Preparation of glycyrrhizic acid from licorice extracts

Балтина, Л. А.; Serdyuk, N. G.; Krasnova, L.; Кондратенко, Р. М.; Толстиков, Г. А.

doi:10.1007/bf02219211

Cited by 4 publications

(6 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Bioactive compounds are separated from licorice extract by a few methods such as adsorption separation with different adsorbents (7), electrophoresis (8), two and three-liquid-phase extraction system (9), solvent extraction (10), high-speed countercurrent chromatography (11), simulated moving-bed chromatography (12), acidification (13), on-membrane quantitative analysis system (14) and nonionic surfactant mediated extraction (15). These methods are very often time consuming, high cost, having low recovery, and make new pollution (1,15).…”

Section: Introductionmentioning

confidence: 99%

Separation of Liquiritin from Glycyrrhizic Acid in Licorice Root Extract by Nanofiltration Membrane

Madaeni

Sohrabi

Khosravi

et al. 2011

Separation Science and Technology

View full text Add to dashboard Cite

The aim of this work was to study the separation of liquiritin (LQ) from glycyrrhizic acid (GA), in licorice aqueous solutions using nanofiltration (NRT-7450) membrane. The LQ and GA components are the main active ingredients of licorice root extract with various pharmacological effects, The effects of transmembrane pressure, feed temperature, feed pH, and cross-flow velocity on permeate flux and recovery were determined. A lab scale cross-flow set up using flat-sheet configuration membrane was employed for all experiments. SEM micrographs showed the changes in the fouled surface during operating time. The applied transmembrane pressure, feed temperature, feed pH, and cross-flow velocity were varied from 4 to 10 bars, 30 to 40 C, 3 to 9, and 0.8 to 3.1 m s À1 respectively. The obtained recoveries for GA and LQ varied between 0.65 to 1.86% and 16.89 to 41.65%, respectively. The optimum operating conditions for separation LQ from GA in licorice aqueous solutions using NRT-7450 nanofiltration membrane were 1.8 m s À1 cross-flow velocity, 8 bars transmembrane pressure, 40 C of feed temperature and pH 7.

show abstract

Section: Introductionmentioning

confidence: 99%

Separation of Liquiritin from Glycyrrhizic Acid in Licorice Root Extract by Nanofiltration Membrane

Madaeni

Sohrabi

Khosravi

et al. 2011

Separation Science and Technology

View full text Add to dashboard Cite

show abstract

“…The full or selective esterification of hydroxyl groups of the carbohydrate part of GL, its salts or trimethyl ester (17) was carried out using chlorides of various aromatic acids in pyridine, pyridine -triethylamine or pyridine -tributylamine to form esters (27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39)(40)(41)(42) [66,67].…”

Section: Synthesis Of Glycyrrhizic Acid Estersmentioning

confidence: 99%

“…GL with 85-90% purity was produced from the commercial licorice extract by the extraction with acetone in the presence of mineral acids and the subsequent precipitation of glycoside as tri-and monopotassium salts [51,52]. Purified GL (92±2%) was produced from commercial monoammonium salt (75±2% purity) using 1.…”

Section: Isolation Of Glycyrrhizic Acid From Raw Materials and Its Stmentioning

confidence: 99%

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

Балтина

2003

CMC

222

160

View full text Add to dashboard Cite

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.

show abstract

“…Previously, we developed a method for obtaining purified GA (87 -89%) from a commercial dry licorice root extract containing 26 -28% of GA [22,23]. In this paper, we propose an improved method for obtaining high-purity (90.5 ± 1.5%) crystalline GA from a commercial licorice root extract with a GA content of 20.0 ± 1.5% (Fig.…”

mentioning

confidence: 96%

“…Then, the acetone extract was concentrated by evaporating the solvent to~1/2 of the initial volume and the target glycoside was precipitated in the form of a tripotassium salt (3K + GA salt, II) with a 10% KOH solution in methanol, followed by conversion into a monopotassium salt (1K + GA salt, III) via recrystallization from glacial acetic acid (AcOH) as described in [22,23]. Use of a 1% H 2 SO 4 solution in acetone in the first step of extraction allowed the amount of solvent to be reduced~1.5 times as compared to that in the extractant (0.1% H 2 SO 4 solution in acetone) proposed previously [22,23]. In the next stage, the technical 1K + GA salt was treated with a 1.5% aqueous H 2 SO 4 solution at 100°C, which yielded a technical product containing 66.9 ± 1.5% GA.…”

mentioning

confidence: 99%

Obtaining Glycyrrhizic Acid and Its Practically Useful Salts from a Commercial Licorice Root Extract

et al. 2005

Self Cite

View full text Add to dashboard Cite

show abstract

Preparation of glycyrrhizic acid from licorice extracts

Cited by 4 publications

References 5 publications

Separation of Liquiritin from Glycyrrhizic Acid in Licorice Root Extract by Nanofiltration Membrane

Separation of Liquiritin from Glycyrrhizic Acid in Licorice Root Extract by Nanofiltration Membrane

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

Obtaining Glycyrrhizic Acid and Its Practically Useful Salts from a Commercial Licorice Root Extract

Contact Info

Product

Resources

About