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The synthesis and hepatoprotective activity of esters of the lupane group triterpenoids

Abstract

Hemisuccinates, hemiphthalates, acetylsalicylates, cinnamates, andp-methoxycinnamates of lupeol, betulin, and 3-O-acetylbetulin were synthesized via interaction with corresponding acid anhydrides or acid chlorides. A number of betulin esters in position 3 and 28 were shown to exhibit a pronounced hepatoprotective effect similar to that of betulin and silibor. These experimental data were in a good agreement with the computer prediction of their biological activity. Betulin 3,28-bishemiphthalate was more effective than carsil in models of experimental hepatitis caused by carbon tetrachloride, tetracycline, and ethanol.

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Correspondence to O. B. Flekhter.

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Flekhter, O.B., Karachurina, L.T., Poroikov, V.V. et al. The synthesis and hepatoprotective activity of esters of the lupane group triterpenoids. Russ J Bioorg Chem 26, 192–200 (2000). https://doi.org/10.1007/BF02786345

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  • DOI: https://doi.org/10.1007/BF02786345

Key words

  • lupane group triterpenoid esters
  • computer prediction of biological activity
  • hepatoprotective activity