Chemical Constituents of  Yashtimadhu

 

·     A flavanone rhamnoglucoside, mp. 132o, was isolated from roots; it is used as smooth muscle relaxant in pharmaceutical composition (Brit. 901,085 (1962) July 11; Chem Abstr. 1962,57, 11317 h); twenty seven flavonoids present were found to be in roots; of these six were isolated and three identified. as 4',7-dihydroxyflavanone (liquiritigenin), its 4'-b-D-glucoside (liquiritin) and 2,4,'- trihydroxychalcone (isoliquiritigenin); other three are new flavonoids, L-1, mp. 164o, L-5, mp. 150o                                                                                           and L-7 ( zxhch. khim. 1963, 33, 296; Chem. Abstr. 1963, 59, 1744 b); aglycones (90%) obtained by hydrolysis of flavonoid L-1, were separated into liquiritigenin, mp. 2070 and isoliquiritigenin, mp. 199o (Zh. Obshch. khim. 1963,33,4014; Chem. Abstr. 1964,60, 9347 g); two new chalcone glucosides were isolated and characterised as trans-isoliquiritigenin-4'-b-D-glucopyranoside (isoliquiritin), mp. 187o  and trans-isoliquiritigenin-4-b-D-glucopyranoside (neoisoliquiritin), mp. 230o (Dokl. Akad. Nauk SSSR 1964, 155, 600, Chem. Abstr. 1964, 60, 14579 e); liquiritigenin, liquiritin and isoliquiritigenin were detected by PC (Deut. Apoth. Ztg. 1965, 105,644; Chem. Abstr. 1965,63,6784b); 7-hydroxy-4'-methoxyisoflavone (formonetin) was isolated from roots  (Experientia 1966, 22, 359); a new flavonoid glycoside, licuraside, mp. 150o was characterised as trans-isoliquiritigenin- 4-0-(-0-b-D-glucopyranosyl-2-b-D-apiofuranoside) (Dokl. Akad. Nauk SSSR 1966,169,347; Chem. Abstr. 1966,65,13811d); ten flavonoids were identified in plant by PC and saponaretin was characterised (isovitexin) (Khim. Prir. Soedin. 1967,3,56; Chem. Abstr. 1967, 67, 112930 x); isolation and structure of new flavonone glycoside, rhamnoliquiritin were reported (,Pharm. Tijdschr. Belg. 1968, 45, 137; Chem. Abstr. 1969, 70, 106822 e).

 

·     A new triterpenoid, liquoric acid was isolated from roots and its structure elucidated (Tetrahedron 1965, 21, 2109); isolation of two triterpenoid acids,11-deoxoglycyrrhetic acid and liquiritic acid, mp. 298o, were characterised as C-20 epimer of glycyrrhetic acid (Gazz. Chem. Ital. 1966,96,833; Chem. Abstr. 1966,65,15435 f); structure of isoglabrolide, mp. 3180 was reported (Gazz. Chim. Ital. 1966,96,843; Chem. Abstr. 1966,65,154.36 c); new lactones, glabrolide, mp. 360o, deoxoglabrolide, mp. 274o and isoglabrolide  were obtained from acid hydrolysate of crude glucosides (Gazz. Chim. Ital. 1966, 96, 772, Chem. Abstr. 1966, 65, 15435 b); glycyrrhizic acid was isolated from rhizomes and roots (Vop. Izuch. Ispolz. Solodki SSSR 1966, 123, Chem. Abstr. 1968,68,66396 u); isolation of glycyrrhetol, mp. 304o and 21a-hydroxy-isoglabrolide and their structure elucidation were reported (Gazz. Chem. Ital. 1967, 97, 1347; Chem. Abstr. 1968, 68, 49810 g); synthesis of glycyrrhizic acid derivatives were reported (Zh. Obshch. khim. 1967,37,329; Chem. Abstr. 1968, 68,13202w); 18a-hydroxyglycyrrhetic acid was isolated from acid fraction of plant extract (Gazz. Chim. Ital. 1967, 97, 769; Chem. Abstr. 1968, 68, 13206 a); 24-hydroxy-11-deoxyglycyrrhetic and 24-hydroxyglycyrrhetic acids were isolated as their Me esters (Gazz. Chim. Ital. 1967,97,1359; Chem. Abstr. 1968, 68, 49811 h); structures of 24-hydroxyliquiritic and liquiridiolic acids were determined (Gazz. Chm. Ital. 1968, 98, 712; Chem. Abstr. 1968, 59439c); preparation of Me- glabrate from Me- glycyrrhetate was reported (Acta Chem. 1968,58,75; Chem. Abstr. 1969, 70, 29115 x).

