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Russian Chemical Bulletin

, Volume 68, Issue 5, pp 1052–1060 | Cite as

Synthesis, hypolipidemic and antifungal activity of tetrahydroberberrubine sulfonates

  • I. V. NechepurenkoEmail author
  • E. D. Shirokova
  • M. V. Khvostov
  • T. S. Frolova
  • O. I. Sinitsyna
  • A. M. Maksimov
  • R. A. Bredikhin
  • N. I. Komarova
  • D. S. Fadeev
  • O. A. Luzina
  • T. G. Tolstikova
  • N. F. Salakhutdinova
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Abstract

The paper describes the synthesis of new tetrahydroberberrubine derivatives containing polyfl uorophenyl- or alkylsulfonate groups at the O(9) position as well as those containing or not containing a bromine atom at the C(12) position. In a model of acute Triton-induced hyperlipidemia, tetrahydroberberrubine 9-O-(heptafluoro-4’-toluene)sulfonate was shown to reduce the cholesterol level by 23.5%, which is comparable with the eff ect of Simvastatin. At a concentration of 32 μg mL−1, tetrahydroberberrubine 9-O-pentafluorobenzenesulfonate inhibits the growth of the fungus Cryptococcus neoformans by 81.3±3.5%.

Key words

berberine berberrubine sulfonate cholesterol hyperlipidemia antifungal activity Cryptococcus neoformans cytotoxicity 

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Copyright information

© Springer Science+Business Media, Inc. 2019

Authors and Affiliations

  • I. V. Nechepurenko
    • 1
    Email author
  • E. D. Shirokova
    • 1
    • 2
  • M. V. Khvostov
    • 1
    • 2
  • T. S. Frolova
    • 2
    • 3
  • O. I. Sinitsyna
    • 2
    • 3
  • A. M. Maksimov
    • 1
  • R. A. Bredikhin
    • 1
  • N. I. Komarova
    • 1
  • D. S. Fadeev
    • 1
  • O. A. Luzina
    • 1
  • T. G. Tolstikova
    • 1
  • N. F. Salakhutdinova
    • 1
    • 2
  1. 1.N. N. Vorozhtsov Novosibirsk Institute of Organic ChemistrySiberian Branch of the Russian Academy of SciencesNovosibirskRussian Federation
  2. 2.Novosibirsk State UniversityNovosibirskRussian Federation
  3. 3.Institute of Cytology and GeneticsSiberian Branch of the Russian Academy of SciencesNovosibirskRussian Federation

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