Determination and Comparison of Bioactive Compounds in Different Parts of Glycyrrhiza Species

Abstract

Glycyrrhiza spp., one of the most widely used herbal medicine for centuries in the world, contain a large number of bioactive such as triterpene saponins and flavonoids which are the main constituents and show broad biological activity. The present study aimed to evaluate the phytochemical profile of extracts from different parts (roots, stems and leaves) of all wild Glycyrrhiza spp. grown in Turkey and to reveal that other parts besides the roots are a rich source of bioactive compounds with potential use in the pharmaceutical and food industries. For this purpose, extracted bioactive compounds from different parts of five Glycyrrhiza spp. collected in different provinces of Turkey were determined and compared. The microwave-assisted extraction method, which is mentioned as a green technique and requires low solvent and extraction time, was applied. Determination of bioactives was performed using liquid chromatography- electrospray ionisation tandem mass spectrometry (LC-ESI-MS/MS). Among the collected Glycyrrhiza spp.; in leaf parts, the highest glycyrrhizin (GL) (2.05±0.07 mg g-1) and glycyrrhetinic acid (GA) (0.107±0.005 mg g-1) contents were found in Glycyrrhiza flavescens ssp. flavescens; the highest carbenoxolone (CBX) (0.133±0.006 mg g-1) and liquiritin (LQ) (1.644±0.014mg g-1) contents were in Glycyrrhiza glabra grown in Polatlı. In stem parts, the highest GL (2.735±0.04 mg g-1), CBX (0.069±0.004 mg g-1) and LQ (0.602±0.010 mg g-1) contents were determined in G. glabra plant growing in Ankara. In root parts, the highest GL (14.68±0.09 mg g-1) and LQ (9.735±0.046 mg g-1) contents were detected in G. glabra plant growing in Gaziantep while the highest GA (0.136±0.005 mg g-1) and CBX (0.188±0.067 mg g-1) contents in Glycyrrhiza flavescens ssp. antalyensis. Thus, it was determined which location in Turkey and which parts of Glycyrrhiza spp. that grow wild in Turkey can be used as a priority for the food and pharmaceutical industry with this study.

Keywords

• Glycyrrhiza
• microwave-assisted extraction
• bioactive compounds
• LC-ESI-MS/MS

References

1. Alsaadi DHM., Raju A, Kusakari K, Karahan F, Sekeroglu N, Watanabe T (2020). Phytochemical Analysis and Habitat Suitability Mapping of Glycyrrhiza glabra L. Collected in the Hatay Region of Turkey. Molecules 25, 1–13. https://doi.org/10.3390/molecules25235529
2. Bharathala S, Kotarkonda LK, Singh VP, Singh R, Sharma P (2021). In silico and experimental studies of bovine serum albumin-encapsulated carbenoxolone nanoparticles with reduced cytotoxicity. Colloids Surfaces B Biointerfaces 202, 111670. https://doi.org/10.1016/j.colsurfb.2021.111670
3. Cheel J, Antwerpen PV, Tůmová L, Onofre G, Vokurková D, Zouaoui-Boudjeltia K, Vanhaeverbeek M, Nève J (2010). Free radical-scavenging, antioxidant and immunostimulating effects of a licorice infusion (Glycyrrhiza glabra L.). Food Chemistry 122, 508–517. https://doi.org/10.1016/j.foodchem.2010.02.060
4. Cho HJ, Lim SS, Lee YS, Kim JS, Lee CH, Kwon DY, Park JHY (2010). Hexane/ethanol extract of Glycyrrhiza uralensis licorice exerts potent anti-inflammatory effects in murine macrophages and in mouse skin. Food Chemistry 121, 959–966. https://doi.org/10.1016/j.foodchem.2010.01.027
5. Cinatl J, Morgenstern B, Bauer G, Chandra P, Rabenau H, Doerr HW (2003). Glycyrrhizin, an active component of liquorice roots, and replication of SARS-associated coronavirus. Lancet 361, 2045–2046. https://doi.org/10.1016/S0140-6736(03)13615-X
6. Csuk R, Schwarz S, Kluge R, Ströhl D (2010). Synthesis and biological activity of some antitumor active derivatives from glycyrrhetinic acid. European Journal of Medicinal Chemistry 45, 5718–5723. https://doi.org/10.1016/j.ejmech.2010.09.028
7. Duran A, Martin E, Kucukoduk M (2012). Cytotaxonomical study in some taxa of the genus Glycyrrhiza L . ( Fabaceae ).
8. Hosseinzadeh H, Nassiri-Asl M (2015). Pharmacological Effects of Glycyrrhiza spp. and Its Bioactive Constituents: Update and Review. Phytotherapy Research 29, 1868–1886. https://doi.org/10.1002/ptr.5487