 

·     Glycyrrhetic, liquiritic, 18a-glycyrrhetic, 24-hydroxyglycyrrhetic, 11-deoxyglycyrrhetic and 21,24-dihydroxy-11-deoxyglycyrrhetic acids were identified in hydrolysed root extract;  the percentage of  glycyrrhectic acid present in roots was found to be  1.84-2.75% and  in licorice total extract was 3.94% (Fitoterapia 1979, 50, 11); roots contained both glycyrrhizine (4.0-11.0%) and total flavonoids (0.282-0.818%); liquiritigenin, isoliquiritigenin and 4-hydroxychalcone were also isolated (Pazhoohandeh 1979,23, 9; Chem. Abstr 1980, 92, 143254 w); a process was developed for separation and purification of glycyrrhizin (Jpn. 8,013,217; Chem. Abstr 1980,92,31773 d); glabridin, glabrol, glabrene, 3-hydroxyglabrol, 4'-0-methyl glabridin, 3'-methoxyglabridin, formononetin, phaseolinisoflavin, hispaglabridin A, hispaglabridin B, salicylic acid and 0-acetylsalicylic acid were isolated; structures of.hispaglabridins A and B, 4'-0-methylglabridin, 3'-methoxyglabridin and 3-hydroxyglabrol were proposed (J. Nat. Prod. 1980, 43, 259); glycyrrhetinic acid was isolated by paper electrophoresis (Kimfarmzh. 1980, 14, 104; Chem. Abstr 1981, 94, 52759 q); synthesis of rac-4'-0-methylglabridin were reported  (Ann. Chem. 1983,2034); two new saponins, glabranins A and B  were isolated from roots and  partial structures assigned (Int. J. Crude Drug Res. 1983,21,169).

 

·     Liquiritigenin-4'-apiosyl(1®2)glucoside and liquiritigenin-7,4' diglucoside were isolated along with apigenin-6,8-di-C-glucoside (Phytochemistry 1984,23,2108); galangin, naringenin, genistein, 5,7-dihydroxy-6-(gg-dimethylallyl) flavanone, pinocembrin and glabranin were obtained from aerial parts (Khim. prir. Soedin. 1986, 111; Chem. Abstr 1986, 104, 203930 s); determination of hexanoic acid (31.57), g-nonalactone (1.33), cumic alcohol (0.79), indole (0.25), anethole (0.23), eugenol (0.21) and estragole (0.18%) were detected in root essential oil by GC-MS (Nippon Nogei Kagaku KWshi 1987, 61, 1119;  Chem. Abstr 1988, 108, 62302 g); glycyrrhisoflavanone and glycyrrhisoflavone were isolated from roots and characterised; licochalcone B was also isolated (Chem. Pharm. Bull. 1988, 36, 2090); licuroside, previously isolated from roots, has now been shown to be a mixture of isomers, neolicuroside (isoliquiritigenin-4b-apiofuranosyl-2"-b-glucoside) and isoliquiritigenin-4'-b-apiofuranosyl-2"-b-glucoside (Arch. Pharm. 1989,322, 141; Chem. Abstr 1989, 111, 4253 t).

 

·     Isolation and structure determination of licopyranocoumarin, licoarylcoumarin and glisoflavone; kaempferol 3-0-methyl ether and licocoumarone were also isolated (Chem. Pharm. Bull 1989, 37, 3005); roots afforded liquiritigenin, isoliquiritigenin, liquiritin and isoliquiritin (Jpn. 1, 175,942; Chem. Abstr. 1990, 112, 164941 q); process was developed for isolation of yellow pigment containing glycyrrhetinic acid and flavone from roots (CN 1,033,459 ;Chem.Abstr.1990,113,103376h); four new isoprenoid, substituted phenolic constituents  semilicoisoflavone B, 1 -methoxyficifolinol, isoangustone A and licoriphenone  were isolated from roots and their structures elucidated (Heterocycles 1990, 31, 629); a new coumarin, GU-12 - along with echinatin, naringenin, licoricone, glycyrin and isoliquiritigenin were isolated from roots and its structure determined (Planta Med. 19901 56, 254); a process was developed for extraction of glycyrrhizin from roots (Chem. Mikrobiol. Technol. Lebensm. 1990,12,179; Chem.Abstr. 1990, 113, 197742 z); a new pentacyclic triterpenoid (1) was isolated from roots and its structure established (Z Naturforsch. 1990, 45C, 937; Chem. Abstr. 1991, 114, 78648 j); process for extraction of triterpene oligoglycosides (II and III) was developed (Jpn. 2,72,187; Chem. Abstr. 1990, 113, 103375g); isolation of 5,7-dihydroxy-5 -(gg-dimethylallyl) fiavanone, pinocembrin , prunctin and lupeol from vegetative parts was reported (Egypt J. Pharm. Sci. 1991, 32, 275; Chem. Abstr. 1992, 117, 239584 q); crystal structure of 18a-glycyrrhetinic acid was determined (J. Chem. Soc. Perkin 2 1992, 65); five new flavonoids, glucoliquiritin apioside, prenyllicoflavone A, shinflavanone, shinpterocarpin and I-methoxyphascolin  were isolated from air-dried roots and their structures elucidated (Chem. Pharm. Bull. 1994, 42, 1056).

