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Current Bioactive Compounds

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ISSN (Online): 1875-6646

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Research Article

Chemicals Constituents of the Algerian Glycyrrhiza glabra L. Root Extracts and their Antioxidant, Antibacterial and Anticholinesterase Activities

Author(s): Saïd Barek*, Mohammed N. Rahmoun, Mohammed Aissaoui, Chawki Bensouici, Imad A. El Haci, Ridha Hassaine and Noureddine Choukchou-Braham

Volume 16, Issue 8, 2020

Page: [1215 - 1224] Pages: 10

DOI: 10.2174/1573407216666200127125123

Price: $65

Abstract

Background: Glycyrrhiza glabra L. is an important medicinal plant endowed with various pharmacological virtues. This study aimed to investigate the antioxidant, antibacterial, and anticholinesterase activities of the Algerian Glycyrrhiza glabra L. roots extracts.

Methods: The chemical composition of both chloroformic (LCh) and ethyl acetate (LAE) extracts were analyzed by RP-HPLC-PDA and 1H NMR spectroscopy. The antioxidant activity was evaluated using hydrogen atoms transfer methods (DPPH) and single electron transfer (ABTS and CUPRAC assays). The antibacterial activity was realized against different strains via the Minimal Inhibitory Concentration (MIC), when the anticholinesterase activity was performed through the acetylcholinesterase and butyrylcholinesterase enzymes inhibition.

Results: The chemical analysis revealed the presence of phenolic acids (gallic acid, p-coumaric acid) and a hydroxycinnamic compound (ferulic acid). However, flavonoids were represented by quercetin, rutin (flavonol), and glabridin (isoflavane). The 1H NMR of the L4 fraction from LCh extract allowed to characterize the structure of glabridin.

The antioxidant assays revealed that LCh extract is the best among other extracts with IC50 DPPH of 33.94 μg/mL, IC50 ABTS of 3.45 μg/mL and CUPRAC A0.5 of 21.78 μg/mL. The LCh extract displayed an effective antibacterial activity with MIC’s of 19.5 μg/mL against seven gram positive and negative bacteria strains. The same extract showed a potent butyrylcholinesterase inhibitory activity with IC50= 4.72 ± 0.72 μg/mL, which is too strong than the standard drug.

Conclusion: The study demonstrated that G. glabra root extracts had a high antibacterial, and free radical scavenging. It was also able to inhibit cholinesterase enzymes, which confirm the effectiveness of phytoconstituents present in the plant, especially flavonoids.

Keywords: 1H NMR spectroscopy, ABTS, Butyrylcholinesterase inhibitory activity, Glabridin, Glycyrrhiza glabra L, Minimal Inhibitory Concentration (MIC), RP-HPLC-PDA.

