Pharmacological and therapeutic properties of licorice preparations (A review)

Pharmaceutical Chemist~ Journal Vol. 33, No. 8, 1999

MEDICINAL PLANTS

PHARMACOLOGICAL AND THERAPEUTIC PROPERTIES OF LICORICE PREPARATIONS (A REVIEW)

G. V. Obolentseva, l V. I. Litvinenko, 1 A. S. Ammosov, 1 T. P. Popova , 1 and A. M. Sampiev 2

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 33, No. 8, pp. 24 - 31, August, 1999.

Original article submitted June I, 1998.

Remarkable therapeutic properties of licorice (herbs of the Glycyrrhiza genus) as a medicinal plant are known from very ancient times. Licorice roots have been used as a raw plant material for medicinal purposes for several thousand years. Modern folk medicine employs licorice roots both in- dependently and in dozens of multicomponent preparations (teas) possessing cholagogic, diaphoretic, expectorant, anal- gesic, wound-healing, antiseptic, antidotal, antiallergic, and tonic properties, used for the treatment of disorders in lungs, respiratory tracts, stomach, kidneys, and other organs [1 - 5]. With respect to the number of available and widely used preparations, licorice presently occupies the first line in the list of medicinal plants [6, 7].

Composition and Properties of Licorice

During the past century, a number of components, including both complexes of biologically active substances and hundreds of individual compounds belonging to various chemical classes and representing groups possessing different pharmacotherapeutic properties, were isolated from licorice.

Among these components, the first to be mentioned is a water-soluble complex of biologically active substances which account for 4 0 - 50% of the total dry raw material weight [8]. In this complex, a considerable part is made up of triterpene saponins, flavonoids, polysaccharides, pectins, simple sugars, amino acids, mineral salts, microelements, and some other substances.

The list of individual compounds isolated by now from various licorice herbs (13 botanical species of the world flora) includes more than 50 triterpenoids, above 200 individual phenolic compounds, dozens of polysaccharides and amino acids~ and many others. The content of glycyrrhizin (a

I State Drug Research Center, Kharkov, Ukraine;. 2 State Pharmaceutical Academy, Perm, Russia.

427

compound of the triterpenoid series accounting for the char- acteristic sickly sweet taste of the licorice root), representing (in the natural form) a mixture of potassium-calcium-magne- sium salts of glycyrrhizic acid, varies within a 2 - 25% range. The content of phenolic compounds in the raw plant material generally amounts to 3 - 6% [4, 9]. Among the other impor- tant biologically active substances and complexes, it is neces- sary to mention carbohydrates (simple sugars, pectins, and polysaccharides) - amounting to 20%, proteins, amino acids, and bases - up to 10%, and lipids - up to 3 - 4% [4, 8, 10].

Isolation of the complexes of biologically active substances and their separation into fractions and individual compounds would allow researchers to establish more clearly the components responsible for particular types of phanna- cotherapeutic action. This review is one of the first attempts at systematization of the data available on this subject, since only fragmentary data on the biological activity of substances and complexes, as well as of the final drug preparations based on these licorice components, were reported in the literature [11 - 16]. The main purpose of this review was to systema- tize information about the main types of pharmacological action and the use of well-characterized biologically active substances and complexes and to summarize data on some non- traditional types of biological activity. As for other related aspects, such as the synthetic derivatives of glycyrrhizic acid and the patented drugs and preparations, the data are re- stricted to simple listing or referencing to original sources.

The biological and pharmacological properties of compounds contained in medicinal plants are related to a considerable degree with their structural similarity to metabolites and substrates present in the human and animal organisms. Among the natural saponins, this is clearly illustrated by the molecule of glycyrrhizic acid comprising a hydrophilic part (two molecules of glucuronic acid) and a hydrophobic fragment (glycyrrhetic acid). Similarity of glycyrrhetic acid (the

0091-I 50X/99/3308-0427522.00 ~_~ 2000 Kluwer Academic/Plenum Publishers

428 G.V. Obolentseva et ai.

glycyrrhizic acid aglycon) to the structure of hormones se- creted by the adrenal gland cortex accounts for the mineralo- eorticoid and glucocorticoid activity of glycyrrhizic acid.

