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Preparation of new 18α-oleanane alcohols: synthesis, characterization, and cytotoxic activity

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Abstract

New oleanane alcohols and their acetates were prepared using classical reductive reagents (LiAlH4, NaBH4, and B2H6-DMS). In this research, we also studied the influence of these reagents on the stereoselectivity of reduction. All compounds prepared were fully characterized by 1H and 13C NMR spectra, IR spectra, MS, and elemental analysis. These products were tested for cytotoxic activity against T-lymphoblastic leukemia (CEM), human erythromyeloblastoid leukemia (K562), and human melanoma (SK-MEL1) cell lines. One of the compounds prepared exhibits significant cytotoxic activity against the mesenchymal type of cancer cell lines.

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References

  1. Dzubak P, Hajduch M, Vydra V, Hustova A, Kvasnica M, Biedermann D, Markova L, Urban M, Sarek J (2006) Nat Prod Rep 23:394

    Article  CAS  Google Scholar 

  2. Sakai K, Fukuda Y, Matsunaga S, Tanaka R, Yamari T (2004) J Nat Prod 67:1088

    Article  CAS  Google Scholar 

  3. Sun H-X, Ye Y-P, Pan Y-J (2004) J Ethnopharmacol 90:2

    Article  Google Scholar 

  4. Akihisa T, Tabata K, Banno N, Tokuda H, Nishihara R, Nakamura Y, Kimura Y, Yasukawa K, Suzuki T (2006) Biol Pharm Bull 29:1976

    Article  CAS  Google Scholar 

  5. Tu J, Sun H-X, Ye Y-P (2006) Chem Biodivers 3:69

    Article  CAS  Google Scholar 

  6. Suh N, Wang Y, Honda T, Gribble GW, Dmitrovsky E, Hickey WF, Maue RA, Place AE, Porter DM, Spinella MJ, Williams CR, Wu G, Dannenberg AJ, Flanders KC, Letterio JJ, Mangelsdorf DJ, Nathan CF, Nguyen L, Porter WW, Ren RF, Roberts AB, Roche NS, Subbaramaiah K, Sporn MB (1999) Cancer Res 59:336

    CAS  Google Scholar 

  7. Fourie TG, Snyckers FO (1989) J Nat Prod 52:1129

    Article  CAS  Google Scholar 

  8. Pinducciu G, Serra C, Cagetti MG, Cotti M, Deidda D, Pinza M, Pompei R (1995) Med Microbiol Lett 4:83

    CAS  Google Scholar 

  9. Adnyana IK, Tezuka Y, Banskota AH, Tran KQ, Kadota S (2000) Biol Pharm Bull 23:1328

    CAS  Google Scholar 

  10. Platanov VG, Zorina AD, Gordon MA, Chizhov NP, Balykina LV, Mikhailov YD, Ivanen DR, Kvi TK, Shavva AG (1995) Khim Farm Zh 29:42

    CAS  Google Scholar 

  11. Honda T, Janosik T, Honda Y, Han J, Liby KT, Williams CR, Couch RD, Anderson AC, Sporn MB, Gribble GW (2004) J Med Chem 47:4923

    Article  CAS  Google Scholar 

  12. Kim YK, Yoon SK, Ryu SY (2000) Planta Med 66:485

    Article  CAS  Google Scholar 

  13. Ringbom T, Segura L, Noreen Y, Perera P, Bohlin L (1998) J Nat Prod 61:1212

    Article  CAS  Google Scholar 

  14. Liu Y, Kreppel H, Liu J, Choudhuri S, Klaassen CD (1993) J Pharmacol Exp Ther 266:400

    CAS  Google Scholar 

  15. Salvi M, Fiore C, Armanini D, Toninello A (2003) Biochem Pharmacol 66:2375

    Article  CAS  Google Scholar 

  16. Farina C, Pinza M, Pifferi G (1998) Farmaco 53:22

    Article  CAS  Google Scholar 

  17. Sundharsan PT, Mythili Y, Selvakumar E, Varalakshmi P (2006) Mol Cell Biochem 282:23

    Article  Google Scholar 

  18. Streffer JR, Bitzer M, Schabet M, Dichgans J, Keller M (2001) Neurology 56:1219

    CAS  Google Scholar 

  19. Sailer ER, Subramanian LR, Rall B, Hoernlein RF, Ammon HPT, Safayhi H (1996) Br J Pharmacol 117:615

    CAS  Google Scholar 

  20. Giner-Larza EM, Manez S, Recio MC, Giner RM, Prieto JM, Cerda-Nicolas M, Rios JL (2001) Eur J Pharmacol 28:137

    Article  Google Scholar 

  21. Sarek J, Klinot J, Dzubak P, Klinotova E, Noskova V, Krecek V, Korinkova G, Thomson JO, Janostakova A, Wang S, Parsons S, Fischer PM, Zhelev NZ, Hajduch M (2003) J Med Chem 46:5402

    Article  CAS  Google Scholar 

  22. Kvasnica M, Sarek J, Klinotova E, Dzubak P, Hajduch M (2005) Bioorg Med Chem 13:3447

    Article  CAS  Google Scholar 

  23. Sarek J, Kvasnica M, Urban M, Klinot J, Hajduch M (2005) Bioorg Med Chem Lett 15:4196

    Article  CAS  Google Scholar 

  24. Lacaille-Dubois MA, Mitaine-Offer AC (2005) Phytochem Rev 4:2

    Article  Google Scholar 

  25. Yang J-H, Wang Y-S, Huang R, Luo S-D, Zhang H-B, Li L (2006) Helv Chim Acta 89:2830

    Article  CAS  Google Scholar 

  26. Efferth T, Kahl S, Paulus K, Adams M, Rauh R, Boechzelt H, Hao X, Kaina B, Bauer R (2008) Mol Cancer Ther 7:152

    Article  CAS  Google Scholar 

  27. Iwu MM, Anyanwu BN (1982) Fitoterapia 53:25

    CAS  Google Scholar 

  28. Kvasnica M, Tislerova I, Sarek J, Sejbal J, Cisarova I (2005) Collect Czech Chem Commun 70:1447

    Article  CAS  Google Scholar 

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Acknowledgments

This study was supported by A/CZ0046/1/0022 of FM EEA/Norska, the Czech Science Foundation (203/05/P025 and 305/09/1216), and GAAS KAN200200651. Indirect costs were paid from the Czech Ministry of Education (MSM 6198959216). We are grateful to Stanislav Hilgard for measurement of IR spectra. We also thank Bohunka Sperlichova for measurement of optical rotation.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 16610, Prague 6, Czech Republic

    Miroslav Kvasnica

  2. Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 12843, Praha 2, Czech Republic

    Iva Rudovska

  3. Laboratory of Experimental Medicine, Departments of Pediatrics and Oncology, Faculty of Medicine, Palacky University in Olomouc, Puskinova 6, 77520, Olomouc, Czech Republic

    Marian Hajduch

  4. Department of Organic Chemistry, Faculty of Science, Palacky University in Olomouc, Trida Svobody 8, 77200, Olomouc, Czech Republic

    Jan Sarek

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  1. Miroslav Kvasnica
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  2. Iva Rudovska
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  4. Jan Sarek
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Correspondence to Jan Sarek.

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Kvasnica, M., Rudovska, I., Hajduch, M. et al. Preparation of new 18α-oleanane alcohols: synthesis, characterization, and cytotoxic activity. Monatsh Chem 141, 233–244 (2010). https://doi.org/10.1007/s00706-009-0249-9

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  • DOI: https://doi.org/10.1007/s00706-009-0249-9

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