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

• Published in: Russian journal of bioorganic chemistry Vol. 26; no. 3; pp. 192 - 200
• Main Authors: Flekhter, O. B., Karachurina, L. T., Poroikov, V. V., Nigmatullina, L. P., Baltina, L. A., Zarudii, F. S., Davydova, V. A., Spirikhin, L. V., Baikova, I. P., Galin, F. Z., Tolstikov, G. A.
• Format: Journal Article
• Language: English
• Published: New York Springer Nature B.V 2000
• Subjects: Acidic oxides; Biological activity; Carbon tetrachloride; Esters; Ethanol
• ISSN: 1068-1620; 1573-9163; 1608-330X
• DOI: 10.1007/BF02786345

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.