Variations in the chemical profile and biological activities of licorice (Glycyrrhiza glabra L.), as influenced by harvest times

• Autorzy: Cheel J , Tumowa L. , Areche C. , Van Antwerpen P. , Neve J. , Zouaoui-Boudjeltia K. , San Martin A. , Vokral I. , Wsol V. , Neugebauerova J.
• Języki publikacji: EN

Abstrakty

EN

This study investigates the variations in the chemical profile, free radical scavenging, antioxidant and gastroprotective activities of licorice extracts (LE) from plants harvested during the months of February to November. Correlations between biological properties and the chemical composition of LE were also investigated. The results showed that the total contents of phenols, flavonoids and tannins in LE varied at different harvest times. Liquiritin and glycyrrhizin, the major components of LE, varied in the range of 28.65–62.80 and 41.84–114.33 mg g-1, respectively. The relative proportion of glycyrrhizin derivative (3), glabridin (4), glabrene (5) and liquiritigenin derivative (6), varied in the range of 0.88–11.38 %, 1.86–10.03 %, 1.80–18.40 % and 5.53– 16.31 %, respectively. These fluctuations correlated positively with changes in the antioxidant and free radical scavenging activities of licorice. In general, the samples from May and November showed the most favorable free radical scavenging and antioxidant effects, whereas the best gastroprotective effect was in May. Liquiritin and glycyrrhizin, the major constituents in the February and May LE, appeared to contribute to the superoxide radical scavenging and gastroprotective effects. Glabridin and glabrene, the compounds with the highest relative proportion in the November LE, accounted for the antioxidant and DPPH scavenging activities of licorice. It is concluded that the chemical profile of licorice quantitatively varied at different harvest times and these fluctuations determined changes in its bioactivities. These data could pave the way to optimize harvesting protocols for licorice in relation with its health-promoting properties.

• Wydawca: -
• Czasopismo: Acta Physiologiae Plantarum
• Rocznik: 2013
• Tom: 35
• Numer: 04
• Opis fizyczny: p.1337-1349,fig.,ref.

Twórcy

autor

Cheel J

• Department of Pharmacognosy, Faculty of Pharmacy, Charles University in Prague, Heyrovske´ho 1203, 500 05 Hradec Kra´love´, Czech Republic
• Department of Research and Development, Contipro Biotech s.r.o, Dolnı´ Dobroucˇ 401, 561 02 Dolnı´ Dobroucˇ, Czech Republic

autor

Tumowa L.

• Department of Pharmacognosy, Faculty of Pharmacy, Charles University in Prague, Heyrovske´ho 1203, 500 05 Hradec Kra´love´, Czech Republic

autor

Areche C.

• Departamento de Quı´mica, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile

autor

Van Antwerpen P.

• Laboratory of Pharmaceutical Chemistry and Analytical Platform of the Faculty of Pharmacy, Universite Libre de Bruxelles, 1050 Brussels, Belgium

autor

Neve J.

• Laboratory of Pharmaceutical Chemistry and Analytical Platform of the Faculty of Pharmacy, Universite Libre de Bruxelles, 1050 Brussels, Belgium

autor

Zouaoui-Boudjeltia K.

• Laboratory of Experimental Medicine, CHU Charleroi, Universite Libre de Bruxelles, 6110 Montigny-le-Tilleul, Belgium

autor

San Martin A.

• Departamento de Quı´mica, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile

autor

Vokral I.

• Department of Pharmacology and Toxicology, Faculty of Pharmacy, Charles University, Heyrovske´ho 1203, 500 05 Hradec Kra´love´, Czech Republic

autor

Wsol V.

• Department of Biochemical Sciences, Faculty of Pharmacy, Charles University, Heyrovske´ho 1203, 500 05 Hradec Kra´love´, Czech Republic

autor

Neugebauerova J.

• Faculty of Horticulture, Mendel University in Brno, Valticka´ 337, 691 44 Lednice, Czech Republic