Graphical Abstract

[1]
Carocho, M.; Ferreira, I.C.F.R. A review on antioxidants, prooxidants and related controversy: Natural and synthetic compounds, screening and analysis methodologies and future perspectives. Food Chem. Toxicol., 2013, 51, 15-25.
[http://dx.doi.org/10.1016/j.fct.2012.09.021] [PMID: 23017782]
[2]
Sakat, S.; Juvekar, A.R.; Gambhire, M.N. In vitro antioxidant and anti-inflammatory activity of methanol extract of Oxalis corniculata Linn. Int. J. Pharm. Pharm. Sci., 2010, 2, 146-155.
[3]
Yang, J.; Martinson, T.E.; Liu, R.H. Phytochemical profiles and antioxidant activities of wine grapes. Food Chem., 2009, 116, 332-339.
[http://dx.doi.org/10.1016/j.foodchem.2009.02.021]
[4]
Khalfallah, A.; Berrehal, D.; Bensouici, C.; Kabouche, A.; Semra, Z.; Voutquenne-Nazabadioko, L.; Alabdul Magid, A.; Kabouche, Z. Flavonoids, cytotoxic, antioxidant and antibacterial activities of Evax pygmaea. Pharm. Biol., 2017, 55(1), 2292-2296.
[http://dx.doi.org/10.1080/13880209.2017.1405997] [PMID: 29191075]
[5]
Vats, S.; Kamal, R. Identification of flavonoids from plant parts and callus culture of Gymnema sylvestre R.Br.: An antidiabetic plant. Curr. Bioact. Compd., 2016, 12, 264-268.
[http://dx.doi.org/10.2174/1573407212666160425150831]
[6]
Fawcett, J.R.; Bordayo, E.Z.; Jackson, K.; Liu, H.; Peterson, J.; Svitak, A.; Frey, W.H., II Inactivation of the human brain muscarinic acetylcholine receptor by oxidative damage catalyzed by a low molecular weight endogenous inhibitor from Alzheimer’s brain is prevented by pyrophosphate analogs, bioflavonoids and other antioxidants. Brain Res., 2002, 950(1-2), 10-20.
[http://dx.doi.org/10.1016/S0006-8993(02)02981-5] [PMID: 12231224]
[7]
Mukherjee, P.K.; Kumar, V.; Mal, M.; Houghton, P.J. Acetylcholinesterase inhibitors from plants. Phytomedicine, 2007, 14(4), 289-300.
[http://dx.doi.org/10.1016/j.phymed.2007.02.002] [PMID: 17346955]
[8]
Saklani, A.; Kutty, S.K. Plant-derived compounds in clinical trials. Drug Discov. Today, 2008, 13(3-4), 161-171.
[http://dx.doi.org/10.1016/j.drudis.2007.10.010] [PMID: 18275914]
[9]
Demkura, P.V.; Ballaré, C.L. UVR8 mediates UV-B-induced Arabidopsis defense responses against Botrytis cinerea by controlling sinapate accumulation. Mol. Plant, 2012, 5(3), 642-652.
[http://dx.doi.org/10.1093/mp/sss025] [PMID: 22447155]
[10]
Jia, P.; Sheng, R.; Zhang, J.; Fang, L.; He, Q.; Yang, B.; Hu, Y. Design, synthesis and evaluation of galanthamine derivatives as acetylcholinesterase inhibitors. Eur. J. Med. Chem., 2009, 44(2), 772-784.
[http://dx.doi.org/10.1016/j.ejmech.2008.04.018] [PMID: 18550228]
[11]
Ramesh, B.N.; Rao, T.S.S.; Prakasam, A.; Sambamurti, K.; Rao, K.S.J. Neuronutrition and Alzheimer’s disease. J. Alzheimers Dis., 2010, 19(4), 1123-1139.
[http://dx.doi.org/10.3233/JAD-2010-1312] [PMID: 20308778]
[12]
Gali, L.; Bedjou, F. antioxidant and anticholiesterase effects of the ethanol extract, ethanol extract fractions and total alkaloids from the cultivated Ruta chalepensis. S. Afr. J. Bot., 2019, 120, 163-169.
[http://dx.doi.org/10.1016/j.sajb.2018.04.011]
[13]
Muralidharan, P.; Balamurgan, G.; Babu, V. Cerebroprotective effect of Glycyrrhiza glabra L. root extract on hypoxic rats. Bangladesh J. Pharmacol., 2009, 4, 60-64.
[14]
Kataria, Hemraj,. R.; Singh, G.; Gupta, A.; Jalhan, S.; Jindal, A. Pharmacological activities on Glycyrrhiza glabra- A review. Asian. J. Pharm. Clin. Res, 2013, 6, 5-7.
