacopoeia of the People's Republic of China, China Medical and Technology Press, Beijing, 2010.
17. [17]
  [17] C.Y. Shen, Y. Li, Circular dichroism study of Qinghaosu and its derivatives, Acta Chim. Sin. 49 (1991) 183-186.
18. [18]
  [18] A.F. Beecham, Circular dichroism in lactones, Tetrahedron Lett. 9 (1968) 2355-2360.
19. [19]
  [19] M.B. Huang, H.U. Suter, Ab initio study of dimethyl peroxide, J. Mol. Struct. Theochem. 337 (1995) 173-178.
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沈阳化工大学材料科学与工程学院沈阳 110142