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Theoretical investigation of the radical scavenging activity of shikonin and acylshikonin derivatives

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Abstract

The radical scavenging activity of shikonin and acylshikonin derivatives was studied by using density functional theory. The hydrogen bond property of the studied structures was investigated using the atoms in molecules (AIM) theory. It turned out that the hydrogen bond is important for good radical scavenging activity. The hydrogen atom transfer for shikonin and acylshikonin derivatives is difficult to obtain because of the high bond dissociation energy (BDE). However, shikonin and acylshikonin derivatives appear to be good candidates for the one-electron-transfer. The introduction of acyl groups for shikonin decreases the ionization potential (IP) values compared with that of shikonin. The acylshikonin derivatives with 1H-pyrrole, furan, and thiophene groups are expected to be of the highest radical scavenging activity among the compounds investigated in this study. Taking this system as an example, we present an efficient method for the investigation of radical scavenging activity from theoretical point of view.

The radical scavenging activity of shikonin has been theoretically investigated. Six acylshikonin derivatives have been designed by introducing different acyl groups with the aim to design good candidates for radical scavenging activity.

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References

  1. Thomson RH (1971) Naturally occurring quinones. Academic, London, UK

    Google Scholar 

  2. Assimopoulou AN, Karapanagiotis I, Vasiliou A, Kokkini S, Papageorgiou VP (2006) Biomed Chromatogr 20:1359–1374

    Article  CAS  Google Scholar 

  3. Deng R, Tang J, Xie BF, Feng GK, Huang YH, Liu ZC, Zhu XF (2010) Intern J Cancer 127:220–229

    Article  CAS  Google Scholar 

  4. Ravelo AG, Estevez-Braun A, Chavez-Orellana H, Perez-Sacau E, Mesa-Siverio D (2004) Curr Top Med Chem 4:241–265

    Article  CAS  Google Scholar 

  5. Garuti L, Roberti M, Pizzirani D (2007) Mini Rev Med Chem 7:481–489

    Article  CAS  Google Scholar 

  6. Plyta ZF, Li T, Papageorgiou VP, Mellidis AS, Assimopoulou AN, Pitsinos EN, Couladouros EA (1998) Bioorg Med Chem Lett 8:3385–3390

    Article  CAS  Google Scholar 

  7. Ahn BZ, Baik KU, Kweon GR, Lim K, Hwang BD (1995) J Med Chem 38:1044–1047

    Article  CAS  Google Scholar 

  8. Kong Y, Zhang L, Yang Z, Han C, Hu L, Jiang H, Shen X (2008) Acta Pharmacol Sin 29:870–876

    Article  CAS  Google Scholar 

  9. Sasaki K, Abe H, Yoshizaki F (2002) Biol Pharm Bull 25:669–670

    Article  CAS  Google Scholar 

  10. Kim BH, Yoo J, Park SH, Jung JK, Cho H, Chung Y (2006) Arch Pharm Res 29:123–130

    Article  CAS  Google Scholar 

  11. Singh B, Sharma MK, Meghwal PR, Sahu PM, Singh S (2003) Phytomedicine 10:375–380

    Article  CAS  Google Scholar 

  12. Cui XR, Tsukada M, Suzuki N, Shimamura T, Gao L, Koyanagi J, Komada F, Saito S (2008) Eur J Med Chem 43:1206–1215

    Article  CAS  Google Scholar 

  13. An S, Park YD, Paik YK, Jeonga TS, Lee WS (2007) Bioorg Med Chem Lett 17:1112–1116

    Article  CAS  Google Scholar 

  14. Kajimoto S, Hori M, Manabe H, Masuda Y, Shibayama-Imazu T, Nakajo S, Gong XF, Obama T, Itabe H, Nakaya K (2008) BBA-Mol Basis Dis 1782:41–50