9. Jiang Z, Wang Y, Zheng Y, Yang J, Zhang L (2016). Ultra high performance liquid chromatography coupled with triple quadrupole mass spectrometry and chemometric analysis of licorice based on the simultaneous determination of saponins and flavonoids. Journal of Separation Science 39, 2928–2940. https://doi.org/10.1002/jssc.201600246
10. Kim JK, Oh SM, Kwon HS, Oh YS, Lim SS, Shin HK (2006). Anti-inflammatory effect of roasted licorice extracts on lipopolysaccharide-induced inflammatory responses in murine macrophages. Biochemical and Biophysical Research Communications 345, 1215–1223. https://doi.org/10.1016/j.bbrc.2006.05.035
11. Krausse R, Bielenberg J, Blaschek W, Ullmann U (2004). In vitro anti-Helicobacter pylori activity of Extractum liquiritiae, glycyrrhizin and its metabolites. Journal of Antimicrobial Chemotherapy 54, 243–246. https://doi.org/10.1093/jac/dkh287
12. Li G, Nikolic D, Van Breemen RB (2016). Identification and Chemical Standardization of Licorice Raw Materials and Dietary Supplements Using UHPLC-MS/MS. Journal of Agricultural and Food Chemistry 64, 8062–8070. https://doi.org/10.1021/acs.jafc.6b02954
13. Liao WC, Lin YH, Chang TM, Huang WY (2012). Identification of two licorice species, Glycyrrhiza uralensis and Glycyrrhiza glabra, based on separation and identification of their bioactive components. Food Chemistry 132, 2188–2193. https://doi.org/10.1016/j.foodchem.2011.12.051
14. Maatooq GT, Marzouk AM, Gray AI, Rosazza JP (2010). Bioactive microbial metabolites from glycyrrhetinic acid. Phytochemistry 71, 262–270. https://doi.org/10.1016/j.phytochem.2009.09.014
15. Messier C, Epifano F, Genovese S, Grenier D (2012). Licorice and its potential beneficial effects in common oro-dental diseases. Oral Disease 18, 32–39. https://doi.org/10.1111/j.1601-0825.2011.01842.x
16. Montoro P, Maldini M, Russo M, Postorino S, Piacente S, Pizza C (2011). Metabolic profiling of roots of liquorice (Glycyrrhiza glabra) from different geographical areas by ESI/MS/MS and determination of major metabolites by LC-ESI/MS and LC-ESI/MS/MS. Journal of Pharmaceutical and Biomedical Analysis 54, 535–544. https://doi.org/10.1016/j.jpba.2010.10.004
17. Özcan FŞ, Özcan N, Us AA, Sağdiç O (2020). Comparison of extraction methods optimised by RSM for extraction of some bioactives from liquorice samples. Turkish Journal of Agriculture and Forestry 44, 24–38. https://doi.org/10.3906/tar-1903-46
18. Quintana SE, Hernández DM, Villanueva-Bermejo D, García-Risco MR, Fornari T (2020). Fractionation and precipitation of licorice (Glycyrrhiza glabra L.) phytochemicals by supercritical antisolvent (SAS) technique. Lwt 126, 109315. https://doi.org/10.1016/j.lwt.2020.109315
19. Russo M, Serra D, Suraci F, Di Sanzo R, Fuda S, Postorino S (2014). The potential of e-nose aroma profiling for identifying the geographical origin of licorice (Glycyrrhiza glabra L.) roots. Food Chemistry 165, 467–474. https://doi.org/10.1016/j.foodchem.2014.05.142
20. Sasaki H, Takei M, Kobayashi M, Pollard RB, Suzuki F (2002). Effect of glycyrrhizin, an active component of licorice roots, on HIV replication in cultures of peripheral blood mononuclear cells from HIV-seropositive patients. Pathobiology 70, 229–236. https://doi.org/10.1159/000069334
21. Wang ZY, Nixon DW (2001). Licorice and cancer. Nutrition and Cancer 39, 1–11. https://doi.org/10.1207/S15327914nc391_1
22. Yang R, Wang LQ, Yuan BC, Liu Y (2015). The Pharmacological Activities of Licorice. Planta Medica 81, 1654–1669. https://doi.org/10.1055/s-0035-1557893
23. Zhang Q, Ye M (2009). Chemical analysis of the Chinese herbal medicine Gan-Cao (licorice). Journal of Chromatography A 1216, 1954–1969. https://doi.org/10.1016/j.chroma.2008.07.072