Synthesis of glycyrrhizic acid conjugates containing L-lysine

Балтина, Л. А.; Кондратенко, Р. М.; Plyasunova, O. A.; Галин, Ф. З.; Толстиков, Г. А.

doi:10.1007/s10600-006-0210-7

Cited by 18 publications

(19 citation statements)

References 7 publications

(13 reference statements)

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“…Glycyrrhizic acid (glycyrrhizin, 18␤-GL or GL) and 18␤glycyrrhetinic acid (18␤-GA or GA) were purchased from Sigma-Aldrich Chemie GmbH, Germany. The synthesis of GL derivatives was reported previously (Baltina, 2003;Baltina et al, 2006;Kondratenko et al, 2006). l-Aminoacids were used for the synthesis of GL glycopeptides.…”

Section: Chemicalsmentioning

confidence: 99%

Inhibitory effects of some derivatives of glycyrrhizic acid against Epstein-Barr virus infection: Structure–activity relationships

et al. 2008

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Glycyrrhizic acid (18beta-GL or GL) is a herbal drug with a broad spectrum of antiviral activities and pharmacological effects and multiple sites of action. Previously we showed that GL inhibits Epstein-Barr virus (EBV) infection in vitro by interfering with an early step of the EBV replication cycle (possibly attachment/penetration). Here we tested the effects of 15 GL derivatives against EBV infection by scoring the numbers of cell expressing viral antigens and quantifying EBV DNA copy numbers in superinfected Raji cells. The derivatives were made either by transformation of GL on carboxyl and hydroxyl groups or by conjugation of amino acid residues into the carbohydrate part. We identified seven compounds active against EBV and all showed dose-dependent inhibition as determined by both assays. Among these active compounds, the introduction of amino acid residues into the GL carbohydrate part enhanced the antiviral activity in three of the seven active compounds. However, when Glu(OH)-OMe was substituted by Glu(OMe)-OMe, its antiviral activity was completely abolished. Introduction of potassium or ammonium salt to GL reduced the antiviral activity with no significant effect on cytotoxicity. The alpha-isomer (18alpha-GL) of 18beta-GL was as potent as the beta-form, but its sodium salt lost antiviral activity. The metabolic product of GL, 18beta-glycyrrhetinic acid (18beta-GA or GA), was 7.5-fold more active against EBV than its parental compound GL but, concomitantly, exhibited increased cytotoxicity resulting in a decreased therapeutic index.

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Section: Chemicalsmentioning

confidence: 99%

Inhibitory effects of some derivatives of glycyrrhizic acid against Epstein-Barr virus infection: Structure–activity relationships

et al. 2008

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“…31,36 Target compounds were isolated by column chromatography (CC) on silica gel (SL) with 55-60% yields. 39,40 tert-Butyl ester groups of protected conjugates 10 and 12 were deleted with 50% CF 3 COOH in DCM and pure compounds 11 and 13 were isolated by CC on SL. There are signals of free 30-COOH at 180.3-180.8 ppm as in the 13 C NMR GA. 37 Analytical and spectral data for new compounds 5-7 are given in the References and notes.…”

Section: Introductionmentioning

confidence: 99%

Glycyrrhizic acid derivatives as influenza A/H1N1 virus inhibitors

Baltina

Zarubaev

Балтина

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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This Letter describes the synthesis and antiviral activity study of some glycyrrhizic acid (GL) derivatives against influenza A/H1N1/pdm09 virus in MDCK cells. Conjugation of GL with l-amino acids or their methyl esters, and amino sugar (d-galactose amine) dramatically changed its activity. The most active compounds were GL conjugates with aromatic amino acids methyl esters (phenylalanine and tyrosine) (SI=61 and 38), and S-benzyl-cysteine (SI=71). Thus modification of GL is a perspective route in the search of new antivirals, and some of GL derivatives are potent as anti-influenza A/H1N1 agents.

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“…3,4 Exploring the chemical versatility of this saponin, Baltina Jr. et al 9 employed the technique described in Schemes 1-3 to obtain GL-lysine conjugate in the viral surface. Compounds 55-58 were also found to be cytotoxic against VERO cell cultures.…”

Section: Antiviral Derivativesmentioning

confidence: 99%

Glycyrrhizin and glycyrrhetic acid: scaffolds to promising new pharmacologically active compounds

Graebin¹,

Verli²,

Guimarães³

2010

J. Braz. Chem. Soc.

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O ácido glicirrizínico (GL), também conhecido como glicirrizina, é uma saponina triterpênica, um produto natural encontrado na raiz de Glycyrrhyza glabra L. ("licquorice" ou "alcaçuz"), utilizada mundialmente como edulcorante e também na medicina tradicional do Oriente. Este artigo de revisão enfoca os novos compostos sintetizados usando GL ou sua aglicona, o ácido glicirretínico (GLA), como materiais de partida e as atividades farmacológicas descritas para os mesmos e seus derivados.Glycyrrhizinic acid (GL), also known as glycyrrhizin, is a triterpene saponin, a natural product found on the root of Glycyrrhyza glabra L. ("licquorice"), used worldwide as sweetener and in the traditional eastern medicines. This review is focused on a series of new derivatives synthesized using GL and its aglycon, glycyrrhetinic acid (GLA), as starting materials, the pharmacological activities described for those compounds, as well as new activities reported for GL and GLA themselves.

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Synthesis of glycyrrhizic acid conjugates containing L-lysine

Cited by 18 publications

References 7 publications

Inhibitory effects of some derivatives of glycyrrhizic acid against Epstein-Barr virus infection: Structure–activity relationships

Inhibitory effects of some derivatives of glycyrrhizic acid against Epstein-Barr virus infection: Structure–activity relationships

Glycyrrhizic acid derivatives as influenza A/H1N1 virus inhibitors

Glycyrrhizin and glycyrrhetic acid: scaffolds to promising new pharmacologically active compounds

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