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Chemistry of Natural Compounds

, Volume 46, Issue 4, pp 576–582 | Cite as

Synthesis and anti-HIV activity of triterpene 3-O-galactopyranosides, analogs of glycyrrhizic acid

  • L. A. BaltinaJr.
  • L. A. Baltina
  • R. M. Kondratenko
  • O. A. Plyasunova
  • S. A. Nepogodiev
  • R. A. Field
Article

A new method for synthesizing triterpene 3-O-galactosides, analogs of glycyrrhizic acid (GA) based on 18βglycyrrhetic acid (GLA) methyl esters and 18,19-dehydro-GLA, using 2,3,4,6-tetra-O-acetyl-a-Dgalactopyranosyl bromide as the glycosyl donor, I–Br promoter, and 4-Å molecular sieves was developed. The method could produce primarily 3-O-α-D- or β-D-galactopyranosides depending on the reaction conditions. The 3-O-α-D-galactopyranoside of GLA exhibited an index of selectivity (IS) 2.9 times greater than that of GA for inhibition of accumulation of virus-specific protein p24 of HIV-1. β-D-Galactopyranoside of GLA was more cytotoxic for MT-4 cells and exhibited weak anti-HIV-1 activity.

Keywords

triterpeneglycosides,glycyrrhizicacid,glycyrrhetic acid glycosylation iodine monobromide anti-HIV-1 activity 

Notes

Acknowledgment

The work was financed by the Royal Society of Great Britain (Project gt/fSU17p), the Federal Agency for Science and Innovation (State Contract 02.434.11.7060), and the RFBR (08-03-13514ofi-ts).

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Copyright information

© Springer Science+Business Media, Inc. 2010

Authors and Affiliations

  • L. A. BaltinaJr.
    • 1
    • 2
  • L. A. Baltina
    • 1
    • 2
  • R. M. Kondratenko
    • 1
  • O. A. Plyasunova
    • 3
  • S. A. Nepogodiev
    • 4
  • R. A. Field
    • 4
  1. 1.Bashkir State Medical UniversityUfaRussia
  2. 2.Institute of Organic ChemistryUfa Scientific Center, Russian Academy of SciencesUfaRussia
  3. 3.State Scientific Center of Virusology and Biotechnology “Vector”KoltsovoRussia
  4. 4.Center for Carbohydrate Chemistry, School of Chemical and Pharmaceutical SciencesUniversity of East EnglandNorwichUnited Kingdom

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