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

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

Manchester Institute of Biotechnology

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

Abstract

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.

Original language	Undefined
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 - 2010

Keywords

triterpeneglycosides
glycyrrhizicacid
glycyrrhetic acid
glycosylation
iodine monobromide

Research Beacons, Institutes and Platforms

Manchester Institute of Biotechnology

UN SDGs

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

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10.1007/s10600-010-9679-1

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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 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-{\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 = "triterpeneglycosides, glycyrrhizicacid, glycyrrhetic acid, glycosylation, iodine monobromide",

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

year = "2010",

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

language = "Undefined",

volume = "46",

pages = "576--582",

journal = "Chemistry of Natural Compounds",

publisher = "Springer Nature",

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TY - JOUR

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

AU - Baltina Jr, L.A.

AU - Baltina, L.A.

AU - Kondratenko, R.M.

AU - Plyasunova, O.A.

AU - Nepogodiev, S.A.

AU - Field, R.A.

PY - 2010

Y1 - 2010

N2 - 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.

AB - 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.

KW - triterpeneglycosides

KW - glycyrrhizicacid

KW - glycyrrhetic acid

KW - glycosylation

KW - iodine monobromide

UR - http://www.scopus.com/inward/record.url?eid=2-s2.0-78149459369&partnerID=MN8TOARS

U2 - 10.1007/s10600-010-9679-1

DO - 10.1007/s10600-010-9679-1

M3 - Article

VL - 46

SP - 576

EP - 582

JO - Chemistry of Natural Compounds

JF - Chemistry of Natural Compounds

IS - 4

ER -

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

Abstract

Keywords

Research Beacons, Institutes and Platforms

UN SDGs

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