Bibliografia

• Adams RP (1987) Yields and seasonal variation of phytochemicals from Juniperus species of the United States. Biomass 12: 129–139
• Afreen F, Zobayed SMA, Kozai T (2005) Spectral quality and UV-B stress stimulate glycyrrhizin concentration of Glycyrrhiza uralensis in hydroponic and pot system. Plant Physiol Biochem 43:1074–1081
• Areche C, Theoduloz C, Yáñez T, Souza-Brito ARM, Barbastefano V, De Paula D, Ferreira AL, Schmeda-Hirschmann G, Rodrı´guez JA (2008) Gastroprotective activity of ferruginol in mice and rats: effects on gastric secretion, endogenous prostaglandins and non-protein sulfhydryls. J Pharm Pharmacol 60:245–251
• Belinky PA, Aviram M, Fuhrman B, Rosenblat M, Vaya J (1998a) The antioxidative effects of the isoflavan glabridin on endogenous constituents of LDL during its oxidation. Atherosclerosis 137:49–61
• Belinky PA, Aviram M, Mahmood S, Vaya J (1998b) Structural aspects of the inhibitory effect of glabridin on LDL oxidation. Free Radic Biol Med 24:1419–1429
• Cheel J, Theoduloz C, Rodrı´guez JA, Caligari PDS, Schmeda-Hirschmann G (2007) Free radical scavenging activity and phenolic content in achenes and thalamus from Fragaria chiloensis ssp. chiloensis, F. vesca and F. x ananassa cv. Chandler. Food Chem 102:36–44
• Cheel J, Van Antwerpen P, Tůmová L, Onofre G, Vokurková D, Zouaoui-Boudjeltia K, Vanhaeverbeek M, Néve J (2010) Free radical scavenging, antioxidant and immunostimulating effects of a licorice infusion (Glycyrrhiza glabra L.). Food Chem 122:508–517
• Chrtková A (1995) Glycyrrhiza L. In: Slavı´k B (ed) Kvétena České republiky, vol 4. Academia, Praha, pp 378–380
• Ҫyrak C, Radušienė J, Ivanauskas L, Janulis V (2007) Variation of bioactive secondary metabolites in Hypericum origanifolium during its phenological cycle. Acta Physiol Plant 29:197–203
• Di Mambro VM, Fonseca MJV (2005) Assays of physical stability and antioxidant activity of a topical formulation added with different plant extracts. J Pharm Biomed Anal 37:287–295
• Dong TTX, Cui XM, Song ZH, Zhao KJ, Ji ZN, Lo CK, Tsim KWK (2003) Chemical assessment of roots of Panax notoginseng in China: regional and seasonal variations in its active constituents. J Agric Food Chem 51:4617–4623
• Fiore C, Eisenhut M, Ragazzi E, Zanchin G, Armanini D (2005) A history of the therapeutic use of liquorice in Europe. J Ethnopharmacol 99:317–324
• Hayashi H, Hiraoka N, Ikeshiro Y, Yamamoto H, Toshikawa T (1998) Seasonal variation of glycyrrhizin and isoliquiritigenin glycosides in the root of Glycyrrhiza glabra L. Biol Pharm Bull 21:987–989
• Hertog MGL, Hollman PCH, Katan MB (1992) Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in the Netherlands. J Agric Food Chem 40:2379–2383
• Incerti A, Navari-Izzo F, Pardossi A, Izzo R (2009) Seasonal variations in polyphenols and lipoic acid in fruits of tomato irrigated with sea water. J Sci Food Agric 89:1326–1331
• Isbrucker RA, Burdock GA (2006) Risk and safety assessment on the consumption of licorice root (Glycyrrhiza sp.), its extract and powder as a food ingredient, with emphasis on the pharmacology and toxicology of glycyrrhizin. Regul Toxicol Pharmacol 46:167–192
• Ishii T, Ishii N (2006) Aging and age-related diseases caused by superoxide anion production from mitochondria. Seikagaku 78:201–207
• Kato T, Horie N, Hashimoto K, Satoh K, Shimoyama T, Kaneko T, Kusama K, Sakagami H (2008) Bimodal effect of glycyrrhizin on macrophage nitric oxide and prostaglandin E2 production. In Vivo 22:583–586
• Kitagawa I, Chen W-Z, Taniyama T, Harada E, Hori K, Kobayashi M, Ren J (1998) Quantitative determination of constituents in various licorice roots by means of high performance liquid chromatography. Yakugaku Zasshi 118:519–528
• Kondo K, Shiba M, Nakamura R, Morota T, Shoyama Y (2007) Constituent properties of licorices derived from Glycyrrhiza uralensis, G. glabra, or G. inflata identified by genetic information. Biol Pharm Bull 30:1271–1277
• Nakamura R, Kase Y, Hashimoto K, Sakakibara I, Amagaya S, Aburada M (2003) Elucidation of anti-gastric ulcer constituents of Glycyrrhizae Radix. Nat Med 57:172–177
• Nassiri-Asl M, Hosseinzadeh H (2008) Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds. Phytother Res 22:709–724
• Nassiri-Asl M, Saroukhani S, Zamansoltani F (2007) Anticonvulsant effects of aqueous extract of Glycyrrhiza glabra root in PTZinduced seizure in mice. Int J Pharmacol 3:432–434
