Trisubstituted salts of β-glycyrrhizic acid having antiinflammatory and antiulcerous activity

Балтина, Л. А.; Davydova, V. A.; Толстикова, Т. Г.; Zarudyi, F. S.; Murinov, Yu. I.; Bondarev, A. I.; Толстиков, Г. А.

doi:10.1007/bf00772023

Cited by 3 publications

(7 citation statements)

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“…It was not allergic, teratogenic or mutagenic, and did not change blood indexes and plasma enzymes activity when administered per os (7 mg/kg30 times) [99][100][101]. GL derivatives were low toxic compounds too (LD 50 = 800-8000 mg/kg per os) [63,[68][69][70][71][72][73]76].…”

Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 99%

“…Triacylisocianate (67) reacted with primary amines forming appropriate triacylthioureids (68)(69)(70)(71), and with hydrazines formed acylthiocemicarbazides (72-77) (scheme 1) [73].…”

Section: Synthesis Of Acylthioureides and Semicarbazidesmentioning

confidence: 99%

“…The synthesis of glycopeptides (89-140) was carried out by the condensation of GL (1) with alkyl (methyl, ethyl, propyl, butyl, tert-butyl) or benzyl (4-nitrobenzyl) esters of L-amino acids and dipeptides as hydrochlorides, tosylates and benzolsulphonates using an activated esters method, Nhydroxysuccinimide (HOSu) -DCC or Nhydroxybenzotriazole (HOBt)-DCC, in the presence of small excess (1-3 mmol) of triethylamine (Et 3 N) or Nmethylmorpholine (NMM) [76][77][78][79][80]. The yield of carboxyl protected glycopeptides was higher (80-95 %) when HOBt-DCC has been used for the activation of COOH-groups of GL [78][79][80].…”

Section: Synthesis Of Glycyrrhizic Acid Glycopeptidesmentioning

confidence: 99%

“…Some of the GL glycopeptides were found as immunomodulators [76,78,[80][81][82]. Compounds containing methyl esters of amino acids (AlaOMe, LeuOMe, GluOMeOMe) stimulated the primary immune response in mice on 2 mg per kg dose (intraperitoneous) 2-3 times, as compared to the control and in the stress conditions [113].…”

Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 99%

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Chemical Modification of Glycyrrhizic Acid As A Route to New Bioactive Compounds for Medicine

Балтина

2003

CMC

222

160

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Glycyrrhizic Acid (GL) is the major bioactive triterpene glycoside of licorice root (Glycyrrhiza Radix) extracts possessing a wide range of pharmacological properties (anti-inflammatory, anti-ulcer, anti-allergic, anti-dote, anti-oxidant, anti-tumor, anti-viral etc.). Official sources of GL are Glycyrrhiza glabra L. and Gl. uralensis Fish. (Leguminosae). The content of GL in licorice root is 2-24% of the dry weight. GL is one of the leading natural compounds for clinical trials of chronic active viral hepatitis and HIV infections (preparation Stronger Neo-Minophagen C, SNMC), and its monoammonium salt (glycyram, tussilinar) is used as an anti-inflammatory and anti-allergic remedy. The synthetic transformations of GL on carboxyl and hydroxyl groups were carried out to produce new bioactive derivatives for medicine. GL esters were produced containing fragments of bioactive acids (4-nitrobenzoic, cinnamic, salycilic, acetylsalycilic, nicotinic, isonicotinic). Bioactive amides of GL were synthesized using chloroanhydride technique and N,N'-diciclohexylcarbodiimide (DCC) method. The synthesis of acylthioureids and semicarbazones was carried out via the reaction of triacylisothiocianate of penta-O-acetyl-GL with primary amines and hydrazines. The chain of transformations of trichloranhydride of penta-O-acetyl-GL was made with the introduction of diazoketone groups in the molecule. A new group of GL derivatives to be triterpene glycopeptides was prepared by the activated esters method (N-hydrohysuccinimide-DCC or N-hydroxybenzotriazol-DCC) using alkyl (methyl, ethyl, propyl, butyl, tert-butyl) or benzyl (4-nitrobenzyl) esters of amino acids. The glycyrrhizyl analogs of the known immunostimulator, N-acetyl-muramoyldipeptide (MDP), were synthesized using Reagent Woodward K. A series of ureids and carbamates of GL was synthesized containing 5-amino-5-desoxy-D-xylopyranose units. The synthesis of 4-nitro-4-desoxy-glycosides, modified analogs of GL, was carried out by the oxidative splitting of the carbohydrate part of GL with NaIO(4). Triterpene 2-desoxy-D-glycosides, analogs of GL, were prepared by the glycal method in the presence of iodine-containing promoters or sulfonic acid cation-exchange resin KU-2-8 (H+) and LiBr. New anti-inflammatory and anti-ulcer agents were found among GL derivatives such as esters, amides, ureids, carbamates, thioureids and glycopeptides. GL glycopeptides are of interest as immunomodulators. Some of the chemically modified GL derivatives (salts, amides, glycopeptides) were potent HIV-1 and HIV-2 inhibitors in vitro. Preparation niglizin (penta-O-nicotinate of GL) was studied clinically as an anti-inflammatory agent and is of interest for studies as hepatoprotector and HIV inhibitor.