 

·     In vivo antigranulomatus effects of glycyrrhizin make it useful for treatment of such diseases (J. Exp. PathoL 1992, 6, 25; Chem. Abstr. 1992, 117, 62544 y); glycyrrhizin (0.61 mM) inhibited plaque formation by HSV-1 and HSV-2. Same results obtained with Chandipura, measles and polio types 1, 2 and 3 of both wild and Sabins vaccine strains, at a concentration of 1.21 MM (Indian J. Pharmacol 1994, 26, 194); administration of aqueous extract (1.0% in drinking water) to female mice afforded significant protection against benzoalpyrene or NDFA-induced lung acrid forestoniach tumorigenesis. Feeding glycyrrhizin (0.05%) in drinking water to female mice gave substantial protection against D\MBA-induced skin tumor initiation. Glycyrrhetinic acid typically applied to female mice inhibited DNBA-induced skin tumor initiation as well as TPA- induced skin tumor promotion (ACS. Symp.Ser. 1994,547,329;Chem.Abstr. 1994,120,95010 m); antitumor effect of glycyrrhizin on human hepatoma cell lines (PLC/PRF/5, Hep-G2), human liver cells and human pancreatic cancer line (BXPC-3) were investigated. IC5O for PLC/PRF5 was 1.0 ng/ml (Cancer Lett. 1994, 86, 9 1; Chem. Abstr. 1994, 121, 292196 y). Isoliquiritigenin inhibited rat lens aldose-reductase (IC5O 0,32 mM) using DL- glyceraldehyde as substrate. It also inhibited sorbitol accumulation in human red blood cells in vitro with IC50 of 2.0 mM. Administration of isoliquiritigenin via intragastric tube to diabetic rats suppressed sorbitol accumulation in red blood cells, sciatic nerve and rat lens (Planta Med. 1990, 56, 254); isoliquiritigenin inhibited platelet aggregation, phosphorylation of proteins and formation of 12(S)-hydroxy-5,8, 10-heptadecatrienoic acid, 12-hydroxyeicosatetraenoic acid and thromboxane B2. Results indicate that it elicits antiplatelet action by inhibiting not only cyclooxygenase but also lipoxygenase or peroxidase activity in platelets. It also showed anti- platelet action in vivo (Eur. J. Pharmacol. 1992, 212, 87); licochalcones A and B, licopyranocoumarin, licoarylcoumarin, licocoumarone, glycyrrhisoflavone and glisoflavone inhibited xanthine oxidase, IC50 values ranged from 13.0 to 56.0 gM (Chem. Pharm. Bull. 1989, 37, 3005); licochalcone A inhibited growth of both Leishmania major and L. donovani promastigotes and amastigotes. Growth of L. major promastigotes was totally inhibited in 20 hr incubation with licochalcone A at 50.0 mg/ml. At 0.5 g/ml it markedly reduced infection rate of human peripheral blood monoclonal derived macrophages and U937 cells by L. major promastigotes and exhibited strong intracellular killing of parasite (Antimicrob. Agents Chemother. 1993, 37, 2550; Chem. Abstr. 1994, 120, 68923 e); licochalcone A inhibited in vitro growth of both chloroquine-susceptible (3D7) and chloroquine-resistant (Ddz) strains of Plasmodium falciparum to the same extent in 3H-hypoxanthine uptake assay. Growth of parasites at all stages was inhibited by licochalcone A. Administered i.p. or orally for 3 to 6 days, it protected mice from P. yoelii infection. These results demonstrate that licochalcone A possesses potent antimalarial activity (Antimicrob. Agents Chemother. 1994, 38, 1470; Chem. Abstr. 1994, 121, 73154 c).

 

·     A simple method for the distinction of 3 types of licorices was devised by use of TLC.  Glycyrrhizin  [1405-86-3] contents of licorice roots and of Chinese medicine preparations including licorice extracts were measured by HPLC.  The Sinkiang licorice root was distinguished from Tongpei and the Seipei roots by TLC.  When the TLC plate was sprayed with a color reagent and gradually heated, the spot of licochalcone A  [58749-22-7] which was the ingredient specific to the Sinkiang sample changed from yellow to red.  Glycyrrhizin contents of the licorice roots were: 7.4 (Tongpei licorice), 6.4 (Seipei licorice), and 5.2% (Sinkiang licorice).  Glycyrrhizin contents of the prepns. were 2.6-5.2 mg/g (Saikeishikankyoto), 2.3~6.4 mg/g (Kamishoyosan), 2.0~4.1 mg/g (Saikokeishito), and 3.2~5.2 mg/g (Otsujito). (Nagasaki-ken Eisei Kogai Kenkyushoho, 27, 77, 1985. Chem Abstr 106,219431)

 

·     Reversed-phase HPLC was used to determine the content of glycyrrhizin in G. uralensis.  A LiChrosorb RP-18 column was used.  The mobile phase contained MeOH-H2O-HOAc (71:28:1).  A refractometric detector or an UV detector was used. G. uralensis From different areas showed glycyrrhizin contents of 1.16-6.11%.  Exts. (industrial product) of the plant contained 6.2-15.2% glycyrrhizin. (Zhongcaoyao, 18(4),157, 1987; Chem Abstr 107,102744).

