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Original Paper Identification and Profile of Furanocoumarins from The _ Food Science and Technology Research, 21 (1), 67 75, 2015 Copyright © 2015, Japanese Society for Food Science and Technology doi: 10.3136/fstr.21.67 http://www.jsfst.or.jp Original paper Identification and Profile of Furanocoumarins from the Ribbed CeleryApium ( Graveolens L Var. Dulce Mill./ Pers.) 1* 1 1 2 1 3 Agnieszka NAJDA , Jan DYDUCH , Klaudia Świca , Magdalena Kapłan , Rafał paplińsKi , Monika sachadyn-Król 4 and Kamila KlimeK 1 Department of Vegetable Crops and Medicinal Plants, University of Life Sciences in Lublin, 20-950 Lublin, Leszczyńskiego Street 58, Poland 2 Department of Seed Production and Nurseries, University of Life Sciences in Lublin, 20-950 Lublin, Leszczyńskiego Street 58, Poland 3 Department of Chemistry University of Life Sciences in Lublin, 20-950 Lublin, Akademicka Street 15, Poland 4 Department of Applied Mathematics and Informatics, University of Life Sciences in Lublin, 20-612 Lublin, Głęboka Street 28, Poland Received July 22, 2014 ; Accepted September 9, 2014 The aim of this study was to identify and determine the qualitative and quantitative composition of furanocoumarins in anatomical parts (blade and petiole) of two cultivars of ribbed celery, depending on the age of the plant. Two accurate, precise and inexpensive techniques for analytical detection of coumarin in a relatively short period of time were used in the present study. TLC - the method considered as preliminary, showed the presence of psolaren, bergapten, xanthotoxin and simple coumarin – umbelliferone. Additionally, isopimpinellin was detected by HPLC method. Chromatographic analysis of ribbed celery leaves showed the presence of four furanocoumarins. Psoralen and isopimpinellin are dominant in the leaf blades, wherein content is correlated with the term of harvesting. Bergapten was dominant in petioles regardless of the harvesting time and cultivar. Keywords: Apiaceae, cultivars, harvest, furanocoumarin, HPLC methods Introduction 2002). Leafy vegetables are an important group of plants in the daily Plants from the family Apiaceae contain compounds with diet. Less known species like endive, chicory, arugula, rochet and multidirectional biological activity: antimicrobial, anti-cancer, for chard has become popular among consumers. Also ribbed celery the liver agents and cyclooxygenase inhibitors (Chen et al., 1995; (Apium graveolens L. var. Dulce Mill. / Pers.), valued for its Strohl, 2000). The presence of these substances is responsible for the attractive appearance, taste and the nutritional composition sealing properties and capillary walls strengthens, improving blood resulting from the rich mineral and vitamin composition is circulation in the myocardium, spasmolytic, diuretic, platelet classified to this group (Vogel, 1996). In part for consumption anticoagulation, anti-ulcer, anti-allergic, anti-inflammatory, anti- (petioles and partially leaf blades) contains many valuable hepatotoxic, antifungal and antiviral effects (Trumble and Quiros, biologically active substances such as phenolic acids, flavonoids, 1988, Zheng et al., 1993). tannins, mono-and sesquiterpenes which make them useful in the Coumarins are fairly common in many fruits and vegetables, treatment of certain dermatological diseases, arthritic-rheumatic, especially in the families Apiaceae and Rutaceae (Zobel and Brown, urinary and digestive system (Williamson, 1999; Wolski et al., 1990; Ojala, 2001). These group of compounds are important from *To whom correspondence should be addressed. E-mail: [email protected] 68 A. NAJDA et al. the therapeutic point of view (Leal et al., 2000; Waksmundzka- carried out on two dates i.e. I – after 100 (August) and II – after Hajnos et al., 2004). Currenly, furanocoumarins of natural origin 120 days (September) of two growing seasons: in 2011 and 2012. are used in PUVA therapy of vitiligo and psoriasis; furthermore, they In a two-year cycle, the experimental average air temperature in are active Ca+2 channel blockers (Murray et al., 1982; Vuorela et the growing seasons of 2011 and 2012 showed a little varied. The al., 1988; Coven et al., 1999) . Furanocoumarins are characterized average air temperature in the period May-September was 17.2℃ by a broad spectrum of biological activity. They reduce the platelet (Table 1). The range of rainfall in years of research was at a agregation in in vitro test (Chen et al.,1996), they induce apoptosis similar level. Average monthly temperatures in May and June in human promyelocytic leukemia, HL-60 cells (Bogucka-Kocka and were higher than the perennial average, it has the second decade of Kocki, 2002; Pae et al., 2002) and they work as hepatoprotective July to the end of the growing season showed a gradual decrease in agents (Jagiełło-Wójtowicz et al., 2004) . Photosensitizer effect of temperatures that were higher than the average perennial. Research these substances (particularly psoralen derivative) is used in medicine material consisted blades and petioles of celery; 25 plants from and the treatment of many dermatological disorders (Towers and each cultivar (5 plants × 5 replications) in each year. Samples were Abramowski, 1983; Bhatnagar et al., 2007; Serrano-Perez et al., dried in a conventional dryer at 35℃ to dry mass of raw material. 