[Synthesis of baicalin derivatives and evaluation of their anti-human immunodeficiency virus (HIV-1) activity]

Yao Xue Xue Bao. 1998;33(1):22-7.
[Article in Chinese]

Abstract

The aglycone baicalien(1) and the key intermediate 5,6-O-dibenzyl-baicalien(3) were prepared from baicalin in order to evaluate the influence of different glycosyloxies linked to baicalien on anti-HIV activity. Four new flavone-glycosides namely 5-hydroxyl-6-O-benzyl-flavone-7-beta-D-glucoside(12), 5-hydroxyl-6-O-benzyl-flavone-7-beta-D-galactoside(13), 5-hydroxyl-6-O-benzyl-flavone-7-alpha-D-mannoside(14) and 5-hydroxyl-6-O-benzyl-flavone-7-alpha-D-arabinoside (15) were synthesized by condensation of the corresponding protected glycosyl bromides with (3). Biological activity test showed that (a) both baicalin and baicalien inhibited HIV-1 RT; (b) the 6-hydroxyl substitution of baicalin and baicalien is necessary for their inhibitory activity on HIV-1 RT; (c) the HIV-1 inhibitory activity and cytotoxicity of baicalien were higher than those of baicalin, the two compounds were found to have almost identical therapeutic index.

Publication types

  • English Abstract
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Enzyme Inhibitors / chemical synthesis
  • Flavanones*
  • Flavonoids / chemical synthesis*
  • Flavonoids / pharmacology
  • HIV Reverse Transcriptase / metabolism
  • HIV-1 / drug effects*
  • HIV-1 / enzymology
  • Humans

Substances

  • Antiviral Agents
  • Enzyme Inhibitors
  • Flavanones
  • Flavonoids
  • baicalin
  • baicalein
  • HIV Reverse Transcriptase