 

·     Aerial parts of G. astragalina afforded 2',4'-dihydroxychalcone (I) and pinocembrin.  Identification was based on UV-visible spectra and mass spectrometry; IR and co-chromatog. with an authentic std. were used to confirm the presence of I. (An. Asoc. Quim. Argent., 75(1),7, 1987; Chem Abstr 107:112718)

 

·     Supercrit. fluid extraction was applied to the pigments of Lithospermum root and those of licorice root.  Shikonin derivs., the red pigments of Lithiospermum root, were effectively extracted with supercritical CO2 without using entrainer.  An application of entrainer (EtOH or H2O) reduced efficiency in this extractraction.  The amounts of the substances which are immobile on TLC and regarded as oxidized products of shikonin derivatives, were significantly smaller than that obtained by the ordinary extraction with organic solvent (ether) when extracted with supercritical fluid without using entrainer, indicating an advantage of the latter extraction.  Liquiritigenin of Sipei licorice (licorice root from the northwest region of China) and Tongpei licorice (licorice root from the Northeast region of China), was extracted with supercritical CO2  in the presence of the entrainer (5% EtOH).  However, isoliquiritigenin possessing 3 phenolic OH groups was not extd. with supercritical fluid with or without entrainers (H2O or EtOH).  Licochalcone A was extracted from Sinkiang licorice , with CO2 only, but the extn. of licochalcone B required addn. of EtOH as entrainer. (YakugakuZasshi, 107(7), 506, 1987. Chem Abstr 107:205004)

 

·     A new triterpenoid lactone, named uralenolide (I), m. 302~303°, was isolated after acid hydrolysis from exts. of the rhizomes of G. uralensis..  The structure 1 as 3 b, 22 b, 24-trihydroxy-olean-11, 13(18)-dien-30-oic acid (30,22 b)-lactone, was confirmed by spectroscopic data .  Another known sapogenin, Me- 18a-hydroxy glycyrrhetate, was also identified.  (Yaoxue Xuebao, 22(7), 512, 1987. Chem Abstr 107:214819)

 

·     A method for the separation. and determination of glycyrrhizin from licorice roots is based on the use of TLC on silica gel G, development of the chromatogram with BuOH-HOAc-H2O (5:1:4), extraction of the separated glycyrrhizin from the TLC plates with MeOH, and measurement of the absorbance at 258 nm.  The av. recovery was 98.7%, and the standard  deviation was 0.56. (J. Pharm. (Lahore), 7(1-2), 21, 1986; Chem Abstr 107:223358z)

 

·     Two active compounds that inhibit mitochondrial monoamine oxidase (MAO) of rat liver were isolated from G. uralensis roots and identified as liquiritigenin and isoliquiritigenin.  The latter compd. was more active than the former, showing a substrate-competitive inhibition of MAO (Ki = 2.11 mM).  Studies on the structure-activity relationship suggested that the inhibitory activity of the chalcone derivs. can be attributed to either 4- or 4'-OH group and the possible coplanarity between the Ph ring and the adjacent conjugated ketone.  (Planta Med., 53(1), 5,1987; Chem Abstr 107:35544)

 

·     Glycyrol, glycyrin, isoglycyrol and glycycoumarin isolated from the methanolic ext. of licorice roots (Glycyrrhiza uralensis) had potent antibacterial action against a cariogenic bacterium, S. mutans.  The former two compds. completely inhibited bacterial growth at 6.25% mg/mL and the latter two at 12.5 mg/mL, detd. by the tube diln. technique.  The four coumarins were contained in licorice roots from the North-East and South-East regions of China, but not in those from Sinkiang, the Soviet Union and Afghanistan. (Shoyakugaku Zasshi, 40(4), 406,1986; Chem Abstr 107:46132).

 

·     Glycyrrhizic acid in licorice extracts was extracted with acetone containing 3% trichloroacetic acid and determined by a.c. oscillopolarog.; the recovery was 100.4% and the variation coeff. was <1.9%.  The results were comparable to those detd. by the pharmacopeia method. (Yaowu Fenxi Zazhi, 7(2), 108(Chinese) 1987. Chem Abstr 107:83975)

 

·     A HPLC method was developed for the determiniation of glycyrrhetinic acid contained in licorice powder.  Glycyrrhetinic acid, which is the hydrolyzate of glycyrrhizin extracted from licorice powder, was determined with good results by HPLC using 2-bromoacetyltriphenylene labeling reagent.  The glycyrrhetinic acids were labeled with 2-bromoacetyltriphenylene in MeCN using 18-crown-6-ether and KOH as a catalyst.  Derivatized glycyrrhetinic acids were sepd. from the extd. licorice powder on a reversed-phase column (Chemopak C18) by using 100% MeCN as a mobile phase and monitored by an UV detector at 268 nm.  The calibration curve was obtained for 5-20 ng, and the lower limit of detection was 2 ng.  The recovery of glycyrrhetinic acid in licorice powder was ~99.3%.  This method was sensitive, reliable, and useful for the detn. of glycyrrhetinic acid. (Yakhak Hoechi, 31(5), 315 (Korean) 1987. Chem Abstr 108:127851)