[15]
Kaur, R. Glycyrrhiza glabra: A phytopharmacological review. I.J.P.S.R., 2013, 4, 2470-2477.
[16]
Jahan, Y.; Siddique, H.H. Study of antitussive potential of Glycyrrhiza glabra and Adhotha vasica using a cough model induced by SO2 gaz in mice. I.J.P.S.R. 2012, 3, 1668-1674.
[17]
Murray, W.J. Herbal medications for gastrointestinal problems, Herbal Medicinals- A Clinician’s guide; Pharmaceutical Products Press: New York, 1998.
[18]
Vaya, J.; Belinky, P.A.; Aviram, M. Antioxidant constituents from licorice roots: isolation, structure elucidation and antioxidative capacity toward LDL oxidation. Free Radic. Biol. Med., 1997, 23(2), 302-313.
[http://dx.doi.org/10.1016/S0891-5849(97)00089-0] [PMID: 9199893]
[19]
van Rossum, T.G.; Vulto, A.G.; de Man, R.A.; Brouwer, J.T.; Schalm, S.W. Review article: Glycyrrhizin as a potential treatment for chronic hepatitis C. Aliment. Pharmacol. Ther., 1998, 12(3), 199-205.
[http://dx.doi.org/10.1046/j.1365-2036.1998.00309.x] [PMID: 9570253]
[20]
Ates, D.A.; Erdoglu, O.T. Antimicrobial activities of various medicinal and commercial plant extract. Turk. J. Biol., 2003, 27, 157-162.
[21]
Statti, G.A.; Tundis, R.; Sacchetti, G.; Muzzoli, M.; Bianchi, A.; Menichini, F. Variability in the content of active constituents and biological activity of Glycyrrhiza glabra. Fitoterapia, 2004, 75(3-4), 371-374.
[http://dx.doi.org/10.1016/j.fitote.2003.12.022] [PMID: 15158998]
[22]
Aly, A.M.; Al-Alousi, L.; Salem, H.A. Licorice: A possible anti-inflammatory and anti-ulcer drug. AAPS PharmSciTech, 2005, 6(1), E74-E82.
[http://dx.doi.org/10.1208/pt060113] [PMID: 16353966]
[23]
Shin, Y.W.; Bae, E.A.; Lee, B.; Lee, S.H.; Kim, J.A.; Kim, Y.S.; Kim, D.H. In vitro and in vivo antiallergic effects of Glycyrrhiza glabra and its components. Planta Med., 2007, 73(3), 257-261.
[http://dx.doi.org/10.1055/s-2007-967126] [PMID: 17327992]
[24]
Ram, S.A. Bibliometric assessement of licorice (Glycyrrhiza glabra) research trends. Ann. Lib. Info. Stu, 2015, 62, 27-32.
[25]
Vermerius, W.; Nicholson, R. Bibliometric assessement of licorice (Glycyrrhiza glabra) research trends. Ann. Lib. Info. Stu, 2006, 62, 27-32.
[26]
Topçu, G.; Ay, A.; Bilici, A.; Sarikürkcü, C.; Öztürk, M.; Ulubelen, A. A new flavon from antioxidant extracts of Pistacia terebinthus. Food Chem., 2007, 103, 816-822.
[http://dx.doi.org/10.1016/j.foodchem.2006.09.028]
[27]
El Haci, I.A.; Mazari, W.; Atik-Bekkara, F.; Mouttas-Bendimerad, F.; Hassani, F. Bioactive compounds from the flower part of Polygonum maritimum L. collected from Algerian coast. Curr. Bioact. Compd., 2020, 16(4), 543-545.
[28]
Lekhal, H.; Boudiar, T.; Kabouche, A.; Laggoune, S.; Kabouche, Z.; Topçu, G. Flavonoids and antioxidant activity of Stachys ocymastrum. Chem. Nat. Compd., 2011, 46, 964-966.
[http://dx.doi.org/10.1007/s10600-011-9797-4]
[29]
Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic. Biol. Med., 1999, 26(9-10), 1231-1237.
[http://dx.doi.org/10.1016/S0891-5849(98)00315-3] [PMID: 10381194]
[30]
Apak, R.; Güçlü, K.; Ozyürek, M.; Karademir, S.E. Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method. J. Agric. Food Chem., 2004, 52(26), 7970-7981.
[http://dx.doi.org/10.1021/jf048741x] [PMID: 15612784]
[31]
Rhee, K.; Van de Meent, M.; Ingkaninan, K.; Verpoorte, R. Screening for Acetylcholinesterase inhibitors using silica gel chromatography in combination with bioactive staining. J. Chromatogr. A, 2001, 915, 217-223.
