Synthesis of the New Derivatives of Usnic Acid and Investigation of Their Hypoglycemic Properties
S. A. BORISOV, O. A. LUZINA, M. V. KHVOSTOV, T. G. TOLSTIKOVA, N. F. SALAKHUTDINOV
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia
Keywords: usnic acid, enamines, hypoglycemic action, diabetes mellitus
Pages: 579-584
Abstract
In view of the 2nd type diabetes mellitus "epidemic" developing over the world, and the absence of any efficient and safe drug therapy, the search for new hypoglycemic agents is a highly relevant task. Usnic acid produced by lichens, in addition to its diverse biological effects, also exhibits hypoglycemic action, though only in high doses. To decrease the effective hypoglycemic dose and reduce the risk of side effects, in the present work usnic acid was modified through reactions with the amino acid β-alanine and its derivatives. The hypoglycemic effect of the synthesized enamine derivatives of usnic acid was investigated in mice with alloxan-induced diabetes mellitus. It was determined that the derivative containing the amide fragment in the substituent exhibited a clearly pronounced hypoglycemic effect at the dose of 50 mg/kg. Neither of the studied compounds exhibited activity in the oral glucose-tolerance test in mice without any carbohydrate metabolism disorders.
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