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<p>Aldol condensation of 24-norallobetulon with 4-bromo-, 4-chloro-, 2,3-dimethoxybenzaldehydes or 3-pyridinecarboxaldehyde was used to synthesize a series of triterpenoids modified in ring A with 2<i>E</i>-benzylidene moieties containing 3-oxo-, 4α-hydroxy-3-oxo-, and 3β,4α-dihydroxy groups. Derivatives of norallobetulin significantly exceeding acarbose in inhibitory activity against α-glucosidase of <i>Saccharomyces cerevisiae</i> were identified. 2-(4-Chlorobenzylidene)-19β,28-epoxy-4α-hydroxy-23-nor-18α-olean-3-one was found to be the most active from the synthesized compounds with IC<sub>50</sub> of 35.41 µmol L<sup>−1</sup>, with showing no cytotoxicity against mouse peritoneal macrophages C57bl/6j, which indicates its high potential in the design of medicinal agents for the treatment of type 2 diabetes. Based on molecular modeling data, it was shown that the presence of a hydroxy group at position C(4) of norallobetulin led to a significant increase in inhibitory activity against α-glucosidase.</p>

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2E-Benzylidene-19,28-epoxynoroleananes: synthesis and inhibition of α-glucosidase

  • 期刊论文

  • 发表日期：

    2025年5月1日

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  • L. M. Zakirova,
  • R. D. Danilov,
  • I. P. Baikova,
  • A. V. Lukyanov,
  • D. A. Babkov,
  • O. B. Kazakova

摘要

Aldol condensation of 24-norallobetulon with 4-bromo-, 4-chloro-, 2,3-dimethoxybenzaldehydes or 3-pyridinecarboxaldehyde was used to synthesize a series of triterpenoids modified in ring A with 2E-benzylidene moieties containing 3-oxo-, 4α-hydroxy-3-oxo-, and 3β,4α-dihydroxy groups. Derivatives of norallobetulin significantly exceeding acarbose in inhibitory activity against α-glucosidase of Saccharomyces cerevisiae were identified. 2-(4-Chlorobenzylidene)-19β,28-epoxy-4α-hydroxy-23-nor-18α-olean-3-one was found to be the most active from the synthesized compounds with IC50 of 35.41 µmol L−1, with showing no cytotoxicity against mouse peritoneal macrophages C57bl/6j, which indicates its high potential in the design of medicinal agents for the treatment of type 2 diabetes. Based on molecular modeling data, it was shown that the presence of a hydroxy group at position C(4) of norallobetulin led to a significant increase in inhibitory activity against α-glucosidase.