Mineralocorticoid Action of Licorice

Licorice preparations, similarly to the adrenocortical hormones, affect the water - salt balance in the organism [ 17 - 19]. As long ago as 1948, F. E. Revers (using a licorice extract for the therapy of patients with duodenal ulcers) observed for the first time a delay in urination on the back- ground of decreased content of potassium ions, increased content of sodium ions, and increased arterial pressure [20], which was evidence of the deoxycorticosterone-like properties of the licorice extract. Later, it was established that the mechanism of action of the licorice preparations consists in their ability to enhance the effect of endogenous adrenocortical hormones on water - salt metabolism [2 l, 22]. The mineralocorticoid action of licorice is much like the syndrome of excess mineralocorticoid hormones. This phenomenon is known under the name of "pseudoaldosteronism." It was suggested that licorice saponins are capable of potentiating the aldosterone action and binding partly to the mineralocorticoid receptors of kidneys [23]. The pseudoaldosteronism syndrome is believed to result from inhibition of the activity of 11-hydroxystemid dehydrogenase [24, 25], an agent responsible for the cortisol to cortisone transformation [26].

The mineralocorticoid activity of licorice preparations was studied in various aspects, including the mechanisms of reactions of triterpene derivatives in polynuclear human leu- kocytes [27], the effect of saponins upon the mineralocorticoid and glucocorticoid receptors [28, 29], the influence of glycyrrhizin on the inhibiting activity of cortisol in the adrenal mucosa [30] and on the dexamethasone-induced atrophy in adrenal cortex [31, 32], and the mineralocorticoid effect of glycyrrhizic acid in healthy humans [33]. The results of these investigations allowed licorice saponins to be successfully used for the treatment of Addison's disease and Simmonds' syndrome [20, 34]. Some of these investigations were per- formed in the USSR. For example, in the 1960s Desenko et al. [35] studied the effect of some glycyrrhetic acid derivatives (deoxyglycyrrhetic acid methyl ester, olean-12-eno- 3,30-diol) on water-mineral metabolism and the detoxicat- ing function of liver. Siryachenko and Ryzhenkov [36] studied the properties of glucocorticoid and antiinflammatory properties of sodium and ammonium salts of echinatic, mace- donic, and meristotropic acids-triterpenoids isolated from various licorice species.

Levin and Kabakov [37] reported on the results of clinical tests of the drug liquiriton (a purified sum of flavonoid glycosides from licorice roots) for the treatment of stomach and duodenal ulcers. Acute ulcer attack is accompanied by in- sufficient mineralocorticoid activity, which was restored (si- multaneously with ulcer healing) as a result of the drug administration. These data led researchers to a conclusion that liquiriton possesses a mineralocorticoid activity.

The mechanism of the antiulcerous action of licorice flavonoids is considered in more detail below.

Effect of Licorice on the Metabolism of Steroidal Hormones

Data gained in the 1960s revealed the estrogen activity both of the total licorice extract and of some individual components. This phenomenon was studied both in the USSR [38 - 42 ] and in other countries [43 -45]. However, neither the chemical carrier of this activity nor the mechanism of action were unambiguously established at that time. Some prelimi- nary data showed that the carriers are probably compounds having a low-polarity phenol nature, such as the isoflavonoids isolated from the above-ground part of licorice. Note that glycyrrhetic acid as such exhibits an antiestrogen effect [46- 48], as manifested by inhibition of the effect of estra- diol upon the uterus in test animals and by suppression of the [3-glucuronidase activity in animals with removed ovaries. At the same time, glycyrrhetic acid produced no significant effects upon the serum globulins or upon the androgen and estrogen receptors of sex hormones [49].

Antiinfiammatory and Antiulcerous Activi~ of Licorice

The licorice saponins possess high antiinflammato U and antiulcerous activity [50 - 52]. In particular, ammonium glycyrrhizate (glycyrram) and sodium glycyrrhizate are capable of suppressing formalin-induced edema in both intact and ad- renalectomized animals [51]. The effects of glycyrrhizic acid and its aglycon (glycyrrhetic acid) observed on the model of formalin arthritis in rats was similar to the action ofhydrocor- tisone, while effects of the former triterpenoids on the model of carrageenan-induced inflammation were less pronounced as compared to the hydrocortisone action [53]. It is interesting to note that the 18-R-H-isomer of glycyrrhetic acid is more active than the 18-~-H-isomer [54-56]. Glycyrrhetic acid and its derivatives exhibit the properties of cortisone antagonists, in particular, block the antigranulomatous action of glucocorticoids, potentiate the effect of exogenous adrenocortical hormones, suppress the oxidative phosphorylation and biosynthesis of sulfonated mucopolysaccharides, inhibit the activity of phosphoIipase A2, and increase the activity of glutamine transaminase [57, 58].

