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Quantitative Determination of Ellagic Acid and Gallic Acid in Geum Rivale L. and G. Urbanum L

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Quantitative Determination of Ellagic Acid and Gallic Acid in Geum Rivale L. and G. Urbanum L ACTA BIOLOGICA CRACOVIENSIA Series Botanica 56/2: 74–78, 2014 DOI: 10.2478/abcsb-2014-0021 QUANTITATIVE DETERMINATION OF ELLAGIC ACID AND GALLIC ACID IN GEUM RIVALE L. AND G. URBANUM L. ALEKSANDRA OWCZAREK*, MONIKA ANNA OLSZEWSKA, AND JAN GUDEJ Department of Pharmacognosy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, Poland Received December 12, 2013; revision accepted March 15, 2014 Hydrolyzable tannins and products of their hydrolysis, ellagic acid (EA) and gallic acid (GA), are important con- stituents of many medicinal plants and exhibit various biological activities. Geum rivale and G. urbanum are traditional herbal remedies rich in tannin compounds. The aim of the study was to quantitate free and total EA and GA in aerial and underground parts of G. rivale and G. urbanum. After optimization of extraction, both compounds were quantitated by reversed phase HPLC (RP-HPLC). EA was more abundant than GA in the inves- tigated material, and underground parts of G. rivale were the richest source of total EA and GA. Key words: Geum rivale, Geum urbanum, phenolic acid, Rosaceae. INTRODUCTION G. urbanum is sometimes used to flavor alcoholic beverages (Mackù and Krejèa, 1989; Strzelecka and Ellagic acid (EA) and gallic acid (GA) are two impor- Kowalski, 2000). tant phenolic compounds present in many medici- Analyses of the chemical composition of those nal plants. They show a large variety of biological species have revealed the presence of some triter- activities including antioxidant, antimicrobial and penes, sterols and flavonoids, as well as small anticancer activity (Faried et al., 2007; Wansi et al., amounts of essential oil (Vollmann and Schultze, 2010; Hagiwara et al., 2010). EA and GA can exist in 1995; Panizzi et al., 2000). It is tannins, however, that plant material in free form but the main sources of are considered to be the main group of constituents these compounds are hydrolyzable tannins (ellagi- responsible for the activity and medicinal usefulness tannins and gallotannins), which upon hydrolysis of the plants (Blinova, 1954; Strzelecka and release a sugar and a respective acid moiety Kowalski, 2000). Previously we determined total tan- (Haslam, 2007; Serrano et al., 2009). Hydrolytic nin content (by gravimetric method with the use of degradation of hydrolyzable tannins can occur in the hide powder) in the plants, at 31.4–136.1 mg/g gastrointestinal tract after ingestion of the medicine depending on the species and plant organ (Owczarek (Clifford and Scalbert, 2000; Cerdá et al., 2005). EA and Gudej, 2013). Most of them are believed to be and GA, as the major products of hydrolyzable tan- hydrolyzable gallo- and ellagitannins (Blinova, 1954). nin degradation, might therefore have a significant Free EA and GA have also been isolated from the effect on the activity of herbal remedies containing plants (Gstirner and Widenmann, 1964; Panizzi et al., large amounts of hydrolyzable tannins. 2000). G. rivale and G. urbanum could be rich Rosaceae is a plant family known to contain sources of EA and GA and this might be reflected in large amounts of tannin compounds (Hegnauer, their activity. To the best of our knowledge, EA and 1973). Here we study the chemical composition of GA content has been studied in G. rivale and two species of the genus Geum (Rosaceae) – Geum G. urbanum only fragmentarily, and the methods rivale and G. urbanum. Both plants are perennial used were not optimized or validated (Oszmianski et herbs widely distributed in temperate regions of the al., 2007; Kuczerenko et al., 2011). Northern Hemisphere. Rhizomes of the plants are The aim of our study was to determine the con- used in traditional medicine as astringent, anti- tent of free EA and GA, as well as their total content inflammatory and antiseptic agents. Due to its char- after hydrolytic degradation of tannins, in aerial and acteristic clove-like aroma the rhizome of underground parts of G. rivale and G. urbanum. *e-mail: [email protected] PL ISSN 0001-5296 © Polish Academy of Sciences and Jagiellonian University, Cracow 2014 Unauthenticated Download Date | 2/12/16 11:01 AM Ellagic acid and gallic acid in Geum rivale and G. urbanum 75 MATERIALS AND METHODS for 60 min. The obtained extract was filtered and the residue was heated twice with 20 mL water for 15 min. PLANT MATERIAL The combined extracts were diluted to 100 mL. Aerial and underground parts of G. rivale and G. urbanum were collected in Lodz in May 2010. HPLC ANALYSES The material was identified by Prof. Jan Gudej, The analyses employed a Hewlett-Packard 1100 Department of Pharmacognosy, Medical University series chromatograph equipped with an HP1311A of Lodz, Poland. Voucher specimens are deposited quaternary pump, HP1322A vacuum degasser, in the Department of Pharmacognosy, Medical HP1314A variable wavelength UV/VIS detector and University of Lodz, Poland. 