 

·     Glycyrrhizic acid was separated from licorice and glycyrrhiza extracts by Amberite XAD-8 resin and purified by recrystallisation from AcOH with active charcoal, resin, or H2O2; the total yield was 65-75%, and the purities were c. 90%. (Yiyao Gongye, 18(11), 481, 1987; Chem Abstr 108,26864)

 

·     The root oil of G. glabra was obtained in 0.047% yield and 82 components were identified by gas chromatog.(GC) and GC-mass spectrometry. The main component was hexanoic acid (31.57%) and the main characteristic aroma was due to mix. of estragole 0.18, anethole 0.23, eugenol 0.21, indole 0.45, g-nonalactone 1.33, and cumic alc. 0.79%. (Nippon Nogei Kagaku Kaishi, 61(9), 1119, 1987;Chem Abstr 108:62302).

 

·     The glycyrrhizin content of extracts of licorice root was enriched by fermantation with A. niger.  The sugars and flavonoid glycosides are consumed, leaving glycyrrhizin.  Fermantation conditions were adjusted so that an extract titer of 54.5% glycyrrhizin was obtained in 156 h of fermn.  This titer is higher than in com. glycyrrhizin.  (Ann.Pharm. Fr., 45(3), 249,1987. Chem Abstr 108:73680)

 

·     Flavonoids, triterpenoids and a phytosterol were isolated from the roots of G. inflata gathered from Jinta county, Gansu province.  On the basis of chem. and spectroscopic data, their structures were identified as licochalcone A and B, licoflavone, liquiritin, liquiritigenin, isoliquiritigenin, 4',7-dihydroxyflavone, ononin, glycyrrhizic acid, glycyrrhetinic acid, 11-deoxyglycyrrhetinic acid and b -sitosterol.  Licochalcone A was the major component among the flavonoids.  Its 13C-NMR data were recorded. (Zhiwu Xuebao, 30(2), 176, 1988; Chem Abstr 109,107754)

 

·     Glycyrrhizin was determined by HPLC using a YQG C18H37 column, MeOH-H2O-36% AcOH (58:42:2) as mobile phase, biphenyl as the internal std., and detection at 254 nm.  Several Radix Glycyrrhizae samples and its formulation were detd.  The coeff. of variation of the results is <2%.  The method of crude drug treatment was investigated simultaneously.  Samples in China were assayed.  This detn. method is simple, rapid and accurate. (Yaowu Fenxi Zazhi, 8(3), 137, 1988. Chem Abstr 109,135046)

 

·     Four compounds, including 2 new flavonoids, were isolated from Sipei licorice (licorice from the North-Western region of China).  The structures of the 2 new flavonoids, glycyrrhisoflavanone and glycyrrhisoflavone, were determined as (I, R = H) and (II R = H), resp.  Glycyrrhisoflavone was one of the tannic substances as detd. by the measurement of the binding activity to Hb (relative astringency).  Licochalcone B was isolated from the fraction which showed the highest binding activity to Hb among the fractions obtained by centrifugal partition chromatography of the extract of Sinkiang licorice (licorice from Sinkiang in China).  Licochalcone B also showed the highest activity as a radical scavenger in the expt. using 1,1-diphenyl-2-picrylhydrazyl radical, among 10 tested compounds obtained from several licorices.  The order of the radical scavenging effects was the same as the order of the inhibitory effects on the 5-lipoxygenase-dependent peroxidn. in arachiconate metab. [licochalcone B > licochalcone A »isoliquiritigenin >liquiritigenin]. (Chem.Pharm. Bull., 36(6), 2090, 1988; Chem Abstr 109:142029)

 

·     Five phenolics isolated from licorice inhibited the cytopathic activity of a human immunodeficiency virus.  One of these, a coumarin derivative named licopyranocoumarin, isolated from Xi-bei licorice, had structure I, based on the chem. and spectroscopic evidence. (Chem.Pharm. Bull., 36(6), 2286, 1988. Chem Abstr 109:162965)

 

·     A review, with 11 references, on Sankanon as a food preservative has been published (Gekkan Fudo Kemikaru, 4(2), 75, 1988. Chem Abstr 109:169024)

 

·     A number of compounds with acidic properties were isolated from roots and stems of licorice (Glycyrrhiza glabra).  Six individual fractions were obtained using preparative thin-layer chromatography.  The most active is a fraction of fatty oxyacids which consists of two components identified, using combined gas chromatog.-mass spectrometry as,  9,12,13-trihydroxy-10-octadecenoic and 9,12,13-trihydroxy-10,11-epoxyoctadecanoic acids.  The fraction of fatty oxyacids increases the endurance of intact and stressed rats in doses 400 times less than the licorice ext. (Izv. Akad. Nauk SSSR, Ser. Biol.,(6), 932, 1988. Chem Abstr 110:108136)

 

·     Ten new oleanene-type triterpene oligoglycosides were isolated from the dried root of G. uralensis., and the structures of 5 oligoglycosides, named licorice-saponins A3 (I), B2, C2, D3, and E2, have been detd. on the basis of chem. and physicochem. evidence. (Chem. Pharm. Bull., 36(9), 3710, 1988; Chem Abstr 110:111680)

 

·     A new prenylated flavanone named licoflavanone (I) was isolated, together with pinocembrin (II), from the leaves of G. glabra typica as an antimicrobial agent.  I and II were not so active against Bacillus subtilis, Staphylococcus aureus, and Candida albicans, and were inactive against Escherichia coli.  (Chem. Pharm. Bull., 36(10), 4174,1988; Chem Abstr 110:111699).