Glycyrrhizic acid, glycyrrhetic acid, and their derivatives affect (similarly to nonsteroidal antiinflammatory agents) the arachidonic acid cycle [59], thus inhibiting the biosynthesis ofprostaglandins [60]. The glycyrrhizic acid derivatives usu- ally exhibit no ulcerogenic effect, which is the undesired side effect of some widely used nonsteroidal antiinflammatory drugs (such as acetylsalicylic acid, voltaren, indomethacin, etc. [61]). Significant antiinflammatory and antiulcerous activity was reported for semisynthetic amides, peptides, and ureides of glycyrrhizic acid [62 - 68]. Also synthesized were several highly effective salts [15, 67] and esters [68] of glycyrrhizic acid, including pentacinnamate and pentanicotinate (niglizin). The latter drug was successfully used for the treat-

Pharmacological and Therapeutic Properties of Licorice Preparations 429

ment of rheumatoid arthritis, deforming arthrosis, Bek- hterev's disease, and nonspecific polyarthritis [69]. Pre- viously, similar effects were reported for glycyrrhizin [70] and glycyrrhetie acid [71 ].

As for licorice flavonoids, data were reported on the antiinflammatory, antiulcerous, and spasmolytic properties of licorice root extract preliminarily deprived of glycyrrhizin [67, 72] and then of some flavonoid fractions [67, 73 - 77]. Similar investigations were also conducted in the USSR: in the early 1960s, a series of about ten individual flavanone and ehalcone compounds were isolated from licorice roots (at the Kharkov Chemico-Pharnaaceutical Research Institute). Among these, there were compounds possessing antiulcerous and spasmolytic activity (approaching that ofpapaverine), the most effective being licuroside (licurazid). These flavonoids were studied under preclinical and clinical test conditions [78 -96] . Based on these data, three original drugs were suggested for further thorough investigation and use in clinical practice: liquiriton (tablets) and flacarbin (granules) for the treatment of stomach and duodenal ulcers, and lavalon (tablets and capsules) for the treatment of inflammatory disorders in liver [97]. Methods developed for the production ofliquiri- ton and flacarbin, as well as liquiritigenin, liquiritin, licuroside, liquiriton, and chalcorin (developed at the State Drug Research Center), were patented [67].

Data published abroad include a cycle of works devoted to the antiulcerous activity of a combined preparation re- ferred to as FM- 100 [75, 98 - 102] and a fraction called "xan- thoglabrol" [ 103].

Antiallergic Properties of Licorice

Some of glycyrrhizic and glycyrrhetic acid derivatives exhibit properties of antagonists of Hi-histamine receptors, which makes these compounds effective agents for the treatment of eczema, psoriasis, urticaria, allergic dermatoses and dermatites, and bronchial asthma [104-106]. There were several communications concerning the use of glycyrrhetic acid and its derivatives as antiallergic preparations in derma- tology and cosmetology [107 - 110] and for the treatment of psoriasis [111]. More extended information was published in the domestic literature. In particular, there are experimental data on the dynamics of burned and purulent skin wound healing under the action of licorice extract [112, 113], on the application of licorice preparations for the treatment of allergic dermatoses [114-121], including the use of ointments with glycyrram [122], dense extract [123], and gliderinin [124], and on the use of biologically active substances ex- tracted from licorice herbs (Glycyrrhiza glabra) for the fabri- cation of antifungal fiber materials [ 125, 126] and antiinflammatory phytocomplexes [127- 131]. A considerable volume of data was accumulated on the drug gliderinin [132- 134]. At the same time, it was reported that infection was observed on skin wounds treated with a licorice root extract [135] and a contact dermatitis was caused by contact with licorice [136].