20 μl manual injector. A Nucleodur C18 HPLC col- The plant material was dried under normal con- umn (250 × 4.6 mm, 5 μm; Machery-Nagel) was used. ditions and powdered using an electric grinder. The mobile phase consisted of solvent A [0.5% (v/v) water solution of H3PO4] and solvent B (methanol) CHEMICALS AND REAGENTS with the following elution profile: 0–8.5 min: 5–14% B in A, 8.5–25 min: 14–70% B in A, 25–30 min: EA and GA were purchased from Sigma-Aldrich 70% B in A. Elution was carried out at room tem- (Germany). Solvents used for HPLC analysis were perature at a flow rate of 1.0 mL/min. Injection vol- obtained from POCH (Gliwice, Poland). Other sol- ume was 20 μl and detection wavelength 254 nm. vents were of analytical grade and were obtained Before HPLC analysis all samples were filtered from Chempur (Piekary Slaskie, Poland). through a PFTE syringe filter (13 mm, 0.2 μm, Whatman). Identification of EA and GA was based PREPARATION OF STANDARD CURVE on comparison of retention time with standards, and their content was calculated based on the cor- Stock solutions of EA and GA were prepared by dis- responding peak areas and injected concentra- solving the reference substances in methanol to final tions. concentrations of 103.28 μg/mL for EA and 221 μg/mL for GA. The stock solutions were then diluted to appropriate concentration ranges and VALIDATION used to establish calibration curves. Each concen- Measurements of intra- and inter-day variability were tration was injected three times and the calibration used to determine the precision of the methods. The curves were plotted using linear regression of the assessments were made for a sample of G. rivale rhi- mean peak area versus the concentration. zomes before and after hydrolysis. Each solution was injected five times. Intra-day repeatability was exam- OPTIMIZATION OF SAMPLE PREPARATION ined by analyzing each sample on the same day with- To optimize extraction of free EA and GA we com- in 24 h. Inter-day repeatability was determined on five pared different extraction solvents [methanol, 75%, different days. The measure of repeatability was the 50%, 25% methanol/water (v/v), water] and two relative standard deviation (RSD). extraction methods (mechanical shaking, refluxing). A recovery study was made to determine accura- To optimize hydrolysis we compared different cy. Known quantities of the standard solutions at solvents [methanol, 75%, 50%, 25% methanol/water three different concentrations were added to known (v/v), water], acid concentrations [6, 8, 10 mL amounts of pulverized rhizomes of G. rivale, and the 25% (v/v) HCl in 20 mL solvent] and extraction times samples were extracted and analyzed by the estab- (60, 90, 120 min). lished HPLC method. Percentage recovery was calcu- lated as the ratio of detected versus added amounts. The limit of detection (LOD) and the limit of DETERMINATION OF FREE EA AND GA quantification (LOQ) were found by successively Dried and ground plant material (500 mg) was diluting the standard stock solutions to the concen- mechanically shaken with 30 mL methanol for tration giving the smallest detectable peak. These 20 min. The obtained extract was filtered and the concentrations were used to calculate the 3-σ signal- residue was shaken twice with 20 mL methanol for to-noise (S/N) ratio for the LOD, and the 10-σ S/N 15 min. The combined extracts were diluted with ratio for the LOQ. methanol to 100 mL. STATISTICAL ANALYSIS DETERMINATION OF TOTAL EA AND GA All analyses were done in triplicate and are Dried and ground plant material (50–100 mg) was expressed as means ±SD. Statistical analyses refluxed with 20 mL water with 6 mL 25% (v/v) HCl employed StatisticaPL software (StatSoft Inc., Unauthenticated Download Date | 2/12/16 11:01 AM 76 Owczarek et al. TABLE 1. Linearity of standard curves and retention parameters of ellagic and gallic acid TABLE 2. Precision data, LOD and LOQ for ellagic and gallic acid Poland). The significance of differences between aerial than in the underground parts. The free GA means was analyzed by ANOVA. content of aerial parts of G. urbanum was too low for quantitation and in the other plant materials was virtually undetectable (Tab. 3). In their screening of RESULTS AND DISCUSSION various G. urbanum populations, Kuczerenko et al. (2011) reported average 0.4 mg/g free EA and 0.3 Preliminary optimization studies showed that mg/g GA in aerial parts of the plant, and 0.5 mg/g EA adding water to the extraction solution caused a and 0.6 mg/g GA in underground parts. The rela- steady increase of the concentrations of both tively small differences between studies are probably acids, especially during refluxing, when the extrac- explained by variability between plants growing in tion time was extended.
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