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

L. A. Baltina; L. A. Baltina; R. M. Kondratenko; O. A. Plyasunova; S. A. Nepogodiev; R. A. Field

doi:10.1007/s10600-010-9679-1

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

L. A. Baltina, L. A. Baltina, R. M. Kondratenko, O. A. Plyasunova, S. A. Nepogodiev, R. A. Field

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

A new method for synthesizing triterpene 3-O-galactosides, analogs of glycyrrhizic acid (GA) based on 18β- glycyrrhetic acid (GLA) methyl esters and 18,19-dehydro-GLA, using 2,3,4,6-tetra-O-acetyl-α-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.

Original language	English
Pages (from-to)	576-582
Number of pages	7
Journal	Chemistry of Natural Compounds
Volume	46
Issue number	4
DOIs	https://doi.org/10.1007/s10600-010-9679-1
Publication status	Published - Sep 2010

Keywords

Anti-HIV-1 activity
Glycosylation
Glycyrrhetic acid
Glycyrrhizic acid
Iodine monobromide
Triterpene glycosides

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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@article{7ba9329e08d547b79217207ec3e47819,

title = "Synthesis and anti-HIV activity of triterpene 3-o-galactopyranosides, analogs of glycyrrhizic acid",

abstract = "A new method for synthesizing triterpene 3-O-galactosides, analogs of glycyrrhizic acid (GA) based on 18β- glycyrrhetic acid (GLA) methyl esters and 18,19-dehydro-GLA, using 2,3,4,6-tetra-O-acetyl-α-Dgalactopyranosyl bromide as the glycosyl donor, I-Br promoter, and 4-{\AA} 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 = "Anti-HIV-1 activity, Glycosylation, Glycyrrhetic acid, Glycyrrhizic acid, Iodine monobromide, Triterpene glycosides",

author = "Baltina, {L. A.} and Baltina, {L. A.} and Kondratenko, {R. M.} and Plyasunova, {O. A.} and Nepogodiev, {S. A.} and Field, {R. A.}",

note = "Funding Information: 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).",

year = "2010",

month = sep,

doi = "10.1007/s10600-010-9679-1",

language = "English",

volume = "46",

pages = "576--582",

journal = "Chemistry of Natural Compounds",

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publisher = "Springer",

number = "4",

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TY - JOUR

T1 - Synthesis and anti-HIV activity of triterpene 3-o-galactopyranosides, analogs of glycyrrhizic acid

AU - Baltina, L. A.

AU - Kondratenko, R. M.

AU - Plyasunova, O. A.

AU - Nepogodiev, S. A.

AU - Field, R. A.

N1 - Funding Information: 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).

PY - 2010/9

Y1 - 2010/9

N2 - A new method for synthesizing triterpene 3-O-galactosides, analogs of glycyrrhizic acid (GA) based on 18β- glycyrrhetic acid (GLA) methyl esters and 18,19-dehydro-GLA, using 2,3,4,6-tetra-O-acetyl-α-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.

AB - A new method for synthesizing triterpene 3-O-galactosides, analogs of glycyrrhizic acid (GA) based on 18β- glycyrrhetic acid (GLA) methyl esters and 18,19-dehydro-GLA, using 2,3,4,6-tetra-O-acetyl-α-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.

KW - Anti-HIV-1 activity

KW - Glycosylation

KW - Glycyrrhetic acid

KW - Glycyrrhizic acid

KW - Iodine monobromide

KW - Triterpene glycosides

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U2 - 10.1007/s10600-010-9679-1

DO - 10.1007/s10600-010-9679-1

M3 - Article

AN - SCOPUS:78149459369

VL - 46

SP - 576

EP - 582

JO - Chemistry of Natural Compounds

JF - Chemistry of Natural Compounds

SN - 0009-3130

IS - 4

ER -

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

Abstract

Keywords

UN SDGs

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