Hepatoprotector and Antidotal Activity of Licorice

Data gained in the middle of the 1970s sharply increased the interest of researchers toward the hepatoprotector properties of licorice triterpenoids, in particular, of glycyrrhizin [137- 141]. It was established that the hepatoprotector effect, which consists of the inhibition of lactate dehydrogenase of lipid peroxides in the liver, depends on the presence of a glucuronic acid residue in the terminal part of a (natural or semisynthetic) saponin molecule. Indeed, glycosides free of glucuronic acid residues exhibit virtually no activity of this type. A different structure of the carbohydrate fragment ren- ders the aglyeon incapable of fixing on the cell surface, which either reduces the cytoprotector effect or leads to damage of the cell membrane [15].

In recent years, some communications were published that refined the mechanism of interaction between glycyrrhetic acid and the tissues and cell structures of liver. In particular, Bastrom et al. [57] studied the effect of glycyrrhizin on the secretion of arylsulfatase and hyaluronidase from liver lysosomes. Irie [142] and Akao [143] reported on the effects of glycyrrhetic acid and some related compounds on the ac-

tivity of 11-c~- and 3-~-hydroxysteroidal dehydrogenases in rat liver microsomes. The glycyrrhetic acid derivatives were found to suppress the 11-[3- and 3-c~-hydroxysteroidal dehydrogenases in rat liver [144]. Glycyrrhizin produces a selec- tive stimulating effect upon the extrathymus T-cells in liver [145- 148]. In addition, data indicative of a hepatoprotector action of glycyrrhizin were reported for chemical liver damage in rats [149], for patients with ischemic heart disease [150], and in cases of hepatitis B relapse accompanying liver transplantation [ 151 - 153]. Hepatoprotector activity was also observed for licorice root extract [154] and glycyrrhetic acid methyl ester [155]. Interesting data were reported con- ccming the use of glycyrram for the therapy of patients with cholelithiasis [152, 156] and on the hepatoprotector effect of the drug "phospholiv," containing phospholipids from sun- flower seeds and licorice saponins [153J.

Antitumor Properties of Licorice

It was reported that glycyrrhetic acid produced an antitumor effect with respect to some skin tumors [156 - 158], and

18-]3-, 3-oxo-18-c~-, 18-]3-, and l l-deoxo-18-13-glycyrrhetic acids exhibited activity with respect to the models of Ober- ling melanoma, sarcoma 180, and leukemia 1210 [159]. The mechanism of action in those cases consisted of inhibiting the phosphotransferase activity of protein kinase C, which is a re- ceptor-promotor of tumors [160]. In connection with this, it was suggested to use glycyrrhizic and glycyrrhetic acids for the prophylaxis of some human tumors [67, 161,162].

Kaempferol isolated from the above-ground part of licorice herbs was suggested for administration as an antimu- tagen agent capable of preventing mutations induced by the use of some food products containing cyclic amines, while

430 G . V . Obolentseva et al.

glabren, liquiritin, and glabroside were recommended as remedies for the treatment of skin melanism [67].

Immunotropic Activity

lmmunomodulating properties were observed for licorice roots (in various teas and mixtures with other herbs) [67], polysaccharides [163, 164], a polysaccharide UA fraction ex- tracted from licorice root (Glycyrrhiza uralensis ) [165], and glycyrrhizie acid and its derivatives [15]. Glycyrrhizic and glycyrrhetic acids and their derivatives were reported to stimulate the production of antibodies (in a human lympho- cyte culture), y-interferon (in a monocyte cell culture), and lymphocytes (in a culture of human macrophages), to stimulate the proliferation ofT- and B-lymphocytes (in a culture of splenic cells from mice), to enhance the phagocytosis of macrophages, and to increase the activity oflysozyme and the titer of antibodies. All these properties indicate that licorice preparations can be used as stimulants of nonspecific immu- nity [15, 166- 168].

Hypolipidemic Action of Licorice

Based on the specific affinity of triterpene saponins with respect to cholesterol and the ability of saponin to break the complexes of cholesterol with proteins and some other lipid complex compounds in the blood serum, it was suggested that cholesterol may serve as a specific antidote in the case of intoxication with saponins, while the latter compounds can be used as a remedy for the treatment of atherosclerosis [ 169].