2008) . Furanocoumarins content in the plant varies depending on the 85 g of dry raw material were obtained from 1000 g of fresh degree of its development, and is different in different vegetative petioles and 170 g from 1000 g of fresh blades. Dry plant material phases (Borkowski, 1973; Bogucka-Kocka and Kocki, 2002). was pulverized and extracted. Increase in the content of furanocoumarins in different organs was Chemical reagents Solvents for extraction were purchased observed in many species of plants under stress conditions due to from POCh SA (Gliwice, Poland) or J.T. Baker (USA). Standards various factors: biotic (fungi, bacteria, viruses), abiotic (heavy metals, of high purity were purchased from Sigma–Aldrich Chemie GmbH detergents, acid rain) or physical (UV radiation, low temperature). (Munich, Germany), Merck (Darmstadt, Germany) and from other The diverse biological activity of furanocoumarins and the role they suppliers. fulfill in the life of the plant tend to clarify the relationship between Solid phase extraction Analysis of free furanocoumarin the plant defense system and external conditions. Stress metabolites arrangements was performed in dry and powdered whole leaves, named phytoalexins including furanocoumarins are formed as a result leaf blades, and petioles of leaf celery plants. Extraction was of defense property (Hain et al., 1993; Dixon and Lamb, 1999). conducted in liquid-solid system, while extract purification by The aim of this study was to identify and determine the means of SPE method (Solid Phase Extraction). qualitative and quantitative composition of furanocoumarins in Samples of 50 g powdered and dried leaves, leaf blades, and anatomical parts (blade and petiole) of two cultivars of ribbed petioles of two leaf celery cultivars were weighed and put into celery, depending on the age of the plant. Two accurate, precise the tubes for extraction. After preliminary maceration for 24 and inexpensive techniques for analytical detection of coumarin in hours, material was extracted using petroleum ether (1:10 v/v) a relatively short period of time were used in the present study. and processed in Soxhlet’s apparatus for 36 hours. The petroleum ether was evaporated till dry then. Dry residue of Material and Methods petroleum ether were purified on a SPE column (BackerBond RP Plant material Two original Polish varieties of celery Zefir 18). Microcolumns were mounted in a set of vacuum filtration (J and Helios (company PlantiCo Zielonka) were tested in this study. Beaker) and further conditioned successively with 5 mL of Plants for analysis were obtained from outdoor experience of the methanol, 5 mL of double-distilled water, then dissolved extracts Department of Vegetable and Medicinal Plants, University of Life were applied (100 mg / 3 mL of double-distilled water). Elution Sciences in Lublin, Poland (N 51 ° 16’ E 22 ° 34’). Cultivation was carried out by washing the bed of pollutant 30 mL of double- was carried out in the ecological system on luvisol soil formed distilled water for removal of the ballast. Furanocoumarin from loess, containing 1.6% organic matter. Crops harvesting was compounds elution was performed 10 mL of methanol solution Table 1. Mean monthly air temperatures and total amount of precipitation at ES Felin in the years 2011-2012 Temperature ℃ Amount of precipitation mm Month 2011 2012 Mean for 1951-2000 2011 2012 Mean for 1951-2000 V 14.9 15.0 13.0 80.5 81.5 58.3 VI 18.1 18.1 16.5 87.8 87.8 65.8 VII 19.1 19.2 17.9 87.0 87.0 78.0 VIII 18.8 19.2 17.1 65.3 37.6 68.6 IX 15.2 15.0 12.6 5.4 35.5 51.6 Mean 17.2 17.3 15.4 65.2 65.88 64.46 Identification and Profile of Furanocoumarins from the Ribbed Celery 69 containing 0.3 mL of 25% ammonia. The eluents were evaporated method. HPLC chromatogram of standards furanocoumarins to dryness and the residue was dissolved in 10 mL of methanol. distribution is presented in Fig. 2. Fig. 3 shows the UV The thus obtained samples were analyzed by TLC and HPLC for spectroscopic spectrums. Tab. 2. contains the average retention the presence of furanocoumarins. times for the different standards of furanocoumarins and Thin layer chromatography TLC was performed on 60G Si furanocoumarins isolated from extracts of the tested materials. The gel, cellulose and polyamide plates (Merck, Germany). Samples presence of three furanocoumarins in the petioles of both studied were applied using Autosampler3 (Camag, Switzerland). The cultivars and four furanocoumarins such as psoralen, bergapten, plates were developed in the chromatographic chambers: flat type isopimpinellin and xanthotoxin in the leaf blades were found. Fig. DS (Chromdes, Poland) and vertical (Camag, Switzerland). 4 and 5 show chromatograms representing furanocoumarins Developing phase was n-heptane:dichloromethane:ethyl acetate content in the tested raw materials. Analysed petioles of tested (40:40:20 v/v/v).
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