    Article  CAS  Google Scholar 

  15. YoshidaL S, Kawada T, Irie K, Yuda Y, Himi T, Ikemoto F, Takano-Ohmuro H (2010) J Pharm Sci 112:343–351

    Article  Google Scholar 

  16. Assimopoulou AN, Boskou D, Papageorgiou VP (2004) Food Chem 87:433–438

    Article  CAS  Google Scholar 

  17. Kourounakisa AP, Assimopoulou AN, Papageorgiou VP, Gavalasa A, Kourounakis PN (2002) Arch Pharm Med Chem 6:262–266

    Article  Google Scholar 

  18. Han J, Weng X, Bi K (2008) Food Chem 106:2–10

    Article  CAS  Google Scholar 

  19. Gao D, Kakuma M, Oka S, Sugino K, Sakurai H (2000) Bioorg Med Chem 8:2561–2569

    Article  CAS  Google Scholar 

  20. Ordoudi SA, Tsermentseli SK, Nenadis N, Assimopoulou AN, Tsimidou MZ, Papageorgiou VP (2011) Food Chem 124:171–176

    Article  CAS  Google Scholar 

  21. Assimopoulou AN, Papageorgiou VP (2005) Phytother Res 19:141–147

    Article  CAS  Google Scholar 

  22. Visioli F, Bellomo G, Galli C (1998) Biochem Biophys Res Commun 247:60–64

    Article  CAS  Google Scholar 

  23. Leopoldini M, Russo N, Chiodo S, Toscano M (2006) J Agric Food Chem 54:6343–6351

    Article  CAS  Google Scholar 

  24. Tejero I, González-García N, González-Lafont A, Lluch JM (2007) J Am Chem Soc 129:5846–5854

    Article  CAS  Google Scholar 

  25. Leopoldini M, Pitarch IP, Russo N, Toscano M (2004) J Phys Chem A 108:92–98

    Article  CAS  Google Scholar 

  26. Halliwell B, Gutteridge JMC (1989) Free radicals in biology and medicine. Oxford University, Oxford

    Google Scholar 

  27. Gugumus F (1990) Oxidation inhibition in organic mMaterials. CRC, Boca Raton

    Google Scholar 

  28. Nenadis N, Sigalas MP (2008) J Phys Chem A 112:12196–12202

    Article  CAS  Google Scholar 

  29. Russo N, Toscano M, Uccella N (2000) J Agric Food Chem 48:3232–3237

    Article  CAS  Google Scholar 

  30. Yang F, Chen Y, Duan W, Zhang C, Zhu H (2006) J Ding Int J Cancer 119:1184–1193

    Article  CAS  Google Scholar 

  31. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09. Gaussian Inc, Wallingford, CT

    Google Scholar 

  32. Bader RFW (1991) Chem Res 91:893–928

    Article  CAS  Google Scholar 

  33. Bader RFW (1998) J Phys Chem A 102:7314–7323

    Article  CAS  Google Scholar 

  34. AIM2000 designed by Friedrich Biegler-Konig (2000) University of Applied Sciences, Bielefeld, Germany

  35. Steiner T, Desiraju GR (1998) Chem Commun 8:891–892

    Article  Google Scholar 

  36. Steiner T (2002) Angew Chem Int Edn 41:48–76

    Article  CAS  Google Scholar 

  37. Wright JS, Johnson ER, Di Labio GA (2001) J Am Chem Soc 123:1173–1183

    Article  CAS  Google Scholar 

  38. Abramov YA (1997) Acta Crystallogr A 53:264–272

    Article  Google Scholar 

  39. Bader RFW (1994) Atoms in Molecules: A Quantum Theory. Clarendon, Oxford, UK

    Google Scholar 

  40. Espinosa E, Molins E, Lecomte C (1998) Chem Phys Lett 285:170–173

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial support from the Research Program of Sciences at Universities of Inner Mongolia Autonomous Region (NJzy08148) is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Chifeng University, Chifeng, 024000, China

    Ruifa Jin

  2. Medical College, Chifeng University, Chifeng, 024000, China

    Yin Bai

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  1. Ruifa Jin
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  2. Yin Bai
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Correspondence to Ruifa Jin.

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Jin, R., Bai, Y. Theoretical investigation of the radical scavenging activity of shikonin and acylshikonin derivatives. J Mol Model 18, 1401–1408 (2012). https://doi.org/10.1007/s00894-011-1170-9

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  • DOI: https://doi.org/10.1007/s00894-011-1170-9

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