Some researchers reported on the hypolipidemic properties of isoflavonoids and licorice preparations (glycyrram, sodium glycyrrhenate, glycyrrhizic acid acetate, glycyrrhetic acid and its 3-amino derivative [9, 67, 170 - 174]), which can be related to inhibition of phospholipase A2 activity [175, 176] and acceleration of the synthesis of bile acids [66, 177].

Antioxidant Activity of Licorice

The licorice root and flavonoids isolated from this material possess antioxidant and antiradical properties [178- 182]. In addition, it was reported that these agents are capable of acting upon various enzyme systems, including monoanaine oxidase [ 183 - 185], xanthine oxidase [ 183, 186, 187], and hyaluronidase [ 188].

Chemotherapeutic Properties of Licorice

Beginning with the 1980s, there is an increasing amount of data concerning the antiviral properties (including the activity with respect to retrovimses, influenza and hepatitis vi- ruses, and the Marburg vims) of glycyrrhizic and glycyrrhetic acids [189 - 192], glycyrrhizin [158, 193 - t96], glycyrram and niglizin [ 195 - 198], glycyrrhizic acid derivatives [ 199 - 204], and carbenoxolone and SNMC preparation (a mixed so- lution of 0.2% glycyrrhizic acid, 0.1% cysteine, 2% glycine,

and 5% glucose) [ 15]. Peptide derivatives ofglycyrrhizic acid were reported to possess a higher anti-HIV- 1 activity than az- idothymidine [15, 67].

The group of new registered anti-AIDS drugs includes liquiritigenin, glabroside, isoliquiritigenin, isoliquiritin, licuroside, licochalcone A [67], as well as complexes of glycyrrhizic acid with isolicoflavonol, glycocoumarin, and licochalcone A [205].

The mechanism of the anti-AIDS action of glycyrrhizic acid and its derivatives is based on the ability of saponins to enhance the formation of interferon in the blood plasma [167, 168, 206], and the anti-HSV effect is related to the ability to inhibit HSV protein kinase activity [ 15].

It should be noted that licorice flavonoids (isolated from Glyeyrrhiza echinata [207, 208], the leaves of Gtycyrrhiza glabra [209], and the herbs of Glycyrrhiza uralensis and Gly- cyrrhiza chinganica [178, 179]), glepidonin C (isolated from Glycyrrhiza eehinata [210]), and licorice chalcones also possess antibacterial properties [211 ]. The latter compounds may also exhibit antileishmaniasis activity [212].

Various Properties

The expectorant activity of licorice is the basis for the use of liquid licorice root extracts and glycyrrhizin for the treatment of pulmonary tuberculosis [213- 215]. Glaucine glycyrrhizate, glycyrrhetic acid, and its derivatives were reported to possess antitussive properties comparable to those of codeine [216 - 218]. There are data that glycyrrhetic acid may affect the acoustic function of the internal ear [219] and the aggregation of formed elements in the blood [220], while glycyrrhizin, glycyrrhizic acid, and carbenoxolone influence the cardiovascular system [221 - 224].

It was suggested that licorice mixtures with other herbs may be used for the treatment of chronic pyelonephritis [225] and hyperglycemia [226 - 228].

Although both licorice as such and its preparations, as well as glycyrrhizic and glycyrrhetic acid derivatives, are low-toxicity substances (LDs0 = 800 - 6500 mg/kg), their administration for a prolonged time or in large doses may give rise to side effects. In particular, there were cases of hy- pokalemia [225, 229 - 231] and acute myopathy [232, 233].

Thus, licorice as a whole and its purified total preparations (glycyrrhizin, liquiriton, chalcorin), as well as the individual substances (flavonoids, glycyrrhizic and glycyrrhetic acids, and their derivatives) and related molecular complexes, possess various types of phamlacological activity (antiinflammatory, antiulcerous, antiallergic, hepatoprotective, antidotal, antitumorigenic, immunotropic, hypolipidemic, antioxidant, antiviral, and mineralocorticoid), which is the basis of their use in medical practice.

Licorice based preparations are also widely used in per- fumery, cosmetology, and food industry for enhancing the characteristics of products.


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Pharmacological and therapeutic properties of licorice preparations (A review)

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