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Changes of Furanocoumarins Content in Vegetables During Storage

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Changes of Furanocoumarins Content in Vegetables During Storage Czech J. Food Sci. Vol. 22, Special Issue Changes of Furanocoumarins Content in Vegetables during Storage P. BOTEK*, V. SCHULZOVÁ*, R. PEROUTKA and J. HAJŠLOVÁ Department of Food Chemistry and Analysis, Institute of Chemical Technology, Prague, Czech Republic, *E-mail: [email protected], [email protected] Abstract: Long term experiments, which simulated storage of celery (Apium graveolens) under industrial (air- conditioned store)/household (common cellar) conditions, were carried out. Several celery cultivars from both organic and/or conventional production were monitored for furanocoumarins levels for 16–26 weeks. The increase of furanocoumarin concentrations during the storage of all the tested celery cultivars was observed, nevertheless, the extent of toxicants accumulation differed among tested cultivars. The changes of furanocoumarin levels occur- ring during processing of vegetables were studied, too. Levels of both linear (psoralen, bergapten, xanthotoxin, trioxsalen, isopimpinellin) and angular (angelicin, sphondin, isobergapten) furanocoumarins in tested vegetable were determined by validated GC/MS (SIM) method. The detection limits (LODs) obtained by this analytical method were around 0.003 mg/kg. Keywords: furanocoumarins; storage; vegetable; gas chromatography INTRODUCTION biologically active compounds, linear and angular furanocoumarins, can be recognized. Furanocoumarins are present in several plant Furanocoumarins are classified as phototoxic families such as Apiaceae, Rutaceae and Moraceae compounds, after exposure to UV light forma- [1]. The most widely consumed vegetable with tion of adducts with DNA can take place [1–3]. high content of these natural toxins are celery, In addition, mutagenic and carcinogenic effects parsley and parsnip. Considering their chemical were demonstrated in experimental animals when structure (Figure 1, Table 1), two groups of these exposed to high doses of furanocoumarins. groups of these biologically active compounds, linear and angular furanocoum 2 A R2R B O O O O O O Figure 1. General structures 2 R2R of linear (A) and angular (B) R1R1 1 R1R furanocoumarins recognized. Table 1. Structure of common furanocoumarins Linear: Angular: Psoralen (R1 = H, R2 = H) Angelicin (R1 = H, R2 = H) 1 2 1 2 Bergapten (R = OCH3, R = H) Isobergapten (R = OCH3, R = H) 1 2 1 2 Xanthotoxin (R = H, R = OCH3) Sphondin (R = H, R = OCH3) 1 2 1 2 Isopimpinellin (R = OCH3, R = OCH3) Pimpinellin (R = OCH3, R = OCH3) Proc. Chemical Reaction in Food V, Prague, 29. 9.–1. 10. 2004 219 Vol. 22, Special Issue Czech J. Food Sci. As regards humans, the dietary intake largely Indofine (USA). Isobergapten and sphondin were depends not only on a variety of celery consumed identified on the basis of mass spectra, and quanti- but also on its storage and processing. As shown in fied using bergapten and xanthotoxin for calibra- our study, concentrations of these toxins in respec- tion. Standards were dissolved in ethyl acetate, tive crop may increase significantly under stress stock solution at concentration 50 µg/ml was stored conditions (attack of insects or fungi, mechanical at 4°C. damage, unfavourable climatic/storage factors etc.) Chemicals – Ethyl acetate for residue pesticide [1, 4, 5] and no significant decrease can be expected analysis was obtained from Scharlau (Spain), sodi- as a result of cooking since furanocoumarins are um sulphate was from Penta (Czech Republic). relatively stable under common heat treatment Methods – Five bulbs (washed, bottom and upper conditions [5]. parts removed) or 100 g of celery leaves from five plants were homogenized to obtain representative EXPERIMENTAL sample. 10 g of homogenized sample was extract- ed with ethyl acetate (2 × 40 ml) by shaking for Material. Stored celery – Two storage experiments 30 min. Combined extracts were filtered through (starting in October) were carried out: anhydrous sodium sulphate and transferred into (i) Four celery cultivars (Maxim, Radiant, Dia- 100 ml volumetric flasks. mand, Neon) were purchased from a private pro- GC/MS analyses of extracts were carried out ducer. Samples were stored at household conditions using Agilent HP 6890 gas chromatograph with in a cellar for 26 weeks at 2–13°C. Dry matter of Mass Selective detector HP 5973 (Agilent, USA) celery bulbs at the beginning of experiment was operated in SIM mode. GC conditions were as fol- around 12% (year 2002 – high rainfall). Relative lows: fused silica capillary column DB5-MS 60 m × standard deviation (sum of furanocoumarins) for 0.25 mm × 0.25 µm; column temperature program bulbs was 7% at the beginning of storage experiment 68°C (hold for 2 min) to 250°C at 20°C/min, and and 53% at the end of storage experiment. hold for 5 min, then 20°C/min to 285°C (hold for (ii) Six cultivars (3 root celery – Albin, Kompakt, 15 min); carrier gas He with constant flow 2 ml/min; Maxim, 2 petiolate celery – Malachit, Avalon and injection temperature 250°C; injection volume 1 µl 1 leafy celery – Jemny) both of organic and con- using splitless injection mode (splitless time 2 min). ventional origin were purchased from the Czech For detection characteristic m/z values were used: University of Agriculture in Prague. Samples were angelicin (186), psoralen (186), sphondin (216), stored at industrial (air-conditioned store) condi- xanthotoxin (216), isobergapten (216), bergapten tions at 4°C. Bulbs were stored for 16 weeks, rela- (216), trioxsalen (228), isopimpinellin (231). tive standard deviation (sum of furanocoumarins) Methods performance characteristic – detection lim- for bulbs was 32% at the beginning of experiment, its were in the range 0.001–0.008 mg/kg, recovery 49% at the end. Dry matter of bulbs at the begin- 89–97% (spiking level 10 mg/kg), relative standard ning of experiment was around 25% (year 2003 deviation 3.9–4.7% – low rainfall during growing period). Leaves were stored for 4 weeks, dry matter at the beginning of RESULTS AND DISCUSSION experiment was 21–34%, at the end 31–76%. Grated celery – Samples were purchased from the In celery samples the following components were retail market. Grated celery and parsnip root were determined: psoralen, xanthotoxin, bergapten, stored ten days in refrigerator at 4°C. Samples isopimpinellin; in parsnip angelicin, psoralen, were packed in food stretch film, dry matter was sphondin, xanthotoxin, isobergapten, bergapten, constant during the experiment. trioxsalen, isopimpinellin. In the next results, the Processing of celery – Samples (cultivar President) sum of these furanocoumarins is presented. were purchased from various phase of sterilization processing from industrial producer. Product was Storage of celery at household conditions a grated pickled celery (pH 4). Chemicals and methods. Standards – Standards As shown in Figure 2 successive increase of fura- of psoralen, angelicin, xanthotoxin, bergapten, nocoumarin levels occurred during storage in all trioxsalen were purchased from Sigma-Aldrich celery varieties, the most pronounced was recog- (Germany), isopimpinellin was obtained from nized in the cultivar Maxim: after 10 weeks their 220 Proc. Chemical Reaction in Food V, Prague, 29. 9.–1. 10. 2004 Czech J. Food Sci. Vol. 22, Special Issue 200 16 Figure 2. Storage of celery bulbs at household conditions (total Radiant furanocoumarins in fresh mat- ) ) Maxim g C ° k Neon ter) ( / 150 12 g Diamand e r m u ( Temperature t a n r o e i t p a r m t 100 8 e n t e e c g n a o r C o t 50 4 S 0 0 0 5 10 15 20 25 30 Weeks content was even 17 times higher as compared to conventionally grown cultivar Maxim a�er 16 weeks. that determined after harvest. Expressed on dry ma�er the highest levels of furano- coumarins were found a�er 12 weeks of storage. Storage of celery under industrial conditions Conventionally grown cultivars Albin (63.7 mg/kg) (air conditioned store held at 4°C) and Kompakt (38.0 mg/kg) were analyzed only a�er harvesting. Content of furanocoumarins a�er Similarly to the previous experiment the gradual harvest was higher (1.3–2.8 times) in conventional increase of furanocoumarins was observed dur- grown bulbs compared to organic ones. ing the storage period (Figure 3). The dynamics of In celery leaves higher accumulation of furano- toxicants in conventionally grown cultivar Maxim coumarins was found after 4 weeks of storage was rather different as compared to other samples. (14 times higher expressed on fresh matter, 9 times Rather surprisingly, the content of furanocoumarins higher on dry matter). Expressed on dry matter in in the same cultivar obtained from the organic farm- some samples the levels of the furanocoumarins ing system was distinctly lower. The maximal ac- did not change. The influence of growing condi- cumulation (14 times higher concentrations than in tions on furanocoumarin levels was not signifi- bulbs a�er harvest) of furanocoumarins occurred in cant. 200 Albin org. Kompakt org. ) g 150 Maxim org. k / g Maxim conv. m ( n o i t 100 a r t n e c n o C 50 0 Figure 3. Storage of celery bulbs in 0 5 10 15 refrigerator20 (total furanocoumarins Weeks on fresh ma�er) Proc. Chemical Reaction in Food V, Prague, 29. 9.–1. 10. 2004 221 Vol. 22, Special Issue Czech J. Food Sci. 100 Figure 4. Thermodynamics of furano- coumarins in grated celery and parsnip Parsnip stored at 4°C (total furanocoumarins on Celery fresh ma�er) ) g 75 k / g m ( n o i t 50 a r t n e c n o C 25 0 0 2 4 6 Days 8 10 12 Storage of grated celery and parsnip their reductions in a diet is peeling and blanching of bulbs, the breakdown during thermo sterilization Rapid increase of furanocoumarin levels oc- does not take place. Since successive increase of curred 6th day of storage of grated vegetables at furanocoumarins may occur in grated celery and 4°C (Figure 4); in day 10 the levels of toxicants parsnip, the period before processing or consump- were 270% in parsnip and 1330% in celery storage tion of these vegetables should be shortened as as compared to the original content (day 0).
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