• Okada K, Tamura Y, Yamamoto M, Inoue Y, Takagaki R, Takahashi K, Demizu S, Kajiyama K, Hiraga Y, Kinoshita T (1989) Identification of antimicrobial and antioxidant constituents from licorice of Russian and Xinjiang origin. Chem Pharm Bull 37:2528–2530
• Ozkan G, Baydar H, Erbas S (2010) The influence of harvest time on essential oil composition, phenolic constituents and antioxidant properties of Turkish oregano (Origanum onites L.). J Sci Food Agric 90:205–209
• Parr AJ, Bolwell GP (2000) Phenols in the plant and in man. The potential for possible nutritional enhancement of the diet by modifying the phenols content or profile. J Sci Food Agric 80:985–1012
• Sabbioni C, Mandrioli R, Ferranti A, Bugamelli F, Saracino MA, Forti GC, Fanali S, Raggi MA (2005) Separation and analysis of glycyrrhizin, 18b-glycyrrhetic acid and 18a-glycyrrhetic acid in liquorice roots by means of capillary zone electrophoresis. J Chromatogr A 1081:65–71
• Salminen JP, Ossipov V, Haukioja E, Pihlaja K (2001) Seasonal variation in the content of hydrolysable tannins in leaves of Betula pubescens. Phytochemistry 57:15–22
• Schempp H, Weiser D, Kelber O, Elstner EF (2006) Radical scavenging and anti-inflammatory properties of STW 5 (Iberogast) and its components. Phytomedicine 13:36–44
• Schindhelm RK, Van Der Zwan LP, Teerlink T, Scheffer PG (2009) Myeloperoxidase: a useful biomarker for cardiovascular disease risk stratification? Clin Chem 55:1462–1470
• Simons R, Vincken JP, Bakx EJ, Verbruggen MA, Gruppen H (2009) A rapid screening method for prenylated flavonoids with ultrahigh-performance liquid chromatography/electrospray ionisation mass spectrometry in licorice root extracts. Rapid Commun Mass Spectrom 23:3083–3093
• Slimestad R, Verheul B (2009) Review of flavonoids and other phenolics from fruits of different tomato (Lycopersicon esculentum Mill.) cultivars. J Sci Food Agric 89:1255–1270
• Suja KP, Jayalekshmy A, Arumughan C (2005) Antioxidant activity of sesame cake extract. Food Chem 91:213–219
• Toor RK, Savage GP, Lister CE (2006) Seasonal variation in the antioxidant composition of greenhouse grown tomatoes. J Food Compos Anal 19:1–10
• Valentão P, Fernandes E, Carvalho F, Andrade PB, Seabra RM, Bastos ML (2001) Antioxidant activity of Centaurium erythraea infusion evidenced by its superoxide radical scavenging and xanthine oxidase inhibitory activity. J Agric Food Chem 49: 3476–3479
• Van Antwerpen P, Moreau P, Zouaoui-Boudjeltia K, Babar S, Dufrasne F, Moguilevsky N, Vanhaeverbeek M, Ducobu J, Néve J (2008a) Development and validation of a screening procedure for the assessment of inhibition using a recombinant enzyme. Talanta 75:503–510
• Van Antwerpen P, Prévost M, Zouaoui-Boudjeltia K, Babar S, Legssyer I, Moreau P, Moguilevsky N, Vanhaeverbeek M, Ducobu J, Néve J, Dufrasne F (2008b) Conception of myeloperoxidase inhibitors derived from flufenamic acid by computational docking and structure modification. Bioorg Med Chem 16:1702–1720
• Vaya J, Belinky PA, Aviram M (1997) Antioxidant constituents from licorice roots: isolation, structure elucidation and antioxidative capacity toward LDL oxidation. Free Radic Biol Med 23:302–313
• Witztum JL, Steinberg D (1991) Role of oxidized low density lipoprotein in atherogenesis. J Clin Invest 88:1785–1792
• Yamamoto Y, Tani T (2006) Brief survey of Glycyrrhiza plant resources in Xinjiang, China. J Trad Med 23:27–35
• Yao L, Caffin N, D’arcy B, Jiang Y, Shi J, Singanusong R, Liu X, Datta N, Kakuda Y, Xu Y (2005) Seasonal variations of phenolic compounds in Australia-grown tea (Camellia sinensis). J Agric Food Chem 53:6477–6483
• Yesil-Celiktas O, Girgin G, Orhan H, Wichers HJ, Bedir E, Vardar-Sukan F (2007) Screening of free radical scavenging capacity and antioxidant activities of Rosmarinus officinalis extracts with focus on location and harvesting times. Eur Food Res Technol 224:443–451
• Zeng L, Zhang RY, Meng T, Lou ZC (1990) Determination of nine flavonoids and coumarins in licorice root by high-performance liquid chromatography. J Chromatogr 513:247–254
• Zhang Q, Ye M (2009) Chemical analysis of the Chinese herbal medicine Gan-Cao (licorice). J Chromatogr A 1216:1954–1969
• Zhang R, Brennan ML, Shen Z, MacPherson JC, Schmitt D, Molenda CE (2002) Myeloperoxidase functions as a major enzymatic catalyst for initiation of lipid peroxidation at sites of inflammation. J Biol Chem 277:46116–46122

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