[http://dx.doi.org/10.1016/S0021-9673(01)00624-0] [PMID: 11358251]
[32]
Methods for Antimicrobial Susceptibility Tests for Bacteria that Growth Aerobically 2009.
[33]
Wijngaad, H.H.; Brunton, N. The optimization of solid-liquid extraction of antioxidants from the apple pomace by response surface methodology. J. Food Eng., 2010, 96, 134-140.
[http://dx.doi.org/10.1016/j.jfoodeng.2009.07.010]
[34]
Damle, M. Glycyrrhizaglabra (Liquorice)-A potent medicinal herb. Int. J. Herb. Med, 2014, 2, 132-136.
[35]
Shanker, K.; Fatima, A.; Negi, A.S.; Gupta, M.; Darokar, M.P.; Gupta, M.M.; Khanuja, S.P.S. RP-HPLC method for quantitation of Glabridin in Yashti-madhu (Glycyrrhiza glabra). Chromatographia, 2007, 65, 771-774.
[http://dx.doi.org/10.1365/s10337-007-0230-x]
[36]
Liao, W.C.; Lin, Y.H.; Chang, T.M.; Huang, W.Y. Identification of two llicoroce species, Glycyrrhiza uralensis and Glycyrrhiza glabra, based on separation and identification of their bioactive components. Food Chem., 2012, 132, 2188-2193.
[http://dx.doi.org/10.1016/j.foodchem.2011.12.051]
[37]
Hatano, T.; Fukuda, T.; Liu, Y.Z.; Noro, T.; Okuda, T. Phenolic constituents of licorice. IV. Correlation of phenolic constituents and licorice specimens from various sources, and inhibitory effects of licorice extracts on xanthine oxidase and monoamine oxidase. Yakugaku Zasshi, 1991, 111(6), 311-321.
[http://dx.doi.org/10.1248/yakushi1947.111.6_311] [PMID: 1941536]
[38]
Hayashi, H.; Hattori, S.; Inoue, K.; Khodzhimatov, O.; Ashurmetov, O.; Ito, M.; Honda, G. Field survey of Glycyrrhiza plants in Central Asia (3). Chemical characterization of G. glabra collected in Uzbekistan. Chem. Pharm. Bull. (Tokyo), 2003, 51(11), 1338-1340.
[http://dx.doi.org/10.1248/cpb.51.1338] [PMID: 14600388]
[39]
Ksouri, R.; Megdiche, W.; Falleh, H.; Trabelsi, N.; Boulaaba, M.; Smaoui, A.; Abdelly, C. Influence of biological, environmental and technical factors on phenolic content and antioxidant activities of Tunisian halophytes. C. R. Biol., 2008, 331(11), 865-873.
[http://dx.doi.org/10.1016/j.crvi.2008.07.024] [PMID: 18940702]
[40]
Ksouri, R.; Falleh, H.; Megdiche, W.; Trabelsi, N.; Mhamdi, B.; Chaieb, K.; Bakrouf, A.; Magné, C.; Abdelly, C. Antioxidant and antimicrobial activities of the edible medicinal halophyte Tamarix gallica L. and related polyphenolic constituents. Food Chem. Toxicol., 2009, 47(8), 2083-2091.
[http://dx.doi.org/10.1016/j.fct.2009.05.040] [PMID: 19500639]
[41]
Ali, R.; Hossain, M.; Kuri, S.; Islam, M.S. Evaluation of total Phenolic content, free radical scavenging activity and phyto-chemical screening of different extracts of Averhoa bilimbi (fruits). Int. Curr. Pharm. J., 2013, 2, 92-96.
[http://dx.doi.org/10.3329/icpj.v2i4.14058]
[42]
Ju, H.S.; Li, X.J.; Zhao, B.L.; Han, Z.W.; Xin, W.J. Effects of glycyrrhiza flavonoid on lipid peroxidation and active oxygen radicals. Yao Xue Xue Bao, 1989, 24(11), 807-812.
[PMID: 2618676]
[43]
Badkhan, Y.; Yadar, A.S.; Bajaj, A.; Ajit, K.; Sharma, V.; Raghuwanshi, D.K. Glycyrrhiza glabra L. A miracle medicinal herb. Indo. Am. J. Pharm. Res, 2014, 4, 5808-5816.
[44]
Lateef, M.; Iqbal, L.; Fatima, N.; Siddiqui, K.; Afza, N.; Zia-ul-Haq, M.; Ahmad, M. Evaluation of antioxidant and urease inhibition activities of roots of Glycyrrhiza glabra. Pak. J. Pharm. Sci., 2012, 25(1), 99-102.