 

·     A prenylated isoflavan isolated from Sipei licorice (Glycyrrhiza species, Leguminosae, Seihoku Kanzo in Japanese) was found to be identical with the already known compd. licoricidin.  From the spectral data, the structure of licoricidin should be revised to the structure (I).  (Heterocycles, 27(10), 2309, 1988. Chem Abstr 110:121179).

 

·     Glycyrrhizin was determined in commonly available licorice confectionery and dried extracts and powdered roots of the licorice plant (Glycyrrhiza glabra) following extraction with H2O and without further purification by isotachophoresis with electrocondition detection (UV detection was not possible because of interference effects) with mean reproducibilities and recoveries of ±2.3 and 100.7%, resp.  With the exception of sorbic,  L-ascorbic, and gluconic acids and cyclamate, good separations were obtained from other preservatives (e.g. benzoic acid, p-hydroxybenzoic acid esters, propionic acid), organic acids (citric, lactic, and tartaric), and sweetening agents (acesulfame K, aspartame, saccharin) tested.  The method is thus simple and suited for routine analyses. (Ernaehrung (Vienna), 13(2), 82, 1989. Chem Abstr 110:211091)

 

·     Licorice root is often co-prescribed with Bupleuri radix (Bupleurum root) for decoctions used in oriental traditional medicine.  The water solubility of saikosaponin A, the active principle of Bupleurum roots, was increased in the presence of the water ext. or the saponin fraction of licorice root and this solubilizing effect was due to glycyrrhizin, the major active saponin of this plant drug.  A solubilizing effect on saikosaponin A was also observed with the 30-b-glucoside ester and  30-b-glucuronide ester of glycyrrhizin.  The 30-b-glucoside ester improved the solubilizing property of glycyrrhizin.  Aqueous solutions of the 30-b-glucoside ester and the 30-b-glucuronide ester solubilized dl-b-tocopherol and oleanolic acid, both of which are almost insol. In water. (Chem. Pharm. Bull.,36(9), 3491, 1988. Chem Abstr 110:44800)

 

·     A new 2-arylbenzofuran deriv. named licocoumarone (I) was isolated from com. available xibei licorice (seihoku kanzo) along with a known 3-arylcoumarin deriv., glycycoumarin.  The structure of I was elucidated as 2-(2,4-dihydroxyphenyl)-6-hydroxy-4-methoxy-5-(3-methyl-2-butenyl)coumarone on the basis of spectroscopic and chem. studies.  Both I and glycycoumarin exhibited antimicrobial activities, whereas only I had antioxidant activity. (Chem. Pharm. Bull.,36(9), 3474, 1988. Chem Abstr 110,54473)

 

·     The principal constituent of liquorice to which it owes its characteristic sweet taste is glycyrrhizin which is present in different varieties in a concentration of 2-14%. This principle is not found in the aerial parts of the plant. Spanish liquorice  contains  6-8%  glycyrrhizin,  while Russian liquorice contains 10-14%; the     concentration of bitter principles is much less in the former. Liquorice from plants experimentally grown in Srinagar was found to contain 3.6% glycyrrhizin. Other  constituents  present  in liquorice are: glucose  (up to 3.8%), sucrose (2.4-6.5%), mannite, starch (c. 30% ), asparagine, bitter principles, resins  (2-4%), a volatile oil (0.03-0.035%) and colouring matter. The yellow colour is due to the     anthoxanthin glycoside, isoliquiritin [C22H22O9; m.p., 185-86° (decomp.)] which, undergoes partial conversion to liquiritin (m.p., 212°) during drying and storage of roots. Isoliquiritin gives on hydrolysis isoliquiritigenin (2,4,4'-trihydroxy chalcone, C15H12O4, m.p.202-4°) while liquiritin gives liquiritigenin (7-4'-dihydroxy flavone, C15H12O4; m.p., 207°) as aglucone. Both isoliquiritin and     liquiritin are bitter with a sweet after-taste and stimulate the salivary glands. Commercial samples contain c. 2.2% of isoliquiritin. A steroid estrogen, possibly estriol, is also reported to be present in liquorice. The presence in the inner bark of a haemolytically active saponin has been reported. Chinese liquorice     contains a substance (C20H12O9; m.p., 202-4°) which is hydrolysed by acids to lapachol derivatives ( Thorpe, VII, 362;     Kapur et al., loc. cit.; Trease, 393; McIlroy, 40; Puri & Seshadri, J.Sci. industr. Res., 1954, 13B, 475; Chem. Abstr., 1950, 44, 4635).

