Pharmacological properties of novel glycopeptides of glycyrrhizic acid

Davydova, V. A.; Zarudii, F. S.; Балтина, Л. А.; Ryzhova, S. A.; Толстиков, Г. А.

doi:10.1007/bf02219463

Cited by 4 publications

(7 citation statements)

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“…Potent anti-inflammatory agents were found among GL esters, amides, glycopeptides and ureides [68][69][70][103][104][105][106]. The anti-inflammatory activity of penta-O-cinnamate (34) and penta-O-(4-nitro)benzoate (27) was more pronounced in the carrageenan and formaldehyde induced models of inflammation in mice, than that of GL [103].…”

Section: Pharmacological Properties Of Glycyrrizic Acid Derivativs Anmentioning

confidence: 99%

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

Балтина

2003

CMC

219

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%

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

Балтина

2003

CMC

219

160

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“…or by the intragastric introduction of acetylsalicylic acid (2 x 150 mg, p.o.) [6]. Prior to the reproduction of experimental ulcers, the animals were deprived of food for two days.…”

Section: Experimental Pharmacological Partmentioning

confidence: 99%

“…In the previous works we have demonstrated that glycyrrhizic acid derivatives exhibit a high antiinflammatory activity, produce no irritation of the mucous membrane of the stomach, and are efficient antiulcer agents [6,7]. Searching for new compounds possessing high antiinfiammatory and antiulcer activity, we have studied the pharmacological properties of two modified derivatives ofglycyrrhizic acid, representing 13-D-glucopyranosyl-(l--~ 2)-13-Dglucopyranosides of glycyrrhetic acid methyl ether (I) and 1813-olean-9(11)12(13)-dien-313-ol (II).…”

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confidence: 99%

Antiinflammatory and antiulcer properties of 3-O-(β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside) derivatives of steroidal alcohols

et al. 1997

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“…We have previously synthesized glucopeptide conjugates (GC) with various amino acids and dipeptides, among which were found stimulators of the primary immune response [3][4][5] and anti-inflammatory, antiulcer, and anti-HIV agents [6][7][8].…”

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confidence: 99%

“…In continuation of our research on the synthesis of new biologically active GA derivatives, we synthesized new conjugates (2)(3)(4)(5)(6)(7)(8) with an amide bond formed through the α-NH 2 group of N ε -carbobenzyloxy-L-lysine or its esters containing two or three amino components. Lys(Z)-OH = C 6 H 5 CH 2 OCONH 5 CH 2 4 CH 2 3 CH 2 2 CH 2 1 CH(COOH)NH-Conjugate 2 was synthesized by condensation of GA with the trifluoroacetate of N ε -carbobenzyloxy-L-lysine methyl ester [Lys(Z)-OMe·CF 3 COOH] using N-hydroxybenzotriazole (HOBt)-N,N′-dicyclohexylcarbodiimide (DCC) in the presence of triethyloamine (Et 3 N) as described previously [9].…”

mentioning

confidence: 99%