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Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 99%

“…Triacylisocianate (67) reacted with primary amines forming appropriate triacylthioureids (68)(69)(70)(71), and with hydrazines formed acylthiocemicarbazides (72-77) (scheme 1) [73].…”

Section: Synthesis Of Acylthioureides and Semicarbazidesmentioning

confidence: 99%

Section: Synthesis Of Glycyrrhizic Acid Glycopeptidesmentioning

confidence: 99%

Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 99%

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Chemical Modification of Glycyrrhizic Acid As A Route to New Bioactive Compounds for Medicine

Балтина

2003

CMC

222

160

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“…and G. glabra L. as the main Glycyrrhiza Radix (licorice root) sources are documented in the China Pharmacopoeia, and extensively used in clinic for anti-inflammatory, anti-viral, anti-allergenic, anti-ulcer, anti-oxidative, anticarcinogenic, memory-strengthening activity and antihepatotoxic. [1][2][3][4][5][6][7][8] The main compounds in G. uralensis Fisch. are triterpenoids, such as glycyrrhizic acid, and flavones including liquiritin and neoliquiritin.…”

Section: Introductionmentioning

confidence: 99%

Studies on Triterpenoids and Flavones in Glycyrrhiza uralensis Fisch. by HPLC‐ESI‐MSⁿ and FT‐ICR‐MSⁿ

Meng

Song³

et al. 2009

Chin. J. Chem.

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Seven compounds, four flavones and three triterpenoids from Glycyrrhiza uralensis Fisch. extract are identified by high performance liquid chromatography coupled with electrospray ionization multi-tandem mass spectrometry (HPLC-ESI-MS n ). The fragmentation pathways of these compounds are investigated by ESI-MS n and Fourier transform ion cyclotron resonance multiple-stage tandem mass spectrometry (FT-ICR-MS n ). Comparing the retention times (t R ) and mass spectra with those of reference compounds, seven components are identified in Glycyrrhiza uralensis Fisch. and their MS n data proposed plausible schemes for their fragmentation. All the experimental results show that ESI-MS n and FT-ICR-MS n are powerful tools for the structural characterization of triterpenoids and flavones.Scheme 1 Structures of compounds in Glycyrrhiza uralensis Fisch. Sample preparationG. uralensis Fisch. was purchased from the Baicheng Mashi Glycyrrhizea base. G. uralensis Fisch. of 1 g was powdered (ca. 60 mesh) and ultrasonically extracted with 20 mL of 75% ethanol for 30 min at room temperature. The extraction was repeated three times. After combining them together, the extract solution was diluted with 75% ethanol to 100 mL in a volumetric flask. The solution was filtered with a 0.45 µm filter and 20 µL of the filtrate was injected into the HPLC-MS system for analysis.

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Hypoglycemic Activity of Glycyrrhizic Acid and Some of its Derivatives in the Alloxan Diabetes Model in Rats

et al. 2021

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The hypoglycemic activity of glycyrrhizic acid (GA, I), its trisodium (II) and sodium-dilithium salts (III), and a conjugate with L-methionine methyl ester (IV) was studied using an alloxan diabetes model after peroral administration to male Wistar rats. It was found that GA and its conjugate IV at a dose of 100 mg/kg exhibited hypoglycemic activity and reduced the blood glucose content of the animals by 35.5 and 42.6%, respectively, after 120 min. GA conjugate IV had low toxicity and hypoglycemic activity superior to those of GA and acarbose.

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Trisubstituted salts of β-glycyrrhizic acid having antiinflammatory and antiulcerous activity

Cited by 3 publications

References 0 publications

Chemical Modification of Glycyrrhizic Acid As A Route to New Bioactive Compounds for Medicine

Chemical Modification of Glycyrrhizic Acid As A Route to New Bioactive Compounds for Medicine

Studies on Triterpenoids and Flavones in Glycyrrhiza uralensis Fisch. by HPLC‐ESI‐MSⁿ and FT‐ICR‐MSⁿ

Hypoglycemic Activity of Glycyrrhizic Acid and Some of its Derivatives in the Alloxan Diabetes Model in Rats

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Trisubstituted salts of β-glycyrrhizic acid having antiinflammatory and antiulcerous activity

Cited by 3 publications

References 0 publications

Chemical Modification of Glycyrrhizic Acid As A Route to New Bioactive Compounds for Medicine

Chemical Modification of Glycyrrhizic Acid As A Route to New Bioactive Compounds for Medicine

Studies on Triterpenoids and Flavones in Glycyrrhiza uralensis Fisch. by HPLC‐ESI‐MSn and FT‐ICR‐MSn

Hypoglycemic Activity of Glycyrrhizic Acid and Some of its Derivatives in the Alloxan Diabetes Model in Rats

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Studies on Triterpenoids and Flavones in Glycyrrhiza uralensis Fisch. by HPLC‐ESI‐MSⁿ and FT‐ICR‐MSⁿ