 

·     Glycyrrhizin occurs in liquorice as the calcium or potassium salt of the trihydroxy acid, glycyrrhizic acid (C42H62O16; m.p., 205°). It is nearly 50 times as sweet as cane sugar and its sweetness is perceptible even in a dilution of 1: 20,000. A solution of glycyrrhizin in hot water gelatinizes on cooling. On hydrolysis it yields glycyrrhetic acid (C30H46O4) and mannuronic  acid. The former appears to exist in two forms (m.p., 283° and 296°) and is a triterpene related to oleanolic     acid. It has a haemolytic action, though glycyrrhizic acid itself does not cause haemolysis (Chem. Abstr., 1937, 31, 3057; 1939, 33, 2528; The Merck Index, 470).

 

·     Spent pulp left after the extraction of the water-soluble matter is subjected to a second extraction with dilute caustic soda solution and the secondary extract utilized in the manufacture of Fire foam Liquid, used as foam stabilizer in fire extinguishers. The secondary extract may be used as a wetting and foaming agent in ore beneficiation by the froth flotation process and as a wetting, spreading and sticking agent in insecticide  formulations. The spent pulp may be hydrolysed by     acids to fermentable sugars and used for the production of alcohol or used in culture media for food yeast. The exhausted pulp may be used for the culture of mushrooms and for the manufacture of insulation board, boxwood and other fibre products (Hill, 247; Chem. Abstr., 1952, 46, 8815).

 

·     Several compounds have been isolated from the roots, such as:18a-hydroxyglycyrrhetic acid, glabrolide, deoxyglabrolide, isoglabrolide,     glycyrrhetol, liquiritic acid, liquiritogenine, liquiritoside,     isoliquiritoside, uralenic acid, methyl glycyrrhetinate, liquiritin,     isoliquiritin, licoricidin, isoshaftoside (0.12%), shaftoside (0.015%), violanthin (0.015%) and ononin (0.032%) (Miyazawa & Kameoka, Flavour & Fragrance J, 1990, 5, 157; Yang et al, Acta Pharm Sin, 1990, 25 840).

 

·     Soyasaponins were isolated from the hypocotyl, rootlet and seed. Cell     suspension cultures also produce soyasaponins I and II and betulinic acid;  they fail to produce glycyrrhizin (Hayashi et al, Planta Med, 1993, 59, 351; Hayashi et al, Phytochemistry, 1990, 29, 3127).

 

·     The air-dried root of G. glabra var. glandulifera Regel & Herder from China yielded 0.03% of yellowish-green volatile oil. It contained 81 volatile components of which 35% were terpenoids. The main constituents were octanoic acid (11.4%), paeonol (8.9%), octadecane (8.6%),     benzaldehyde (7.5%), a-terpineol (7.5%) and 4-terpineol (7.2%)     (Miyazawa & Kameoka, Flavour & Fragrance J, 1990, 5, 157).

 

      A reverse phase HPLC method developed to deter­mine glycyrrhizin in Glycyrrhiza glabra and its extract has been described. The method involves separation of com­pound using the mobile phase acetonitrile: water.phosphoric acid:32:67:l and detection of chromato-gram at 250 nm using photodiode array detector. The sensitivity of the method was observed to be 2.0 microg and the linearity was observed in the range of 2.0 microg-16.0 microg/ul. The proposed method being precise, sensitive and reproducible, can be used for detection, monitoring and quantification of glycyrrhizin in G.glabra and its extract. (Chauhan, S.K.et.al, Indian Drugs, 36(8), 521,1999 )

 

·     Two new 3-arylcoumarin derivatives were isolated  from the root of Glycyrrhiza glabra (licorice; Fabaceae),  and their structures were elucidated as 2',4'-dihydroxy-  {6",6"-dimethylpyranol(2",3":7m8)}-3-arylcoumarin and  {6",6"-dimethylprano(2",3":7,8)}-2'-hydroxy-4'-methox  y-3-arylcoumarin on the basis of spectroscopic evidence.  Chemical syntheses of these two pyrano-3-arylcpumarins  are described. Two other known iso-flavonoids glabrene and  glabrone were also obtained, and the structure of the former  is revised based on 13C-NMR analysis and NOE experiments. (Kinoshita, T. et.al.; Natural Product Letters,  9(4),  289, 1997)

 

The following triterpenes and phenolic compounds were isolated from G.glabra inaadition to the above compounds mentioned.