[PMID: 22186315]
[45]
Visavadiya, N.P.; Soni, B.; Dalwadi, N. Evaluation of antioxidant and anti-atherogenic properties of Glycyrrhiza glabra root using in vitro models. Int. J. Food Sci. Nutr., 2009, 60(Suppl. 2), 135-149.
[http://dx.doi.org/10.1080/09637480902877998] [PMID: 19384750]
[46]
Howes, M.J.R.; Perry, N.S.L.; Houghton, P.J. Plants with traditional uses and activities, relevant to the management of Alzheimer’s disease and other cognitive disorders. Phytother. Res., 2003, 17(1), 1-18.
[http://dx.doi.org/10.1002/ptr.1280] [PMID: 12557240]
[47]
Dasmalchi, K.; Dorman, H.J.D.; Vuorela, H.; Hilttunen, R. Plants as potential sources for drug development against Alzheimer’s disease. Int. J. Biomed. Pharm. Sci, 2007, 1, 83-104.
[48]
Vinutha, B.; Prashanth, D.; Salma, K.; Sreeja, S.L.; Pratiti, D.; Padmaja, R.; Radhika, S.; Amit, A.; Venkateshwarlu, K.; Deepak, M. Screening of selected Indian medicinal plants for acetylcholinesterase inhibitory activity. J. Ethnopharmacol., 2007, 109(2), 359-363.
[http://dx.doi.org/10.1016/j.jep.2006.06.014] [PMID: 16950584]
[49]
Taylor, P.; Camp, S.; Radić, Z. Acetylcholinester-ase.Encyclopedia of Neuroscience; Larry, R.S., Ed.; Academic Press: Oxford, 2009.
[50]
Demizu, S.; Kajiyama, K.; Takahashi, K.; Hiraga, Y.; Yamamoto, S.; Tamura, Y.; Okada, K.; Kinoshita, T. Antioxidant and antimicrobial constituents of licorice: Isolation and structure elucidation of a new benzofuran derivative. Chem. Pharm. Bull. (Tokyo), 1988, 36(9), 3474-3479.
[51]
Poltrai, O. Antioxidants and free radicals scavengers of natural origin. Curr. Org. Chem., 1997, 1, 415-440.
[52]
Murugan, T.; Wins, J.A.; Murugan, M. Antibacterial activity and phytochemical constituents of leaf extract of Cassia auriculata. Indian J. Pharm. Sci., 2013, 75(1), 122-125.
[http://dx.doi.org/10.4103/0250-474X.113546] [PMID: 23901174]
[53]
Sharma, V.; Agrawal, R.C.; Pandey, S. Phytochemical screening and determination of antibacterial and antioxidant potential of Glycyrrhiza glabra root extracts. J. Environ. Res. Dev., 2013, 7, 1552-1558.
[54]
Deepika, T.; Jain, A.; Ghoshal, G. Evaluation of phytochemical, antioxidant and antimicrobial properties of Glycyrrhizin extracted from roots of Glycyrrhiza glabra. J. Sci. Res, 2016, 75, 487-494.
[55]
Asl, M.N.; Hosseinzadeh, H. Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds. Phytother. Res., 2008, 22(6), 709-724.
[http://dx.doi.org/10.1002/ptr.2362] [PMID: 18446848]
[56]
Cowan, M.M. Plant products as antimicrobial agents. Clin. Microbiol. Rev., 1999, 12(4), 564-582.
[http://dx.doi.org/10.1128/CMR.12.4.564] [PMID: 10515903]
[57]
Manoj, M.; Nitalikar, K.C.; Balaji, M.; Dhore, V.; Sajid, N. Shikalgar. Studies of antibacterial activities of Glycyrrhiza glabra root extract. Int. J. Pharm. Tech. Res., 2010, 2, 899-901.
[58]
Zablotowicz, R.M.; Hoagland, R.E.; Wagner, S.C. Effect of saponins on the growth and activity of rhizosphere bacteria. Adv. Exp. Med. Biol., 1996, 405, 83-95.
[http://dx.doi.org/10.1007/978-1-4613-0413-5_8] [PMID: 8910697]
[59]
Patil, S.M.; Patil, M.B.; Sapkale, G.N. Antimicrobial activity of Glycyrrhiza glabra linn roots. Int. J. Chem. Sci, 2009, 7, 585-591.
[60]
Shimada, T. Salivary proteins as a defense against dietary tannins. J. Chem. Ecol., 2006, 32(6), 1149-1163.
[http://dx.doi.org/10.1007/s10886-006-9077-0] [PMID: 16770710]

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