 

      ·           Triterpenes

Liquiritic acid (Cononica et al, Gazzchim. Ital. 96, 843,1966); 11-Deoxoglabrolide (Canonica et. al., Gazz Chem. Ital., 96, 772,1966); 11-Deoxoglycyrrhetin acid (Canonica et al, Gazz. Chim Ital 96,  772, 833, 843 ,1966); 3b-Hydroxy-11, 13 (18)-Oleanadien-30-oic acid(Canonica et al, Gazz. Chem. Ital. 97,769, 1347, 1359, 1967); Russo G., Corsi Semin Chim, 20,1968); 24-Hydroxy-11-deoxo-glycyrrhetic acid (Canonica et al Gazz. Chem. Ital., 97, 1359, 1967); 18a-Hydroxyglycyrrhetic acid (Canonica et al, Gazz. Chem. Ital, 97,  769, 1967); Liquiridiolic acid (Canonica et al, Gazz Chem. Ital 98,  712, 1968); 24-Hydroxyliquiritic acid (Canonica et al, Gazz. Chem. Ital, 97, 1359, 1967); Glabric acid,  (Beaton and Spring, J. Chem.Soc., 2417,1956); 3,24-Dihydroxy-11, 13 (18)-Oleanodien-30-oic acid - (Bogatkina et al, Khim-Prir. Soedin, 101,1974; Chem. Nat. Compds. 10, 114,1976); Uralenic acid (Belaus et al Chem. Abs. 62,13186a, 1965); 28-Hydroxyglycyrrhetic acid (Elgamal and EI Tawil,  Planta Med, 27,159, 1975).

 

·     Phenolic compounds

Liquirtin (Shinoda and Ueeda, yakugaku Zoashi 54,  707,1934; Shinoda and Ueeda, Chem. Ber. 67, 434, 1934 ; Puri and Seshadri,  J. Sci. Ind. Res., 13B,  475, 1954); Liquirigenin (Litvienko and Obolentseva, Chem. Abstr., 62,  8286a ,1965; Arakawa and Nakakazaki, Chem.. Ind. 73, 1960;  Gaffield,  Tetrahed  26,  4093,1970); Neoisoliquiritin, Neoliquiritin, Liquiritinapioside, Liquiritigenin 7-apisoylgucoside, Rhamnoisoliquiritin, Liquraside, Licurazid (Litvinenko and Obolentseva,  Chem. Abs. 62, 8286a, 1965); Litvinenko  (Chem. Abs. 60, 14579,1964; Afchar et al.,  Plant Med. Phytother, 14, 46,1980; Nakanishi et al., Phytochem 24,  339, 1985; Meithing et al., Chem. Abs. 115, 994271991; Van Hulle et al., Planta Med., 20,  278,1971; Litvinenko, Chem. Abs. 60, 6700, 1964; Livinenko and Kovalev. Kokl. Akad. Nauk SSSR, 169, 347,1966; Miething and Speicher-Brinker, Arch Pharm. 322, 141, 1989; Shibata S., Int. J. Pharmacog 32, 75,1994); Liqcoumarin (Bhardwaj et al., Phytochem 15,  352, 1976; Bhardwaj et al.,Phytochem,15,1182, 1976; Bhardwaj et al., Curr. Sci., 46, 754, 1977; Bhardwaj et al Phytochem 16, 402,1977); Glabridin, Glabrol (Sitoh et al., Chem. Pharm. Bull., 24, 752,1976); 3-Hydroxyglabrol (Mitscher et al., Heterocycles 9,  1533,1978; Mitscher et al., J. Nat. Prod., 43,  259,1980), 3'-Hydroxy-4'-O-Methyl glabridin (Kinoshita, Heterocycles,43, 581,1996); Kanzonol U, Kanzonol V (Asada et al., Phytochem 34,1049,1993); Kanzonol X, Kanzonol Y, Glabrene (Fukui et al., Phytochem., 43,  1119, 1996); Methylhispaglabridin B, Prenyllicoflavone A, Shinflavanone (Kitagawa et al., Chem. Pharm. Bull., 42,1056, 1994); Kanzonol, Kanzonol T (Fukai et al., Heterocycles 38, 1089,1994; Fukai et al., Phytochem 43,  531,1996); Glabranin, Licoflavanone  (Kattaev and Nikonov, Khim Prir Soedin, 805, 1972; Fukui et al., Chem. Pharm Bull, 36,  4174,1988); Folerogenin  (Litvinenko and Nadezhina, Chem.  Abs., 76  124123 f, 1972); Glyphoside (Bohm B A,  The Flavonoids, 597; Chapman and Hall 1975); Isomucronulatol (Ingham J. L., Phytochem, 16, 1957, 1977); Kanzonol  Y and Kanzonol Z.  (Fukui et al.,  Phytochem.,  49 (7), 2005,1998); 3,3'-Di-g,  g-Dimethylallyl-2',4,4'-trihydroxychalcone and [6", 6"- Dimethylpyrano (2",2":4, 5)]-3'-g, g-dimethyallyl-2',3,4'-trihydroxychalcone, glabrocoumarone A and glabrocoumarone B (Kinoshita et al., Chem. Pharm Bull, 1218, 1997); Licoagrochalcone A and Licoagrocarpin (Asada et al., Phytochem,  47 (3), 389,1998); Licoagrone, Afrormosin, Odoratin, Phaseol and Echinatin (Asada et al., Phytochem., 50, 1015,1999).